107793-04-4

Basic information

• Product Name: 1,4-bis(2-bromophenyl)-1,3-butadiyne
• Synonyms: 1,4-bis(2-bromophenyl)-1,3-butadiyne
• CAS NO: 107793-04-4
• Molecular Weight: 360.048
• Mol File: 107793-04-4.mol
• Article Data: 17

Chemical Properties

• CAS DataBase Reference: 1,4-bis(2-bromophenyl)-1,3-butadiyne(CAS DataBase Reference)
• NIST Chemistry Reference: 1,4-bis(2-bromophenyl)-1,3-butadiyne(107793-04-4)
• EPA Substance Registry System: 1,4-bis(2-bromophenyl)-1,3-butadiyne(107793-04-4)

Safety Data

• Hazardous Substances Data: 107793-04-4(Hazardous Substances Data)

Upstream product

• 766-46-1 2-bromo-1-ethynylbenzene 
• 38274-16-7 2-bromo-1-(trimethylsilylethynyl)benzene 
• 2142-69-0 2-bromophenyl methyl ketone 
• 153140-75-1 1-bromo-2-[(Z)-2-bromoethenyl]benzene 
• 213599-19-0 1-bromo-2-(2,2-dibromovinyl)benzene 
• 583-55-1 1-Bromo-2-iodobenzene 

Downstream Products

• 155587-94-3 1,4-bis[2-(2-trimethylsilylethynyl)phenyl]buta-1,3-diyne 
• 97976-81-3 1,4-bis(2-ethynylphenyl)buta-1,3-diyne 
• 1356907-39-5 1,4-bis(2-(dimethyl-(2-(4-fluorophenyl)ethynyl)silyl)phenyl)buta-1,3-diyne 
• 1356907-38-4 1,4-bis(2-(dimethyl-(2-(4-methoxyphenyl)ethynyl)silyl)phenyl)buta-1,3-diyne 
• 1356907-37-3 1,4-bis(2-(dimethyl(2-phenylethynyl)silyl)phenyl)buta-1,3-diyne 
• 1356917-98-0 ethyl 9,9-dimethyl-3-(3-(2-(ethoxycarbonyl)ethynyl)napht-2-yl)-4-(2-(2-(dimethyl-(2-phenylethynyl)silyl)phenyl)ethynyl)-1-phenyl-silafluorene-2-carboxylate 
• 1356917-97-9 ethyl 9,9-dimethyl-3-(2-(2-(ethoxycarbonyl)ethynyl)phenyl)-4-(2-(2-(dimethyl-(2-(4-fluorophenyl)ethynyl)silyl)phenyl)ethynyl)-1-(4-fluoro)phenyl-silafluorene-2-carboxylate 
• 1356917-96-8 ethyl 9,9-dimethyl-3-(2-(2-(ethoxycarbonyl)ethynyl)phenyl)-4-(2-(2-(dimethyl-(2-(4-methoxyphenyl)ethynyl)silyl)phenyl)ethynyl)-1-(4-methoxy)phenyl-silafluorene-2-carboxylate 
• 107793-02-2 2,5-bis(2-formylphenyl)thiophene 
• 107793-03-3 2,5-bis(2-bromophenyl)-thiophene 

Relevant articles and documents

Transition-metal-free variant of Glaser- and Cadiot-Chodkiewicz-type Coupling: Benign access to diverse 1,3-diynes and related molecules

Efficient and transition-metal-free transformations towards the synthesis of 1,3-diynes have been described from their corresponding terminal acetylenes or 1,1-dibromo-1-alkenes. The efficiency of molecular iodine as catalyst in aqueous medium, driven the transformation to afford 1,3-diynes in moderate to good yields. The developed reaction conditions revealed appreciable functional group tolerance in aqueous medium. Further, the scope of the transition-metal-free approach for the synthesis of 1,3-enynes has been investigated using terminal alkynes as easy available precursors.

Partially oxidized gold nanoparticles: A catalytic base-free system for the aerobic homocoupling of alkynes

The mechanism of alkyne homocoupling over gold nanoparticles and clusters, isolated and supported on CeO2, has been theoretically investigated by means of periodic DFT calculations. The theoretical study indicates that O2 dissociation on gold generates basic O atoms able to abstract the proton of the alkyne, and cationic Auδ+ and Au+ species that decrease the activation barrier for the CC bond forming step. Kinetic results show that the base-free homocoupling of alkynes is effectively catalyzed by gold nanoparticles supported on different solids, and confirm the theoretical prediction that the dissociation of oxygen on the gold nanoparticle is the controlling step of the global reaction.

Synthesis of symmetrical 1,3-diynes in water-soluble ionic liquid [DMIM]Me2PO4

Treatment of a variety of arynes in water-soluble ionic liquid [DMIM]Me2PO4 in the presence of catalytic amount of CuI and inexpensive NH3·H2O under aerobic conditions afforded the corresponding symmetrical 1,3-diynes in high yields. The ionic liquid could be reused for at least five times without apparent decrease of the yield.

Copper(i) chloride catalysed room temperature Csp-Csp homocoupling of terminal alkynes mediated by visible light

We developed a technique mediated by visible light for the aerobic homocoupling of terminal alkynes to synthesize 1,3-conjugated diynes using a copper(i) chloride catalyst at room temperature. Compared with previously reported thermal processes, this photochemical method is simple, uses only mild reaction conditions, produces high yields and works well for substrates with electron-withdrawing groups without the need for bases/ligands, oxidants or palladium catalysts.

One-pot desilylation/dimerization of ethynyl- and butadiynyltrimethylsilanes. Synthesis of tetrayne-linked dehydrobenzoannulenes

Addition of K2CO3 to standard Eglinton coupling conditions effects a one-pot desilylation/dimerization reaction of alkynyltrimethylsilanes. Use of this procedure on substituted phenylbutadiynylsilanes ultimately leads to the formation of dehydrobenzoannulenes possessing an unprecedented number of acetylene linkers.

Synthesis, Characterization of Spirocyclic λ3-Iodanes and Their Application to Prepare 4,1-Benzoxazepine-2,5-diones and 1,3-Diynes

Herein, a [3+2] cycloaddition of aza-oxyallylic cations with ethynylbenziodoxolones for synthesis of new λ3-iodanes containing spirocyclic 4-oxazolidinone has been developed. This cyclic λ3-iodanes display stability in air and excellent solubility in organic solvent. Using them as substrate, both the 4,1-benzoxazepine-2,5-diones and symmetrical 1,3-diynes derivatives were afforded in high yield under copper(I)-catalyzed conditions.

Metallomicelle catalyzed aerobic tandem desilylation/Glaser reaction in water

PEG-grafted nitrogen ligands were synthesized. The corresponding copper complexes serve as metallomicellar nanoreactors for the aerobic tandem desilylation/Glaser coupling of TMS-protected alkynes in water. The protocol is also suitable for base-free homocoupling of terminal alkynes. The metallomicellar catalyst could be recycled 5 times with minor loss of reactivity.