21788-36-3

Basic information

• Product Name: methyl (2Z)-2-bromo-3-phenylprop-2-enoate
• Synonyms: 2-Propenoic acid, 2-bromo-3-phenyl-, methyl ester; 2-propenoic acid, 2-bromo-3-phenyl-, methyl ester, (2Z)-; Cinnamic acid, .alpha.-bromo-, methyl ester; Methyl (2Z)-2-bromo-3-phenylacrylate
• CAS NO: 21788-36-3
• Molecular Formula: C₁₀H₉BrO₂
• Molecular Weight: 241.0813
• Mol File: 21788-36-3.mol
• Article Data: 27

Chemical Properties

• Boiling Point: 295°C at 760 mmHg
• Flash Point: 132.2°C
• Density: 1.475g/cm³
• Vapor Pressure: 0.00157mmHg at 25°C
• Refractive Index: 1.603
• CAS DataBase Reference: methyl (2Z)-2-bromo-3-phenylprop-2-enoate(CAS DataBase Reference)
• NIST Chemistry Reference: methyl (2Z)-2-bromo-3-phenylprop-2-enoate(21788-36-3)
• EPA Substance Registry System: methyl (2Z)-2-bromo-3-phenylprop-2-enoate(21788-36-3)

Safety Data

• Hazardous Substances Data: 21788-36-3(Hazardous Substances Data)

Upstream product

• 67-56-1 methanol 
• 15813-24-8 (Z)-2-bromo-3-phenylacrylic acid 
• 21770-48-9 rac-(R,S)-methyl 2,3-dibromo-3-phenylpropanoate 
• 141-52-6 sodium ethanolate 
• 186581-53-3 diazomethane 
• 21770-48-9 methyl 2,3-dibromo-3-phenylpropanoate 
• 93682-01-0 methyl erythro-2-bromo-3-chloro-3-phenylpropanoate 
• 52777-73-8 Methyl erythro-2,3-dibromo-3-phenylpropanoate 
• 52742-03-7 Methyl threo-2,3-dibromo-3-phenylpropanoate 
• 114642-85-2 methyl erythro-2-bromo-3-fluoro-3-phenylpropanoate 
• 93682-01-0 methyl 2-bromo-3-chloro-3-phenylpropanoate 
• 52742-04-8 methyl erythro-3-acetoxy-2-bromo-3-phenylpropanoate 
• 52742-04-8 methyl threo-3-acetoxy-2-bromo-3-phenylpropanoate 
• 120235-81-6 methyl erythro-2-bromo-3-chloroacetoxy-3-phenylpropanoate 

Downstream Products

• 7029-82-5 3-phenyl-2,3-dipiperidino-propionic acid methyl ester 
• 15813-24-8 (Z)-2-bromo-3-phenylacrylic acid 
• 76311-71-2 5-Oxo-3-phenyl-tetrahydro-furan-2,4-dicarboxylic acid dimethyl ester 
• 76311-73-4 1-Dimethylcarbamoyl-3-phenyl-cyclopropane-1,2-dicarboxylic acid dimethyl ester 
• 101235-88-5 (2R,3S,4R,5R)-2-Methyl-3,5-diphenyl-1-aza-bicyclo[2.1.0]pentane-2,4-dicarboxylic acid dimethyl ester 
• 136132-17-7 (Z)-methyl α-bromo-β-nitrocinnamate 
• 136132-16-6 (E)-methyl α-bromo-β-nitrocinnamate 
• 75698-15-6 1-(2-methoxycarbonyl)ethyl-2-methoxycarbonyl-3-phenylaziridine 
• 75698-15-6 1-(2-methoxycarbonyl)ethyl-2-methoxycarbonyl-3-phenylaziridine 
• 103-26-4 methyl cinnamate 
• 58808-66-5 methyl (Z)-3-phenyl-2-(phenylsulfanyl)prop-2-enoate 
• 58808-71-2 methyl (E)-3-phenyl-2-phenylthiopropenoate 
• 882-33-7 diphenyldisulfane 
• 34863-30-4 trans-1-isopropyl-2-methoxycarbonyl-3-phenylaziridine 

Relevant articles and documents

Visible light-mediated metal-free double bond deuteration of substituted phenylalkenes

Various bromophenylalkenes were reductively photodebrominated by using 1,3-dimethyl-2-phenyl-1H-benzo-[d]imidazoline (DMBI) and 9,10-dicyanoanthracene. With deuterated DMBI analogs (the most effective was DMBI-d11), satisfactory to excellent isotopic yields were obtained. DMBI-d11 could also be regenerated from the reaction mixtures with a recovery rate of up to 50%. The combination of the photodebromination reaction with conventional methods for bromoalkene synthesis enables sequential monodeuteration of a double bond without the necessity of a metal catalyst. This journal is

A new convenient synthetic route towards 2-(hetero)aryl-substituted thieno[3,2-b]indoles using Fischer indolization

A number of 2-(hetero)aryl-substituted thieno[3,2-b]indoles have been successfully prepared using an efficient transition-metal-free strategy, involving the Fiesselmann synthesis of methyl 5-(hetero)aryl-3-hydroxythiophene-2-carboxylates from 2-bromo-3-(hetero)arylacrylates and methyl thioglycolate, and the transformation of the synthesized 3-hydroxyesters into the corresponding thiophen-3(2H)-ones, followed by their treatment with arylhydrazines to directly form the targeted structures via Fischer indolization. At the same time, structural variety of the obtained thieno[3,2-b]indoles has been achieved due to a wide range of available starting materials, including both 2-bromo-3-(hetero)arylacrylates and arylhydrazines. In addition, two π-extended molecules, namely 1,4-bis(4H-thieno[3,2-b]indol-2-yl)benzene and 2,5-bis(4H-thieno[3,2-b]indol-2-yl)thiophene, have been synthesized in line with the current approach towards 2-(hetero)arylated thieno[3,2-b]indoles.

Ru-catalyzed highly chemo- and enantioselective hydrogenation of γ-halo-γ,δ-unsaturated-β-keto esters under neutral conditions

Finely-tuned ruthenium-catalyzed highly chemoselective and enantioselective hydrogenation of γ-halo-γ,δ-unsaturated-β-keto esters at the carbonyl group was achieved under neutral reaction conditions (ee up to 97%). Both olefin and alkenyl halogen moieties, which are labile under hydrogenation conditions, remained untouched during the reaction.