3D Mol Similar

Phenoxyacetyl chloride

: Iupac Name：2-phenoxyacetyl chloride; CAS No.: 701-99-5; Molecular Weight：170.59300; Modify Date.: 2022-11-29 03:08; Introduction:
Phenoxyacetyl chloride, with the chemical formula C8H7ClO2 and CAS registry number 701-99-5, is a compound known for its applications in various chemical processes. This colorless liquid, also referred to as 2-Chloro-1-(2,4,5-trichlorophenoxy)ethanone, is characterized by its chlorine and phenoxy functional groups. It is commonly used as a reagent in organic synthesis, offering a versatile platform for the introduction of phenoxyacetyl moieties into different molecules. Phenoxyacetyl chloride is primarily used in the production of herbicides, specifically as an intermediate in the synthesis of phenoxyacetic acid herbicides. It is also utilized in the manufacturing of pharmaceuticals and agrochemicals. As with any chemical compound, proper handling and safety precautions should be followed when working with phenoxyacetyl chloride.
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1. Names and Identifiers

: 1.1 Name; Phenoxyacetyl chloride; 1.2 Synonyms; 2-Phenoxyacetyl chloride Acetyl chloride, 2-phenoxy- Acetyl chloride, phenoxy- Acetylchloride,phenoxy- Acyl chloride kind AKOS BBS-00003927 LABOTEST-BB LT00643586 NSC 9808 Phenoxyacetic acid chloride phenoxy-acetylchlorid Phenoxyethanoyl chloride Phenyloxyacetyl chloride; View all

1.3 CAS No.: 701-99-5

1.4 CID: 69703

1.5 EINECS(EC#): 211-862-4

1.6 Molecular Formula: C8H7ClO2 (isomer)

1.7 Inchi: InChI=1S/C8H7ClO2/c9-8(10)6-11-7-4-2-1-3-5-7/h1-5H,6H2

1.8 InChIkey: PKUPAJQAJXVUEK-UHFFFAOYSA-N

1.9 Canonical Smiles: C1=CC=C(C=C1)OCC(=O)Cl

1.10 Isomers Smiles: C1=CC=C(C=C1)OCC(=O)Cl

2. Properties

2.1 Density: 1.235g/mLat 25°C(lit.)

2.1 Melting point: 28 - 30ºC

2.1 Boiling point: 225-226°C(lit.)

2.1 Refractive index: n20/D 1.534(lit.)

2.1 Flash Point: 227°F

2.1 Precise Quality: 170.01300

2.1 PSA: 26.30000

2.1 logP: 1.83080

2.1 Appearance: Clear slightly yellow to brown Liquid

2.2 Storage: Moisture Sensitive. Store under Nitrogen. Ambient temperatures.

2.3 Chemical Properties: Colorless to brown liquid

2.4 Color/Form: Clear slightly yellow to brown

2.5 Water Solubility: Reacts with water.

2.6 Stability: Stable under normal temperatures and pressures.

2.7 StorageTemp: Store at RT.

3. Use and Manufacturing

3.1 Purification Methods: If it has no OH band in the IR then distil it in a vacuum, taking precautions for the moisture-sensitive compound. If it contains free acid (due to hydrolysis, OH bands in the IR), then add an equal volume of redistilled SOCl2, reflux for 2-3hours, evaporate and distil the residue in a vacuum as before. The amide has m 101o. [McElvain & Carney J Am Chem Soc 68 2592 1946, Beilstein 6 III 613.] Phenoxyacetyl chlorideSupplier

4. Safety and Handling

4.1 Hazard Codes: C

4.1 Risk Statements: R14; R34; R36/37

4.1 Safety Statements: S26-S36/37/39-S45

4.1 Packing Group: II

4.1 Hazard Class: 8

4.1 Hazard Declaration: H314-H335

4.1 RIDADR: UN 3265 8/PG 2

4.1 Caution Statement: P261-P280-P305 + P351 + P338-P310

4.1 WGK Germany: 3

4.1 Sensitive: Moisture Sensitive

4.2 Specification

The Phenoxyacetyl chloride, with the CAS registry number 701-99-5, is also known as Acetyl chloride, 2-phenoxy-. It belongs to the product categories of Biochemistry; Nucleosides, Nucleotides & Related Reagents; Protecting Agents for Hydroxyl and Amino Groups; Protecting Agents, Phosphorylating Agents & Condensing Agents; Acid Halides; Carbonyl Compounds; Organic Building Blocks. Its EINECS registry number is 211-862-4. Its IUPAC name and systematic name are the same which is called 2-phenoxyacetyl chloride. This chemical is colorless to brown liquid.

Physical properties of Phenoxyacetyl chloride: (1)ACD/LogP: 2.07; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 2.07; (4)ACD/LogD (pH 7.4): 2.07; (5)#H bond acceptors: 2; (6)#Freely Rotating Bonds: 3; (7)Index of Refraction: 1.525; (8)Molar Refractivity: 42.44 cm³; (9)Molar Volume: 138.4 cm³; (10)Surface Tension: 39.5 dyne/cm; (11)Density: 1.232 g/cm³; (12)Flash Point: 84 °C; (13)Enthalpy of Vaporization: 46.29 kJ/mol; (14)Boiling Point: 226.3 °C at 760 mmHg; (15)Vapour Pressure: 0.0823 mmHg at 25°C; (16)Storage Temp.: Store at RT. ; (17)Sensitive: Moisture Sensitive.

Preparation: this chemical can be prepared by phenoxyacetic acid. This reaction will need reagent (COCl)₂, DMF and solvent CH₂Cl₂. The reaction time is 1 hours with reaction temperature of 20 ℃.

Uses of Phenoxyacetyl chloride: it can be used to produce phenoxy-acetic acid-(2-hydroxy-anilide) at ambient temperature. This reaction will need reagent NaHCO₃ and solvent diethyl ether, H₂O. The yield is about 60%

When you are using this chemical, please be cautious about it as the following:
This chemical may destroy living tissue on contact. Secondly, it reacts violently with water and can cause burns. In case of contact with eyes, you should rinse immediately with plenty of water and seek medical advice. Whenever you will contact it, please wear suitable protective clothing, gloves and eye/face protection. In case of accident or if you feel unwell seek medical advice immediately (show the label where possible).

You can still convert the following datas into molecular structure:
(1)Canonical SMILES: C1=CC=C(C=C1)OCC(=O)Cl
(2)InChI: InChI=1S/C8H7ClO2/c9-8(10)6-11-7-4-2-1-3-5-7/h1-5H,6H2
(3)InChIKey: PKUPAJQAJXVUEK-UHFFFAOYSA-N

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5. MSDS

2.Hazard identification

2.1 Classification of the substance or mixture

Skin corrosion, Category 1B

Specific target organ toxicity \u2013 single exposure, Category 3

2.2 GHS label elements, including precautionary statements

Pictogram(s)
Signal word	Danger
Hazard statement(s)	H314 Causes severe skin burns and eye damage H335 May cause respiratory irritation
Precautionary statement(s)
Prevention	P260 Do not breathe dust/fume/gas/mist/vapours/spray. P264 Wash ... thoroughly after handling. 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.
Response	P301+P330+P331 IF SWALLOWED: Rinse mouth. Do NOT induce vomiting. P303+P361+P353 IF ON SKIN (or hair): Take off immediately all contaminated clothing. Rinse skin with water [or shower]. P363 Wash contaminated clothing before reuse. P304+P340 IF INHALED: Remove person to fresh air and keep comfortable for breathing. P310 Immediately call a POISON CENTER/doctor/\u2026 P321 Specific treatment (see ... on this label). P305+P351+P338 IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. P312 Call a POISON CENTER/doctor/\u2026if you feel unwell.
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

13C NMR : Predict

1H NMR : Predict

Predict 1H proton NMR

Mass spectrum (electron ionization)

7. Synthesis Route

701-99-5Total: 4 Synthesis Route

122-59-8 174 Suppliers

701-99-5 50 Suppliers

Literatures:
Wharton, Clifford J.; Wrigglesworth, Roger; Rowe, Michael Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1984 , # 1 p. 29 - 39
Yield: ~37%

139-02-6 24 Suppliers

701-99-5 50 Suppliers

Literatures:
Journal of the Indian Chemical Society, , vol. 69, # 1 p. 45 - 46
Yield: null

108-95-2 253 Suppliers

701-99-5 50 Suppliers

Literatures:
Journal of the Indian Chemical Society, , vol. 68, # 6 p. 358 - 359
Yield: null

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8. Precursor and Product

precursor:

108-95-2

122-59-8

139-02-6

10026-13-8

product :

7695-63-8

100880-66-8

62283-07-2

107637-99-0

7169-34-8

621-88-5

14231-45-9

87-08-1

2555-49-9

25774-60-1

7170-38-9

58903-18-7

132-98-9

19090-04-1

62372-04-7

721-04-0

62372-05-8

189057-67-8

13468-02-5

2315-05-1

122-99-6

2120-70-9

5426-70-0

3598-14-9

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9. Other Information

9.0 Usage: Acylation of D- and DL-WV with phenoxyacetyl chloride, followed by cleavage of the t-butyl ester,afforded the penultimate penicilloic acids. Phenoxyacetyl chloride was used in the synthesis of series of macrocyclic bis-β-lactams, 5-phenyl-6-epiphenoxymethylpenicillin benzyl ester, N-protected guanosine derivatives, useful in RNA synthesis, phenyloxyketene, for cycloaddition to imines leading to β-lactams. Treatment of iminophosphoranes with phenoxyacetyl chloride afforded respectively the trans- and cis-3-(acylamino)-p-lactams. By the oxidative addition of stannous fluoride to allyliodide, with 1, 2-O-isopropylidene-D-glyceraldehyde and phenoxyacetyl chloride results in the predominant formation of erythro homoallylester, which is in turn converted into 2-deoxy-D-ribose. The 4-disubstituted P-lactams (4a-c and 6a-b) were prepared through the reaction of N,N-diphenylhydrazones and N-methyl-N-phenylhydrazones of ketones with phenoxyacetyl chloride/Et3N in dichloromethane.

9.1 Manufacturing Info: Acetyl chloride, 2-phenoxy-: ACTIVE

10. Computational chemical data

Molecular Weight: 170.59300g/mol
Molecular Formula: C₈H₇ClO₂
Compound Is Canonicalized: True
XLogP3-AA: null
Exact Mass: 170.0134572
Monoisotopic Mass: 170.0134572
Complexity: 130
Rotatable Bond Count: 3
Hydrogen Bond Donor Count: 0
Hydrogen Bond Acceptor Count: 2
Topological Polar Surface Area: 26.3
Heavy Atom Count: 11
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: AAADcYBwMAAEAAAAAAAAAAAAAAAAAAAAAAAwAAAAAAAAAAABAAAAGgIAAAAACAagkAIwBoAABACIAGBaAAICCAAgIAAIiABGCYgMJiKEMR6COCCkwBEIqAeAQAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAA==