2789-89-1

Basic information

• Product Name: Bis(4-bromophenyl)acetylene
• Synonyms: BIS(4-BROMOPHENYL)ACETYLENE;4,4'-DIBROMO-TOLANE;4,4'-DIBROMODIPHENYLACETYLENE;4-(2-(4-BROMOPHENYL)ETHYNYL)BROMOBENZENE;Bis-(p-bromophenyl)acetylene;Bis(4-bromophenyl)acetylene,97%;Bis(4-bromophenyl)acetylene4,4'-Dibromotolane;Bis(4-bromophenyl)acetylene ,96%
• CAS NO: 2789-89-1
• Molecular Formula: C₁₄H₈Br₂
• Molecular Weight: 336.02
• Product Categories: Aromatic Hydrocarbons (substituted) & Derivatives;Miscellaneous
• Mol File: 2789-89-1.mol
• Article Data: 73

Chemical Properties

• Melting Point: 182 °C
• Boiling Point: 383.6 °C at 760 mmHg
• Flash Point: 217.2 °C
• Appearance: Off-white/Crystalline Powder
• Density: 1.74 g/cm³
• Vapor Pressure: 9.62E-06mmHg at 25°C
• Refractive Index: 1.697
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• Solubility: Chloroform, Ethyl Acetate (Sparingly)
• CAS DataBase Reference: Bis(4-bromophenyl)acetylene(CAS DataBase Reference)
• NIST Chemistry Reference: Bis(4-bromophenyl)acetylene(2789-89-1)
• EPA Substance Registry System: Bis(4-bromophenyl)acetylene(2789-89-1)

Safety Data

• Statements: 36/37/38
• Safety Statements: 26-37/39
• Hazardous Substances Data: 2789-89-1(Hazardous Substances Data)

Usage

Chemical Properties

Off-white crystalline powder

Uses

Bis(4-bromophenyl)acetylene is used as a reactant in the synthesis of ethynylarene analogs containing 2-(1,2,3-triazol-4-yl)pyridine as selective ''turn-on'' fluorescent chemosensors for Ni(II).

InChI:InChI=1/C14H8Br2/c15-13-7-3-11(4-8-13)1-2-12-5-9-14(16)10-6-12/h3-10H

Upstream product

• 5405-28-7 meso-4,α,4',α'-tetrabromo-bibenzyl 
• 103-29-7 1,1'-(1,2-ethanediyl)bisbenzene 
• 62247-77-2 1-bromo-4-(dibromomethyl)benzene 
• 78238-16-1 α,α',4,4'-tetrabromostilbene 
• 114263-88-6 silver p-bromophenylcyanomethylenenitronate 
• 76-83-5 trityl chloride 
• 26204-09-1 1,1-bis-(4-bromo-phenyl)-2-chloro-ethene 
• 5216-53-5 1,1-dichloro-2,2-bis(p-bromophenyl)ethane 
• 5405-28-7 1,2-di(4-bromophenyl)-1,2-dibromoethane 
• 589-87-7 1,4-bromoiodobenzene 
• 74-86-2 acetylene 
• 23773-30-0 (4-bromophenyl)-1-propyne 
• 1066-54-2 trimethylsilylacetylene 
• 91110-68-8 1-bromo-4-((phenylsulfonyl)methyl)benzene 

Downstream Products

• 7150-10-9 4,4'-dibromo-1,2-diphenylethanone 
• 96871-50-0 4,4'-Bis-(diphenyl-hydroxymethyl)-tolan 
• 19057-50-2 4,4''-dibromo-3',4',5',6'-tetrakis(4-bromophenyl)-1,1':2',1''-terphenyl 
• 96970-04-6 p,p'-Bis-(α-hydroxy-β-phenyl-ethyl)-tolan 
• 35578-47-3 4,4'-dibromobenzil 
• 136118-17-7 4,4'-Bis(trimethylsilyl)diphenylacetylene 
• 253202-78-7 1,2-bis(4-bromophenyl)cyclobutene 
• 886-66-8 1,4-diphenyl-1,3-butadiyne 
• 106785-01-7 4,4'-bis(phenylethynyl)diphenylethyne 
• 347390-12-9 4,4'-bis(3,7-dimethyloctanyl)diphenylacetylene 
• 325834-47-7 1,2-bis(4-(triisopropylsilylethynyl)phenyl)ethyne 
• 647851-32-9 1,2-bis(4'-(trimethylsilyl)-[1,1'-biphenyl]-4-yl)ethyne 
• 732276-65-2 4,4'-bis(2-decyltetradecyl)diphenylacetylene 
• 849681-64-7 (1,2-bis(4-(4,4,5,5-tetramethyl--1,3,2-dioxaborolan-2yl)phenyl)acetylene) 

Relevant articles and documents

Synthesis and thermal properties of an acetylenic monomer containing boron and silicon

To improve the thermo-oxidative stability of acetylenic aromatic compounds, 1,2-bis(4-trimethylsilylethynylphenyl)-carborane (CBTMS) was designed, synthesized and characterized by FT-IR, 1H-NMR, 13C-NMR and mass spectrometry. The analysis of the DSC results showed that the acetylenic monomer had a melting point at 195.5 °C. The cross-linking process of CBTMS included a Diels-Alder cycloaddition reaction confirmed by FT-IR spectroscopy. Nonisothermal DSC studies showed CBTMS has an activation energy similar to that of the phenylethynyl-terminated compound. The thermoset and ceramic derived from the acetylenic monomer exhibited extremely thermo-oxidatively stable properties studied using thermogravimetric analysis (TGA). The thermoset showed a weight gain in air at elevated temperature and char yield of 98.8% at 1000 °C in air, and the ceramic residue had almost no weight loss up to 1000 °C in air. We demonstrated that trimethylsilylethynyl could be used as a crosslinking group for thermosetting polymers.

Mechanochemical Synthesis of Diarylethynes from Aryl Iodides and CaC 2

A mechanochemical synthesis of diarylethynes from aryl iodides and calcium carbide as acetylene source is reported. The reaction is catalyzed by a palladium catalyst in the presence of copper salt, base, and ethanol as liquid assisting grinding (LAG) additive. Various aryl and heteroaryl iodides have been converted in up to excellent yields.

Rh(iii)-Catalyzed three-component cascade annulation to produce theN-oxopropyl chain of isoquinolone derivatives

Developing powerful methods to introduce versatile functional groups at theN-substituents of isoquinolone scaffolds is still a great challenge. Herein, we report a novel three-component cascade annulation reaction to efficiently construct theN-oxopropyl chain of isoquinolone derivativesviarhodium(iii)-catalyzed C-H activation/cyclization/nucleophilic attack, with oxazoles used both as the directing group and potential functionalized reagents.

Synthesis of Diarylethynes from Aryldiazonium Salts by Using Calcium Carbide as an Alkyne Source in a Deep Eutectic Solvent

An efficient method for the synthesis of diarylethynes from aryldiazonium salts by using calcium carbide as an alkyne source at room temperature in a deep eutectic solvent is described. The salient features of this protocol are an inexpensive and easy-to-handle alkyne source, a nonvolatile and recyclable solvent, mild conditions, and a simple workup procedure.