Phenacyl acetate

Base Information

• Chemical Name: Phenacyl acetate
• CAS No.: 2243-35-8
• Molecular Formula: C10H10O3
• Molecular Weight: 178.188
• NSC Number: 9837
• DSSTox Substance ID: DTXSID20862889
• Nikkaji Number: J135.668B
• Wikidata: Q72500774
• Mol file: 2243-35-8.mol

Synonyms:Phenacyl acetate;2-Oxo-2-phenylethyl acetate;2243-35-8;Ethanone, 2-(acetyloxy)-1-phenyl-;alpha-Acetoxyacetophenone;2-Hydroxyacetophenoneacetate;PHENACYLACETATE;Acetophenone, 2-hydroxy-, acetate;omega-Acetoxyacetophenone;.omega.-Acetoxyacetophenone;2-(Acetyloxy)-1-phenyl-ethanone;NSC 9837;2-Acetoxy-1-phenylethanon;a-acetoxy acetophenone;Acetic acid phenacyl ester;Acetophenone, acetate;2--Acetoxyacetophenone;alpha-acetoxy acetophenone;2-Acetoxy-1-phenylethanone;2-Oxo-2-phenylethylacetate;2-acetoxy-1-phenyl-ethanone;SCHEMBL1907159;DTXSID20862889;NSC9837;CAA24335;MFCD00026205;AKOS003609122;Acetic Acid 2-oxo-2-phenyl-ethyl Ester;AS-59088;FT-0634160;A878538

Chemical Property of Phenacyl acetate

Chemical Property:

• Vapor Pressure: 0.000899mmHg at 25°C
• Melting Point: 48-50 °C
• Refractive Index: 1.473
• Boiling Point: 270.7 °C at 760 mmHg
• Flash Point: 115.8 °C
• PSA: 43.37000
• Density: 1.131 g/cm³
• LogP: 1.43240
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility.: Chloroform (Slightly), Methanol (Slightly)
• XLogP3: 1.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 4
• Exact Mass: 178.062994177
• Heavy Atom Count: 13
• Complexity: 192

Purity/Quality:

99% ^*data from raw suppliers

2-(Acetyloxy)-1-phenylethanone ^*data from reagent suppliers

Safty Information:

• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)OCC(=O)C1=CC=CC=C1
• Uses: 2-(Acetyloxy)-1-phenylethanone is used in the synthesis of enol phosphates. Also used in the preparation of triazole antifungals such as (-)-Genazonazole.

Technology Process of Phenacyl acetate

There total 91 articles about Phenacyl 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: 97.0%

potassium acetate (127-08-2) + 1-chloroacetophenone (532-27-4,108321-66-0,164322-25-2) → 2-acetoxyacetophenone (2243-35-8)

Guidance literature:

With [bmim]Br; at 20 ℃; for 0.5h;

DOI:10.1016/j.tetlet.2004.10.015

Reference yield: 94.0%

α-bromoacetophenone (70-11-1) → 2-acetoxyacetophenone (2243-35-8)

Guidance literature:

With silver(I) acetate; In acetonitrile; at 50 ℃; for 2.5h; Inert atmosphere; Darkness;

DOI:10.1055/s-0033-1338551

Reference yield: 93.0%

[bis(acetoxy)iodo]benzene (3240-34-4) + phenylacetylene (536-74-3) → 2-acetoxyacetophenone (2243-35-8)

Guidance literature:

With silver(I) acetate; In acetonitrile; at 25 ℃; for 14h; Solvent; Reagent/catalyst;

DOI:10.1016/j.tet.2013.04.122

upstream raw materials:

iodoacetophenone

potassium acetate

methanol

2-bromo-1-phenyl-3-[2]pyridyl-propane-1,3-dione

Downstream raw materials:

2,2-dimethyl-4-oxo-3-phenyl-butyric acid

3-hydroxy-2-phenylquinoline-4,8-dicarboxylic acid

6-chloro-3-hydroxy-2-phenyl-chromenylium

2-Hydroxy-1,3,5-triphenyl-1,5-pentanedione

Refernces

• 1、 Doxsee, Kenneth M.,Ferguson, Cynthia M.,Wash, Paul L.,Saulsbery, Robin L.,Hope, Hakon. "Calcium Complexation by α-Hydroxy Ketones. Characterization of a Calcium Complex of Phenacyl Alcohol". . p. 7557 - 7561. Retrieved 1993.
• 2、 Huang, Xin,Zhang, Yage,Zhang, Chaoshen,Zhang, Lei,Xu, Ying,Kong, Lichun,Wang, Zhi-Xiang,Peng, Bo. "The ortho-Difluoroalkylation of Aryliodanes with Enol Silyl Ethers: Rearrangement Enabled by a Fluorine Effect". . p. 5956 - 5961. Retrieved 2019.
• 3、 Adam, Waldemar,Arnold, Markus A.,Nau, Werner M.,Pischel, Uwe,Saha-Moeller, Chantu R.. "A comparative photomechanistic study (spin trapping, EPR spectroscopy, transient kinetics, photoproducts) of nucleoside oxidation (dG and 8-oxodG) by triplet-excited acetophenones and by the radicals generated from α-oxy-substituted derivatives through no". . p. 3893 - 3904. Retrieved 2002.
• 4、 Ochiai, Masahito,Kunishima, Munetaka,Fuji, Kaoru,Nagao, Yoshimitsu. "Conjugate Addition of Acyloxy Groups to Alkynylphenyliodonium Tetrafluoroborates under Both Basic and Acidic Conditions. Synthesis of α-Acyloxy Ketones". . p. 4038 - 4041. Retrieved 1989.
• 5、 Vil’, Vera A.,Merkulova, Valentina M.,Ilovaisky, Alexey I.,Paveliev, Stanislav A.,Nikishin, Gennady I.,Terent’ev, Alexander O.. "Electrochemical Synthesis of Fluorinated Ketones from Enol Acetates and Sodium Perfluoroalkyl Sulfinates". supporting information. p. 5107 - 5112. Retrieved 2021/06/30.
• 6、 Chen, Xin,Xin, Yangchun,Zhao, Zhi-Wei,Hou, Yu-Jian,Wang, Xiang-Xiang,Xia, Wen-Jin,Li, Ya-Min. "Decarboxylative Oxyacyloxylation of Propiolic Acids: Construction of Alkynyl-Containing α-Acyloxy Ketones". supporting information. p. 8216 - 8225. Retrieved 2021/06/28.