356759-39-2

Basic information

• Product Name: (Z)-4-(β-bromovinyl)benzoic acid methyl ester
• Synonyms: (Z)-4-(β-bromovinyl)benzoic acid methyl ester
• CAS NO: 356759-39-2
• Molecular Weight: 241.084
• Mol File: 356759-39-2.mol
• Article Data: 9

Chemical Properties

• CAS DataBase Reference: (Z)-4-(β-bromovinyl)benzoic acid methyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: (Z)-4-(β-bromovinyl)benzoic acid methyl ester(356759-39-2)
• EPA Substance Registry System: (Z)-4-(β-bromovinyl)benzoic acid methyl ester(356759-39-2)

Safety Data

• Hazardous Substances Data: 356759-39-2(Hazardous Substances Data)

Upstream product

• 253684-21-8 1,1-dibromo-2-(4-methoxycarbonylphenyl)ethene 
• 1571-08-0 methyl 4-formylbenzoate 
• 3034-86-4 4-ethynylbenzoic acid methyl ester 
• 117390-07-5 (E)-4-(methoxycarbonyl)cinnamic acid 

Downstream Products

• 3034-86-4 4-ethynylbenzoic acid methyl ester 
• 1616973-22-8 methyl 4-{1-[(4-methylphenyl)sulfonyl]-1H-1,2,3-triazol-4-yl}benzoate 

Relevant articles and documents

Regio- and stereoselective synthesis of bromoalkenes by homolytic hydrobromination of alkynes with hydrogen bromide

Homolytic hydrobromination of terminal and internal alkynes with a commercially available solution of hydrogen bromide in acetic acid has been investigated for regio- and stereoselective synthesis of bromoalkenes. Under an aerobic atmosphere at room temperature, the reaction of ethynylarenes with a small excess of HBr efficiently gave (2-bromoethenyl)arenes with good to high E-selectivity. (Alk-1-ynyl)arenes, or internal alkynes bearing both phenyl and alkyl groups at the sp-carbons also underwent the air-initiated hydrobromination to exhibit high Z-selectivity under kinetic conditions using a half equivalent of HBr.

Ohmic Heating and Ionic Liquids in Combination for the Indium-Promoted Synthesis of 1-Halo Alkenyl Compounds: Applications to Pd-Catalysed Cross-Coupling Reactions

We have explored the combination of ohmic heating (ΩH) with ionic liquids for indium-promoted reactions and report herein the indium-promoted dehalogenation of gem-dibromo alkenes and the indium-mediated reductive elimination of chlorohydrins for the synthesis of 1-halo alkenyl derivatives. Heck, Stille, Suzuki, Kumada and Sonogashira couplings of the resulting 1-halo-1-alkenes with appropriate reagents were carried out to give alkenes, dienes and enynes. We report herein the combination of ohmic heating (ΩH) with ionic liquids for the indium-promoted dehalogenation of gem-dibromo alkenes and the indium-mediated reductive elimination of chlorohydrins. The 1-halo alkenyl derivatives synthesized were then submitted to a series of cross-coupling reactions to give conjugated alkenes, dienes and enynes.

Nickel(II)-magnesium-catalyzed cross-coupling of 1,1-dibromo-1-alkenes with diphenylphosphine oxide: One-pot synthesis of (E)-1-alkenylphosphine oxides or bisphosphine oxides

A novel nickel(II)-magnesium-mediated cross-coupling of diphenylphosphine oxide with a variety of 1,1-dibromo-1-alkenes has been developed, which provides a powerful and general methodology for the stereoselective synthesis of various (E)-1-alkenylphosphine oxides or bisphosphine oxides, with operational simplicity of the procedure, good to high yields and broad substrate applicability. Mechanistic studies reveal that the reaction might involve a Hirao reduction, cross-coupling and Michael addition. Copyright