Methyl phenylacetate

Base Information

• Chemical Name: Methyl phenylacetate
• CAS No.: 101-41-7
• Molecular Formula: C9H10O2
• Molecular Weight: 150.177
• Hs Code.: H3 MOL WT. 150.18
• European Community (EC) Number: 202-940-9
• NSC Number: 401667,9405
• UNII: D4PDC41X96
• DSSTox Substance ID: DTXSID1044352
• Nikkaji Number: J363H
• Wikipedia: Methyl_phenylacetate
• Wikidata: Q390681
• Metabolomics Workbench ID: 45656
• ChEMBL ID: CHEMBL3189123
• Mol file: 101-41-7.mol

Synonyms:methyl phenylacetate

Chemical Property of Methyl phenylacetate

Chemical Property:

• Appearance/Colour: colourless liquid
• Vapor Pressure: 0.129mmHg at 25°C
• Melting Point: 218 °C(lit.)
• Refractive Index: 1.507
• Boiling Point: 218 °C at 760 mmHg
• Flash Point: 93.9 °C
• PSA: 26.30000
• Density: 1.055 g/cm³
• LogP: 1.40210
• Storage Temp.: Store below +30°C.
• Solubility.: Chloroform (Slightly), Methanol (Slightly)
• Water Solubility.: Miscible with water.
• XLogP3: 1.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 3
• Exact Mass: 150.068079557
• Heavy Atom Count: 11
• Complexity: 126

Purity/Quality:

98% ^*data from raw suppliers

Methyl phenylacetate ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 21-R21
• Safety Statements: 23-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Other Classes -> Esters, Other
• Canonical SMILES: COC(=O)CC1=CC=CC=C1
• Description: Methyl phenylacetate belongs to an ester compound form between the methanol and phenylacetate. It chemical formula is C6H5CH2COOCH3. It is generally found in brandy, capsicum, honey, pepper, some wine, coca and coca products. It is mainly used as a flavouring agent, and is also supplemented into perfumes to enhance honey scents. It can also be used as the precursor for the manufacture of synthetic perfumes. In addition, as an acylating agent, it can participate in the enantioselective acylation reaction of beta-lactam intermediate catalyzed by the penicillin G amidase.
• Uses: Methyl phenylacetate is utilized for partition coefficient measurement experiments. It is mainly used in the flavor industry and in perfumes to impart honey scents. Further, it acts as a precursor to prepare synthetic perfumes. It acts as an acylating agent and involved in the enantioselective acylation of beta-lactam intermediate using penicillin G amidase.

Technology Process of Methyl phenylacetate

There total 305 articles about Methyl phenylacetate 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: 84.0%

2-methoxycyclohexane (931-56-6) → cyclohexyl chloride (542-18-7) + benzeneacetic acid methyl ester (101-41-7)

Guidance literature:

With phenylacetyl chloride; zinc; In Petroleum ether; at 28 ℃; for 4h; Yields of byproduct given;

DOI:10.1021/jo00108a048

Reference yield: 84.0%

2-methoxycyclohexane (931-56-6) + phenylacetyl chloride (103-80-0) → cyclohexyl chloride (542-18-7) + benzeneacetic acid methyl ester (101-41-7)

Guidance literature:

With zinc; In Petroleum ether; at 28 ℃; for 4h; Yields of byproduct given;

DOI:10.1021/jo00108a048

Reference yield: 74.0%

methanol (67-56-1) + carbon monoxide (201230-82-2) + benzyl bromide (100-39-0) → benzyl methyl ether (538-86-3) + benzeneacetic acid methyl ester (101-41-7)

Guidance literature:

organopalladium catalyst; at 55 ℃; under 2587.71 Torr;

DOI:10.1016/j.tetlet.2005.10.038

upstream raw materials:

diazomethane

phenylacetic acid

methanol

2-diazo-acetophenone

Downstream raw materials:

N-phenethyl-2-phenylacetamide

N,N-bis(2-hydroxyethyl)-2-phenylacetamide

N-Allyl-2-phenylethanamide

dimethyl 2-phenylmalonate

Refernces

• 1、 Jia, Rong,Ren, Jiawen,Liu, Xiaohui,Lu, Guanzhong,Wang, Yanqin. "Design and synthesis of sulfonated carbons with amphiphilic properties". . p. 11195 - 11201. Retrieved 2014.
• 2、 McElvain,Stevens. "-". . p. 1917,1921. Retrieved 1946.
• 3、 Hidai,M. et al.. "-". . p. 2075 - 2077. Retrieved 1975.
• 4、 Remme, Nicole,Koschek, Katharina,Schneider, Christoph. "Scandium triflate catalyzed transesterification of carboxylic esters". . p. 491 - 493. Retrieved 2007.
• 5、 Midura, Wanda H.,Rzewnicka, Aneta,Krysiak, Jerzy A.. "Phenylsilane as an effective desulfinylation reagent". . p. 1513 - 1517. Retrieved 2017.
• 6、 Luo, Fen-Tair,Jeevanandam, Arumugasamy. "Simple transformation of nitrile into ester by the use of chlorotrimethylsilane". . p. 9455 - 9456. Retrieved 1998.
• 7、 Fisher, Thomas J.,Dussault, Patrick H.. "Fragmentation of chloroperoxides: Hypochlorite-mediated dehydration of hydroperoxyacetals to esters". . p. 5615 - 5617. Retrieved 2010.
• 8、 Balasubramanian, P. N.,Bruice, Thomas C.. "Oxygen Transfer Involving Non-Heme Iron. The reaction of (EDTA)Fe(III) with m-Chloroperbenzoic Acid". . p. 5495 - 5503. Retrieved 1986.
• 9、 Stille,Wong. "". . p. 532. Retrieved 1975.
• 10、 Shieh, Wen-Chung,Dell, Steven,Repic, Oljan. "Nucleophilic catalysis with 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) for the esterification of carboxylic acids with dimethyl carbonate". . p. 2188 - 2191. Retrieved 2002.