2,2-Difluoro-1-phenylethanone

Base Information

• Chemical Name: 2,2-Difluoro-1-phenylethanone
• CAS No.: 395-01-7
• Molecular Formula: C8H6F2O
• Molecular Weight: 156.132
• Hs Code.: 2914700090
• European Community (EC) Number: 641-292-5
• NSC Number: 118411
• DSSTox Substance ID: DTXSID80960133
• Nikkaji Number: J753.861H
• Mol file: 395-01-7.mol

Synonyms:395-01-7;2,2-difluoro-1-phenylethanone;2,2-difluoroacetophenone;2,2-difluoro-1-phenyl-ethanone;alpha,alpha-difluoroacetophenone;2,2-difluoro-1-phenylethan-1-one;A,A-Difluoroacetophenone;Ethanone, 2,2-difluoro-1-phenyl-;MFCD06246879;2,2-bis(fluoranyl)-1-phenyl-ethanone;difluoromethyl phenyl ketone;difluoroacetophenone;NSC118411;, -Difluoroacetophenone;Acetophenone, 2,2-difluoro;SCHEMBL1492635;DTXSID80960133;BBL100593;STL554387;AKOS005254888;NSC-118411;AM803835;AS-39499;SY061919;CS-0095863;FT-0677386;EN300-316968;A824576;W65

Chemical Property of 2,2-Difluoro-1-phenylethanone

Chemical Property:

• Vapor Pressure: 0.439mmHg at 25°C
• Melting Point: 48-50°C
• Refractive Index: 1.4955
• Boiling Point: 194.6 °C at 760 mmHg
• Flash Point: 71.9 °C
• PSA: 17.07000
• Density: 1.18g/cm³
• LogP: 2.13440
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• Water Solubility.: Immiscible with water.
• XLogP3: 2.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 156.03867113
• Heavy Atom Count: 11
• Complexity: 139

Purity/Quality:

98%,99%, ^*data from raw suppliers

2,2-Difluoroacetophenone ^*data from reagent suppliers

Safty Information:

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

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)C(=O)C(F)F
• Uses: 2,2-Difluoroacetophenone acts as an intermediate in the preparation of various substances such as pharmaceuticals. Further, it is used in the one-pot synthesis of difluoromethylated arenes from aryl chlorides and bromides. In addition to this, it undergoes reduction with (-)-diisopinocampheylchloroborane chloride to get R-alcohols of purity 85% ee.

Technology Process of 2,2-Difluoro-1-phenylethanone

There total 87 articles about 2,2-Difluoro-1-phenylethanone 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: 94.0%

2,2,2-Trifluoroacetophenone (434-45-7) → 2,2-difluoro-1-phenylethanone (395-01-7)

Guidance literature:

With chloro-trimethyl-silane; tetrabutylammomium bromide; tetraethylammonium hexafluorophosphate; In acetonitrile; at 20 ℃; Electrochemical reaction;

DOI:10.1039/d1sc01574e

Reference yield: 91.0%

difluoroacetonitrile (359-12-6) + benzene (71-43-2,26181-88-4,54682-86-9,13967-78-7,174973-66-1) → 2,2-difluoro-1-phenylethanone (395-01-7)

Guidance literature:

difluoroacetonitrile; benzene; With trifluorormethanesulfonic acid; In chloroform; at 20 ℃; Inert atmosphere;

With water; In chloroform; Cooling with ice;

DOI:10.1016/j.tetlet.2011.07.125

Reference yield: 90.0%

1-Phenyl-4,4,4-trifluorobutane-1,3-dione (326-06-7) → 2,2-difluoro-1-phenylethanone (395-01-7)

Guidance literature:

1-Phenyl-4,4,4-trifluorobutane-1,3-dione; With Selectfluor; In acetonitrile; at 90 ℃; for 3h; Inert atmosphere;

With water; In acetonitrile; for 0.25h; Inert atmosphere; Reflux;

With triethylamine; In acetonitrile; at 20 ℃; for 16h; regioselective reaction; Inert atmosphere;

DOI:10.1039/c5ob02468d

upstream raw materials:

Difluoroacetic acid

2,2-dichloroacetophenone

acetophenone

difluoroacetyl chloride

Downstream raw materials:

2,2-difluoro-1-phenyl-ethanol

(1,1-dichloro-2,2-difluoro-ethyl)-benzene

4-[2,2-Difluoro-1-phenyl-eth-(Z)-ylidene]-2-phenyl-4H-oxazol-5-one

2,2-difluoro-3-hydroxy-1,3-diphenylpropan-1-one

Refernces

• 1、 Li, Jinshan,Xi, Wenxue,Zhong, Rong,Yang, Jianguo,Wang, Lei,Ding, Hanfeng,Wang, Zhiming. "HFIP-catalyzed direct dehydroxydifluoroalkylation of benzylic and allylic alcohols with difluoroenoxysilanes". . p. 1050 - 1053. Retrieved 2021.
• 2、 Demir, Ayhan S.,Eymur, Serkan. "Addition of trifluoromethyltrimethylsilane to acyl phosphonates: Synthesis of TMS-protected 1-alkyl-1-trifluoromethyl-1-hydroxy phosphonates and 1-aryldifluoroethenyl phosphates". . p. 8527 - 8530. Retrieved 2007.
• 3、 Médebielle, Maurice,Kato, Katsuya,Dolbier Jr., William R.. "Difluoromethylation reactions of ethyl pyruvate with the TDAE - A mild approach to the synthesis of 3,3-difluoro-2-hydroxy-2-methyl-4-oxo-butyric ethyl esters derivatives". . p. 1541 - 1543. Retrieved 2002.
• 4、 Ispizua-Rodriguez, Xanath,Munoz, Socrates B.,Krishnamurti, Vinayak,Mathew, Thomas,Prakash. "Direct Synthesis of Tri-/Difluoromethyl Ketones from Carboxylic Acids by Cross-Coupling with Acyloxyphosphonium Ions". supporting information. p. 15908 - 15913. Retrieved 2021/10/07.