932-87-6

Usage

Uses

Used in Pharmaceutical Industry:
Phenylbromoethyne is used as a key intermediate in the synthesis of various pharmaceuticals for its ability to facilitate the creation of complex molecular structures that can exhibit therapeutic properties.
Used in Agrochemical Industry:
In the agrochemical sector, Phenylbromoethyne is employed as a precursor in the development of compounds that can be used in pest control and crop protection, leveraging its reactivity to form new agrochemical entities.
Used in Heterocyclic Compound Preparation:
Phenylbromoethyne is utilized as a starting material in the preparation of heterocyclic compounds, which are important in various fields such as medicine, dyes, and plastics due to their diverse chemical and biological properties.
Used as a Reagent in Chemical Reactions:
As a reagent, Phenylbromoethyne is applied in a variety of chemical reactions to facilitate specific transformations, such as cross-coupling reactions, which are crucial for the formation of carbon-carbon bonds in organic molecules.

InChI:InChI=1/C8H5Br/c9-7-6-8-4-2-1-3-5-8/h1-5H

Upstream product

• 6738-06-3 phenylethynylmagnesium bromide 
• 506-68-3 bromocyane 
• 512-35-6 benzenesulfonic anhydride 
• 1950-69-2 toluene-p-sulfonyl bromide 
• 1004-22-4 (phenylethynyl)sodium 
• 536-74-3 phenylacetylene 
• 7436-90-0 2,2-dibromostyrene 
• 358-23-6 trifluoromethylsulfonic anhydride 
• 72591-21-0 2,2,2-tribromoethylbenzene 
• 3201-60-3 α-bromobenzoylmethylene triphenylphosphorane 
• 75-61-6 dibromodifluoromethane 
• 93588-79-5 tetrabutylammonium tetramethylsuccinimide - N-bromotetramethylsuccinimide complex 
• 4440-01-1 lithium phenylacetylide 
• 7726-95-6 bromine 

Downstream Products

• 542-11-0 aniline hydrobromide 
• 1129-65-3 (hex-1-yn-1-yl)benzene 
• 673-32-5 1-Phenylprop-1-yne 
• 62217-45-2 1-phenylocta-1,3-diyne 
• 92496-23-6 2-methyl-8-phenylocta-3,5,7-triyn-2-ol 
• 536-74-3 phenylacetylene 
• 91059-48-2 5-phenyl-penta-2,4-diynoic acid amide 
• 7200-00-2 7-phenyl-hept-2t-ene-4,6-diynoic acid 
• 4300-27-0 1-phenyl-hepta-1,3,5-triyne 
• 92024-81-2 6-phenyl-hexa-3,5-diynoic acid 
• 962-57-2 1-nitro-4-(phenylbuta-1,3-diyn-1-yl)benzene 
• 95820-61-4 1,1,7-triphenyl-hepta-2,4,6-triyn-1-ol 
• 119722-38-2 10-hydroxy-10-phenylbutadiynyl-anthrone 
• 18499-58-6 9,10-bis-phenylbutadiynyl-9,10-dihydro-anthracene-9r,10t-diol 

Relevant academic research and scientific papers

Substituent effect of bis(pyridines)iodonium complexes as iodinating reagents: Control of the iodocyclization/oxidation process

This work was supported by a Grant-in-Aid for Young Scientists (B) from MEXT. T.O. also acknowledges support from the Society of Iodine Science.

β-Bromoenol phosphate as a new precursor for the modular regioselective synthesis of substituted furans

Owing to its importance in various realms of chemistry, furan occupies a position of eminence among heterocycles. Despite the availability of many methodologies for the synthesis of variably substituted furans, a modular convenient synthesis of 2,4-disubstituted furans remains challenging. The present work attempts to bridge that gap through a novel annulation-based approach using feedstock chemicals such as methyl ketones and their easily available derivatives, β-bromoenol phosphates. We have demonstrated a hitherto unknown reactivity of β-bromoenol phosphates which is responsible for the observed regioselectivity. The reaction requires only sodium hydride as the base under mild conditions. The scope of the reaction was found to be broad with the possibility of obtaining even tri-substituted furans besides a variety of 2,4-disubstituted furans. The methodology was applied to obtain synthetically challenging 3-acylfuran derivatives as well. The newly developed methodology is characterized by the modularity, regioselectivity as well as its practicality owing to easily available starting materials and fast reaction times.

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.

Method for preparing 1-halogenated alkyne under catalysis of heterogeneous Ag catalyst at room temperature

The invention discloses a novel method for preparing 1-halogenated alkyne under the catalysis of a heterogeneous Ag catalyst at room temperature. The method comprises the steps of mixing terminal alkyne compounds containing different substituent groups, N

Nickel-Catalyzed Difunctionalization of Alkynyl Bromides with Thiosulfonates and N -Arylthio Succinimides: A Convenient Synthesis of 1,2-Thiosulfonylethenes and 1,1-Dithioethenes

An efficient nickel-catalyzed vicinal thiosulfonylation of 1-bromoalkynes with thiosulfonates in the presence of cesium carbonate is described. An operationally simple and highly regioselective atom transfer radical addition (ATRA) of alkynyl bromides provides a wide range of (E)-1,2-thiosulfonylethenes (α-aryl-β-thioarylvinyl sulfones) in moderate to high yields. The extensive substrate scope of both alkynyl bromides and thiosulfonates is explored with a broad range of functional groups. Indole-derived 1,1-bromoalkenes were also successfully explored in this 1,2-thiosulfonylation process. Moreover, the nickel-catalyzed geminal -dithiolation of alkynyl bromides with N -arylthio succinimides provides 1,1-dithioalkenes in high yields. The present protocol is reliable on gram scale, and a sequential one-pot bromination and thiosulfonylation of phenylacetylene is achieved in a scale-up synthesis. Following control experiments, a plausible mechanism is proposed to rationalize the experimental outcome and the vicinal thio-sulfonylation.

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.

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.).

Biogenic synthesis of Pd-nanoparticles using Areca Nut Husk Extract: a greener approach to access α-keto imides and stilbenes

An eco-friendly green method for a one-step synthesis of palladium nanoparticles and their synthetic utility are reported. Phytochemicals like amines, alcohols, and phenols present in the Areca Nut Husk extract facilitate the reduction of Pd(ii) to Pd(0). The phytochemicals serve as stabilising agents and ligands for palladium reduction and the need for an external ligand is avoided. The Field Emission Scanning Electron Microscopy and Transmission Electron Microscopy of newly synthesized palladium nanoparticles revealed a spherical morphology. The catalytic activity of the nanoparticles was tested for 1,2-difunctionalization of ynamides, Heck coupling, denitrogenative coupling of phenylhydrazine and C-H arylation of indole. Moreover, catalyst recyclability, control experiments, mechanistic elucidation, and gram-scale synthesis are elaborated.

Decatungstate as Direct Hydrogen Atom Transfer Photocatalyst for SOMOphilic Alkynylation

A versatile approach for the alkynylation of a variety of aliphatic hydrogen donors, including alkanes, is reported. We used tetrabutylammonium decatungstate as photocatalyst to generate organoradicals from C-H/Si-H bonds via hydrogen atom transfer. The l

Base-Mediated Generation of Ketenimines from Ynamides: [3+2] Annulation with Azaallyl Anions

Under basic conditions and heat, ynamides can serve as precursors to ketenimines, whose synthetic potential is often hampered by their difficulty of access. Herein, we report that they can undergo a [3+2] cycloaddition with 2-azaallyl anions, obtained from benzylimines under the same reaction conditions. This reaction between two highly reactive intermediates, both generated in situ from bench stable starting materials, gives access to various nitrogen-rich heterocycles. The reaction usually proceeds with excellent diastereoselectivity, in favor of the cis adduct. Deuteration experiments and DFT calculations helped rationalize the regio- and stereoselectivity of the process as well as the formation of side products. (Figure presented.).