ChemicalBook > Product Catalog > Organic Chemistry > Carboxylic acids and derivatives > Cyclic carboxylic acids > Phenylacetic acid
- Product Name:Phenylacetic acid
- Synonyms: Tropicamide EP Impurity D benzenaceticacid benzeneethanoicacid ethanoicacid,phenyl- Kyselina fenyloctova kyselinafenyloctova omega-Phenylacetic acid omega-phenylaceticacid
- Product Categories: Building Blocks C8 Carbonyl Compounds Carboxylic Acids Chemical Synthesis Citrus aurantium (Seville orange) Nutrition Research Organic Building Blocks Phytochemicals by Plant (Food/Spice/Herb) API
- Mol File:103-82-2.mol
Phenylacetic acid Chemical Properties
- 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)
- refractive index 1.5120 (estimate)
- FEMA 2878 | PHENYLACETIC ACID
- Flash point:132°C
- storage temp. Store at RT.
- form neat
- pka4.28(at 18℃)
- Specific Gravity1.081
- Water Solubility 15 g/L (20 ºC)
- Merck 14,7268
- JECFA Number1007
- BRN 1099647
- Stability:Stable. Incompatible with strong oxidizing agents.
- CAS DataBase Reference103-82-2(CAS DataBase Reference)
- NIST Chemistry ReferenceBenzeneacetic acid(103-82-2)
- EPA Substance Registry SystemBenzeneacetic acid(103-82-2)
Phenylacetic acid Usage And Synthesis
- DescriptionNaturally 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 Propertieswhite crystals with a honey-like odour
- Chemical PropertiesPhenylacetic 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
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 PropertiesPhenylacetic 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.
- OccurrenceReported 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.
- UsesPhenylacetic 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.
- UsesPhenylacetic Acid is used in the synthesis of Diclofenac (D436450) and its metabolite 4'-Hydroxydiclofenac (H825225), which is the principal human metabolite of Diclofenac.
- DefinitionChEBI: A monocarboxylic acid that is toluene in which one of the hydrogens of the methyl group has been replaced by a carboxy group.
- PreparationBy the treatment of benzyl cyanide with dilute sulfuric acid and other processes.
- Aroma threshold valuesDetection: 1 ppm
- Taste threshold valuesTaste characteristics at 30 ppm: sweet, floral, chocolate, honey and tobacco.
- Safety ProfileModerately 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
- Purification MethodsCrystallise 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.]
Phenylacetic acid Preparation Products And Raw materials
- Raw materialsSodium hydroxideHydrochloric acidSulfuric acid Sodium cyanideBenzyl chlorideDimethylamineBenzeneacetonitrileAmmonium hydrogen sulfate(R,R)-(+)-HYDROBENZOIN
- Preparation ProductsPropiophenone4-Aminosalicylic acidPhenylacetic acid ethyl esterPhenylacetaldehydePhenthoateMethyl phenylacetatePhenylacetoneCefaclor monohydratePotassium benzylpenicillinPenicillin G sodium saltPhenylacetyl chloride2-Phenylacetamide7-HYDROXYISOFLAVONEDIPHACINONEIpriflavoneAmitriptyline hydrochloride 2-Bibenzylcarboxylic acidETHYL ALPHA-CHLOROPHENYLACETATE2-(METHYLSULFANYL)-5-PHENYLPYRIMIDINEp-Tolyl phenylacetateTamoxifen citrateIsopentyl phenylacetateRofecoxibALLYL PHENYLACETATEPhenylacetic acid isobutyl esterDL-2-Phenylpropionic acidBENZALPHTHALIDEPhenethyl phenylacetateBUTYL PHENYLACETATECyproheptadine hydrochloride 2-PHENYL-ETHANESULFONYL CHLORIDE
- Acetophenone Benzeneacetonitrile Ethyl 2-(Chlorosulfonyl)acetate Ascoric Acid 4-Methoxyphenylacetic acid 2-Chlorophenylacetic acid 9-HYDROXYFLUORENE-9-CARBOXYLIC ACID Benzocyclobutyl-1-carboxylic acid 1-Phenyl-1-cyclopropanecarboxylic acid 1-(4-CHLOROPHENYL)-1-CYCLOPROPANECARBOXYLIC ACID 1-Phenylcyclopentanecarboxylic acid 1-(4-CHLOROPHENYL)-1-CYCLOPENTANECARBOXYLIC ACID 1-(4-CHLOROPHENYL)-1-CYCLOBUTANECARBOXYLIC ACID 9-Carboxyfluorene 4-Hydroxyphenylacetic acid 4-Biphenylacetic acid α-Lipoic Acid 4-Chlorophenylacetic acid