139616-16-3

Basic information

• Product Name: Benzeneacetic acid, a-[(4-bromophenyl)methylene]-, methyl ester, (E)-
• CAS NO: 139616-16-3
• Molecular Formula: C16H13BrO2
• Molecular Weight: 317.182
• Mol File: 139616-16-3.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: Benzeneacetic acid, a-[(4-bromophenyl)methylene]-, methyl ester, (E)-(CAS DataBase Reference)
• NIST Chemistry Reference: Benzeneacetic acid, a-[(4-bromophenyl)methylene]-, methyl ester, (E)-(139616-16-3)
• EPA Substance Registry System: Benzeneacetic acid, a-[(4-bromophenyl)methylene]-, methyl ester, (E)-(139616-16-3)

Safety Data

• Hazardous Substances Data: 139616-16-3(Hazardous Substances Data)

Upstream product

• 22979-35-7 Methyl phenyldiazoacetate 
• 589-15-1 1-bromomethyl-4-bromobenzene 
• 1122-91-4 4-bromo-benzaldehyde 
• 139616-15-2 C₁₂H₁₇O₅P 
• 4358-87-6 (RS)-methyl mandelate 
• 100-52-7 benzaldehyde 
• 532-28-5 (RS)-mandelonitrile 
• 873-75-6 4-bromobenzenemethanol 
• 15206-55-0 methyl 2-oxo-2-phenylacetate 
• 1251532-38-3 methyl α-(4-bromobenzyl)diazoacetate 
• 98-80-6 phenylboronic acid 

Relevant articles and documents

P(NMe2)3-Mediated Umpolung Alkylation and Nonylidic Olefination of α-Keto Esters

A commercial phosphorus-based reagent (P(NMe2)3) mediates umpolung alkylation of methyl aroylformates with benzylic and allylic bromides, leading to either Barbier-type addition or ylide-free olefination products upon workup. The reaction sequence is initiated by a two-electron redox addition of the tricoordinate phosphorus reagent with an α-keto ester compound (Kukhtin-Ramirez addition). A mechanistic rationale is offered for the chemoselectivity upon which the success of this nonmetal mediated C-C bond forming strategy is based.

Palladium-catalyzed cross coupling reaction of benzyl bromides with diazoesters for stereoselective synthesis of (E)-α,β-diarylacrylates

(Chemical Equation Presented) A Pd-catalyzed cross-coupling reaction of benzyl bromides with α-aryldiazoesters is described, and E-α,β-diarylacrylates were obtained in good yields and excellent E-to-Z selectivity (>20:1).