Phenylacetic Acid

Base Information

• Chemical Name: Phenylacetic Acid
• CAS No.: 103-82-2
• Molecular Formula: C8H8O2
• Molecular Weight: 136.15
• Hs Code.: 2916.33
• European Community (EC) Number: 203-148-6
• ICSC Number: 1260
• NSC Number: 139637,125718
• UNII: ER5I1W795A
• DSSTox Substance ID: DTXSID2021656
• Nikkaji Number: J10.117F
• Wikipedia: Phenylacetic_acid
• Wikidata: Q410842
• NCI Thesaurus Code: C77487
• RXCUI: 33332
• Metabolomics Workbench ID: 37136
• ChEMBL ID: CHEMBL1044
• Mol file: 103-82-2.mol

Synonyms:phenylacetate;phenylacetic acid;phenylacetic acid, ammonium salt;phenylacetic acid, calcium salt;phenylacetic acid, cesium salt;phenylacetic acid, lithium salt;phenylacetic acid, mercury salt;phenylacetic acid, potassium salt;phenylacetic acid, rubidium salt;phenylacetic acid, sodium salt;phenylacetic acid, sodium salt , carboxy-(11)C-labeled cpd;sodium phenylacetate

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Chemical Property of Phenylacetic Acid

Chemical Property:

• Appearance/Colour: White crystals with a honey-like odour
• Vapor Pressure: 1 mm Hg ( 97 °C)
• Melting Point: 76-78 °C(lit.)
• Refractive Index: 1.552
• Boiling Point: 265.499 °C at 760 mmHg
• PKA: 4.28(at 18℃)
• Flash Point: 156.213 °C
• PSA: 37.30000
• Density: 1.165 g/cm³
• LogP: 1.31370
• Storage Temp.: Store at RT.
• Water Solubility.: 15 g/L (20 ºC)
• XLogP3: 1.4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 136.052429494
• Heavy Atom Count: 10
• Complexity: 114

Purity/Quality:

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36-37/39

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Other Classes -> Organic Acids
• Canonical SMILES: C1=CC=C(C=C1)CC(=O)O
• Recent ClinicalTrials: Phenylacetate in Treating Children With Recurrent or Progressive Brain Tumors
• Inhalation Risk: A harmful contamination of the air will not or will only very slowly be reached on evaporation of this substance at 20 °C.
• Effects of Short Term Exposure: The substance is irritating to the eyes. The substance is mildly irritating to the skin.
• 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.
• 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. Phenylacetic acid?has strong fixative agent and can be directly used in low-or-middle-level soap, cosmetics essences. It is usually to confect the substitute for civetta with indole quinoline type and used in acacia, sweet-scented osmanthus, rose, hosta and other floral essences. Phenylacetic Acid is used in the synthesis of Diclofenac (D436450) and its metabolite 4'-Hydroxydiclofenac (H825225), which is the principal human metabolite of Diclofenac.

Technology Process of Phenylacetic Acid

There total 937 articles about Phenylacetic Acid which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 88.0%

ethylbenzene (100-41-4,27536-89-6) + peroxyphenylacetic acid (60538-67-2) → phenylacetic acid (103-82-2) + 1-Phenylethanol (98-85-1,13323-81-4) + acetophenone (98-86-2)

Guidance literature:

With manganese(III)-5,10,15,20-tetrakis(pentafluorophenyl)porphyrin chloride; In water; acetonitrile; at 20 ℃; for 0.166667h; Concentration; Reagent/catalyst; Solvent; Inert atmosphere;

DOI:10.1002/chem.201202640

Reference yield: 83.0%

ethylbenzene (100-41-4,27536-89-6) + peroxyphenylacetic acid (60538-67-2) → phenylacetic acid (103-82-2) + 1-Phenylethanol (98-85-1,13323-81-4) + benzaldehyde (100-52-7) + acetophenone (98-86-2)

Guidance literature:

With (5,10,15,20-tetramesitylporphyrinato)manganese(III) chloride; In water; acetonitrile; at 20 ℃; for 0.166667h; Concentration; Reagent/catalyst; Solvent; Inert atmosphere;

DOI:10.1002/chem.201202640

Reference yield: 68.0%

peroxyphenylacetic acid (60538-67-2) → phenylacetic acid (103-82-2) + benzaldehyde (100-52-7)

Guidance literature:

With (5,10,15,20-tetramesitylporphyrinato)manganese(III) chloride; In water; acetonitrile; at 20 ℃; for 0.166667h; Solvent; Reagent/catalyst; Inert atmosphere;

DOI:10.1002/chem.201202640

upstream raw materials:

diazoacetic acid ethyl ester

sodium ethanolate

diethyl 2-phenylmalonate

propan-1-ol

Downstream raw materials:

4-chlorobutyl phenylacetate

3-methoxy-stilben-4-ol

[4-(2-chloro-propionyl)-phenyl]-acetic acid

2-phenyl-1-o-tolylethanone

Refernces

• 1、 Amer, Ibrahim,Alper, Howard. "Lanthanide-Promoted and Nickel Cyanide Catalyzed Carbonylation Reactions under Phase-Transfer Conditions". . p. 927 - 930. Retrieved 1989.
• 2、 Iwamura, Michiko,Tokuda, Kazuko,Koga, Noboru,Iwamura, Hiizu. "Photoreactivity of 1-Pyrenylmethyl Esters. Dependence on the Structure of the Carboxylic Acid Moieties and the Nature of the Excited States". . p. 1729 - 1732. Retrieved 1987.
• 3、 Matloubi Moghaddam,Ghaffarzadeh. "Microwave-assisted rapid hydrolysis and preparation of thioamides by Willgerodt-Kindler reaction". . p. 317 - 321. Retrieved 2001.
• 4、 Yin, Xu-Guang,Gao, Xiao-Fei,Du, Jing-Jing,Zhang, Xiao-Kang,Chen, Xiang-Zhao,Wang, Jian,Xin, Ling-Ming,Lei, Ze,Liu, Zheng,Guo, Jun. "Preparation of Protein Conjugates via Homobifunctional Diselenoester Cross-Linker". . p. 5796 - 5799. Retrieved 2016.
• 5、 Freeman, Fillmore,Lin, Doris K.,Moore, Gregory R.. "Permanganate Ion Oxidations. 14. Kinetics and Mechanism of the Oxidation of Aliphatic Aldehydes in Acid Media". . p. 56 - 59. Retrieved 1982.
• 6、 Yukawa et al.. "". . p. 2618,2619. Retrieved 1967.
• 7、 Chemat, Farid. "Towards the rehabilitation of the Mathews' 'dry' hydrolysis reaction using microwave technology". . p. 5555 - 5557. Retrieved 2002.
• 8、 Gilman,Pacevitz,Baine. "-". . p. 1514,1519. Retrieved 1940.
• 9、 Guranda, Dorel T.,Khimiuk, Andrey I.,Van Langen, Luuk M.,Van Rantwijk, Fred,Sheldon, Roger A.,Svedas, Vytas K.. "An 'easy-on, easy-off' protecting group for the enzymatic resolution of (±)-1-phenylethylamine in an aqueous medium". . p. 2901 - 2906. Retrieved 2004.
• 10、 Shim, Sang Chul,Doh, Chil Hoon,Park, Woo Hyun,Kwon, Young Gil,Lee, Hyung Soo. "Cobalt carbonyl catalyzed carbonylation of benzal bromides by phase transfer catalysis". . p. 419 - 421. Retrieved 1990.