85433-90-5

Usage

Physical state

Colorless liquid

Common uses

a. Organic synthesis
b. Pharmaceutical research
c. Production of chemical compounds (pharmaceuticals, agrochemicals, and industrial chemicals)

Applications

Versatile properties make it an important building block in the development of new chemicals and materials

Safety precautions

Proper handling and storage required to avoid harm if not used properly

Upstream product

• 14774-77-7 p-methoxyphenyllithium 
• 696-62-8 para-iodoanisole 
• 60059-95-2 C₉H₇ClF₂O 

Relevant academic research and scientific papers

The stereoselective synthesis of (Z)-HFC=CFZnI and stereospecific preparation of (E)-1,2-difluorostyrenes from (Z)-HFC=CFZnI via an unusual Pd(PPh3)4-Cu(I)Br co-catalysis approach or (Z)-HFC=CFSnBu3

(Z)-HFCCFZnI was stereoselectively synthesized from activated zinc dust and (Z)-HFCCFI that was synthesized from chlorotrifluoroethene in a sequential manner. Compared to (E)-HFCCFZnI, (Z)-HFCCFZnI was more challenging to prepare in terms of sluggish metallation and formation of by-products, and underwent slower and incomplete Negishi coupling with aryl iodides. In a modification of Negishi coupling, (E)-α,β-difluorostyrenes were stereospecifically prepared in good to excellent yields under mild conditions from aryl iodides and (Z)-HFCCFZnI with the co-catalysis of Pd(PPh3)4/Cu(I)Br. Experimental investigation and mechanistic rationalization suggested that Cu(I)Br would be a scavenger of free ligands for the facilitation of Pd(PPh 3)2 formation, and a supplier of ligand for the metathesis process. Alternatively, (Z)-HFCCFSnBu3 and aryl iodides with an electron-withdrawing group underwent Stille-Liebiskind coupling to afford (E)-α,β-difluorostyrenes.

Stereospecific synthesis of (E)-α,β-difluorostyrenes

Isomerically pure (Z)-HFC=CFZnI undergoes Pd(PPh3)4/CuBr co-catalyzed cross-coupling reactions with aryl iodides in DMAC to give the title compounds in good yields, under mild conditions. In the absence of CuBr, the reaction is slugg

REACTION DE PERHALOSTYRENES AVEC LES ORGANOLITHIENS. PREPARATION D'ARYL-1 ALCYNES-1 RAMIFIES PAR L'INTERMEDIAIRE D'ARYL FLUORO ACETYLENES

Organolithium compounds react with 1-aryl 2-chloro 1,2-difluoroethylene to give derivatives of type Ar-C*C-R'.Hydrolysis of the intermediate carbanionic species yilds the corresponding α,β-difluorostyrenes.