91047-77-7

Basic information

• Product Name: (E)-Ethyl3-(2-bromophenyl)acrylate
• Synonyms: 2-Bromocinnamic Acid Ethyl Ester
• CAS NO: 91047-77-7
• Molecular Formula: C₁₁H₁₁BrO₂
• Molecular Weight: 255.10784
• Mol File: 91047-77-7.mol
• Article Data: 44

Chemical Properties

• Boiling Point: 110-112 °C(Press: 0.55 Torr)
• Appearance: /
• Density: 1.393±0.06 g/cm3(Predicted)
• CAS DataBase Reference: (E)-Ethyl3-(2-bromophenyl)acrylate(CAS DataBase Reference)
• NIST Chemistry Reference: (E)-Ethyl3-(2-bromophenyl)acrylate(91047-77-7)
• EPA Substance Registry System: (E)-Ethyl3-(2-bromophenyl)acrylate(91047-77-7)

Safety Data

• Hazardous Substances Data: 91047-77-7(Hazardous Substances Data)

Usage

Uses

2-Bromocinnamic Acid Ethyl Ester is a useful reagent in many Witting reactions.

Upstream product

• 867-13-0 diethoxyphosphoryl-acetic acid ethyl ester 
• 6630-33-7 ortho-bromobenzaldehyde 
• 136859-33-1 1-bromo-2-(4-tolylsulfonylmethyl)benzene 
• 105-36-2 ethyl bromoacetate 
• 1099-45-2 ethyl (triphenylphosphoranylidene)acetate 
• 1071-46-1 hydrogen ethyl malonate 
• 3959-05-5 2-bromobenzylamine 
• 6091-64-1 2-bromobenzoic acid ethyl ester 
• 64-17-5 ethanol 
• 7345-79-1 2-bromocinnamic acid 
• 583-55-1 1-Bromo-2-iodobenzene 
• 140-88-5 ethyl acrylate 
• 623-73-4 diazoacetic acid ethyl ester 
• 88-65-3 2-bromobenzoic-acid 

Downstream Products

• 52221-92-8 3-(2-bromo-phenyl)-propan-1-ol 
• 378759-68-3 ethyl (E)-3-[2-(3-oxopropyl)phenyl]prop-2-enoate 
• 1070799-53-9 ethyl 2-(2-cyanoethyl)cinnamate 
• 236737-86-3 ethyl (E)-3-bromo-3-<2-(4-oxophenyl)phenyl>prop-2-enoate 

Relevant articles and documents

A One-Pot Synthesis of α,β-Unsaturated Esters From Esters

A convenient method for reductive Horner–Wadsworth–Emmons (HWE) olefination is described. The E-selective HWE homologation of various esters to α,β-unsaturated esters was readily achieved and gave the desired products in good-to-moderate yields under mild conditions. The one-pot reaction proceeds through an in situ generated aldehyde, formed via the partial reduction of an ester with lithium diisobutyl-t-butoxyaluminum hydride. The formation of cyclized metal acetal and subsequent decompose to the aldehyde for the olefination was found to be a crucial step in this C2-carbon homologation protocol.

Solvent role in the lipase-catalysed esterification of cinnamic acid and derivatives. Optimisation of the biotransformation conditions

The esterification of cinnamic acid has been deeply investigated using ethanol as nucleophile and Candida antarctica lipase type B (CAL-B) as suitable biocatalyst. Special attention has been paid to the role that the solvent plays in the production of ethyl cinnamate. Therefore, volatile organic solvents and deep eutectic mixtures were employed in order to find optimal reaction conditions. Once that hexane was selected as the solvent of choice, other parameters that affect the enzyme activity were investigated in order to produce ethyl cinnamate with excellent yield. The CAL-B loading, nucleophile equivalents, temperature and reaction time have been identified as key parameters in the enzyme efficiency, and the potential of lipase-catalysed esterification has been finally exploited to produce a series of ethyl esters with different pattern substitutions on the aromatic ring.

Enantiodivergent One-Pot Synthesis of Axially Chiral Biaryls Using Organocatalyst-Mediated Enantioselective Domino Reaction and Central-to-Axial Chirality Conversion

Enantiodivergent one-pot synthesis of biaryls was developed using a catalytic amount of a single chiral source. A domino organocatalyst-mediated enantioselective Michael reaction and aldol condensation provided centrally chiral dihydronaphthalenes with excellent enantioselectivity, from which an enantiodivergent chirality conversion from central-to-axial chirality was achieved. Both enantiomers of biaryls were obtained with excellent enantioselectivity. All transformations can be conducted in a single reaction vessel. A plausible reaction mechanism for the enantiodivergence is proposed.