115665-72-0

Basic information

• Product Name: Benzene, 1-bromo-3-(2-bromoethenyl)
• Synonyms: Benzene, 1-bromo-3-(2-bromoethenyl);Benzene, 1-broMo-3-[(1E)-2-broMoethenyl]-
• CAS NO: 115665-72-0
• Molecular Formula: C₈H₆Br₂
• Molecular Weight: 262
• Mol File: 115665-72-0.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: Benzene, 1-bromo-3-(2-bromoethenyl)(CAS DataBase Reference)
• NIST Chemistry Reference: Benzene, 1-bromo-3-(2-bromoethenyl)(115665-72-0)
• EPA Substance Registry System: Benzene, 1-bromo-3-(2-bromoethenyl)(115665-72-0)

Safety Data

• Hazardous Substances Data: 115665-72-0(Hazardous Substances Data)

Upstream product

• 14473-91-7 3-Bromocinnamic acid 
• 766-81-4 3-bromophenylacetylene 
• 1253943-66-6 (E)-4,4,5,5-tetramethyl-2-(3-bromophenyl)ethen-1-yl-1,3,2-dioxaborolane 
• 2039-86-3 3-bromostyrene 

Downstream Products

• 1206904-61-1 (E)-1-(2-bromovinyl)-3-iodobenzene 
• 174967-37-4 (E)-1-bromo-3-(2-iodovinyl)benzene 
• 1344717-56-1 (E)-9-benzyl-6-(benzylthio)-8-(3-bromostyryl)-9H-purine 
• 1059544-40-9 2-[2-(3-bromophenyl)vinyl]-5-phenyl-oxazole 

Relevant articles and documents

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.

TsNBr2 promoted decarboxylative bromination of α,β-unsaturated carboxylic acids

A rapid process for decarboxylative bromination of α,β-unsaturated carboxylic acids have been developed using N,N-dibromo-p-toluenesulfonamide (TsNBr2). Treatment of cinnamic acids with TsNBr2 in presence of potassium carbonate in acetonitrile produces corresponding β-bromostyrenes at room temperature. Exclusive formation of (E)-β-bromostyrenes was observed in a stereoselective manner within a very short period of time (5–15 min). This method was further extended for obtaining 1-bromoalkynes from corresponding propiolic acids. Instantaneous formation of bromoalkynes was observed when the reaction was carried out in presence of DBU as a base in acetonitrile at room temperature. A wide variety of cinnamic acids and propiolic acids could be converted to corresponding β-bromostyrenes and 1-bromoalkynes respectively under mild reaction condition with high to excellent yield.

A stereoselective synthesis of (E)- or (Z)-β-arylvinyl halides via a borylative coupling/halodeborylation protocol

A new stereoselective method for the synthesis of (E)-β-arylvinyl iodides and (E)- or (Z)-β-arylvinyl bromides from styrenes and vinyl boronates on the basis of a one-pot procedure via borylative coupling/halodeborylation is reported. Depending on the halogenating agent as well as the mode of the halodeborylation reaction, (E) or (Z) isomers are selectively formed.

Ohmic Heating and Ionic Liquids in Combination for the Indium-Promoted Synthesis of 1-Halo Alkenyl Compounds: Applications to Pd-Catalysed Cross-Coupling Reactions

We have explored the combination of ohmic heating (ΩH) with ionic liquids for indium-promoted reactions and report herein the indium-promoted dehalogenation of gem-dibromo alkenes and the indium-mediated reductive elimination of chlorohydrins for the synthesis of 1-halo alkenyl derivatives. Heck, Stille, Suzuki, Kumada and Sonogashira couplings of the resulting 1-halo-1-alkenes with appropriate reagents were carried out to give alkenes, dienes and enynes. We report herein the combination of ohmic heating (ΩH) with ionic liquids for the indium-promoted dehalogenation of gem-dibromo alkenes and the indium-mediated reductive elimination of chlorohydrins. The 1-halo alkenyl derivatives synthesized were then submitted to a series of cross-coupling reactions to give conjugated alkenes, dienes and enynes.

H-β-zeolite catalyzed synthesis of β-bromostyrenes from styrene bromohydrins

Synthesis of β-bromostyrenes from styrene bromohydrins using H-β-zeolite as catalyst under moderate conditions is reported. The catalyst could be regenerated and reused up to three consecutive cycles.

Microwave-assisted Pd/Cu-catalyzed C-8 direct alkenylation of purines and related azoles: An alternative access to 6,8,9-trisubstituted purines

An efficient microwave-assisted palladium/copper comediated C-8 direct alkenylation of purines with styryl bromides has been developed. The method is regioselective, functional group tolerant, rapid, and compatible with other related azoles. Combined with

Stereoselective direct copper-catalyzed alkenylation of oxazoles with bromoalkenes

(Chemical Equation Presented) A copper-catalyzed direct alkenylation of oxazoles with bromoalkenes has been developed. The method is both regio- and stereoselective and tolerates a variety of functional groups. A wide range of 2-E-vinyl-substituted oxazoles were obtained in high yields including the highly fluorescent alkaloid annuloline.