2789-89-1

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 
• 114263-88-6 silver p-bromophenylcyanomethylenenitronate 
• 76-83-5 trityl chloride 
• 26204-09-1 1,1-bis-(4-bromo-phenyl)-2-chloro-ethene 
• 5405-28-7 1,2-di(4-bromophenyl)-1,2-dibromoethane 
• 589-87-7 1,4-bromoiodobenzene 
• 74-86-2 acetylene 
• 766-96-1 4-bromo-1-ethynylbenzene 
• 623-00-7 4-bromobenzenecarbonitrile 
• 16819-51-5 C₁₄H₁₂Br₂N₄ 
• 75-20-7 calcium carbide 
• 108-86-1 bromobenzene 
• 14630-40-1 Bis(trimethylsilyl)ethyne 
• 1066-54-2 trimethylsilylacetylene 

Downstream Products

• 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 
• 849681-64-7 (1,2-bis(4-(4,4,5,5-tetramethyl--1,3,2-dioxaborolan-2yl)phenyl)acetylene) 
• 36741-17-0 4,5-bis(4-bromophenyl)-2-phenyl-1H-imidazole 
• 25206-02-4 4,5-bis-(4-bromo-phenyl)-2-(4-nitro-phenyl)-1H-imidazole 
• 5140-98-7 4,4′-bis(bromomethyl)tolan 
• 84907-57-3 (4,4’-(ethyne-1,2-diyl)bis(4,1-phenylene))dimethanol 

Relevant academic research and scientific papers

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.

Sky-blue thermally activated delayed fluorescence material employing a diphenylethyne acceptor for organic light-emitting diodes

The strong electronegativity of sp-hybridized carbons, contributed by their large s character (50%), inspired the development of diphenylethyne as an electron acceptor to construct a sky-blue thermally activated delayed fluorescence material, 1,2-bis(4-(10H-phenoxazin-10-yl)phenyl)ethyne (DPE-DPXZ), using 10H-phenoxazine (PXZ) as an electron donor fragment. A sky-blue organic light-emitting diode employing DPE-DPXZ as the emitter demonstrated an external quantum efficiency exceeding 10%. Furthermore, another alkyne derivative, 1,2-bis(4-(9,9-dimethylacridin-10(9H)-yl)phenyl)ethyne (DPE-DDMAc), in combination with 9,9-dimethyl-9,10-dihydroacridine (DMAc) as the donor was also studied to explore the singlet-triplet splitting energy governed by donor-acceptor alternation.

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.

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.

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.

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%.

Selective Synthesis of Non-Aromatic Five-Membered Sulfur Heterocycles from Alkynes by using a Proton Acid/N-Chlorophthalimide System

A multicomponent strategy to achieve two different regioselectivities from alkynes, isothiocyanates and H2O with a proton acid/N-chlorophthalimide (NCPI) system is described to selectively obtain non-aromatic five-membered sulfur heterocycles (1,3-oxathiol-2-imines/thiazol-2(3H)-one derivatives) through multiple bond formations. The process features readily available starting materials, mild reaction conditions, broad substrate scope, good functional-group tolerance, high regio- and chemo- selectivities, gram-scale synthesis and late-stage modifications. Mechanistic studies support the proposal that the transformation process includes a combination of H2O and isothiocyanate, free-radical formation, carbonation and intramolecular cyclization to give the products. Furthermore, the 1,3-oxathiol-2-imine derivatives possess unique fluorescence characteristics and can be used as Pd2+ sensors with a “turn-off” response, demonstrating potential applications in environmental and biological fields.

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.

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.

Stereodivergent Synthesis of Alkenylpyridines via Pd/Cu Catalyzed C-H Alkenylation of Pyridinium Salts with Alkynes

The first Pd/Cu catalyzed selective C2-alkenylation of pyridines with internal alkynes has been developed via the pyridinium salt activation strategy. Importantly, the configuration of the product alkenylpyridines could be tuned by the choice of the proper N-alkyl group of the pyridinium salts, thus allowing for both the Z- and E-alkenylpyridines synthesized with good regio- and stereoselectivity. A plausible mechanism was proposed based on the Hammett study and KIE experiment.