105836-25-7

Basic information

• Product Name: Thiophene, 3-(4-phenyl-1,3-butadiynyl)-
• CAS NO: 105836-25-7
• Molecular Formula: C14H8S
• Molecular Weight: 208.284
• Mol File: 105836-25-7.mol

Chemical Properties

• CAS DataBase Reference: Thiophene, 3-(4-phenyl-1,3-butadiynyl)-(CAS DataBase Reference)
• NIST Chemistry Reference: Thiophene, 3-(4-phenyl-1,3-butadiynyl)-(105836-25-7)
• EPA Substance Registry System: Thiophene, 3-(4-phenyl-1,3-butadiynyl)-(105836-25-7)

Safety Data

• Hazardous Substances Data: 105836-25-7(Hazardous Substances Data)

Upstream product

• 498-62-4 3-thiophene carboxaldehyde 
• 118616-07-2 ((E)-2,3-Dibromo-3-phenyl-allyl)-triphenyl-phosphonium; bromide 
• 105836-22-4 trans-(2,3-dibromo-3-phenyl-2-propen-1-yl)triphenylphosphonium bromide 
• 67237-53-0 3-ethynylthiophene 
• 932-87-6 1-Bromo-2-phenylacetylene 
• 536-74-3 phenylacetylene 
• 2170-06-1 1-Phenyl-2-(trimethylsilyl)acetylene 
• 1374225-73-6 3-(bromoethynyl)thiophene 
• 159087-45-3 4,4,5,5-tetramethyl-2-phenylethynyl-[1,3,2]dioxaborolane 

Relevant articles and documents

Transition metal-free coupling of terminal alkynes and hypervalent iodine-based alkyne-transfer reagents to access unsymmetrical 1,3-diynes

A variety of unsymmetrical 1,3-diynes can easily be accessed in good yields under catalyst- and transition metal-free conditions by reacting terminal alkynes with hypervalent iodine-based electrophilic alkyne-transfer reagents.

Synthesis of Unsymmetrical 1,3-Diynes via Pd/Cu-Catalyzed Cross-Coupling of Terminal Alkynes at Room Temperature

A facile and practical synthetic route of unsymmetrical 1,3-diynes via the PdCl/CuI catalyzed oxidative coupling of two different terminal alkynes has been developed by using 3-(diphenylphosphino)propanoic acid as a ligand in the presence of oxygen. This system is suitable for not only aromatic alkynes but also heteroaromatic and aliphatic alkynes which were transformed into the corresponding unsymmetrical 1,3-diynes in moderate to good yields at room temperature. Moreover, the unsymmetrical 1,3-diynes were also obtained on a multi-gram scale. Mechanistic studies suggest that oxygen plays a key role in the catalytic cycles.

A co-operative Ni-Cu system for Csp-Csp and Csp-Csp2 cross-coupling providing a direct access to unsymmetrical 1,3-diynes and en-ynes

An efficient cross-coupling of alkynes with alkynyl and alkenyl halides catalysed by a Ni-Cu system without any ligand has been achieved. The reaction is suggested to proceed by Ni(0) catalysis assisted by Cu(i). A series of functionalised diaryl, aryl-alkyl, aryl-heteroaryl, diheteroaryl 1,3-di-ynes and en-ynes are obtained in high yields.

Cu-catalyzed Fe-driven Csp-Csp and C sp-Csp2 cross-coupling: An access to 1,3-diynes and 1,3-enynes

An efficient Csp-Csp cross-coupling of alkynyl bromide and pinacol ester of alkynyl boronic acid catalyzed by CuFe 2O4 nanoparticles has been accomplished in dimethyl carbonate to produce unsymmetric 1,3-diynes. This protocol is also extended for the Csp-Csp2 coupling of alkynyl bromide and alkenyl boronic acid to provide conjugated 1,3-enynes. The aliphatic, aromatic, and heteroaromatic alkynes couple with various substituted alkynyl/alkenyl boronates/boronic acids by this procedure to furnish a library of 1,3-diynes and enynes in high yields. The catalyst was easily separated by an external magnet and recycled 10 times.