394-98-9

Basic information

• Product Name: Benzene, (1-chloro-2,2-difluoroethenyl)-
• CAS NO: 394-98-9
• Molecular Formula: C8H5ClF2
• Molecular Weight: 174.578
• Mol File: 394-98-9.mol
• Article Data: 11

Chemical Properties

• CAS DataBase Reference: Benzene, (1-chloro-2,2-difluoroethenyl)-(CAS DataBase Reference)
• NIST Chemistry Reference: Benzene, (1-chloro-2,2-difluoroethenyl)-(394-98-9)
• EPA Substance Registry System: Benzene, (1-chloro-2,2-difluoroethenyl)-(394-98-9)

Safety Data

• Hazardous Substances Data: 394-98-9(Hazardous Substances Data)

Upstream product

• 378-99-4 α,α,β-trichloro-β,β-difluoroethylbenzene 
• 591-50-4 iodobenzene 
• 75-88-7 1,1,1-trifluoro-2-chloroethane 
• 151-67-7 1,1,1-trifluoro-2-bromo-2-chloroethane 
• 79-35-6 1,1'-dichloro-2,2'-difluoroethene 
• 98-80-6 phenylboronic acid 
• 384-67-8 2-chloro-2,2-difluoroacetophenone 
• 434-45-7 2,2,2-Trifluoroacetophenone 
• 405-42-5 2',2'-difluorostyrene 
• 340-03-4 2-chloro-2,2-difluoro-1-phenyl-ethan-1-ol 
• 434-44-6 1,2-dichloro-1-phenyl-2,2-difluoroethane 
• 60-29-7 diethyl ether 
• 75-45-6 Chlorodifluoromethane 
• 98-07-7 Benzotrichlorid 

Downstream Products

• 40193-71-3 (1,2-Dibromo-1-chloro-2,2-difluoro-ethyl)-benzene 
• 58852-20-3 α-Chlor-α-Tritio-β,β,β-trifluoraethylbenzol 
• 78844-54-9 α-Chlor-α-Deutero-β,β,β-trifluoraethylbenzol 
• 384-65-6 1-chloro-2,2,2-trifluoroethylbenzene 

Relevant articles and documents

Reaction of Halothane with sec-butyllithium in the presence of zinc halides - One-pot preparation of chlorodifluorovinylzinc reagent and its derivatization to α-chloro-β,β-difluorostyrene

Halothane, 2-bromo-2-chloro-1,1,1-trifluoroethane, reacts with sec -butyllithium in the presence of zinc halides to afford a chlorodifluorovinylzinc reagent. This zinc reagent reacts with aryl halides in the presence of a palladium catalyst to give chlorodifluorostyrene derivatives in moderate to good yields.

Room temperature preparation of α-chloro-β,β- difluoroethenylzinc reagent (CF2CClZnCl) by the metallation of HCFC-133a (CF3CH2Cl) and a high yield one-pot synthesis of α-chloro-β,β-difluorostyrenes

α-Chloro-β,β-difluorovinylzinc reagent [CF 2CClZnCl] was generated in 91% yield by the metallation of a THF solution of commercially available HCFC-133a (CF3CH2Cl) and zinc chloride at 15-20 °C using LDA as base. The corresponding reaction with Halothane (CF3CHClBr) produced a poor yield of CF 2CClZnCl. The palladium catalyzed coupling reaction of the CF 2CClZnCl with aryl iodides under mild reaction conditions produced α-chloro-β,β-difluorostyrenes in 64-90% isolated yields. The stability of the intermediate CF2CClLi and the nature of the zinc reagents are discussed.

The room temperature preparation of the 1-chloro-2,2-difluorovinylzinc reagent from HCFC-133a (CF3CH2Cl). The first ambient, high yield, one-flask preparation of α-chloro-β,β-difluorostyrenes

The reaction of LDA (2.0 equiv.) with a THF solution of ZnCl2 (1.0 equiv.) and HCFC-133a (CF3CH2Cl) (1.0 equiv.) at 15-20°C gives a 91% yield of [F2C=CClZnCl]. Addition of ArI and Pd(PPh3)4 at rt to 65°C gives 65-85% isolated yields of ArCCl=CF2. This one-flask procedure provides the first room temperature generation of the 1-chloro-2,2-difluorovinylzinc reagent and the first high yield preparation of α-chloro-β,β-difluorostyrenes from a cheap, readily available industrial precursor.