174967-37-4

Basic information

• Product Name: (E)-1-bromo-3-(2-iodovinyl)benzene
• Synonyms: (E)-1-bromo-3-(2-iodovinyl)benzene
• CAS NO: 174967-37-4
• Molecular Weight: 308.944
• Mol File: 174967-37-4.mol

Chemical Properties

• CAS DataBase Reference: (E)-1-bromo-3-(2-iodovinyl)benzene(CAS DataBase Reference)
• NIST Chemistry Reference: (E)-1-bromo-3-(2-iodovinyl)benzene(174967-37-4)
• EPA Substance Registry System: (E)-1-bromo-3-(2-iodovinyl)benzene(174967-37-4)

Safety Data

• Hazardous Substances Data: 174967-37-4(Hazardous Substances Data)

Upstream product

• 2039-86-3 3-bromostyrene 
• 1253943-66-6 (E)-4,4,5,5-tetramethyl-2-(3-bromophenyl)ethen-1-yl-1,3,2-dioxaborolane 
• 115665-72-0 trans-1-(2-bromovinyl)-3-bromobenzene 
• 75-11-6 diiodomethane 
• 823-78-9 meta-bromobenzyl bromide 

Downstream Products

• 36751-46-9 2-(3-bromophenyl)pyrazolo[1,5-a]pyridine 
• 174967-28-3 1-Bromo-3-((1E,3E)-4-phenyl-buta-1,3-dienyl)-benzene 

Relevant articles and documents

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.

Stereoselective Synthesis of Vinyl Iodides through Copper(I)-Catalyzed Finkelstein-Type Halide-Exchange Reaction

An efficient method for the stereoselective synthesis of vinyl iodides is described. The reactions of vinyl bromides with potassium iodide proceed smoothly in the presence of a copper catalyst under mild reaction conditions to produce the corresponding vinyl iodides stereospecifically and in satisfactory to excellent yields.

Synthesis of 2- and 2,3-substituted Pyrazolo[1,5- a ]pyridines: Scope and mechanistic considerations of a domino direct alkynylation and cyclization of n -iminopyridinium ylides using alkenyl bromides, alkenyl iodides, and alkynes

Direct functionalization and tandem processes have both received considerable recent interest due to their cost and time efficiency. Herein we report the synthesis of difficult to obtain 2-substituted pyrazolo[1,5-a] pyridines through a tandem palladium-catalyzed/silver-mediated elimination/direct functionalization/cyclization reaction involving N-benzoyliminopyridinium ylides. As such, these biologically important molecules are prepared in an efficient, high-yielding manner, only requiring a two-step sequence from pyridine. Aryl-substituted alkenyl bromides and iodides are effective ylide coupling partners. Mechanistic studies led to the use of terminal alkynes, which extended the scope of the reaction to include alkyl substitution on the unsaturated reactive site. The optimization, scope, and mechanistic considerations of the process are discussed.

Convenient one-pot synthesis of (E)-β-aryl vinyl halides from benzyl bromides and dihalomethanes

(Chemical Equation Presented) (E)-β-Aryl vinyl iodides are synthesized in high yield with excellent stereoselectivity from benzyl bromides by a one-pot homologation/ stereoselective elimination procedure. Convenient conditions involving the anion of diiodomethane and an excess of base provide complete consumption of the benzyl bromide and elimination from a diiodoalkane intermediate. Similar conditions provide (E)-β-aryl vinyl chlorides and bromides by employing the anions of ICH2CI or CH2Br 2. The functional group tolerance and facile purification allows rapid access to a wide range of functionalized vinyl halides.