3D Mol Similar

3-Chloroaniline

: Iupac Name：3-chloroaniline; CAS No.: 108-42-9; Molecular Weight：127.571; Modify Date.: 2022-11-29 11:43; Introduction: 3-Chloroaniline, with the chemical formula C6H6ClN and CAS registry number 108-42-9, is a compound notable for its applications in organic synthesis and manufacturing processes. This colorless to light amber liquid with a sweet odor, also known as m-Chloroaniline, features a chlorine atom attached to the benzene ring alongside an amino group. It serves as a precursor in the production of various dyes, pigments, and pharmaceuticals, contributing significantly to the chemical industry. 3-Chloroaniline has been studied for its potential environmental and health impacts due to its usage in industrial processes. It is crucial in the synthesis of agricultural chemicals and as an intermediate in the preparation of herbicides and pesticides. View more+

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1. Names and Identifiers

: 1.1 Name; 3-Chloroaniline; 1.2 Synonyms; 1-Amino-3-chlorobenzene 1-Chloro-3-aminobenzene 3-chloro-aniline 3-chlorobenzenamine 3-Chlorophenylamine 3-Cloroaniline 6-amino-2-chlorobenzene Aniline, 3-chloro- Aniline, m-chloro- Azoic diazo component 2, base Benzenamine, 3-chloro- Benzenamine,3-chloro Benzenamine,3-chloro- Benzeneamine, 3-chloro- Blue lips, fingernails and skin. Dizziness. Headache. Shortness of breath. Nausea. Vomiting. Convulsions. Weakness. Confusion. Unconsciousness. MAY BE ABSORBED! Redness. Burning sensation. Further see Inhalation. Redness. Pain. chloro-3aniline Chloroaniline EINECS 203-581-0 m-Aminochlorobenzene m-chloraniline m-Chloroaminobenzene m-Chloroaniline m-Chlorophenylamine MFCD00007765 Orange GC Base; View all

1.3 CAS No.: 108-42-9

1.4 CID: 7932

1.5 EINECS(EC#): 203-581-0

1.6 Molecular Formula: C6H6ClN (isomer)

1.7 Inchi: InChI=1S/C6H6ClN/c7-5-2-1-3-6(8)4-5/h1-4H,8H2

1.8 InChIkey: PNPCRKVUWYDDST-UHFFFAOYSA-N

1.9 Canonical Smiles: C1=CC(=CC(=C1)Cl)N

1.10 Isomers Smiles: C1=CC(=CC(=C1)Cl)N

2. Properties

2.1 Density: 1.216

2.1 Melting point: -11℃

2.1 Boiling point: 13.5° F (NTP, 1992)

2.1 Refractive index: 1.5927-1.5947

2.1 Flash Point: 255° F (NTP, 1992)

2.2 Precise Quality: 127.01900

2.2 PSA: 26.02000

2.2 logP: 2.50340

2.2 Solubility: 6.2g/l

2.3 VaporDensity: Relative vapour density (air = 1): 4.4

2.4 AnalyticLaboratory Methods: THIS METHOD DETECTS ANILINE; DERIVATIVES FORMED AS DEGRADATION PRODUCTS FROM CERTAIN PESTICIDES USING THIN-LAYER CHROMATOGRAPHY.

2.5 Appearance: Clear pale yellow to brown Liquid

2.6 AutoIgnition: >540°C

2.7 Storage: Ambient temperatures.

2.8 Chemical Properties: clear pale yellow to brown liquid

2.9 Color/Form: Colorless to light amber, tends to darken during storage

2.10 Decomposition: When heated to decomposition, it emits toxic fumes of /hydrogen chloride; and nitrogen oxides/.

2.11 Odor: Characteristic sweet odor

2.12 PH: 7.3 (H2O)(saturated aqueous solution)

2.13 Physical: PHYSICAL DESCRIPTION: Colorless to light amber liquid with a sweet odor. (NTP, 1992)

2.14 pKa: 3.46(at 25℃)

2.15 Water Solubility: H2O: 6.8 g/L (20 oC)

2.16 Stability: Tends to darken during storage.

2.17 StorageTemp: Store below +30°C.

3. Use and Manufacturing

3.1 General Description: Colorless to light amber liquid with a sweet odor.

3.2 GHS Classification: Signal: Danger
GHS Hazard Statements
Aggregated GHS information provided by 115 companies from 13 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

H301 (69.57%): Toxic if swallowed [Danger Acute toxicity, oral]
H311 (69.57%): Toxic in contact with skin [Danger Acute toxicity, dermal]
H331 (64.35%): Toxic if inhaled [Danger Acute toxicity, inhalation]
H373 (96.52%): Causes damage to organs through prolonged or repeated exposure [Warning Specific target organ toxicity, repeated exposure]
H400 (97.39%): Very toxic to aquatic life [Warning Hazardous to the aquatic environment, acute hazard]
H410 (67.83%): Very toxic to aquatic life with long lasting effects [Warning Hazardous to the aquatic environment, long-term hazard]

Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown.

Precautionary Statement Codes
P260, P261, P264, P270, P271, P273, P280, P301+P310, P302+P352, P304+P340, P311, P312, P314, P321, P322, P330, P361, P363, P391, P403+P233, P405, and P501; View all

3.3 Methods of Manufacturing: The preparation method is obtained by reduction of m-chloronitrobenzene. The reducing agent can be sodium sulfide or zinc powder and hydrochloric acid. In the reaction kettle, sodium sulfide is dissolved in water, stirred and heated to boiling, and gradually added human chloronitrobenzene, refluxed for 5 h Afterwards, distill the oily liquid to get the finished product.

3.4 Usage: 3-Chlorobenzenamine is used in the synthesis of pyrimidoazepine analogs as serotonin 5-HT2A and 5-HT2C receptor ligands for the treatment of obesity. Also used in the synthesis of novel COX-2 inhibitors.

4. Safety and Handling

4.1 Symbol: GHS06, GHS08, GHS09

4.1 Hazard Codes: T

4.1 Signal Word: Danger

4.1 Risk Statements: R23/24/25;R33;R50/53

4.1 Safety Statements: S28;S36/37;S45;S60;S61

4.1 Packing Group: II

4.1 Fire Hazard: 3-Chloroaniline is combustible.

4.2 Hazard Class: 6.1

4.2 Hazard Declaration: H301-H311-H331-H373-H410

4.2 RIDADR: UN 2019

4.2 Safety Profile: Poison by ingestion, skin contact, subcutaneous, and intravenous routes. Mutation data reported. When heated to decomposition it emits toxic fumes of Cland NOx. See also ANILINE DYES. 3-Chloroaniline Preparation Products And Raw materials Raw materials

4.3 Caution Statement: P261-P273-P280-P301 + P310-P311-P501

4.3 WGK Germany: 2

4.3 RTECS: BX0350000

4.3 Report: EPA Genetic Toxicology Program. Reported in EPA TSCA Inventory.

4.4 Safety: Safety: DANGER: POISON, irritates skin, eyes, lungs
Hazard Codes:?T,N
Risk Statements: 23/24/25-33-50/53 (Toxic by inhalation, in contact with skin and if swallowed; Danger of cumulative effects; Very Toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment)
Safety Statements: 28-36/37-45-60-61-28A (After contact with skin, wash immediately with plenty of ... (to be specified by the manufacturer);
Poison by ingestion, skin contact, subcutaneous, and intravenous routes. Mutation data reported. When heated to decomposition it emits toxic fumes of Cl^? and NO_x. See also ANILINE DYES.

4.5 Specification: ?3-Chloroaniline , its cas register number is 108-42-9. It also can be called 1-Amino-3-chlorobenzene ; m-Aminochlorobenzene ; 3-Chlorophenylamine ; Fast Orange GC base ; and 3-Chlorobenzenamine . It should?be?stored in a tightly closed container. Store in a cool, dry, well-ventilated area away from incompatible substances. It is hazardous, so the first aid measures and others should be known. Such as: When on the skin: first, should flush skin with plenty of water immediately for at least 15 minutes while removing contaminated clothing. Secondly, get medical aid. Or in the eyes: Flush eyes with plenty of water for at least 15 minutes, occasionally lifting the upper and lower eyelids. Then get medical aid soon. While, it's inhaled: Remove from exposure and move to fresh air immediately. Give artificial respiration while not breathing. When breathing is difficult, give oxygen. And as soon as to get medical aid. Then you have the ingesting of the product: Wash mouth out with water, and get medical aid immediately. Notes to physician: Treat supportively and symptomatically.
In addition, 3-Chloroaniline (CAS NO.108-42-9)?darkens on exposure to light and air. It is not compatible with strong oxidizing agents, acids, acid chlorides, acid anhydrides, chloroformates, and you must not take it with incompatible materials. And also prevent it to broken down into hazardous decomposition products:?Hydrogen chloride, nitrogen oxides, carbon monoxide, irritating and toxic fumes and gases, carbon dioxide, nitrogen.; View all

4.6 Toxicity: Oral-rat LD50: 256 mg/kg; Oral-Mouse LD50: 334 mg/kg

5. MSDS

2.Hazard identification

2.1 Classification of the substance or mixture

Acute toxicity - Oral, Category 3

Acute toxicity - Dermal, Category 3

Skin irritation, Category 2

Eye irritation, Category 2

Acute toxicity - Inhalation, Category 3

Specific target organ toxicity \u2013 repeated exposure, Category 2

Hazardous to the aquatic environment, short-term (Acute) - Category Acute 1

2.2 GHS label elements, including precautionary statements

Pictogram(s)
Signal word	Danger
Hazard statement(s)	H301 Toxic if swallowed H311 Toxic in contact with skin H315 Causes skin irritation H319 Causes serious eye irritation H331 Toxic if inhaled H373 May cause damage to organs through prolonged or repeated exposure H400 Very toxic to aquatic life
Precautionary statement(s)
Prevention	P264 Wash ... thoroughly after handling. P270 Do not eat, drink or smoke when using this product. P280 Wear protective gloves/protective clothing/eye protection/face protection. P261 Avoid breathing dust/fume/gas/mist/vapours/spray. P271 Use only outdoors or in a well-ventilated area. P260 Do not breathe dust/fume/gas/mist/vapours/spray. P273 Avoid release to the environment.
Response	P301+P310 IF SWALLOWED: Immediately call a POISON CENTER/doctor/\u2026 P321 Specific treatment (see ... on this label). P330 Rinse mouth. P302+P352 IF ON SKIN: Wash with plenty of water/... P312 Call a POISON CENTER/doctor/\u2026if you feel unwell. P361+P364 Take off immediately all contaminated clothing and wash it before reuse. P332+P313 If skin irritation occurs: Get medical advice/attention. P362+P364 Take off contaminated clothing and wash it before reuse. P305+P351+P338 IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. P337+P313 If eye irritation persists: Get medical advice/attention. P304+P340 IF INHALED: Remove person to fresh air and keep comfortable for breathing. P311 Call a POISON CENTER/doctor/\u2026 P314 Get medical advice/attention if you feel unwell. P391 Collect spillage.
Storage	P405 Store locked up. P403+P233 Store in a well-ventilated place. Keep container tightly closed.
Disposal	P501 Dispose of contents/container to ...

2.3 Other hazards which do not result in classification

none

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6. NMR Spectrum

ESR : OXIDATION WITH PERBENZOIC ACID

13C NMR : in CDCl3

13C NMR : Predict

1H NMR : 400 MHz in CDCl3

1H NMR : Predict

Predict 1H proton NMR

gas

IR : CCl4 solution

IR : liquid film

SOLUTION (10% CCl4 FOR 3800-1800, 10% CS2 FOR 1800-450 CM-1)

Mass

7. Synthesis Route

108-42-9Total: 76 Synthesis Route

95-76-1 166 Suppliers

108-42-9 159 Suppliers

Literatures:
Rhone-Poulenc Agrochimie Patent: US4495368 A1, 1985 ;
Yield: ~99%

95-82-9 121 Suppliers

108-42-9 159 Suppliers

Literatures:
US4193937 A1, ;
Yield: ~%

89-61-2

108-42-9 159 Suppliers

Literatures:
Journal of Organometallic Chemistry, , vol. 208, # 2 p. 145 - 152
Yield: ~%

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8. Precursor and Product

precursor:

541-73-1

618-48-4

625-99-0

141-85-5

636-30-6

139-24-2

139-71-9

95-76-1

95-50-1

608-27-5

535-80-8

634-91-3

108-37-2

108-90-7

121-73-3

101-27-9

95-82-9

View all

product :

825-41-2

712-33-4

823-57-4

86-47-5

108-43-0

101-21-3

456-39-3

606-75-7

86-98-6

625-98-9

54-05-7

625-99-0

86-99-7

695-99-8

671-89-6

139-71-9

654-36-4

101-17-7

932-78-5

953-01-5

611-07-4

95-85-2

108-37-2

121-73-3

121-30-2

View all

9. Other Information

9.0 Usage: 3-Chloroaniline was?the?only?aniline?compound?to?increase?plasmaALT/GPT?activity?at?48?h. It is employed in the bioaugmentation of activated sludge.

9.1 Merck: 14,2118

9.2 BRN: 605969

9.3 Chemical Properties: clear pale yellow to brown liquid

9.4 Uses: 3-Chlorobenzenamine is used in the synthesis of pyrimidoazepine analogs as serotonin 5-HT2A and 5-HT2C receptor ligands for the treatment of obesity. Also used in the synthesis of novel COX-2 inhibito rs.

9.5 Synthesis Reference(s): Tetrahedron Letters, 36, p. 7313, 1995 DOI: 10.1016/0040-4039(95)01474-V

9.6 General Description: Colorless to light amber liquid with a sweet odor.

9.7 Air & Water Reactions: Sensitive to prolonged exposure to air and light and tends to darken during storage. Insoluble in water.

9.8 Reactivity Profile: 3-Chloroaniline is incompatible with acids, acid chlorides, acid anhydrides, chloroformates and strong oxidizing agents.

9.9 Fire Hazard: 3-Chloroaniline is combustible.

9.10 Safety Profile: Poison by ingestion, skin contact, subcutaneous, and intravenous routes. Mutation data reported. When heated to decomposition it emits toxic fumes of Cland NOx. See also ANILINE DYES.

9.11 Storage Conditions: The preparation method is obtained by reduction of m-chloronitrobenzene. The reducing agent can be sodium sulfide or zinc powder and hydrochloric acid. In the reaction kettle, sodium sulfide is dissolved in water, stirred and heated to boiling, and gradually added human chloronitrobenzene, refluxed for 5 h Afterwards, distill the oily liquid to get the finished product.

9.12 Henrys Law Constant: 10.00e-07 atm-m3/mole|Henry's Law constant = 1.0X10-6 atm-cu m/mol at 25 °C

9.13 Dissociation Constants: pKa = 3.521 at 25 °C (conjugate acid)

9.14 Experimental Properties: Heat of decomposition was determined as zero.|Hydroxyl radical reaction rate constant = 7.6X10-11 cu cm/molec-sec at 25 °C /Estimated/

9.15 Reactive Group: Aryl Halides

9.16 Reactivity Profile: M-CHLOROANILINE is incompatible with acids, acid chlorides, acid anhydrides, chloroformates and strong oxidizing agents. (NTP, 1992)

9.17 Autoignition Temperature: >540 °C

9.18 Storage features: The warehouse is ventilated at low temperature and dry; stored separately from oxidants, acids and food additives

9.19 Disposal Methods: SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational exposure or environmental contamination. Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air quality; potential migration in soil or water; effects on animal, aquatic, and plant life; and conformance with environmental and public health regulations.

9.20 Special Reports: Sakamoto Y, Watanabe S; Bull Chem Soc Jpn 59 (10): 3033-8 (1986). The relation between chem structure and carcinogenicity was investigated in 38 polycyclic aromatic cmpd and 44 chlorinated aromatic hydrocarbons by means of (13)C-NMR.

9.21 Fire Hazards: This chemical is combustible. (NTP, 1992)|Combustible. Gives off irritating or toxic fumes (or gases) in a fire.

9.22 Nonfire Spill Response: SMALL SPILLS AND LEAKAGE: If you spill this chemical, FIRST REMOVE ALL SOURCES OF IGNITION. Then, use absorbent paper to pick up all liquid spill material. Your contaminated clothing and absorbent paper should be sealed in a vapor-tight plastic bag for eventual disposal. Solvent wash all contaminated surfaces with 60-70% ethanol followed by washing with a soap and water solution. Do not reenter the contaminated area until the Safety Officer (or other responsible person) has verified that the area has been properly cleaned. STORAGE PRECAUTIONS: You should protect this chemical from exposure to light. Keep the container tightly closed under an inert atmosphere, and store under refrigerated temperatures. STORE AWAY FROM SOURCES OF IGNITION. (NTP, 1992)

9.23 Personal Protective Equipment: RECOMMENDED RESPIRATOR: Where the neat test chemical is weighed and diluted, wear a NIOSH-approved half face respirator equipped with an organic vapor/acid gas cartridge (specific for organic vapors, HCl, acid gas and SO2) with a dust/mist filter. (NTP, 1992)|Wear butyl rubber gloves, protective plastic clothing and self-contained breathing apparatus.

9.24 Fire Fighting Procedures: Water, dry chemical, foam or carbon dioxide. /4-Chloroaniline/

9.25 Preventive Measures: Immediately wash contaminated areas of body with concentrated soap solution. Remove contaminated clothing, dry, then wash with concentrated soap solution or dispose as waste. Contaminated shoes may be disposed of in an incinerator.|...Precaution should be taken to avoid inhalation of vapors.|SRP: The scientific literature for the use of contact lenses in industry is conflicting. The benefit or detrimental effects of wearing contact lenses depend not only upon the substance, but also on factors including the form of the substance, characteristics and duration of the exposure, the uses of other eye protection equipment, and the hygiene of the lenses. However, there may be individual substances whose irritating or corrosive properties are such that the wearing of contact lenses would be harmful to the eye. In those specific cases, contact lenses should not be worn. In any event, the usual eye protection equipment should be worn even when contact lenses are in place.|SRP: Contaminated protective clothing should be segregated in such a manner so that there is no direct personal contact by personnel who handle, dispose, or clean the clothing. Quality assurance to ascertain the completeness of the cleaning procedures should be implemented before the decontaminated protective clothing is returned for reuse by the workers. Contaminated clothing should not be taken home at end of shift, but should remain at employee's place of work for cleaning.; View all

9.26 Spillage Disposal: Personal protection: chemical protection suit including self-contained breathing apparatus. Do NOT let this chemical enter the environment. Collect leaking and spilled liquid in sealable containers as far as possible. Absorb remaining liquid in sand or inert absorbent. Then store and dispose of according to local regulations.

9.27 Safe Storage: Separated from food and feedstuffs. Keep in the dark. Well closed.

9.28 Inhalation Risk: No indication can be given about the rate at which a harmful concentration of this substance in the air is reached on evaporation at 20 °C.

9.29 Effects Of Short Term Exposure: The substance is irritating to the eyes and skin. The substance may cause effects on the blood. This may result in the formation of methaemoglobin. Medical observation is indicated. The effects may be delayed.

9.30 Fire Prevention: NO open flames.

9.31 Exposure Prevention: PREVENT GENERATION OF MISTS!

9.32 Inhalation Prevention: Use ventilation, local exhaust or breathing protection.

9.33 Skin Prevention: Protective gloves. Protective clothing.

9.34 Eye Pprevention: Wear safety goggles or face shield.

9.35 Pollution Sources: 3-Chloroaniline's production and use as an intermediate for azo dyes and pigments, pharmaceuticals, insecticides, and agricultural chemicals(1) may result in its release to the environment through various waste streams(SRC). Chloroanilines may also form in the environment as degradation products of various pesticides(2). 3-Chloroaniline has been identified as a major degradation product of the herbicide chlorpropham during soil field studies(3). Release may also occur from alkaline hydrolysis of the herbicide barban(4) or the anaerobic biodegradation of 3,4-dichloroaniline under methanogenic, but not sulfate-reducing conditions(5), both of which results in the formation of 3-chloroaniline.

9.36 Environmental Fate: TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 250(SRC), determined from a log Kow of 1.88(2) and a regression-derived equation(3), indicates that 3-chloroaniline is expected to have moderate mobility in soil(SRC). However, aromatic amines are expected to bind strongly to humus or organic matter in soils due to the high reactivity of the aromatic amino group(4,5), suggesting that mobility may be much lower in some soils(SRC). 3-Chloroaniline may undergo covalent chemical bonding with humic materials which results in its chemical alteration and tight adsorption(6). There is evidence to suggest that this complexing may extend the residual life of these substances in soil for as much as 10 years(7). Due to this covalent bonding, significant leaching in soil systems is not generally expected to occur(SRC). The pKa of 3-chloroaniline is 3.52(10), indicating that this compound will primarily exist in its nonionic form in the environment. Volatilization of 3-chloroaniline from moist soil surfaces is expected to occur(SRC) given a Henry's Law constant of 1.0X10-6 atm-cu m/mole(8). However, adsorption to soil is expected to attenuate volatilization(SRC). 3-Chloroaniline is not expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 0.066 mm Hg(9). 3-Chloroaniline may degrade in soil by chemical and microbial processes(11). When 3-chloroaniline (30 ppm) was incubated in Guelph loam with water added to 60% water-holding capacity, levels declined rapidly for 2 weeks after which time the rate of loss decreased(11). The percent of 3-chlororaniline remaining in soil after 2 and 8 weeks were 38% and 18%, respectively(11).|AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 250(SRC), determined from a log Kow of 1.88(2) and a regression-derived equation(3), indicates that 3-chloroaniline may adsorb to suspended solids and sediment(SRC). In addition, 3-chloroaniline may undergo chemical bonding with humic materials in the water column and in the sediment(4). Volatilization from water surfaces is expected(3) based upon a Henry's Law constant of 1.0X10-6 atm-cu m/mole(5). Using this Henry's Law constant and an estimation method(3), volatilization half-lives for a model river and model lake are 42 and 310 days, respectively(SRC). However, aromatic amines are expected to bind strongly to humus or organic matter in soils due to the high reactivity of the aromatic amino group(13,14), and volatilization from water surfaces is expected to be attenuated by adsorption to suspended solids and sediment in the water column(SRC). The pKa of 3-chloroaniline is 3.52(6), indicating that this compound will primarily exist in its nonionic form in the environment. According to a classification scheme(7), measured BCF values ranging from 0.8 to 11.5(8,9) suggests the potential for bioconcentration in aquatic organisms is low(SRC). In a 3-day cultivation test using 2 different river waters from Japan and two different sea waters, 50% of initial 3-chloroaniline was degraded; the degradation was paralleled by growth of microbes(9,10). A biotransformation half-life of 0.4 year was determined for 3-chloroaniline in laboratory studies using two pond and one river water samples obtained near Athens, GA(12). Irradiation of an aqueous solution of 3-chloroaniline in a quartz tube with a fluorochemical lamp (wavelengths above 300 nm) resulted in a photodegradation half-life of 2.6 hours(14).|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), 3-chloroaniline, which has a vapor pressure of 0.066 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase 3-chloroaniline is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC); the half-life for this reaction in air is estimated to be 5.1 hours(SRC), calculated from its rate constant of 7.6X10-11 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). 3-Chloroaniline absorbs light with wavelengths >290 nm(4) and may be susceptible to direct photolysis by sunlight(SRC).; View all

9.37 Abiotic Degradation: The rate constant for the vapor-phase reaction of 3-chloroaniline with photochemically-produced hydroxyl radicals has been estimated as 7.6X10-11 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 5.1 hours at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). 3-Chloroaniline is not expected to undergo hydrolysis in the environment due to the lack of hydrolyzable functional groups(2). 3-Chloroaniline absorbs light with wavelengths >290 nm(3) and may be susceptible to direct photolysis by sunlight(SRC). Irradiation of an aqueous solution of 3-chloroaniline in a quartz tube with a fluorochemical lamp (wavelengths above 300 nm) resulted in a photodegradation half-life of 2.6 hours(4). The quantum yield was measured to be 0.0429 at 292 nm in hexane solution with photodegradation to aniline(5). In another study in which 3-chloroaniline in water was irradiated in a photoreactor with a light source with radiation in the 250-300 nm region (Integrated intensity times extinction coefficient = 3512 L/mol-cm, 20 °C), the photohydrolysis rate constant and half-life was 0.393/min and 1.76 min respectively(6). The quantum yield was 0.212 and independent of wavelength(6).; View all

9.38 Bioconcentration: 2.24|The average BCFs in the whole body of carp exposed to 3-chloroaniline in flow-through experiments (25 °C, 12 L/hr) for 24 to 336 hr at high (14.7 ug/L) and low (0.67 ug/L) exposure levels were 0.8 and 2.2, respectively(1). Excretion was rapid with depuration rates and half-lives of 0.21/hr and 3.3 hr, respectively(1). This conclusion is supported by field data in which the concentration of 3-chloroaniline in water and fish were <0.02 - 0.02 ug/L and <2.0 ng/g(1). Uptake was rapid in static tests (0.17 umol/L, 26 °C) on zebrafish and a BCF of 11.5 was obtained for 100 hr exposure (2). Elimination was best described by a two compartment first order model(2). After 52 hr of depuration, the concn of 3-chloroaniline in the zebrafish declined to 10.3% of the steady state value. According to a classification scheme(3), these BCF values suggest the potential for bioconcentration in aquatic organisms is low(SRC).

9.39 Mobility: The Koc of 3-chloroaniline is estimated as 250(SRC), using a log Kow of 1.88(1) and a regression-derived equation(2). According to a classification scheme(3), this estimated Koc value suggests that 3-chloroaniline is expected to have moderate mobility in soil. However, aromatic amines are expected to bind strongly to humus or organic matter in soils due to the high reactivity of the aromatic amino group(4,5), suggesting that mobility may be much lower in some soils(SRC). In laboratory persistence studies using non-sterilized Hagerstown silty clay loam soil, 73% of applied 3-chloroaniline remained chemically bound to soil particles after 64 days of incubation(6). A related chemical, 2-chloroaniline, has been observed to undergo rapid and reversible covalent bonding with humic materials in aqueous solution; the initial bonding reaction is followed by a slower and much less reversible reaction believed to represent the addition of the amine to quinoidal structures followed by oxidation of the product to give an amino-substituted quinone(7).; View all

9.40 Volatilization: The Henry's Law constant for 3-chloroaniline is 1.0X10-6 atm-cu m/mole(1). This Henry's Law constant indicates that 3-chloroaniline is expected to volatilize from water surfaces(2). Based on this Henry's Law constant, the volatilization half-life from a model river (1 m deep, flowing 1 m/sec, wind velocity of 3 m/sec)(2) is estimated as 42 days(SRC). The volatilization half-life from a model lake (1 m deep, flowing 0.05 m/sec, wind velocity of 0.5 m/sec)(2) is estimated as 310 days(SRC). However, volatilization from water surfaces is expected to be attenuated by adsorption to suspended solids and sediment in the water column(SRC). 3-Chloroaniline's Henry's Law constant indicates that volatilization from moist soil surfaces may occur(SRC). However, volatilization is expected to be attenuated by adsorption to soil(SRC). 3-Chloroaniline is not expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 0.066 mm Hg(3). In laboratory persistence studies using non-sterilized Hagerstown silty clay loam soil, 2.5% of applied 3-chloroaniline volatilized over a 49 day period(4).; View all

9.41 Food Survey Values: 3-Chloroaniline was detected in several samples of potato peels, 0.18-0.36 ppb, from potatoes obtained from various geographic locations(1).

9.42 Human Exposure: NIOSH (NOES Survey 1981-1983) has statistically estimated that 851 workers (187 of these are female) are potentially exposed to 3-chloroaniline in the US(1). Occupational exposure to 3-chloroaniline may occur through inhalation and dermal contact with this compound at workplaces where 3-chloroaniline is produced or used(SRC). Monitoring data indicate that the general population may be exposed to 3-chloroaniline via ingestion of food and drinking water(SRC).

9.43 Absorption: m-Chloroaniline is readily absorbed through the skin and also via the gastrointestinal tract and lung. .

9.44 Metabolism: 3-Chloroaniline was excreted /by rats/ in urine as glucuronides and sulfate esters of 4-hydroxy-3-chloroacetanilide (a major metabolite) and 2-hydroxy-5-chloroacetanilide (a minor metabolite).|...In male albino rats after a single oral dose /of 3-chloroaniline/ urine was collected and analyzed. ...TLC showed the presence of 2-amino-4-chlorophenol and 4-amino-2-chlorophenol. ...Acetyl phenols were also identified /as were/ glucuronides and sulfates of the phenols and their acetyl derivatives. ...2-Amino-6-chlorophenol was not found but traces of the glucuronide and sulfate were. ...|Metabolites identified following oral administration of 150 mg/kg in rats: 2-amino-4-chlorophenyl-beta-d-glucuronide, 4-amino-2-chloro phenyl-beta-d-glucuronide, 4-acetylamino-2-chlorophenyl-beta-d-glucuronide, 2-acetylamino-4-chlorophenyl-beta-d-glucuronide, 2-amino-4-chlorophenylsulfate, 4-amino-2-chlorophenylsulfate, 2-acetylamino-4-chlorophenylsulfate, and 4-acetylamino-2-chlorophenylsulfate.|High performance liquid chromatography was used to quantify the metabolism of free chlorpham and its metabolites in isolated rat hepatocyte incubations. ... 10 percent was metabolized to 3-chloroaniline which was broken down to 3-chloroacetanilide. ...|For more Metabolism/Metabolites (Complete) data for 3-CHLOROANILINE (6 total), please visit the HSDB record page.; View all

9.45 Biological Half Life: 0.19 Days

9.46 First Aid

EYES: First check the victim for contact lenses and remove if present. Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center. Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician. IMMEDIATELY transport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) develop. SKIN: IMMEDIATELY flood affected skin with water while removing and isolating all contaminated clothing. Gently wash all affected skin areas thoroughly with soap and water. If symptoms such as redness or irritation develop, IMMEDIATELY call a physician and be prepared to transport the victim to a hospital for treatment. INHALATION: IMMEDIATELY leave the contaminated area; take deep breaths of fresh air. If symptoms (such as wheezing, coughing, shortness of breath, or burning in the mouth, throat, or chest) develop, call a physician and be prepared to transport the victim to a hospital. Provide proper respiratory protection to rescuers entering an unknown atmosphere. Whenever possible, Self-Contained Breathing Apparatus (SCBA) should be used; if not available, use a level of protection greater than or equal to that advised under Protective Clothing. INGESTION: DO NOT INDUCE VOMITING. If the victim is conscious and not convulsing, give 1 or 2 glasses of water to dilute the chemical and IMMEDIATELY call a hospital or poison control center. Be prepared to transport the victim to a hospital if advised by a physician. If the victim is convulsing or unconscious, do not give anything by mouth, ensure that the victim's airway is open and lay the victim on his/her side with the head lower than the body. DO NOT INDUCE VOMITING. IMMEDIATELY transport the victim to a hospital. (NTP, 1992)

Fresh air, rest. Artificial respiration may be needed. Refer for medical attention.

Remove contaminated clothes. Rinse and then wash skin with water and soap. Refer for medical attention .

First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then refer for medical attention.

View all

9.47 Antidote: Methylene blue, alone or in combination with oxygen, is indicated as treatment in nitrite-induced methemoglobinemia.|Basic treatment: Establish a patent airway. Suction if necessary. Watch for signs of respiratory insufficiency and assist ventilations if necessary. Administer oxygen by nonrebreather mask at 10 to 15 L/min. Monitor for shock and treat if necessary ... . Anticipate seizures and treat if necessary ... . For eye contamination, flush eyes immediately with water. Irrigate each eye continuously with normal saline during transport ... . Do not use emetics. For ingestion, rinse mouth and administer 5 ml/kg up to 200 ml of water for dilution if the patent can swallow, has a strong gag reflex, and does not drool. Administer activated charcoal ... . /Aniline and related compounds/|Advanced treatment: Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious. Monitor cardiac rhythm and treat arrhythmias as necessary ... . Start an IV with D5W /SRP: "To keep open", minimal flow rate/. Use lactated Ringer's if signs of hypovolemia are present. Watch for signs of fluid overload. Administer 1% solution methylene blue if patient is symptomatic with severe hypoxia, cyanosis, and cardiac compromise not responding to oxygen. ... . For hypotension with signs of hypovolemia, administer fluid cautiously. Consider vasopressors if hypotensive with a normal fluid volume. Watch for signs of fluid overload ... . Treat seizures with diazepam (Valium) ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Aniline and related compounds/; View all

9.48 Human Toxicity Excerpts: /HUMAN EXPOSURE STUDIES/ In the United Kingdom between 1961 and 1980, chloroaniline, p-toluidine, nitrobenzene, and nitrochlorobenzene were the most common industrial causes of methemoglobinemia. Dermal exposure was a more frequent route of toxicity than inhalation with these compounds. /Chloroaniline/|/SIGNS AND SYMPTOMS/ Symptomatology: Lips, tongue and mucous membranes navy blue to black; skin slate gray, all without signs of cardiac or pulmonary insufficiency. Severe headache, nausea, sometimes vomiting, dryness of throat. Central nervous symptoms: confusion, ataxia, vertigo, tinnitus, weakness, disorientation, lethargy, drowsiness, and finally coma. Convulsions may occur but appear to be uncommon. Cardiac effects: heart blocks, arrhythmias, and shock. Death, although uncommon, is usually due to cardiovascular collapse and not resp paralysis. Urinary signs and symptoms may incl painful micturition, hematuria, hemoglobinuria, and renal insufficiency (usually mild). A late acute hemolytic episode should be anticipated at 6 to 8 days after ingestion. /Aniline/|/SIGNS AND SYMPTOMS/ Acute and long term exposure to m-chloroaniline leads to methemoglobin formation in humans... .; View all

9.49 Mesh Entry Terms: 3-chloroaniline

9.50 Symptoms

Blue lips, fingernails and skin. Dizziness. Headache. Shortness of breath. Nausea. Vomiting. Convulsions. Weakness. Confusion. Unconsciousness.

MAY BE ABSORBED! Redness. Burning sensation. Further see Inhalation.

Redness. Pain.

9.51 Formulations: GRADES: Technical

9.52 Manufacturing Info: Benzenamine, 3-chloro-: ACTIVE

10. Computational chemical data

Molecular Weight: 127.571g/mol
Molecular Formula: C₆H₆ClN
Compound Is Canonicalized: True
XLogP3-AA: null
Exact Mass: 127.0188769
Monoisotopic Mass: 127.0188769
Complexity: 74.9
Rotatable Bond Count: 0
Hydrogen Bond Donor Count: 1
Hydrogen Bond Acceptor Count: 1
Topological Polar Surface Area: 26
Heavy Atom Count: 8
Defined Atom Stereocenter Count: 0
Undefined Atom Stereocenter Count: 0
Defined Bond Stereocenter Count: 0
Undefined Bond Stereocenter Count: 0
Isotope Atom Count: 0
Covalently-Bonded Unit Count: 1
CACTVS Substructure Key Fingerprint: AAADcYBiAAAEAAAAAAAAAAAAAAAAAAAAAAAwAAAAAAAAAAABAAAAHAIQAAAACAqBECAwwIBAAACAACRCQACCAAAgBwAIiAAAZogIICKBk5GAIABgkAAIyAcQAAAAAAAAAAIAAAAAAAAABAAAAAAAAAAAAA==

11. Question & Answer

What are the key aspects of 3-Chloroaniline in the chemical industry? Feb 26 2024
General Description 3-Chloroaniline is a crucial intermediate in the chemical industry, used in the production of herbicides, pharmaceuticals, dyes, pigments, insecticides, and agricultural chemicals...
What are the properties, applications, and storage conditions of 3-Chloroaniline? Apr 23 2023
3-Chloroaniline, also known as 3-Chloroaniline, is a transparent pale yellow to brown liquid at room temperature and pressure. It is insoluble in water but soluble in common organic solvents. As a der..
What is the General Description of 3-Chloroaniline and its Applications? Nov 07 2021
General Description 3-Chloroaniline is a colorless to light amber liquid with a sweet odor. It has a melting point of -11 to -9 ℃ and a boiling point of 230 to 231 ℃ (95 to 96 ℃/1.47 kPa). It is in..

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Benzenamine,3-chloro-