16939-15-4

Basic information

• Product Name: Thiophene, 3-methyl-4-phenyl-
• CAS NO: 16939-15-4
• Molecular Formula: C11H10S
• Molecular Weight: 174.266
• Mol File: 16939-15-4.mol
• Article Data: 11

Chemical Properties

• CAS DataBase Reference: Thiophene, 3-methyl-4-phenyl-(CAS DataBase Reference)
• NIST Chemistry Reference: Thiophene, 3-methyl-4-phenyl-(16939-15-4)
• EPA Substance Registry System: Thiophene, 3-methyl-4-phenyl-(16939-15-4)

Safety Data

• Hazardous Substances Data: 16939-15-4(Hazardous Substances Data)

Upstream product

• 29290-99-1 2-methyl-3-phenylbut-1-en-3-ol 
• 616-44-4 3-Methylthiophene 
• 591-50-4 iodobenzene 
• 98-09-9 benzenesulfonyl chloride 
• 768-32-1 trimethylphenylsilane 
• 30318-99-1 3-bromo-4-methylthiophene 
• 98-80-6 phenylboronic acid 
• 18476-73-8 (3-methylbuta-1,3-dien-2-yl)benzene 
• 769-57-3 α,β,β-trimethylstyrene 

Downstream Products

• 83125-20-6 2,5-dibromo-3-methyl-4-phenylthiophene 
• 215377-86-9 3-methyl-2,4-diphenylthiophene 
• 126954-02-7 2-(α-Carbomethoxy-α-trifluoroacetamidotrifluoroethyl)-3-methyl-4-phenylthiophene 

Relevant articles and documents

Redox-Divergent Construction of (Dihydro)thiophenes with DMSO

Thiophene-based rings are one of the most widely used building blocks for the synthesis of sulfur-containing molecules. Inspired by the redox diversity of these features in nature, we demonstrate herein a redox-divergent construction of dihydrothiophenes, thiophenes, and bromothiophenes from the respective readily available allylic alcohols, dimethyl sulfoxide (DMSO), and HBr. The redox-divergent selectivity could be manipulated mainly by controlling the dosage of DMSO and HBr. Mechanistic studies suggest that DMSO simultaneously acts as an oxidant and a sulfur donor. The synthetic potentials of the products as platform molecules were also demonstrated by various derivatizations, including the preparation of bioactive and functional molecules.

Palladium-catalyzed dehydrogenative coupling of cyclic enones with thiophenes: A rapid access to β-heteroarylated cyclic enones

Dehydrogenative coupling of cyclic enones with heteroarenes has been a longstanding challenge because of the competitive ketone dehydrogenation and conjugated addition. Herein, a dehydrogenative coupling reaction of cyclic enones of different sizes with substituted thiophenes to construct β-thienyl cyclic enone compounds through palladium-catalyzed C-H functionalization under mild reaction conditions is reported. Simple substituted thiophenes with different functional groups can be directly introduced into cyclic enones with predominant regioselectivity at the α position of thiophene moieties and excellent functional group tolerance. Further molecular transformations of the coupling products to synthetically useful meta-heteroarylated phenol derivatives have also been demonstrated.

Selective β-Arylation of Thiophenes with Aryl Iodides Catalyzed by Dinuclear Palladium Carboxylate Complexes

Novel dinuclear palladium complexes bearing acetoxy ligands were synthesized and characterized by X-ray crystal analysis. The complexes were utilized for the arylation of 2-ethylthiophene with iodobenzene to give ethylphenylthiophenes with high β selectiv