934-94-1

Basic information

• Product Name: 1-bromo-4-bromoethynyl-benzene
• Synonyms: 1-bromo-4-bromoethynyl-benzene
• CAS NO: 934-94-1
• Molecular Weight: 259.928
• Mol File: 934-94-1.mol

Chemical Properties

• CAS DataBase Reference: 1-bromo-4-bromoethynyl-benzene(CAS DataBase Reference)
• NIST Chemistry Reference: 1-bromo-4-bromoethynyl-benzene(934-94-1)
• EPA Substance Registry System: 1-bromo-4-bromoethynyl-benzene(934-94-1)

Safety Data

• Hazardous Substances Data: 934-94-1(Hazardous Substances Data)

Upstream product

• 25294-65-9 3-(4-bromophenyl)-2-propynoic acid 
• 7726-95-6 bromine 
• 1200-07-3 trans-4-bromocinnamic acid 
• 136350-66-8 1-bromo-4-(2,2-dibromovinyl)benzene 
• 558-13-4 carbon tetrabromide 
• 1122-91-4 4-bromo-benzaldehyde 
• 16116-78-2 (4-bromophenyl)(trimethylsilyl)acetylene 
• 112595-55-8 (2RS,3SR)-2,3-dibromo-3-(4-bromophenyl)propanoic acid 
• 589-15-1 1-bromomethyl-4-bromobenzene 
• 72591-18-5 p-(2,2,2-Tribromaethyl)-brombenzol 
• 766-96-1 4-bromo-1-ethynylbenzene 

Downstream Products

• 99-73-0 para-bromophenacyl bromide 
• 23464-12-2 5-(p-Bromphenyl)-penta-2,4-diinal-diethylacetal 
• 23463-86-7 5--pentadiin-(2.4)-saeure 
• 934-95-2 1-bromo-4-(iodoethynyl)benzene 
• 1231255-97-2 (Z)-1-bromo-4-(4-bromo-3-propylhept-3-en-1-yn-1-yl)benzene 
• 1231256-16-8 1-((E)-4-bromo-1-(4-bromophenyl)pent-3-en-1-yn-3-yl)cyclohexanol 
• 189099-57-8 1-bromo-4-[2-(4-methoxyphenyl)ethynyl]benzene 
• 1258498-77-9 benzo[d]oxazol-2-yl(4-bromophenyl)methanone 
• 76284-87-2 2-(4-bromobenzyl)benzo[d]oxazole 
• 140935-32-6 benzo[d]thiazol-2-yl(4-bromophenyl)methanone 
• 1327274-39-4 2-(4-bromobenzoyl)-5-methylbenzoxazole 
• 1327274-40-7 2-(4-bromobenzoyl)-5-chlorobenzoxazole 
• 102394-37-6 2-(4-bromobenzyl)-5-chlorobenzoxazole 
• 1338248-68-2 3-(4-bromophenyl)imidazo[1,2-a]pyridine 

Relevant articles and documents

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.

Visible-Light-Promoted Formation of C—C and C—P Bonds Derived from Evolution of Bromoalkynes under Additive-Free Conditions: Synthesis of 1,1-Dibromo-1-en-3-ynes and Alkynylphosphine Oxides

The controllable achievement of C—C and C—P bond formations is developed via visible-light-promoted bromoalkyne dimerization or its further transformation with secondary phosphine oxides. The 1,1-dibromo-1-en-3-ynes are formed when bromoalkyne is exposed to visible-light. While alkynylphosphine oxides are generated when bromoalkynes are mixed with secondary phosphine oxides.

Palladium-Catalyzed Carbonylation in the Synthesis of N-Ynonylsulfoximines

Palladium-catalyzed carbonylation reactions with Cr(CO)6 as carbonyl source are key for the preparation of N-ynonylsulfoximines from NH-sulfoximines and bromoalkynes. The couplings proceed at room temperature with a wide range of substrate combinations affording the corresponding products in good yields. (Figure presented.).

A Unified Approach for Divergent Synthesis of Heterocycles via TMSOTf-Catalyzed Formal [3+2] Cycloaddition of Electron-Rich Alkynes

We present a synthetic protocol for the construction of polysubstituted five-membered heterocycles via TMSOTf-catalyzed formal [3+2] cycloaddition of electron-rich alkynes, which features free from any metal, atom economy and water as the main by-product. Furthermore, alkenyl ether adduct has been verified as the key intermediate. Notably, by utilizing this approach, we can synthesize a broad range of polysubstituted furans, thiophenes and pyrroles, and extend this transformation to deliver fused-polyheterocycles. This reaction can be achieved on a gram scale and the corresponding products are intermediates for producing diverse potentially useful scaffolds. (Figure presented.).

Direct oxidation ofN-ynylsulfonamides intoN-sulfonyloxoacetamides with DMSO as a nucleophilic oxidant

N-Arylethynylsulfonamides are oxidized intoN-sulfonyl-2-aryloxoacetamides directly and efficiently with dimethyl sulfoxide (DMSO) as both an oxidant and solvent with microwave assistance. DFT calculations indicate that DMSO nucleophilically attacks the ethylic triple bond and transfers its oxygen atom to the triple bond to form zwitterionic anionicN-sulfonyliminiums to trigger the reaction. Then it nucleophilically attacks the generated iminium intermediates to accomplish the oxidationviathe second oxygen atom transfer. The current method provides a straightforward and efficient strategy to transform variousN-arylethynylsulfonamides intoN-sulfonyl-2-aryloxoacetamides, sulfonyl oxoacetimides, without any other electrophilic activators or oxidants.

Monobrominated alkyne compound, preparation method and application thereof

The invention belongs to the technical field of synthetic chemistry and discloses a monobrominated alkyne compound, a preparation method and an application thereof. The chemical structure formula of the monobrominated alkyne compound is as follows, wherei

Gold-Catalyzed C(sp2)?C(sp) Coupling by Alkynylation through Oxidative Addition of Bromoalkynes

A gold(I)-catalyzed cascade cyclization–alkynylation of allenoates using alkynyl bromide to generate β-alkynyl-γ-butenolides was investigated. Whereas alkynyl iodides afforded significant amounts of the homo-coupling of two lactone units, alkynyl bromides led to a selective reaction, and a broad functional group tolerance was observed. Under the optimized reaction conditions, it was possible to directly synthesize a large range of β-alkynyl-γ-butenolides in moderate to good yields without the need for any external oxidant.

Gold Catalyzed Photoredox C1-Alkynylation of N-Alkyl-1,2,3,4- tetrahydroisoquinolines by 1-Bromoalkynes with UVA LED Light

A synthetic method that combines [Au2(m-dppm)2]Cl2 (dppm=bis(diphenylphosphanyl)methane) and UVA LED (LED=light emitting diode) light (365 nm) to catalyze the regioselective C1-alkynylation of N-alkyl-1,2,3,4-tetrahydroisoquinolines (THIQs) with alkynyl bromides is described. The reaction mechanism was delineated to involve a reductive quench pathway to generate the two posited radical species of the nitrogen-containing heterocycle and organic halide. In contrast, radical formation via an oxidative quench pathway was suggested to be operative in analogous control experiments with a 1-iodoalkyne. The usefulness of this carbon-carbon bond forming strategy was also exemplified by its application to the formal synthesis of the opioid analgesic drug methopholine and synthesis of a protoberberine alkaloid derivative.

A Micellar Catalysis Strategy for Amidation of Alkynyl Bromides: Synthesis of Ynamides in Water

Copper-catalyzed amidation of alkynyl bromides can be carried out in water for the first time, which is made possible by a micellar catalysis strategy using rosin-based surfactant APGS-550-M. The surfactant can be easily prepared from natural abundant biomass, resin acids. Studies as to substrate scope and reaction aqueous medium recycling showcase the ease and sustainability of this technology.