1236300-58-5

Basic information

• Product Name: (Z)-1-bromo-4-(2-fluorovinyl)benzene
• Synonyms: (Z)-1-bromo-4-(2-fluorovinyl)benzene
• CAS NO: 1236300-58-5
• Molecular Weight: 201.038
• Mol File: 1236300-58-5.mol

Chemical Properties

• CAS DataBase Reference: (Z)-1-bromo-4-(2-fluorovinyl)benzene(CAS DataBase Reference)
• NIST Chemistry Reference: (Z)-1-bromo-4-(2-fluorovinyl)benzene(1236300-58-5)
• EPA Substance Registry System: (Z)-1-bromo-4-(2-fluorovinyl)benzene(1236300-58-5)

Safety Data

• Hazardous Substances Data: 1236300-58-5(Hazardous Substances Data)

Upstream product

• 84750-93-6 1,1-difluoro-2-(4-bromophenyl)ethene 
• 2039-82-9 1-bromo-4-ethenyl-benzene 
• 2366-31-6 (Z)-1-bromo-2-fluoroethylene 
• 1236300-44-9 1-tert-butyl-1H-tetrazol-5-yl fluoromethyl sulfone 
• 1122-91-4 4-bromo-benzaldehyde 

Relevant articles and documents

Stereodivergent hydrodefluorination of: Gem -difluoroalkenes: Selective synthesis of (Z)- and (E)-monofluoroalkenes

We have developed a novel approach for the stereodivergent hydrodefluorination of gem-difluoroalkenes using copper(i) catalysts to obtain stereodefined monofluoroalkenes. Both (Z)- and (E)-terminal monofluoroalkenes were obtained by the hydrodefluorination of gem-difluoroalkenes in the presence of copper(i) catalysts and diboron or hydrosilane, respectively, with high stereoselectivity. DFT calculations were conducted to elucidate the stereoselectivity.

Direct synthesis of Z-alkenyl halides through catalytic cross-metathesis

Olefin metathesis has had a large impact on modern organic chemistry, but important shortcomings remain: for example, the lack of efficient processes that can be used to generate acyclic alkenyl halides. Halo-substituted ruthenium carbene complexes decompose rapidly or deliver low activity and/or minimal stereoselectivity, and our understanding of the corresponding high-oxidation-state systems is limited. Here we show that previously unknown halo-substituted molybdenum alkylidene species are exceptionally reactive and are able to participate in high-yielding olefin metathesis reactions that afford acyclic 1,2-disubstituted Z-alkenyl halides. Transformations are promoted by small amounts of a catalyst that is generated in situ and used with unpurified, commercially available and easy-to-handle liquid 1,2-dihaloethene reagents, and proceed to high conversion at ambient temperature within four hours. We obtain many alkenyl chlorides, bromides and fluorides in up to 91 per cent yield and complete Z selectivity. This method can be used to synthesize biologically active compounds readily and to perform site- and stereoselective fluorination of complex organic molecules.

1-tert-Butyl-1H-tetrazol-5-yl fluoromethyl sulfone (TBTSO2CH2F): A versatile fluoromethylidene synthon and its use in the synthesis of monofluorinated alkenes via JuliaKocienski olefination

1-tert-Butyl-IH-tetrazol-5-yl fluoromethyl sulfone (TBTSO 2CI-12F) has been developed as a new and efficient fluoromethylidene synthon for the synthesis of both terminal and internal monofluoroalkenes via JuliaKocienski olefination reaction. The base-mediated reaction between TBTSO2CI-12F and carbonyl compounds (aldehydes and ketones) provided terminal monofluoroalkenes in good yields with moderate E!Z selectivity. The dominance of E- or Z-fluoroalkenes could be controlled by selection of proper reaction solvent and temperature. TBTSO 2CI-12F reagent was also found to be readily CL-alkylated, acylated, and phenylsulfonylated to give corresponding CL-functionalized fluorosulfones, which could be used in the synthesis of alkyl-, acyl-, and phenylsulfonyl-substituted internal monofluoroalkenes via JuliaKocienski olefination reactions.