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

• 62247-77-2 1-bromo-4-(dibromomethyl)benzene 
• 5216-53-5 1,1-dichloro-2,2-bis(p-bromophenyl)ethane 
• 91110-68-8 1-bromo-4-((phenylsulfonyl)methyl)benzene 
• 1122-91-4 4-bromo-benzaldehyde 
• 623-00-7 4-bromobenzenecarbonitrile 
• 589-87-7 1,4-bromoiodobenzene 
• 75-20-7 calcium carbide 
• 106-40-1 4-bromo-aniline 
• 1066-54-2 trimethylsilylacetylene 
• 5467-74-3 4-Bromophenylboronic acid 
• 4254-18-6 1,2-bis(4-bromophenyl)-2-hydroxyethan-1-one 
• 23773-30-0 (4-bromophenyl)-1-propyne 
• 74-86-2 acetylene 
• 103-29-7 1,1'-(1,2-ethanediyl)bisbenzene 

Downstream Products

• 96871-50-0 4,4'-Bis-(diphenyl-hydroxymethyl)-tolan 
• 35578-47-3 4,4'-dibromobenzil 
• 136118-17-7 4,4'-Bis(trimethylsilyl)diphenylacetylene 
• 347390-12-9 4,4'-bis(3,7-dimethyloctanyl)diphenylacetylene 
• 106785-01-7 4,4'-bis(phenylethynyl)diphenylethyne 
• 854665-63-7 1,2-bis-(4-bromo-phenyl)-propan-2-ol 
• 191978-48-0 [tetrakis(4-bromophenyl)cyclobutadiene]cyclopentadienylcobalt 
• 1000999-86-9 C₃₀H₃₀O₄ 

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.

Palladium-Catalyzed Cascade Dearomative Spirocyclization and C?H Annulation of Aromatic Halides with Alkynes

Described herein is a palladium-catalyzed intermolecular dearomative annulation of aryl halides with alkynes, which provides a rapid approach to a class of structurally unique spiroembedded polycyclic aromatic compounds. The cascade process is accomplished by a sequential alkyne migratory insertion, Heck-type dearomatization, and C-H bond annulation. Further optoelectronic study indicated this fused spirocyclic scaffold could be a potential host material for OLEDs, as exemplified by a fabricated red PhOLED device with a maximum external quantum efficiency of 23.0%.

Rhodium-Catalyzed Regioselective Hydroformylation of Alkynes to α,β-Unsaturated Aldehydes Using Formic Acid

A rhodium-catalyzed hydroformylation of alkynes with formic acid was developed. The method provides α,β-unsaturated aldehydes in high yield and E-selectivity without the need to handle toxic CO gas.