Phenyl acetate

Base Information

• Chemical Name: Phenyl acetate
• CAS No.: 122-79-2
• Molecular Formula: C8H8O2
• Molecular Weight: 136.15
• Hs Code.: 29153900
• European Community (EC) Number: 204-575-0
• ICSC Number: 0539
• NSC Number: 27795
• UNII: 355G9R500Y
• DSSTox Substance ID: DTXSID3051626
• Nikkaji Number: J32.787E
• Wikipedia: Phenyl_acetate
• Wikidata: Q419645
• NCI Thesaurus Code: C1501
• Metabolomics Workbench ID: 49149
• ChEMBL ID: CHEMBL289559
• Mol file: 122-79-2.mol

Synonyms:acetic acid, phenyl ester;phenol acetate;phenyl acetate

Chemical Property of Phenyl acetate

Chemical Property:

• Appearance/Colour: colourless liquid
• Vapor Pressure: 0.418mmHg at 25°C
• Melting Point: 195-196℃
• Refractive Index: n20/D 1.501(lit.)
• Boiling Point: 195.499 °C at 760 mmHg
• Flash Point: 79.73 °C
• PSA: 26.30000
• Density: 1.072 g/cm³
• LogP: 1.61190
• Storage Temp.: Store below +30°C.
• Solubility.: 4g/l practically insoluble
• Water Solubility.: Soluble in water (4 g/L at 20°C).
• XLogP3: 1.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 136.052429494
• Heavy Atom Count: 10
• Complexity: 114

Purity/Quality:

99.9% ^*data from raw suppliers

Phenyl acetate ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn,Xi
• Hazard Codes: Xn,Xi
• Statements: 22
• Safety Statements: 36

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Solvents -> Esters (
• Canonical SMILES: CC(=O)OC1=CC=CC=C1
• Inhalation Risk: No indication can be given about the rate at which a harmful concentration of this substance in the air is reached on evaporation at 20 °C.
• Effects of Short Term Exposure: The substance is mildly irritating to the eyes and skin.
• Uses: Phenyl Acetate is a metabolite of Phenylbutyrate (PB), useful in the treatment of neuroblastoma and lung cancer. An odorant found in strawberries, passion fruit and black tea. Phenyl acetate levels in urine are marker for the diagnosis of some forms of unipolar major depressive disorders. It undergoes Fries rearrangement to form a mixture of o- and p-hydroxyacetophenones which are useful intermediates in manufacture of pharmaceuticals. It is a metabolite of Phenylbutyrate (PB), useful in the treatment of neuroblastoma and lung cancer. An odorant found in strawberries, passion fruit and black tea.

Technology Process of Phenyl acetate

There total 248 articles about Phenyl acetate 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: 76.0%

trimethylsilyl acetate (2754-27-0) + benzenediazonium tetrafluoroborate (369-57-3) → trimethylsilyl fluoride (420-56-4) + triacetoxyborane (4887-24-5) + Phenyl acetate (122-79-2,34474-31-2)

Guidance literature:

In 1,1,2-Trichloro-1,2,2-trifluoroethane; 1.) 0 to 55 deg C very slowly, 2.) sonication, reflux, 16 h;

DOI:10.1055/s-1991-26419

Reference yield: 10.0%

tert-butyl acetylperoxysalicylate (52602-01-4) → 2-acetoxybiphenyl (3271-80-5) + Phenyl acetate (122-79-2,34474-31-2) + salicylic acid (69-72-7,25496-36-0,8052-31-1) + aspirin (50-78-2,98201-60-6)

Guidance literature:

In benzene; at 100 ℃; for 48h;

DOI:10.1139/v82-162

Reference yield: 2.7%

propionic acid anhydride (123-62-6) + benzene (71-43-2,26181-88-4,54682-86-9,13967-78-7,174973-66-1) → phenyl propionate (637-27-4,132899-52-6) + Phenyl acetate (122-79-2,34474-31-2)

Guidance literature:

With peracetic acid; ferrous perchlorate; acetonitrile;

upstream raw materials:

bromobenzene

Acetyl bromide

1-ethyl-4-phenylethylene glycol

[(2-phenoxyethoxy)methyl]benzene

Downstream raw materials:

N-acetylpiperidine

4-bromophenyl acetate

o-bromophenyl acetate

p-benzylphenol

Refernces

• 1、 Kelebekli, Latif,Demir, Uemit,Kara, Yunus. "Direct Synthesis of trans-1,4-Diacetoxycyclohexa-2,5-diene by Electrochemical Reduction of r-1,t-4-Diacetoxy-t-2,c-3-dibromocyclohex-5-ene". . p. 402 - 403. Retrieved 1997.
• 2、 Burton,Munday. "-". . p. 1456,1459. Retrieved 1954.
• 3、 Spring,Vickerstaff. "-". . p. 1873. Retrieved 1935.
• 4、 Voronkov,Trukhina,Vlasova. "Acyl iodides in organic synthesis: II. Reactions with acyclic and cyclic ethers". . p. 1579 - 1581. Retrieved 2002.
• 5、 Jacobson,Mares,Zambri. "BIPHASE AND TRIPHASE CATALYSIS. ARSONATED POLYSTYRENES AS CATALYSTS IN THE BAEYER-VILLIGER OXIDATION OF KETONES BY AQUEOUS HYDROGEN PEROXIDE.". . p. 6938 - 6946. Retrieved 1979.
• 6、 Gonzalez-Nunez, Maria E.,Mello, Rossella,Olmos, Andrea,Asensio, Gregorio. "Baeyer-Villiger oxidation with potassium peroxomonosulfate supported on acidic silica gel". . p. 10879 - 10882. Retrieved 2005.
• 7、 Emmert, Marion H.,Cook, Amanda K.,Xie, Yushu J.,Sanford, Melanie S.. "Remarkably high reactivity of Pd(OAc)2/pyridine catalysts: Nondirected C-H oxygenation of arenes". . p. 9409 - 9412. Retrieved 2011.
• 8、 Gaikwad, Digambar D.,Dake, Satish A.,Kulkarni, Ravibhushan S.,Jadhav, Wamanrao N.,Kakde, Shankar B.,Pawar, Rajendra P.. "Efficient Baeyer-Villiger oxidation of ketones using molecular iodine/H2O2 as heterogeneous catalytic system". . p. 4093 - 4097. Retrieved 2007.
• 9、 Gary, J. Brannon,Cook, Amanda K.,Sanford, Melanie S.. "Palladium catalysts containing pyridinium-substituted pyridine ligands for the C-H oxygenation of benzene with K2S2O8". . p. 700 - 703. Retrieved 2013.
• 10、 Wack, Harald,Drury III, William J.,Taggi, Andrew E.,Ferraris, Dana,Lectka, Thomas. "Nucleophilic Metal Complexes as Acylation Catalysts: Solvent-dependent Switch Mechanisms Leading to the First Catalyzed Staudinger Reaction". . p. 1985 - 1988. Retrieved 1999.