Phenylbromoethyne

Base Information

• Chemical Name: Phenylbromoethyne
• CAS No.: 932-87-6
• Molecular Formula: C8H5Br
• Molecular Weight: 181.032
• Hs Code.: 2903999090
• Mol file: 932-87-6.mol

Synonyms:Benzene,(bromoethynyl)- (6CI,7CI,8CI,9CI);(Bromoethynyl)benzene;1-Bromo-2-phenylacetylene;1-Bromo-2-phenylethyne;1-Phenyl-2-bromoacetylene;2-Bromo-1-phenylacetylene;2-Bromo-1-phenylethyne;2-Bromoethynylbenzene;2-Phenylethynyl bromide;Bromo(phenyl)acetylene;Bromophenylethyne;Phenylacetylene bromide;Phenylbromoacetylene;Phenylethynyl bromide;b-Bromo-a-phenylacetylene;

Chemical Property of Phenylbromoethyne

Chemical Property:

• Vapor Pressure: 0.196mmHg at 25°C
• Refractive Index: 1.615
• Boiling Point: 217.4 °C at 760 mmHg
• Flash Point: 86 °C
• PSA: 0.00000
• Density: 1.51 g/cm³
• LogP: 2.39050
• Storage Temp.: ?20°C

Purity/Quality:

97% ^*data from raw suppliers

(Bromoethynyl)benzene ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 20-41
• Safety Statements: 26-39

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• General Description: Phenylbromoethyne (also known as (bromoethynyl)benzene) is an alkynyl bromide used as a substrate in nickel-catalyzed C-H alkynylation reactions with azoles. It participates in coupling reactions facilitated by nickel catalysts such as Ni(cod)? or Ni(acac)?, often enhanced by ligands like dppbz, to form alkynylated azole derivatives. The compound serves as a key reagent for introducing phenylacetylene groups into heterocyclic frameworks, demonstrating its utility in synthetic organic chemistry for constructing complex molecular architectures.

Technology Process of Phenylbromoethyne

There total 48 articles about Phenylbromoethyne which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 99.0%

aq. ammonium chloride + phenylacetylene (536-74-3) → N4 -(2,2-Dimethyl-1S-methylcarbamoyl-propyl)-2S,N1 -dihydroxy-3R-(5-phenyl-penta-2, 4-diiynyl)-succinamide + 1-Bromo-2-phenylacetylene (932-87-6)

Guidance literature:

With sodium hydroxide; bromine; In tetrahydrofuran;

Reference yield: 96.0%

potassium (2-phenylethynyl)trifluoroborate → 1-Bromo-2-phenylacetylene (932-87-6)

Guidance literature:

With tetra-N-butylammonium tribromide; In tetrahydrofuran; water; at 20 ℃; for 0.333333h; chemoselective reaction;

DOI:10.1021/ol9027144

Reference yield: 96.0%

2,2-dibromostyrene (7436-90-0) → 1-Bromo-2-phenylacetylene (932-87-6)

Guidance literature:

With potassium hydroxide; N-benzyl-N,N,N-triethylammonium chloride; In dichloromethane; for 2h; cooling;

DOI:10.1016/S0040-4020(00)00920-0

upstream raw materials:

phenylethynylmagnesium bromide

bromocyane

benzenesulfonic anhydride

toluene-p-sulfonyl bromide

Downstream raw materials:

1,1,5-Triphenyl-2,4-pentadiin-1-ol

aniline hydrobromide

(hex-1-yn-1-yl)benzene

1-Phenylprop-1-yne

Refernces

Nickel-catalyzed direct alkynylation of azoles with alkynyl bromides

10.1021/ol901684h

The research explores an efficient method for the direct C-H alkynylation of azoles using alkynyl bromides in the presence of a nickel-based catalyst system. The study investigates the effects of various ligands, solvents, and reaction conditions to optimize the yield of the alkynylation products. Key chemicals involved include benzoxazole and various alkynyl bromides such as (bromoethynyl)benzene, which serve as the substrates. The nickel catalysts, specifically Ni(cod)2 and Ni(acac)2, play crucial roles in facilitating the reaction, with the addition of ligands like 1,2-bis(diphenylphosphino)benzene (dppbz) significantly enhancing the catalytic activity. Lithium tert-butoxide (LiO-t-Bu) is used as a base to deprotonate the azoles, generating heteroaryllithium intermediates essential for the transmetalation step. In some cases, a catalytic amount of CuI is added to further accelerate the reaction, suggesting the possible formation of heteroarylcopper species that facilitate the coupling process. The optimized conditions enable the introduction of a wide range of alkynyl groups bearing different substituents to the azole cores, demonstrating the synthetic utility of this transformation for creating complex molecular structures.