671224-97-8

Basic information

• Product Name: Pyridine, 3-[(1E)-2-bromoethenyl]- (9CI)
• Synonyms: Pyridine, 3-[(1E)-2-bromoethenyl]- (9CI)
• CAS NO: 671224-97-8
• Molecular Formula: C7H6BrN
• Molecular Weight: 184.03324
• Product Categories: PYRIDINE
• Mol File: 671224-97-8.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: Pyridine, 3-[(1E)-2-bromoethenyl]- (9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: Pyridine, 3-[(1E)-2-bromoethenyl]- (9CI)(671224-97-8)
• EPA Substance Registry System: Pyridine, 3-[(1E)-2-bromoethenyl]- (9CI)(671224-97-8)

Safety Data

• Hazardous Substances Data: 671224-97-8(Hazardous Substances Data)

Upstream product

• 63671-82-9 3-(2,2-dibromovinyl)pyridine 
• 19337-97-4 trans-3-(3-pyridyl)acrylic acid 
• 500-22-1 3-pyridinecarboxaldehyde 
• 628703-07-1 3-(β-bromovinyl)pyridine 
• 1034-49-7 (bromomethyl)triphenyl phosphonium bromide 
• 767252-41-5 C₈H₇Br₂NO₂ 
• 1126-74-5 3-(pyridin-3-yl)acrylic acid 

Downstream Products

• 1607020-80-3 N-(4-methylphenyl)-3-exo-(3-pyridylidene)tricyclo[3.2.1.02,4]octane-6,7-endo-dicarboximide 
• 628703-07-1 (E)-3-(2-bromovinyl)pyridine 

Relevant articles and documents

Dual nickel- and photoredox-catalyzed reductive cross-coupling of aryl vinyl halides and unactivated tertiary alkyl bromides

A novel reductive cross-coupling of aryl vinyl halides and unactivated tertiary alkyl bromides has been realized via photoredox/nickel dual catalysis to produce vinyl arene derivatives bearing all-carbon quaternary centers with excellent E-selectivity. A stoichiometric metal reductant could be avoided by employing commercially available N,N,N′,N′-tetramethylethylenediamine (TMEDA) as the terminal reductant.

Palladium-Catalyzed Two-Component Domino Coupling Reaction of (Z)-β-Bromostyrenes with Norbornenes: Synthesis of 1,5-Enynes

Polyfunctional molecules, 1,5-enynes, have been achieved via a palladium(0)-catalyzed domino coupling reaction of (Z)-β-bromostyrenes with norbornenes in the presence of cesium carbonate and N,N-dimethylformamide. The process involves a double Heck-type procedure, two-fold C(sp2) H activation and formation of two carbon-carbon bonds. There are possibilities of diversified transformation for the domino coupling of (Z)-β-bromostyrenes with norbornenes, the procedure is successfully driven to 1,5-enynes via accurate adjustment of the reaction conditions. (Figure presented.) .

Nucleophile-selective cross-coupling reactions with vinyl and alkynyl bromides on a dinucleophilic aromatic substrate

A nucleophile-selective cross-coupling reaction on an aromatic compound bearing two metal groups, Bpin and SnMe3, has been developed. Previously, only aryl bromides and iodides could be used as electrophilic components, but in this work, the scope could be extended to vinyl and alkynyl bromides as electrophiles. This means that the roles typical in Sonogashira couplings or Heck reactions of the aromatic ring as the dielectrophile coupling to vinyl and alkynyl metal species are reversed, which presents a new tool for organic synthesis. The first nucleophilic site to react is the stannyl group, and subsequently, a Suzuki-Miyaura cross-coupling reaction can take place on the same molecule.

Palladium(0)-catalyzed methylenecyclopropanation of norbornenes with vinyl bromides

Highly strained methylenecyclopropane derivatives have been achieved via a novel and efficient Pd(0)-catalyzed domino reaction. The formal [2 + 1] cycloaddition reaction of vinyl bromides to norbornenes involves a Heck-type coupling and a C(sp2)-H bond activation.

Synthesis of (Z)-1-bromo-1-alkenes and terminal alkynes from anti-2,3-dibromoalkanoic acids by microwave-induced reaction

(Z)-1-Bromo-1-alkenes were stereoselectively prepared in high yields in a short reaction time by microwave irradiation of the corresponding anti-2,3-dibromoalkanoic acids in a Et3N/DMF system. A one-pot synthesis of terminal alkynes and enynes from 2,3-dibromoalkanoic acids were also developed by microwave-induced reaction.

Practical synthesis of (Z)-polyaromatic and heteroaromatic vinylacetylenes

(Chemical Equation Presented) Two synthetic routes to several (Z)-polyaromatic and heteroaromatic substituted vinylacetylenes are described. The nature of aryl- or heteroaryl-substituted carboxaldehyde used as starting material dictated the choice of Wittig salt employed. A very attractive way to construct polyaromatic and pyridine-containing enynes is the reaction of polyaromatic and pyridine-containing aldehydes with bromomethyltriphenylphosphonium bromide in the presence of potassium tert-butoxide followed by a Sonogashira desilylation procedure (method B).

Diastereoselective synthesis of 2-amino-4-phosphonobutanoic acids by conjugate addition of lithiated schoellkopf's bislactim ethers to vinylphosphonates

Conjugate additions of lithiated bislactim ethers derived from cyclo-[Gly-Val] and cyclo-[Ala-Val] to α, β, or α,β -substituted vinylphosphonates allow direct and stereoselective access to a variety of 3- or 4-monosubstituted and 2,3-, 2,4-, or 3,4-disubstituted 2-amino-4-phosphonobutanoic acids (AP4 derivatives) in enantiomerically pure form. The relative stereochemistry was assigned by X-ray diffraction analysis or NMR study of 1,2-oxaphosphorinane derivatives. Competitive eight-membered "compact" and "relaxed" transition-state structures are invoked to rationalize the stereochemical outcome of the conjugate additions.

Convenient and stereoselective synthesis of (Z)-1-bromo-1-alkenes by microwave-induced reaction

(Z)-1-Bromo-1-alkenes were stereoselectively prepared in high yields in a short reaction time (0.2-1.0 min) by microwave irradiation of the corresponding 2,3-dibromoalkanoic acids in DMF in the presence of triethylamine.

A mild procedure for the stereospecific transformation of trans cinnamic acid derivatives to cis β-bromostyrenes

A new mild procedure has been developed for the synthesis of cis β- bromostyrene analogs with complete Z/E selectivity and good to excellent yields (58.4 - 90.9 %). The process involves carboxyl-halo-elimination of cinnamic acid dibromides by using triethylamine in N,N-dimethylformamide at room temperature. A one-pot procedure has also been described for the direct transformation of cinnamic acids to β-bromostyrenes.

Stereoselective hydrogenolysis of 1,1-dibromo-1-alkenes and stereospecific synthesis of conjugated (Z)-alkenyl compounds

The Pd-catalyzed hydrogenolysis of 1,1-dibromoalkenes with Bu3SnH occurs at room temperature stereoselectively to give (Z)-1-bromo-1-alkenes. We sought to determine the optimal reaction conditions and illustrate the scope of this method with 32 dibromoalkenes including alkenyl- and alkynyl- conjugated 1,1-dibromo-1-alkenes 7a-h and 2,2-disubstituted 1,1-dibromo-1- alkenes 9af. Triphenylphosphine was the best ligand for the Pd-catalyzed hydrogenolysis. A wide range of solvents can be used for this reaction excluding EtOH, AcOH, and CHCl3. However, the reaction proceeds even in these solvents with the addition of a cosolvent or radical scavenger. The reaction of 1,1-diiodo-1-alkene (3) gave a mixture of (Z)-1-iodo-1-alkene (4), (Z)-1-tributylstannyl-1-alkene (5), and a terminal alkene 6, while that of 1,1-dichloroalkene did not occur. This selectivity can be explained by the stereoselective insertion of Pd(0) to a trans bromine-alkenyl carbon bond, successive transmetalation with Bu3SnH, and reductive elimination. The Suzuki and Sonogashira couplings of the resulting (Z)-1-bromo-1-alkenes with alkenyl(dialkoxy)borane and terminal alkyne occurred to give conjugated polyenes and enynes stereospecifically. The Pd-catalyzed hydrogenolysis of 1,1-dibromo-1-alkene and successive cross-coupling can be carried out either in a stepwise manner or in one-pot under the same Pd catalysis. These two processes should be useful for the synthesis of geometrically pure polyene and enyne with a Z-alkenyl unit.