932-87-6

Basic information

• Product Name: Phenylbromoethyne
• Synonyms: Phenylbromoethyne;(Bromoethynyl)benzene;1-Phenyl-2-bromoethyne;Bromoethynylbenzene;Phenylethynyl bromide;2-broMoethynylBenzene;1-Bromo-2-phenylacetylene;1-Bromo-2-phenylethyne
• CAS NO: 932-87-6
• Molecular Formula: C₈H₅Br
• Molecular Weight: 181.0293
• Mol File: 932-87-6.mol
• Article Data: 129

Chemical Properties

• Boiling Point: 217.4 °C at 760 mmHg
• Flash Point: 86 °C
• Appearance: /
• Density: 1.51 g/cm³
• Vapor Pressure: 0.196mmHg at 25°C
• Refractive Index: 1.615
• Storage Temp.: ?20°C
• BRN: 606222
• CAS DataBase Reference: Phenylbromoethyne(CAS DataBase Reference)
• NIST Chemistry Reference: Phenylbromoethyne(932-87-6)
• EPA Substance Registry System: Phenylbromoethyne(932-87-6)

Safety Data

• Hazard Codes: Xn
• Statements: 20-41
• Safety Statements: 26-39
• WGK Germany: 3
• Hazardous Substances Data: 932-87-6(Hazardous Substances Data)

Usage

General Description

Phenylbromoethyne is a chemical compound with the molecular formula C8H5Br. It is a derivative of ethyne and contains a phenyl group and a bromine atom. Phenylbromoethyne is a colorless liquid that is highly reactive and requires careful handling. It is primarily used as a building block in organic synthesis, particularly in the production of pharmaceuticals and agrochemicals. Phenylbromoethyne is also known for its use in the preparation of various heterocyclic compounds and as a reagent in chemical reactions. It is important to note that phenylbromoethyne should be handled with caution due to its reactivity and potential health hazards.

InChI:InChI=1/C8H5Br/c9-7-6-8-4-2-1-3-5-8/h1-5H

Upstream product

• 536-74-3 phenylacetylene 
• 849728-13-8 ethyl hydrogen phenylethynylphosphonate 
• 100-39-0 benzyl bromide 
• 4440-01-1 lithium phenylacetylide 
• 637-44-5 phenylpropyolic acid 
• 75-25-2 Bromoform 
• 93588-79-5 tetrabutylammonium tetramethylsuccinimide - N-bromotetramethylsuccinimide complex 
• 75-61-6 dibromodifluoromethane 
• 3201-60-3 α-bromobenzoylmethylene triphenylphosphorane 
• 72591-21-0 2,2,2-tribromoethylbenzene 
• 6738-06-3 phenylethynylmagnesium bromide 
• 358-23-6 trifluoromethylsulfonic anhydride 
• 7436-90-0 2,2-dibromostyrene 
• 1950-69-2 toluene-p-sulfonyl bromide 

Downstream Products

• 27425-23-6 6-bromo-3-methyl-7-phenyl-1,5-dihydro-pyrano[2,3-d]pyrimidine-2,4-dione 
• 13343-79-8 (E)-1,4-Diphenylbut-1-en-3-yne 
• 77395-43-8 di (2-phenylethynyl) telluride 
• 120880-80-0 bis-(phenyl ethynyl)selenide 
• 588-73-8 (Z)-β-bromostyrene 
• 178944-09-7 (1-Fluoro-3-phenyl-prop-2-ynyl)-phosphonic acid diethyl ester 
• 932-88-7 1-iodo-2-phenylethyne 
• 886-66-8 1,4-diphenyl-1,3-butadiyne 
• 70-11-1 α-bromoacetophenone 
• 673-32-5 1-Phenylprop-1-yne 
• 536-74-3 phenylacetylene 
• 130410-08-1 phenyl(phenylethynyl)iodonium triflate 
• 4604-65-3 1-dimethylamino-2-phenyl-ethyne 
• 27425-25-8 6-bromo-3-(4-nitro-phenyl)-7-phenyl-1,5-dihydro-pyrano[2,3-d]pyrimidine-2,4-dione 

Relevant articles and documents

Substituent effect of bis(pyridines)iodonium complexes as iodinating reagents: Control of the iodocyclization/oxidation process

This work was supported by a Grant-in-Aid for Young Scientists (B) from MEXT. T.O. also acknowledges support from the Society of Iodine Science.

β-Bromoenol phosphate as a new precursor for the modular regioselective synthesis of substituted furans

Owing to its importance in various realms of chemistry, furan occupies a position of eminence among heterocycles. Despite the availability of many methodologies for the synthesis of variably substituted furans, a modular convenient synthesis of 2,4-disubstituted furans remains challenging. The present work attempts to bridge that gap through a novel annulation-based approach using feedstock chemicals such as methyl ketones and their easily available derivatives, β-bromoenol phosphates. We have demonstrated a hitherto unknown reactivity of β-bromoenol phosphates which is responsible for the observed regioselectivity. The reaction requires only sodium hydride as the base under mild conditions. The scope of the reaction was found to be broad with the possibility of obtaining even tri-substituted furans besides a variety of 2,4-disubstituted furans. The methodology was applied to obtain synthetically challenging 3-acylfuran derivatives as well. The newly developed methodology is characterized by the modularity, regioselectivity as well as its practicality owing to easily available starting materials and fast reaction times.

Method for preparing 1-halogenated alkyne under catalysis of heterogeneous Ag catalyst at room temperature

The invention discloses a novel method for preparing 1-halogenated alkyne under the catalysis of a heterogeneous Ag catalyst at room temperature. The method comprises the steps of mixing terminal alkyne compounds containing different substituent groups, N

Regio- and Stereoselective N-addition to an Open Bromo Vinyl Cation

A protocol for the synthesis of thus far inaccessible bromo vinyl triflimides is presented. Our previously reported concept of assisted vinyl cation formation was engaged to achieve both a protonation of relatively electron poor bromo alkynes and a reaction with high regio- and stereoselectivity. To the best of our knowledge, this is the first stereoselective addition of an N-nucleophile to an open β-halovinyl cation.