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Phenylacetic acid

Description References
Phenylacetic acid
Phenylacetic acid structure
Chemical Name:
Phenylacetic acid
FEMA 2878;phenylacetic;Toluylicacid;L-PHENYLALAIN;A-TOLUIC ACID;α-Toluic acid;à-tolylic acid;α-tolylic acid;Fenylazijnzuur;Phenylessigsure
Molecular Formula:
Formula Weight:
MOL File:

Phenylacetic acid Properties

Melting point:
76-78 °C(lit.)
Boiling point:
265 °C(lit.)
1.081 g/mL at 25 °C(lit.)
vapor density 
~4 (vs air)
vapor pressure 
1 mm Hg ( 97 °C)
refractive index 
1.5120 (estimate)
Flash point:
storage temp. 
Store at RT.
4.28(at 18℃)
Specific Gravity
Water Solubility 
15 g/L (20 ºC)
JECFA Number
Stable. Incompatible with strong oxidizing agents.
CAS DataBase Reference
103-82-2(CAS DataBase Reference)
NIST Chemistry Reference
Benzeneacetic acid(103-82-2)
EPA Substance Registry System
Benzeneacetic acid(103-82-2)
  • Risk and Safety Statements
  • Hazard and Precautionary Statements (GHS)
  • NFPA
Hazard Codes  Xi
Risk Statements  36/37/38
Safety Statements  26-36-37/39
WGK Germany  1
RTECS  AJ2430000
HS Code  29163400
Hazardous Substances Data 103-82-2(Hazardous Substances Data)
Toxicity LD50 orally in Rabbit: > 5000 mg/kg LD50 dermal Rabbit > 5000 mg/kg
Signal word: Warning
Hazard statements:
Code Hazard statements Hazard class Category Signal word Pictogram P-Codes
H303 May be harmfulif swallowed Acute toxicity,oral Category 5 P312
H315 Causes skin irritation Skin corrosion/irritation Category 2 Warning P264, P280, P302+P352, P321,P332+P313, P362
H319 Causes serious eye irritation Serious eye damage/eye irritation Category 2A Warning P264, P280, P305+P351+P338,P337+P313P
H335 May cause respiratory irritation Specific target organ toxicity, single exposure;Respiratory tract irritation Category 3 Warning
Precautionary statements:
P261 Avoid breathing dust/fume/gas/mist/vapours/spray.
P304+P340 IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P305+P351+P338 IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.
P405 Store locked up.

NFPA 704

Diamond Hazard Value Description
Flammability   1 Materials that require considerable preheating, under all ambient temperature conditions, before ignition and combustion can occur. Includes some finely divided suspended solids that do not require heating before ignition can occur. Flash point at or above 93.3 °C (200 °F). (e.g. mineral oil, ammonia)
Instability   0 Normally stable, even under fire exposure conditions, and is not reactive with water (e.g. helium,N2)

(NFPA, 2010)

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Phenylacetic acid Chemical Properties,Uses,Production


Naturally occurring in various types of fruits and other plants, phenylacetic acid is a fragrant phenolic used as a perfume agent and food additive.  Its pharmaceutical uses include the treatment of hyperammonemia for patients with deficiencies related to the urea cycle, and as a side chain precursor in the production of penicillin G. It also plays a role in the production of Camylofin, Bendazol, and Triafungin.
Because of its use in the production of phenylacetone (used to manufacture substituted amphetamines, including methamphetamine), it is a controlled substance.


Chemical Properties

white crystals with a honey-like odour

Chemical Properties

Phenylacetic Acid occurs in Japanese peppermint oil, in neroli oil, and in traces in rose oils. It is a volatile aroma constituent of many foods (e.g., honey). It forms colorless crystals (mp 78°C) that have a honey odor.
The common route to phenylacetic acid is conversion of benzyl chloride into benzyl cyanide by reaction with sodium cyanide, followed by hydrolysis. Because of its intense odor, phenylacetic acid is added to perfumes in small quantities for rounding off blossom odors. Addition to fruit aromas imparts a sweet honey note.


Phenylacetic Acid is a flavoring agent that is crystalline (white, glis- tening), with unpleasant, persisting odor resembling geranium leaf and rose when diluted. it is soluble in most fixed oils and glycerin, slightly soluble in water, and insoluble in mineral oil. it is obtained by chemical synthesis. it is also termed a-toluic acid.


Phenylacetic Acid is used in the synthesis of Diclofenac (D436450) and its metabolite 4'-Hydroxydiclofenac (H825225), which is the principal human metabolite of Diclofenac.


ChEBI: A monocarboxylic acid that is toluene in which one of the hydrogens of the methyl group has been replaced by a carboxy group.

Safety Profile

Moderately toxic by ingestion, subcutaneous, and intraperitoneal routes. An experimental teratogen. Combustible liquid. Used in production of drugs of abuse. When heated to decomposition it emits acrid smoke and irritating fumes

Enzyme inhibitor

This phenylalanine-derived metabolite (FWfree-acid = 136.15 g/mol; CAS 103-82-2 (acid) and 114-70-5 (Na salt); pKa = 4.25 at 25°C) has a melting point of 76.5°C, a boiling point of 265.5°C, and is slightly soluble in water (1.6 g per 100 mL at 20°C). It is more soluble in ethanol, chloroform, and diethyl ether. Note: Because phenylacetic acid is a precursor of phenylacetone, which in turn is used in the illicit production of methamphetamine, its purchase is regulated in the U.S. Target (s) : D- amino-acid oxidase; decarboxylase; [branched-chain a-keto-acid dehydrogenase] kinase, or [3-methyl-2-oxobutanoate dehydrogenase (acetyl-transferring) ] kinase; carboxypeptidase A; catechol oxidase; Ca2+-transporting ATPase; choline O-acetyltransferase ; chymotrypsin, weakly inhibited; glutamate decarboxylase ; haloacetate dehalogenase; (S) -2-hydroxy-acid oxidase; hydroxylaminolysis (nonenzymatic) of amino acid esters; imidazoleacetate 4-monooxygenase; (S) -mandelate dehydrogenase ; mandelate racemase, Ki = 0.2 mM; monophenol monooxygenase; Na+/K+-exchanging ATPase; penicillin amidase ; phenylalanine 2-monooxygenase; pyruvate carboxylase ; stearoyl-CoA 9-desaturase; succinate dehydrogenase; tyrosine aminotransferase; tyrosine-ester sulfotransferase; and zeatin 9-aminocarboxyethyltransferase.

Purification Methods

Crystallise the acid from pet ether (b 40-60o), isopropyl alcohol, 50% aqueous EtOH or hot water (m 77.8-78.2o). Dry it in vacuo. It can be distilled under a vacuum. [Beilstein 9 II 294, 9 III 2169.]

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