588-72-7

Basic information

• Product Name: [(Z)-2-bromoethenyl]benzene
• Synonyms: Nsc147118
• CAS NO: 588-72-7
• Molecular Formula: C₈H₇Br
• Molecular Weight: 183.05
• Mol File: 588-72-7.mol
• Article Data: 121

Chemical Properties

• Melting Point: 7°C
• Boiling Point: 201.4°C (rough estimate)
• Appearance: /
• Density: 1.4269
• Refractive Index: 1.6093
• CAS DataBase Reference: [(Z)-2-bromoethenyl]benzene(CAS DataBase Reference)
• NIST Chemistry Reference: [(Z)-2-bromoethenyl]benzene(588-72-7)
• EPA Substance Registry System: [(Z)-2-bromoethenyl]benzene(588-72-7)

Safety Data

• Hazardous Substances Data: 588-72-7(Hazardous Substances Data)

Usage

General Description

[(Z)-2-bromoethenyl]benzene, also known as cis-2-bromoethylene, is a chemical compound with the molecular formula C8H7Br. It is a colorless to pale yellow liquid with a sharp odor. The compound is primarily used as an intermediate in the synthesis of pharmaceuticals, agrochemicals, and specialty chemicals. It is also used as a reagent in organic synthesis. [(Z)-2-bromoethenyl]benzene is considered to be a hazardous substance and should be handled with caution. It is important to use appropriate protective equipment and follow safety procedures when working with this chemical.

Upstream product

• 64-17-5 ethanol 
• 6286-30-2 erythro-2,3-dibromo-3-phenylpropanoic acid 
• 127-09-3 sodium acetate 
• 6286-30-2 (+/-)-2r_F.3t_F-dibromo-3cat_F-phenyl-propionic acid 
• 127-08-2 potassium acetate 
• 623-11-0 1-methyl-4-nitrosobenzene 
• 6286-30-2 2,3-dibromo-3-phenylpropanoic acid 
• 67-56-1 methanol 
• 69967-70-0 3-benzyl-3-bromodiazirine 
• 99281-00-2 benzylbromocarbene 
• 513-35-9 2-methyl-but-2-ene 
• 563-79-1 2,3-Dimethyl-2-butene 
• 691-38-3 (Z)-4-methyl-2-pentene 
• 140-10-3 (E)-3-phenylacrylic acid 

Downstream Products

• 886-65-7 trans,trans-1,4-Diphenyl-1,3-butadiene 
• 1522-13-0 1,1,3-triphenylprop-2-yn-1-ol 
• 52728-09-3 (E)-1-phenyl-2-<2-<(dimethylamino)methyl>phenyl>ethylene 
• 6111-82-6 (E)-1-phenyl-1-hexene 
• 2170-06-1 1-Phenyl-2-(trimethylsilyl)acetylene 
• 14374-45-9 1-heptynylbenzene 
• 37828-71-0 1-phenyl-3-isopropoxy-1-propyne 
• 62839-71-8 (E)-1-phenyl-1-decene 
• 42762-56-1 (E)-5-phenylpent-4-en-2-one 
• 39491-69-5 ((1E,3E)-octa-1,3-dien-1-yl)benzene 
• 29266-25-9 5r-bromo-2,6t-diphenyl-5,6-dihydro-4H-[1,3]oxazine 
• 13141-45-2 (Z)-1,4-diphenylbut-1-ene-3-yne 
• 13343-79-8 (E)-1,4-Diphenylbut-1-en-3-yne 
• 33236-96-3 1,1,2-tribromo-2-phenylethane 

Relevant articles and documents

Regio- and stereoselective synthesis of bromoalkenes by homolytic hydrobromination of alkynes with hydrogen bromide

Homolytic hydrobromination of terminal and internal alkynes with a commercially available solution of hydrogen bromide in acetic acid has been investigated for regio- and stereoselective synthesis of bromoalkenes. Under an aerobic atmosphere at room temperature, the reaction of ethynylarenes with a small excess of HBr efficiently gave (2-bromoethenyl)arenes with good to high E-selectivity. (Alk-1-ynyl)arenes, or internal alkynes bearing both phenyl and alkyl groups at the sp-carbons also underwent the air-initiated hydrobromination to exhibit high Z-selectivity under kinetic conditions using a half equivalent of HBr.

Aminium cation-radical catalysed selective hydration of (E)-aryl enynes

The hydration of carbon-carbon triple bonds is an important and atom economic synthetic transformation. Herein, we report a mild and selective method for the catalytic Markovnikov hydration of (E)-aryl enynes to the corresponding enones, mediated through the bench-stable aminium salt, tris(4-bromophenyl)ammoniumyl hexachloroantimonate (TBPA). The chemoselective and diastereoselective method proceeds under neutral metal-free conditions, delivering excellent product yields from terminal and internal alkyne units. The synthesis of biologically important (E)-3-styrylisocoumarins, including a formal synthesis of the natural product achlisocoumarin III, demonstrates the utility of this novel transformation.

Illuminatinganti-hydrozirconation: controlled geometric isomerization of an organometallic species

A general strategy to enable the formalanti-hydrozirconation of arylacetylenes is reported that mergescis-hydrometallation using the Schwartz Reagent (Cp2ZrHCl) with a subsequent light-mediated geometric isomerization atλ= 400 nm. Mechanistic delineation of thecontra-thermodynamic isomerization step indicates that a minor reaction product functions as an efficientin situgenerated photocatalyst. Coupling of theE-vinyl zirconium species with an alkyne unit generates a conjugated diene: this has been leveraged as a selective energy transfer catalyst to enableE→Zisomerization of an organometallic species. Through anUmpolungmetal-halogen exchange process (Cl, Br, I), synthetically useful vinyl halides can be generated (up toZ?:?E= 90?:?10). This enabling platform provides a strategy to access nucleophilic and electrophilic alkene fragments in both geometric forms from simple arylacetylenes.