19078-73-0

Basic information

• Product Name: (2E)-3-bromo-3-phenylprop-2-enoic acid
• CAS NO: 19078-73-0
• Molecular Formula: C₉H₇BrO₂
• Molecular Weight: 227.0547
• Mol File: 19078-73-0.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 316.7°C at 760 mmHg
• Flash Point: 145.3°C
• Density: 1.603g/cm³
• Vapor Pressure: 0.000169mmHg at 25°C
• Refractive Index: 1.625
• CAS DataBase Reference: (2E)-3-bromo-3-phenylprop-2-enoic acid(CAS DataBase Reference)
• NIST Chemistry Reference: (2E)-3-bromo-3-phenylprop-2-enoic acid(19078-73-0)
• EPA Substance Registry System: (2E)-3-bromo-3-phenylprop-2-enoic acid(19078-73-0)

Safety Data

• Hazardous Substances Data: 19078-73-0(Hazardous Substances Data)

Usage

Description

(2E)-3-bromo-3-phenylprop-2-enoic acid is a chemical compound belonging to the phenylpropanoid class, characterized by its molecular formula C9H7BrO2. It features a phenyl group and a bromine atom attached to a propenoic acid group, forming an unsaturated carboxylic acid with a trans configuration, as indicated by the (2E) in its name.

Uses

Used in Organic Synthesis:
(2E)-3-bromo-3-phenylprop-2-enoic acid is used as a building block in organic synthesis for the creation of various complex organic molecules. Its unique structure and potential reactivity make it a valuable component in the synthesis of pharmaceuticals, agrochemicals, and other specialty chemicals.
Used in Pharmaceutical Research:
In pharmaceutical research, (2E)-3-bromo-3-phenylprop-2-enoic acid is utilized as a starting material or intermediate in the development of new drugs. Its distinct chemical properties allow for the exploration of its potential therapeutic effects and mechanisms of action, contributing to the advancement of medicinal chemistry.
Further studies are required to fully understand the properties and potential uses of (2E)-3-bromo-3-phenylprop-2-enoic acid, expanding its applications across different industries.

Upstream product

• 501-52-0 3-Phenylpropionic acid 
• 993-51-1 trichloro-methanesulfonyl bromide 
• 536-74-3 phenylacetylene 
• 140-10-3 (E)-3-phenylacrylic acid 
• 14804-59-2 3-bromo-3-phenylacrylaldehyde 
• 98-86-2 acetophenone 

Downstream Products

• 886-66-8 1,4-diphenyl-1,3-butadiyne 

Relevant articles and documents

Conceptual approach to the synthesis of symmetrical 1,3-diynes from β-bromo vinyl carboxylic acids

Abstract: A conceptual route has been developed for the synthesis of 1,3-diyne from β-bromo vinyl carboxylic acids. The reaction of the β-bromo vinyl carboxylic acid with palladium catalyst is conceptually similar to the decomposition of 2-diazoniumbenzoic acid to benzyne. In the presence of palladium catalyst, the β-bromo vinyl carboxylic acid undergoes a fragmentation to generate terminal alkyne. The terminal alkyne undergoes dimerisation in the presence of palladium catalysts to produce the product 1,3-diyne. Graphic abstract: A conceptual route has been developed for the synthesis of 1,3-diyne from β-bromo vinyl carboxylic acids. To the best of our knowledge, we are the first ones reporting the synthesis of 1,3-diyne in a catalytic way without the requirement of any prefunctionalized alkyne unit(s).[Figure not available: see fulltext.]

Controlling 6-endo-selectivity in oxidation/bromocyclization cascades for synthesis of aplysiapyranoids and other 2,2,6,6-substituted tetrahydropyrans

A cascade, composed of (i) oxovanadium(V)-catalyzed oxidation of bromide by tert-butyl hydroperoxide and (ii) stereoselective 6-endo-bromocyclization, affords 3-bromo-2-aryl-2,6,6-trimethyltetrahydropyrans from styrene-type tertiary alkenols in synthetically useful yields. (E)-Alkenols add the bromo- and the alkoxy substituent anti-selectively across the double bond, indicating a bromonium ion-mechanism for the ring closure. 6-endo-control of the alkenol cyclization thereby arises from the polar effect of the aryl substituent. Two methyl substituents bound to the alkene terminus are not similarly able to favor 6-endo-cyclization, because strain arising from methyl group repulsion, as the bromonium-activated π-bond and the hydroxyl oxygen approach, directs bromocyclization of tertiary prenyl-type substrates toward tetrahydrofuran formation. A hexasubstituted bromotetrahydropyran prepared from the oxidation/bromocyclization cascade served as starting material for synthesis of racemic aplysiapyranoid A, in a sequence of free radical and polar functional group interconversion.

A CONTRIBUTION TO MECHANISM OF ADDITION OF HYDROGEN BROMIDE TO THE α,β-UNSATURATEDSYSTEM OF 3-PHENYL-2-PROPENOIC ACID

Rate of addition of hydrogen bromide to meta- and para-substituted 3-phenyl-2-propenoic acids I was followed by polarography and UV spectroscopy.Rate of protonation either is the overall rate determining step or is at least comparable with the rate of the subsequent nucleophile attack.