84750-92-5

Basic information

• Product Name: 3-Bromo-beta,beta-difluorostyrene
• Synonyms: 1-Bromo-3-(2,2-difluoroethenyl)benzene
• CAS NO: 84750-92-5
• Molecular Formula: C₈H₅BrF₂
• Molecular Weight: 0
• Mol File: 84750-92-5.mol
• Article Data: 10

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 3-Bromo-beta,beta-difluorostyrene(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Bromo-beta,beta-difluorostyrene(84750-92-5)
• EPA Substance Registry System: 3-Bromo-beta,beta-difluorostyrene(84750-92-5)

Safety Data

• Hazardous Substances Data: 84750-92-5(Hazardous Substances Data)

Upstream product

• 3132-99-8 m-bromobenzoic aldehyde 
• 19740-19-3 chlorodifluoroacetic acid lithium salt 
• 1895-39-2 sodium chlorodifluoroacetate 
• 66107-31-1 3-bromophenyl trifluoromethanesulfonate 
• 120801-75-4 trimethylsilyl-2,2-difluoro-2-(fluorosulphonyl)acetate 
• 371-67-5 2,2,2-trifluorodiazoethane 
• 89598-96-9 (3-bromophenyl)boronic acid 

Downstream Products

• 849015-92-5 3-(2,2-difluoroethenyl)benzaldehyde 
• 1501969-12-5 3,3'-((2RS,3SR)-1,1,1,4,4,4-hexafluorobutane-2,3-diyl)bis(bromobenzene) 
• 1589050-69-0 (E)-1-(2-(3-bromophenyl)-1-fluorovinyl)-1H-benzo[d]imidazole 
• 1589050-75-8 (Z)-1-(2-(3-bromophenyl)-1-fluorovinyl)-1H-benzo[d]imidazole 

Relevant articles and documents

Fluoride-Triggered Synthesis of 1-Aryl-2,2-difluoroalkenes via Desilylative Defluorination of (1-Aryl)-2,2,2-trifluoroethyl-silanes

An efficient route for the synthesis of 1-aryl-2,2-difluoroalkenes via 1,2-desilylative defluorination is disclosed. Only a catalytic amount of fluoride source is required to initiate the desilylation and afford gem-difluoroalkenes in very good to quantitative yields, using mild reaction conditions in dimethyl carbonate as a green solvent. This reaction uses (1-aryl)-2,2,2-trifluoroethyl-silanes, which are easily prepared via the insertion reaction of trifluoroethyl diazo alkanes into the Si-H bond of tertiary organosilanes. (1-Aryl)-perfluoroalkyl-silanes cleanly afford the corresponding (Z)-1-benzylideneperfluoroalkanes, which upon hydrodefluorination furnish the (E)-β(perfluoroalkyl)styrene derivatives with excellent yield and complete stereoselectivity. A one-pot system involving sequential insertion and desilylative-defluorination is also suitable for this transformation. This method demonstrates the usefulness of organosilanes toward the preparation of fluorinated alkenes as synthetically useful targets.

Pd-Catalyzed Selective Carbonylation of gem-Difluoroalkenes: A Practical Synthesis of Difluoromethylated Esters

The first catalyst for the alkoxycarbonylation of gem-difluoroalkenes is described. This novel catalytic transformation proceeds in the presence of Pd(acac)2/1,2-bis((di-tert-butylphosphan-yl)methyl)benzene (btbpx) (L4) and allows for an efficient and straightforward access to a range of difluoromethylated esters in high yields and regioselectivities. The synthetic utility of the protocol is showcased in the practical synthesis of a Cyclandelate analogue using this methodology as the key step.

A versatile difluorovinylation method: Cross-coupling reactions of the 2,2-difluorovinylzinc-TMEDA complex with alkenyl, alkynyl, allyl, and benzyl halides Dedicated to Professor Iwao Ojima on the occasion of his 70th birthday.

A thermally stable 2,2-difluorovinylzinc-TMEDA complex was prepared via a deprotonation-transmetallation sequence starting from commercially available 1,1-difluoroethylene. The complex thus formed was successfully applied to transition metal-catalyzed cross-coupling reactions with a wide range of organic halides, which led to the syntheses of 2,2-difluorovinyl compounds. On treatment with the difluorovinylzinc-TMEDA complex in the presence of an appropriate palladium or copper catalyst, alkenyl, alkynyl, allyl, and benzyl halides effectively underwent difluorovinylation to afford 1,1-difluoro-1,3-dienes, 1,1-difluoro-1,3-enynes, 1,1-difluoro-1,4-dienes, and (3,3-difluoroallyl)arenes, respectively.