3D Mol Similar

2-tert-Butyl-4-methylphenol

: Iupac Name：2-tert-butyl-4-methylphenol; CAS No.: 2409-55-4; Molecular Weight：164.248; Modify Date.: 2022-11-29 09:34; Introduction:
2-tert-Butyl-4-methylphenol, with the chemical formula C11H16O and CAS registry number 2409-55-4, is a compound known for its antioxidant properties. This colorless crystalline solid, also referred to as BHT or butylated hydroxytoluene, is widely used as a food preservative and in various industrial applications. BHT is commonly added to oils, fats, and fatty foods to prevent oxidation and extend their shelf life. It works by inhibiting the formation of free radicals, which can cause spoilage and degradation of the products. BHT is also used in cosmetics, pharmaceuticals, and rubber products for its antioxidant and stabilizing effects. However, it is important to note that BHT has been the subject of some controversy due to potential health concerns, and its usage is regulated in certain countries. Overall, 2-tert-Butyl-4-methylphenol is a versatile compound with significant applications in the preservation and stabilization of various products.
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1. Names and Identifiers

: 1.1 Name; 2-tert-Butyl-4-methylphenol; 1.2 Synonyms; 2-(tert-Butyl)-4-methylphenol 2-butyl-4-methylphenol 2-di-tert-butyl-4-methylphenol 2-t-Butyl-4-methylphenol 2-T-BUTYL-P-CRESOL 2-Terc.butyl-p-kresol 2-tercbutyl-p-kresol(czech) 2-tert-butyl-4-methyl-1-hydroxybenzene 2-tert-butyl-p-creso 2-tert-butyl-p-cresol 4-Methyl-2-(2-methyl-2-propanyl)phenol 4-Methyl-2,6-tert-butylphenol 6-tert-Butyl-4-methylphenol 6-tert-Butyl-p-cresol EINECS 219-314-6 Lowinox MBPC MBPC MFCD00002381 MONOBUTYL-P-CRESOL MTBP o-tert-Butyl-p-cresol p-Butylcresol Phenol, (1,1-dimethylethyl)-4-methyl- Phenol, 2- (1,1-dimethylethyl)-4-methyl- Phenol, 2-(1,1-dimethylethyl)-4-methyl- RALOX 240; View all

1.3 CAS No.: 2409-55-4

1.4 CID: 17004

1.5 EINECS(EC#): 219-314-6

1.6 Molecular Formula: C11H16O (isomer)

1.7 Inchi: InChI=1S/C11H16O/c1-8-5-6-10(12)9(7-8)11(2,3)4/h5-7,12H,1-4H3

1.8 InChIkey: IKEHOXWJQXIQAG-UHFFFAOYSA-N

1.9 Canonical Smiles: CC1=CC(=C(C=C1)O)C(C)(C)C

1.10 Isomers Smiles: CC1=CC(=C(C=C1)O)C(C)(C)C

2. Properties

2.1 Density: 0.961

2.1 Melting point: 50-53℃

2.1 Boiling point: 237℃

2.1 Refractive index: 1.5155 (20 C)

2.1 Flash Point: 105℃

2.1 Precise Quality: 164.12000

2.1 PSA: 20.23000

2.1 logP: 2.99810

2.1 Solubility: methanol: 0.1?g/mL, clear

2.2 AnalyticLaboratory Methods: A SIMPLIFIED QUANTITATIVE METHOD IS DESCRIBED FOR COLLECTION OF AIR POLLUTANTS ON A POROUS POLYMER (TENAX GC;) TRAP, FOR HEAT DESORPTION ONTO A COLUMN, & FOR ANALYSIS BY GAS CHROMATOGRAPHY. THE METHOD WAS APPLIED TO A NUMBER OF VOLATILE INDUSTRIAL SUBSTANCES FROM STACKS & AMBIENT AIR INCLUDING 2-T-BUTYL-4-METHYLPHENOL;.

2.3 Appearance: Liquid

2.4 Storage: Ambient temperatures.

2.5 Chemical Properties: white to yellow-beige crystalline mass

2.6 Color/Form: White to yellow-beige

2.7 PH: 4-5 (H2O, 20℃)(saturated solution)

2.8 pKa: 11?+-.0.18(Predicted)

2.9 Water Solubility: insoluble

2.10 Spectral Properties: IR: 2:583F (Aldrich Library of Infrared Spectra, Aldrich Chemical Co, Milwaukee, WI)
NMR: 4:123C (Aldrich Library of Mass Spectra, Aldrich Chemical Co, Milwaukee, WI)
MASS: 4243 (National Bureau of Standards EPA-NIH Mass Spectra Data Base, NSRDS-NBS-63)
Index of Refraction = 1.4969 at 75 deg C

2.11 Stability: Stable at room temperature in closed containers under normal storage and handling conditions.

2.12 StorageTemp: Keep in dark place,Inert atmosphere,Room temperature

3. Use and Manufacturing

3.1 GHS Classification: Signal: Danger
GHS Hazard Statements
Aggregated GHS information provided by 126 companies from 20 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Reported as not meeting GHS hazard criteria by 3 of 126 companies. For more detailed information, please visit ECHA C&L website

Of the 19 notification(s) provided by 123 of 126 companies with hazard statement code(s):

H314 (94.31%): Causes severe skin burns and eye damage [Danger Skin corrosion/irritation]
H318 (34.15%): Causes serious eye damage [Danger Serious eye damage/eye irritation]
H335 (55.28%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation]
H411 (22.76%): Toxic to aquatic life with long lasting effects [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, P271, P273, P280, P301+P330+P331, P303+P361+P353, P304+P340, P305+P351+P338, P310, P312, P321, P363, P391, P403+P233, P405, and P501; View all

3.2 Methods of Manufacturing: m/p-Cresol with isobutylene (Friedel-Crafts alkylation; co-produced with 6-t-butyl-m-cresol).

3.3 Usage: Chemical intermediate for aldehyde condensates (rubber antioxidants, for 2,2'-methylenebis(4-methyl-6-t-butylphenol), with sulfur dichloride for rubber antioxidants, for a benzotriazole uv light stabilizer, for 6-(5-chlorobenzotriazole) deriv, for diazo derivatives.

4. Safety and Handling

4.1 Symbol: GHS05, GHS09

4.1 Hazard Codes: C; N

4.1 Signal Word: Danger

4.1 Risk Statements: R34;R51/53

4.1 Safety Statements: S26;S29;S36/37/39;S45;S61

4.1 Packing Group: III

4.1 Hazard Class: 8

4.1 Hazard Declaration: H314-H411

4.1 DisposalMethods: SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.

4.2 RIDADR: UN 2430

4.2 Safety Profile: A poison by intraperitoneal and intravenous routes. Moderately toxic by ingestion and skin contact. Questionable carcinogen with experimental neoplastigenic data. A severe skin and eye irritant. Mutation data reported. Flammable liquid when exposed to heat, flame, or oxidizers. To fight fire, use alcohol foam, foam, water spray, fog, dry chemical. When heated to decomposition it emits acrid and irritating fumes. 2-tert-Butyl-4-methylphenol Preparation Products And Raw materials Raw materials

4.3 Caution Statement: P260-P280-P303 + P361 + P353-P304 + P340 + P310-P305 + P351 + P338

4.3 WGK Germany: 2

4.3 RTECS: GO7000000

4.3 Report: Reported in EPA TSCA Inventory.

4.4 Safety: A poison by intraperitoneal and intravenous routes. Moderately toxic by ingestion and skin contact. Questionable carcinogen with experimental neoplastigenic data. A severe skin and eye irritant. Mutation data reported. Flammable liquid when exposed to heat, flame, or oxidizers. To fight fire, use alcohol foam, foam, water spray, fog, dry chemical. When heated to decomposition it emits acrid and irritating fumes.
Hazard Codes: C,N
Risk Statements:34-37-51/53
R34: Causes burns ;
R37:Irritating to the respiratory system ;
R51/53:Toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment ;
Safety Statements:26-36/37/39-45-61-29
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice ;
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection ;
S45:In case of accident or if you feel unwell, seek medical advice immediately(show label where possible) ;
S61:Avoid release to the environment. Refer to special instructions safety data sheet ;
S29:Do not empty into drains ;
RIDADR:UN 2430 8/PG 3
WGK Germany:2
RTECS:GO7000000
F:8-9-23
HazardClass:8
PackingGroup of 2-tert-Butyl-4-methylphenol (CAS NO.2409-55-4): III; View all

4.5 Specification: 2-tert-Butyl-4-methylphenol (CAS NO.2409-55-4), its Synonyms are 2-t-Butyl-4-methylphenol ; 1-Hydroxy-2-tert-butyl-4-methylbenzene ; 2-(1,1-Dimethylethyl)-4-methylphenol ; 2-t-Butyl-p-cresol ; 2-terc.Butyl-p-kresol ; Phenol, 2-(1,1-dimethylethyl)-4-methyl- ; p-Cresol, 2-tert-butyl- . It is white to yellow-beige crystalline mass.

4.6 Toxicity

Organism	Test Type	Route	Reported Dose (Normalized Dose)	Effect	Source
cat	LDLo	oral	940mg/kg (940mg/kg)	PERIPHERAL NERVE AND SENSATION: SPASTIC PARALYSIS WITH OR WITHOUT SENSORY CHANGE BEHAVIORAL: TREMOR BEHAVIORAL: COMA	National Technical Information Service. Vol. OTS0571339,
guinea pig	LD50	oral	1180mg/kg (1180mg/kg)	BEHAVIORAL: SLEEP BEHAVIORAL: ATAXIA LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES	Toksikologiya Novykh Promyshlennykh Khimicheskikh Veshchestv. Toxicology of New Industrial Chemical Substances. For English translation, see TNICS*. Vol. 12, Pg. 124, 1971.
mouse	LD50	intraperitoneal	144mg/kg (144mg/kg)		Journal of Medicinal Chemistry. Vol. 18, Pg. 868, 1975.
mouse	LD50	intravenous	10mg/kg (10mg/kg)		U.S. Army Armament Research & Development Command, Chemical Systems Laboratory, NIOSH Exchange Chemicals. Vol. NX#03020,
mouse	LD50	oral	700mg/kg (700mg/kg)	LUNGS, THORAX, OR RESPIRATION: ACUTE PULMONARY EDEMA GASTROINTESTINAL: ULCERATION OR BLEEDING FROM SMALL INTESTINE	Journal of the American Pharmaceutical Association, Scientific Edition. Vol. 38, Pg. 366, 1949.
rabbit	LDLo	oral	2100mg/kg (2100mg/kg)	PERIPHERAL NERVE AND SENSATION: SPASTIC PARALYSIS WITH OR WITHOUT SENSORY CHANGE BEHAVIORAL: TREMOR BEHAVIORAL: COMA	National Technical Information Service. Vol. OTS0571339,
rabbit	LDLo	skin	2200mg/kg (2200mg/kg)		Journal of the American Pharmaceutical Association, Scientific Edition. Vol. 38, Pg. 366, 1949.
rat	LD50	oral	2500mg/kg (2500mg/kg)	SENSE ORGANS AND SPECIAL SENSES: OTHER CHANGES: OLFACTION BEHAVIORAL: ATAXIA LUNGS, THORAX, OR RESPIRATION: DYSPNEA	Toksikologiya Novykh Promyshlennykh Khimicheskikh Veshchestv. Toxicology of New Industrial Chemical Substances. For English translation, see TNICS*. Vol. 12, Pg. 124, 1971.

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5. MSDS

2.Hazard identification

2.1 Classification of the substance or mixture

Skin corrosion, Category 1C

Serious eye damage, Category 1

Hazardous to the aquatic environment, long-term (Chronic) - Category Chronic 2

2.2 GHS label elements, including precautionary statements

Pictogram(s)
Signal word	Danger
Hazard statement(s)	H314 Causes severe skin burns and eye damage H411 Toxic to aquatic life with long lasting effects
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. P273 Avoid release to the environment.
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. P391 Collect spillage.
Storage	P405 Store locked up.
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 : in CDCl3

1H NMR : 90 MHz in CDCl3

IR : liquid film

Mass

Mass spectrum (electron ionization)

7. Synthesis Route

2409-55-4Total: 29 Synthesis Route

128-37-0 632 Suppliers

2409-55-4 92 Suppliers

Literatures:
Kun, O. B.; Nogina, N. I.; Ostashevskaya, L. A.; Egorov, E. M.; Kuzubova, L. I.; Krysin, A. P. Journal of Organic Chemistry USSR (English Translation), 1984 , vol. 20, p. 2375 - 2378 Zhurnal Organicheskoi Khimii, 1984 , vol. 20, # 12 p. 2608 - 2611
Yield: ~55%

119-47-1 207 Suppliers

2409-55-4 92 Suppliers

Literatures:
Petroleum Chemistry, , vol. 37, # 1 p. 86 - 91
Yield: ~%

128-37-0 632 Suppliers

106-44-5 137 Suppliers

2409-55-4 92 Suppliers

Literatures:
Petroleum Chemistry, , vol. 36, # 1 p. 144 - 154
Yield: ~63%

View all

8. Other Information

8.0 BRN: 1817645

8.1 Chemical Properties: white to yellow-beige crystalline mass

8.2 Safety Profile: A poison by intraperitoneal and intravenous routes. Moderately toxic by ingestion and skin contact. Questionable carcinogen with experimental neoplastigenic data. A severe skin and eye irritant. Mutation data reported. Flammable liquid when exposed to heat, flame, or oxidizers. To fight fire, use alcohol foam, foam, water spray, fog, dry chemical. When heated to decomposition it emits acrid and irritating fumes.

8.3 Storage Conditions: m/p-Cresol with isobutylene (Friedel-Crafts alkylation; co-produced with 6-t-butyl-m-cresol).

8.4 Disposal Methods: SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.

8.5 Pollution Sources: 2-t-Butyl-4-methylphenol's production and use as an antioxidant(1) may result in its release to the environment through various waste streams(SRC).

8.6 Environmental Fate: TERRESTRIAL FATE: Based on a recommended classification scheme(1), an estimated Koc value of 3200(SRC), determined from a structure estimation method(2), indicates that 2-t-butyl-4-methylphenol will have no mobility in soil(SRC). Volatilization of 2-t-butyl-4-methylphenol may be important from moist soil surfaces(SRC) given an estimated Henry's Law constant of 1.5X10-6 atm-cu m/mole(3,SRC). Insufficient data are available to determine the rate or importance of biodegradation of 2-t-butyl-4-methylphenol in soil(SRC).|AQUATIC FATE: Based on a recommended classification scheme(1), an estimated Koc value of 3200(SRC), determined from a structure estimation method(2), indicates that 2-t-butyl-4-methylphenol may adsorb to suspended solids and sediment(SRC) in the water. 2-t-Butyl-4-methylphenol may volatilize from water surfaces based on an estimated Henry's Law constant of 1.5X10-6 atm-cu m/mole(SRC), developed using a fragment constant estimation method(3). Estimated half-lives for a model river and model lake are 31 and 227 days, respectively(4,SRC). An estimated BCF value of 610(4,SRC), from an estimated log Kow(5,SRC), suggests that 2-t-butyl-4-methylphenol will bioconcentrate in aquatic organisms(SRC) according to a recommended classification scheme(6). Insufficient data are available to determine the rate or importance of biodegradation of 2-t-butyl-4-methylphenol in water(SRC).|ATMOSPHERIC FATE: According to a suggested classification scheme(1), an extrapolated vapor pressure of 0.025 mm Hg at 25 °C(2,SRC) indicates that 2-t-butyl-4-methylphenol will exist primarily in the vapor phase in the ambient atmosphere. Vapor-phase 2-t-butyl-4-methylphenol 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 about 7.7 hours(3,SRC). Particulate-phase 2-t-butyl-4-methylphenol may be physically removed from the air by wet and dry deposition(SRC). Reaction of phenols with nitrate radicals may also be an important process(4,SRC).; View all

8.7 Abiotic Degradation: The rate constant for the vapor-phase reaction of 2-t-butyl-4-methylphenol with photochemically produced hydroxyl radicals has been estimated as 5X10-11 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1,SRC). This corresponds to an atmospheric half-life of about 7.7 hours at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1,SRC). Reaction of phenols with nitrate radicals may also be an important process(2,SRC).

8.8 Bioconcentration: An estimated BCF value of 610 was calculated for 2-t-butyl-4-methylphenol(SRC), using an estimated log Kow of 3.97(1,SRC) and a recommended regression-derived equation(2). According to aclassification scheme(3), this BCF value suggests that bioconcentration of 2-t-butyl-4-methylphenol will be high in aquatic organisms(SRC).

8.9 Mobility: Using a structure estimation method based on molecular connectivity indexes(1), the Koc for 2-t-butyl-4-methylphenol can be estimated to be about 3200(SRC). According to a recommended classification scheme(2), this estimated Koc value suggests that 2-t-butyl-4-methylphenol will be immobile in soil(SRC).

8.10 Volatilization: The Henry's Law constant for 2-t-butyl-4-methylphenol is estimated as 1.5X10-6 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This value indicates that 2-t-butyl-4-methylphenol will volatilize from water surfaces(2,SRC). 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) is estimated as approximately 31 days(2,SRC). The volatilization half-life from a model lake (1 m deep, flowing 0.05 m/sec, wind velocity of 0.5 m/sec) is estimated as approximately 227 days(2,SRC). 2-t-Butyl-4-methylphenol's Henry's Law constant(1,SRC) indicates that volatilization from moist soil may occur(SRC).

8.11 Mesh Entry Terms: 2-TBMP

8.12 Production: (1979) PROBABLY GREATER THAN 2.27X10+6 GRAMS|(1981) PROBABLY GREATER THAN 4.54X10+6 GRAMS

8.13 Manufacturing Info: All other basic organic chemical manufacturing|Phenol, 2-(1,1-dimethylethyl)-4-methyl-: ACTIVE|Phenol, (1,1-dimethylethyl)-4-methyl-: ACTIVE

9. Computational chemical data

Molecular Weight: 164.248g/mol
Molecular Formula: C₁₁H₁₆O
Compound Is Canonicalized: True
XLogP3-AA: null
Exact Mass: 164.120115130
Monoisotopic Mass: 164.120115130
Complexity: 146
Rotatable Bond Count: 1
Hydrogen Bond Donor Count: 1
Hydrogen Bond Acceptor Count: 1
Topological Polar Surface Area: 20.2
Heavy Atom Count: 12
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: AAADceBwIAAAAAAAAAAAAAAAAAAAAAAAAAAwAAAAAAAAAAABAAAAGgAACAAADgSAmAAyBoAAAgCAAiBCAAACAAAgIAAIiAAGCIgIJiKCERKAcAAkwBEImAeAwOAPoAACAAAIAABAAAQAABAAAAAAAAAAAA==

10. Question & Answer

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