Description References
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Phenylacetic acid

Description References
Product Name
Phenylacetic acid
CAS No.
103-82-2
Chemical Name
Phenylacetic acid
Synonyms
FEMA 2878;phenylacetic;Toluylicacid;L-PHENYLALAIN;α-Toluic acid;A-TOLUIC ACID;α-tolylic acid;à-tolylic acid;Fenylazijnzuur;Phenylessigsure
CBNumber
CB9699850
Molecular Formula
C8H8O2
Formula Weight
136.15
MOL File
103-82-2.mol
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Phenylacetic acid Property

Melting point:
76-78 °C(lit.)
Boiling point:
265 °C(lit.)
Density 
1.081 g/mL at 25 °C(lit.)
vapor density 
~4 (vs air)
vapor pressure 
1 mm Hg ( 97 °C)
FEMA 
2878 | PHENYLACETIC ACID
refractive index 
1.5120 (estimate)
Flash point:
132°C
storage temp. 
Store at RT.
pka
4.28(at 18℃)
form 
neat
Specific Gravity
1.081
color 
Leaflets on distillation in vac; plates, tablets from pet ether
Odor
disagreeable odor of geranium
Water Solubility 
15 g/L (20 ºC)
Merck 
14,7268
JECFA Number
1007
BRN 
1099647
Stability:
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
Phenylacetic acid (103-82-2)
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Safety

Hazard Codes 
Xi
Risk Statements 
36/37/38
Safety Statements 
26-36-37/39
RIDADR 
UN 3335
WGK Germany 
1
RTECS 
AJ2430000
13
TSCA 
Yes
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
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Hazard statements

H303May be harmfulif swallowed

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P304+P340IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P405Store locked up.

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
8.20993
Product name
Phenylacetic acid
Purity
for synthesis
Packaging
250 g
Price
$24.97
Updated
2021/03/22
Sigma-Aldrich
Product number
W287806
Product name
Phenylacetic acid
Purity
≥99%, FCC, FG
Packaging
1 kg
Price
$67
Updated
2021/03/22
Sigma-Aldrich
Product number
8.20993
Product name
Phenylacetic acid
Purity
for synthesis
Packaging
1 kg
Price
$70.95
Updated
2021/03/22
Sigma-Aldrich
Product number
P6061
Product name
Phenylacetic acid
Purity
plant cell culture tested
Packaging
500g
Price
$101
Updated
2021/03/22
Sigma-Aldrich
Product number
BP1026
Product name
Phenylacetic acid
Purity
British Pharmacopoeia (BP) Reference Standard
Price
$212
Updated
2021/03/22
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Phenylacetic acid Chemical Properties,Usage,Production

Description

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.

References

https://en.wikipedia.org/wiki/Phenylacetic_acid
https://pubchem.ncbi.nlm.nih.gov/compound/phenylacetic_acid
http://www.thegoodscentscompany.com/data/rw1009911.html
https://www.drugbank.ca/drugs/DB09269

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.

Chemical Properties

Phenylacetic acid has a sweet, animal, honey-like odor in dilute solution. The odor is persistent and disagreeable in concentrated solution. It has a sweet, honey-like flavor at high levels. At low levels, it is a sweetener.

Occurrence

Reported found among the constituents of a few essential oils: tobacco, Rosa centifolia, Bulgarian rose, orange flowers absolute, neroli and Mentha arvensis of Japanese origin; also reported present among the volatile constituents of cocoa. Also reported found in guava, papaya, raspberry, strawberry, cooked potato, tomato, peppermint oil, pepper, rye bread, cheddar cheese, Swiss cheese, Gruyere cheese, boiled mutton, beer, cognac, cider, sherry, grape wines, white wine, sake, cocoa, tea, honey soy protein, passion fruit, starfruit, mango, mushroom, malt, wort, roasted chicory root, naranjilla fruit, choke berry, sea buckthorn and Chinese quince.

Uses

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.

Uses

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

Definition

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

Preparation

By the treatment of benzyl cyanide with dilute sulfuric acid and other processes.

Aroma threshold values

Detection: 1 ppm

Taste threshold values

Taste characteristics at 30 ppm: sweet, floral, chocolate, honey and tobacco.

Synthesis Reference(s)

The Journal of Organic Chemistry, 20, p. 440, 1955 DOI: 10.1021/jo01122a005
Tetrahedron Letters, 26, p. 2027, 1985 DOI: 10.1016/S0040-4039(00)94770-1

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

Metabolism

Phenylacetic acid is conjugated in man and the chimpanzee, but probably in no other species, with glutamine. In most other animals, except the hen, it behaves like benzoic acid, forming glycine and glucuronic acid conjugates. In the hen, it conjugates with ornithine, forming phenacetornithuric acid. Phenacetylglutamine and its addition compound with urea were isolated from human urine alter the administration of phenylacetic acid (Williams, 1959).

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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Phenylacetic acid Suppliers

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