91790-32-8

Basic information

• Product Name: BIS(3-BROMOPHENYL)ACETYLENE
• Synonyms: BIS(3-BROMOPHENYL)ACETYLENE
• CAS NO: 91790-32-8
• Molecular Formula: C14H8Br2
• Molecular Weight: 336.03
• Mol File: 91790-32-8.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: BIS(3-BROMOPHENYL)ACETYLENE(CAS DataBase Reference)
• NIST Chemistry Reference: BIS(3-BROMOPHENYL)ACETYLENE(91790-32-8)
• EPA Substance Registry System: BIS(3-BROMOPHENYL)ACETYLENE(91790-32-8)

Safety Data

• Hazardous Substances Data: 91790-32-8(Hazardous Substances Data)

Upstream product

• 591-18-4 1-Bromo-3-iodobenzene 
• 1066-54-2 trimethylsilylacetylene 
• 66107-31-1 3-bromophenyl trifluoromethanesulfonate 
• 3132-99-8 m-bromobenzoic aldehyde 
• 130891-01-9 1-bromo-3-((phenylsulfonyl)methyl)benzene 
• 75-20-7 calcium carbide 
• 766-81-4 3-bromophenylacetylene 
• 18293-53-3 2-trimethylsilylacetonitrile 
• 823-78-9 meta-bromobenzyl bromide 
• 74-86-2 acetylene 

Downstream Products

• 1879010-27-1 C₂₆H₃₂B₂O₄ 

Relevant articles and documents

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.

Ruthenium(ii)-catalyzed intermolecular annulation of alkenyl sulfonamides with alkynes: Access to bicyclic sultams

A ruthenium-catalyzed allylic C(sp3)-H activation strategy has been employed to develop an intermolecular coupling of alkenyl sulfonamides with alkynes. This protocol features the diastereoselective construction of [3.3.0] and [4.3.0] bicyclic sultams in one step.

Synthesis of α-fluoroimines by copper-catalyzed reaction of diarylacetylenes and n-fluorobenzenesulfonimide

Difunctionalization of unsaturated bonds with fluorinating reagents has been regarded as an efficient route to vicdifunctional organic fluorides. Here we report a coppercatalyzed synthesis of α-fluoroimines from diarylacetylenes and N-fluorobenzenesulfonimide. Mechanistically, the reaction initiates from the generation of imidyl radical, which reacts with alkyne to give the product. The resulting α-fluoroimine can easily be transformed into other organic fluorides such as fluoroketone and fluoroamines.

Dichotomy of Manganese Catalysis via Organometallic or Radical Mechanism: Stereodivergent Hydrosilylation of Alkynes

Herein, we disclose the first manganese-catalyzed hydrosilylation of alkynes featuring diverse selectivities. The highly selective formation of E-products was achieved by using mononuclear MnBr(CO)5 with the arsenic ligand, AsPh3. Whereas using the dinuclear catalyst Mn2(CO)10 and LPO (dilauroyl peroxide) enabled the reversed generation of Z-products in good to excellent stereo- and regioselectivity. Such a way of controlling the reaction stereoselectivity is unprecedented. Mechanistic experiments revealed the dichotomy of manganese catalysis via organometallic and radical pathways operating in the E- and Z-selective routes, respectively.

Preparation method of diaryl acetylene compounds

The invention relates to preparation of an organic compound, and aims to provide a preparation method of diaryl acetylene compounds. The preparation method includes steps of adding associated tribromomethylarene compound and copper in a reactor to perform deoxidizing treatment; dissolving polyamine in a proper amount of anhydrous and oxygen-free solvent, and then adding to the reactor; performingcoupling reaction at 30-80DEG C for 3-12 hours; separating and purifying to obtain diaryl acetylene compounds. The preparation is gentle in synthesis condition and the reaction has good compatibilityto different functional groups; the raw material associated tribromomethylarene compound is convenient to compound and has different substituent groups and variable structure; by adopting one raw material, high-quality product can be obtained through simple treatment, and the output is high; by adopting two different raw materials, the asymmetrical diaryl acetylene compound can be prepared.

N-Doped Cationic PAHs by Rh(III)-Catalyzed Double C-H Activation and Annulation of 2-Arylbenzimidazoles with Alkynes

A novel class of N-doped cationic PAHs (polycyclic aromatic hydrocarbons) bearing the benzo[c,d]fluoranthene scaffold has been synthesized by the Rh(III)-catalyzed double-oxidative annulation of 2-arylbenzimidazoles with alkynes. The overall process involves a double C-N bond formation through a double C-H/N-H functionalization.The solid-state structures and electronic properties of the new N-doped PAHs were analyzed. These cationic azapolycycles were readily reduced in the presence of LiAlH4 or by the addition of PhLi to give interesting phenyl and diphenylmethanediamine derivatives.

Synthesis and characterization of symmetrical sulfur-fused polycyclic aromatic hydrocarbons with controlled shapes

Here we report and establish a facile synthetic method for these unprecedented sulfur-fused polycyclic aromatic hydrocarbons (S-PAHs) with symmetrical structures (C2-rectangle and D6h-hexagonal shape). Characterization by laser desor

Small-molecular luminous material with 1,2-diphenyl acetylene as acceptor unit, and preparation and application thereof

The invention belongs to the technical field of luminous materials and discloses a small-molecular luminous material with 1,2-diphenyl acetylene as an acceptor unit, and preparation and applications thereof. The preparation method includes the steps of adding the 1,2-diphenyl acetylene compound, a nitrogen-containing compound and a catalyst into a reaction container filled with a solvent under protection of an inert gas; performing a heated stirring reaction, cooling and extracting a reaction product, and spin-drying an organic phase and performing chromatography to obtain the small-molecular luminous material with the 1,2-diphenyl acetylene as the acceptor unit. The small-molecular luminous material has single structure and definite molecular weight, achieves intramolecular charge transfer and solves a problem of unbalanced charge carriers in a mono-polar luminous material, simplifies device structure and improves device performance. The luminous material is used in organic light-emitting devices.

Palladium nanoparticles catalyzed Sonogashira reactions for the one-pot synthesis of symmetrical and unsymmetrical diarylacetylenes

A variety of symmetrical and unsymmetrical diarylacetylenes are synthesized by ligand-free palladium nanoparticles catalyzed copper-free and amine-free Sonogashira cross-coupling reactions between aryl iodides and trimethylsilylacetylene (TMSA) under mild reaction conditions.

Synthesis of macrocyclic molecular rods as potential electronic devices

The design and synthesis of the macrocycles 1 and 2 as model compounds for the investigation of negative differential conductance phenomena in molecular junctions are reported. The macrocycles 1 and 2 comprise a molecular rod subunit consisting of three ethynyl-linked phenyl rings. While the rotational freedom along the rod axis of both terminal phenyl rings is limited by the macrocyclic frame, the central phenyl ring is revolving. The rod substructure is terminally functionalized with acetyl-protected thiol groups to enable its immobilization between gold contacts. The central phenyl ring is functionalized with one and two nitro groups for 1 and 2, respectively. The nitro groups are of particular importance as i) both macrocycles are model compounds to investigate a hypothetical intramolecular interaction of the nitro group with the opposite macrocyclic subunits and ii) the nitro group(s) result in limited thermal stability of the compounds due to the intramolecular rearrangement to macrocycles comprising isatogen subunits. These highly functionalized macrocycles have been assembled by acetylene scaffolding strategies in combination with functional group transformation chemistry. Wiley-VCH Verlag GmbH & Co. KGaA, 2006.