19099-59-3

Basic information

• Product Name: 1-Chloro-4-((E)-2-chloro-2-fluoro-vinyl)-benzene
• Synonyms: 1-Chloro-4-((E)-2-chloro-2-fluoro-vinyl)-benzene
• CAS NO: 19099-59-3
• Molecular Weight: 191.032
• Mol File: 19099-59-3.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: 1-Chloro-4-((E)-2-chloro-2-fluoro-vinyl)-benzene(CAS DataBase Reference)
• NIST Chemistry Reference: 1-Chloro-4-((E)-2-chloro-2-fluoro-vinyl)-benzene(19099-59-3)
• EPA Substance Registry System: 1-Chloro-4-((E)-2-chloro-2-fluoro-vinyl)-benzene(19099-59-3)

Safety Data

• Hazardous Substances Data: 19099-59-3(Hazardous Substances Data)

Upstream product

• 75-69-4 trichlorofluoromethane 
• 52372-80-2 (4-chlorobenzylidene)hydrazine 
• 104-88-1 4-chlorobenzaldehyde 

Relevant articles and documents

Catalytic olefination reaction of carbonyl compounds. A study on stereoselectivity of alkene formation

The mechanism of formation of alkene stereoisomers in the catalytic olefination reaction of carbonyl compounds was studied. 4-Chlorobenzaldehyde hydrazone 1 stereoselectively reacts with a number of F-, Cl-, Br-, and I-containing polyhaloalkanes in the presence of catalytic amounts of CuCl to give ω-substituted styrenes 2 with the more thermodynamically stable alkene isomer being the major product. A model for the formation of the stereoisomers of alkenes 2 in the olefination reaction is proposed. Stereoselectivity of the reaction is determined by elimination of copper(II) halides from the lowest-lying conformers of organocopper intermediates II. According to quantum-chemical calculations, the elimination should involve the staggered conformations with antiperiplanar arrangement of C-Hal and C-Cu bonds and proceed by the E2 anti-elimination mechanism. The results of quantum-chemical calculations are in good agreement with the experimental E/Z alkene isomer ratios.

A novel approach to 2-chloro-2-fluorostyrenes

A new general catalytic olefination reaction (COR) of aromatic and heteroaromatic aldehydes and ketones was applied to synthesise 2-chloro-2-fluorostyrenes. The two-stage procedure includes the transformation of carbonyl compounds into hydrazones followed by treatment with CFCl3 mediated by copper catalysis. Trichlorofluoromethane was used as a chlorofluoromethylene transfer reagent. The reaction proceeds stereoselectively and the target alkenes were obtained in high yield. A proposed mechanism for the reaction is discussed. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003.