766-96-1

Basic information

• Product Name: 4-Bromophenylacetylene
• Synonyms: 4'-BROMOPHENYL ACETYLENE;4-BROMOPHENYLACETYLENE;(4-BROMPHENYL)-ACETYLEN 97%;(4-Bromophenyl)acetylene,97%;Benzene, 1-broMo-4-ethynyl-;(4-BroMphenyl)acetylene;(4-BroMphenyl)acetylene, 95+%;1-Bromo-4-ethynylbenzene 97%
• CAS NO: 766-96-1
• Molecular Formula: C₈H₅Br
• Molecular Weight: 181.03
• EINECS: -0
• Product Categories: Aromatic Halides (substituted);pharmacetical;Aromatics Compounds;Aromatics;Alkynyl;Halogenated Hydrocarbons;Organic Building Blocks
• Mol File: 766-96-1.mol
• Article Data: 94

Chemical Properties

• Melting Point: 64-67 °C(lit.)
• Boiling Point: 88-90°C 16mm
• Flash Point: 88-90°C/16mm
• Appearance: White to yellow/Powder, Crystalline Powder or Solid
• Density: 1.4255 (rough estimate)
• Vapor Pressure: 0.488mmHg at 25°C
• Refractive Index: 1.6411 (estimate)
• Storage Temp.: -20?C Freezer
• Solubility: Soluble in chloroform, diethyl ether and ethanol.
• BRN: 1209726
• CAS DataBase Reference: 4-Bromophenylacetylene(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Bromophenylacetylene(766-96-1)
• EPA Substance Registry System: 4-Bromophenylacetylene(766-96-1)

Safety Data

• Hazard Codes: Xn,N
• Statements: 22-51/53
• Safety Statements: 61
• RIDADR: UN 3077 9/PG 3
• WGK Germany: 2
• HazardClass: 9
• PackingGroup: III
• Hazardous Substances Data: 766-96-1(Hazardous Substances Data)

Usage

Chemical Properties

Off-White Solid

Uses

Different sources of media describe the Uses of 766-96-1 differently. You can refer to the following data:
1. 4-Bromophenylacetylene, is used as the starting material for second-order nonlinear optical materials, heterocyclotriynes, and unsymmetrical 1,4-diarylbutadiynes.
2. 1-Bromo-4-ethynylbenzene was used in the synthesis of 1-bromo-4-(4′-tetrahydropyranyloxy-1′-ethynylphenyl)benzene.

Synthesis Reference(s)

The Journal of Organic Chemistry, 54, p. 3224, 1989 DOI: 10.1021/jo00274a055Tetrahedron, 62, p. 6673, 2006 DOI: 10.1016/j.tet.2005.12.077

InChI:InChI=1/C8H5Br/c1-2-7-3-5-8(9)6-4-7/h1,3-6H

Upstream product

• 3246-80-8 9-phenyl-9H-xanthene 
• 136482-74-1 C₈H₄BrK 
• 37828-68-5 1,1-dichloro-1-(4'-bromophenyl)ethane 
• 14063-78-6 3-(4-bromophenyl)-3-chloroprop-2-enal 
• 14235-81-5 4-Ethynylaniline 
• 1200-07-3 trans-4-bromocinnamic acid 
• 99-90-1 para-bromoacetophenone 
• 90965-06-3 dimethyl 1-(1-diazo-2-oxopropyl)phosphonate 
• 1122-91-4 4-bromo-benzaldehyde 
• 589-87-7 1,4-bromoiodobenzene 
• 4301-14-8 acetylenemagnesium bromide 
• 76347-62-1 4-(3-hydroxy-3,3-dimethyl-1-propynyl)-1-bromobenzene 
• 56506-90-2 (dibromomethyl)(triphenyl)phosphonium bromide 
• 106-37-6 1.4-dibromobenzene 

Downstream Products

• 31554-57-1 5-(4-bromo-phenyl)-3-(4-chloro-phenyl)-isoxazole 
• 97923-13-2 1-Diphenylhydroxymethyl-4-(3',3'-diphenylhydroxy-1'-propinyl)-benzol 
• 54075-64-8 3-(4-Bromo-phenyl)-1-cyclohepta-2,4,6-trienyl-prop-2-yn-1-ol 
• 1824-00-6 3-bromo-3-(4-bromo-phenyl)-acrylonitrile 
• 62897-32-9 (E)-4,5-Bis-(4-bromo-phenyl)-2,7-dicyano-octa-2,4,6-trienedinitrile 
• 26653-39-4 1-(buta-1,2-dien-1-yl)-4-bromobenzene 
• 42289-91-8 1-Bromo-4-(4-chloro-3,3,4-trifluoro-cyclobut-1-enyl)-benzene 
• 33206-27-8 6-(4-bromo-phenyl)-2-trichloromethyl-[1,3]oxazin-4-one 
• 51556-09-3 1-bromo-4-(chloroethynyl)benzene 
• 934-95-2 1-bromo-4-(iodoethynyl)benzene 
• 934-94-1 1-bromo-4-bromoethynyl-benzene 
• 71420-02-5 3-(p-bromophenyl)-1,2,5-thiadiazole 
• 72234-55-0 3-amino-4-(4-bromophenyl)-1,2,5-thiadiazole 
• 107433-65-8 methyl 5-hydroxy-7-<4-(1-hydroxynonyl)phenyl>hept-6-ynoate 

Relevant articles and documents

Iodonium Cation-Pool Electrolysis for the Three-Component Synthesis of 1,3-Oxazoles

The synthesis of 1,3-oxazoles from symmetrical and unsymmetrical alkynes was realized by an iodonium cation-pool electrolysis of I2 in acetonitrile with a well-defined water content. Mechanistic investigations suggest that the alkyne reacts with the acetonitrile-stabilized I+ ions, followed by a Ritter-type reaction of the solvent to a nitrilium ion, which is then attacked by water. The ring closure to the 1,3-oxazoles released molecular iodine, which was visible by the naked eye. Also, some unsymmetrical internal alkynes were tested and a regioselective formation of a single isomer was determined by two-dimensional NMR experiments.

Decarboxylation-triggered homo-Nazarov cyclization of cyclic enol carbonates catalyzed by rhenium complex

Decarboxylative homo-Nazarov cyclization catalyzed by a Lewis acid was achieved using a cyclic enol carbonate bearing a cyclopropane moiety as a substrate. Various substrates were converted into the corresponding multi-substituted cyclohexenones in good yieldsviadecarboxylation, followed by 6-membered ring formation involving cyclopropane-ring-opening.

Synthesis of alkynes under dry reaction conditions

An easy synthetic method was developed under dry reaction conditions for the preparation of terminal alkynes from 1,1-dibromoalkenes and in the presence of succinimide which acts as a nucleophile and proton donor. It was demonstrated with the synthesis of a broad spectrum of terminal alkynes and extended to synthesize internal alkynes under tandem reaction conditions.