253684-52-5

Basic information

• Product Name: methyl (Z)-4-(2-bromo-2-phenylvinyl)benzoate
• Synonyms: methyl (Z)-4-(2-bromo-2-phenylvinyl)benzoate
• CAS NO: 253684-52-5
• Molecular Weight: 317.182
• Mol File: 253684-52-5.mol

Chemical Properties

• CAS DataBase Reference: methyl (Z)-4-(2-bromo-2-phenylvinyl)benzoate(CAS DataBase Reference)
• NIST Chemistry Reference: methyl (Z)-4-(2-bromo-2-phenylvinyl)benzoate(253684-52-5)
• EPA Substance Registry System: methyl (Z)-4-(2-bromo-2-phenylvinyl)benzoate(253684-52-5)

Safety Data

• Hazardous Substances Data: 253684-52-5(Hazardous Substances Data)

Upstream product

• 934-56-5 trimethyl(phenyl)stannane 
• 253684-21-8 1,1-dibromo-2-(4-methoxycarbonylphenyl)ethene 
• 98-80-6 phenylboronic acid 

Downstream Products

• 1149-18-4 (E)-methyl 4-styrylbenzoate 

Relevant articles and documents

Stereospecific hydrodehalogenation of alkenyl bromides: A new approach to the synthesis of (E)-alkenes

The pair NaBH4-TMEDA and catalytic PdCl2(PPh 3)2 in THF at room temperature is a mild and efficient system for the hydrodebromination of alkenyl bromides, providing a facile reduction procedure that allows completing the process advantageously, leading from aldehydes to (E)-alkenes. This journal is the Partner Organisations 2014.

A modified Suzuki reaction of 1,1-dibromo-1-alkenes

The (E)-bromides in 1,1-dibromo-1-alkenes were stereoselectively coupled with aryl- or alkenylboronic acids to give the corresponding (Z)-1- Aryl(alkenyl)-1-bromo-1-alkenes. Tris(2-furyl)phosphine (TFP) was used as the ligand to palladium, and the combination of 1,4-dioxane and aqueous sodium carbonate produced the best results.

The Stille Reaction of 1,1-Dibromo-1-alkenes: Preparation of Trisubstituted Alkenes and Internal Alkynes

The Stille reaction of 1,1-dibromo-1-alkenes 1 with aryl- and vinylstannanes produces different products depending on the reaction conditions. When the reaction is run in toluene or 1,4-dioxane with tris(2-furyl)phosphine (TFP) as the ligand, (Z)-bromoalkenes 2 are obtained stereospecifically in good to excellent yields with most substrates. However, 2-aryl-1,1-dibromo-1-alkenes (1e,1g) having an electron-donating methoxy group in the para- or ortho- position give poor yields. This method has been applied to the one-pot syntheses of stereospecifically trisubstituted alkenes 5. When the Stille reaction is conducted in a highly dipolar solvent (DMF), monobromides 2 and/or internal alkynes 4 are the products. The less reactive phenylstannane favors the formation of alkynes 4, regardless of which ligand is used. More reactive organostannanes (vinyl, furyl) require a very electron rich ligand, tris(4-methoxyphenyl)phosphine, for the formation of alkynes 4. This new method for internal alkyne preparation is general, requires very mild reaction conditions, and gives high yields.