14300-29-9

Basic information

• Product Name: 4-METHYL-2-PHENYLTHIOPHENE
• Synonyms: 4-METHYL-2-PHENYLTHIOPHENE
• CAS NO: 14300-29-9
• Molecular Formula: C₁₁H₁₀S
• Molecular Weight: 174.26
• Mol File: 14300-29-9.mol

Chemical Properties

• Melting Point: 17.3 °C
• Boiling Point: 280 °C(Press: 773.3 Torr)
• Appearance: /
• Density: 1.1070 g/cm3
• CAS DataBase Reference: 4-METHYL-2-PHENYLTHIOPHENE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-METHYL-2-PHENYLTHIOPHENE(14300-29-9)
• EPA Substance Registry System: 4-METHYL-2-PHENYLTHIOPHENE(14300-29-9)

Safety Data

• Hazardous Substances Data: 14300-29-9(Hazardous Substances Data)

Usage

Synthesis Reference(s)

Journal of Heterocyclic Chemistry, 25, p. 367, 1988 DOI: 10.1002/jhet.5570250203

Upstream product

• 2049-94-7 (3-methylbutyl)benzene 
• 15325-61-8 3-methyl-1-phenyl-1-butene 
• 23806-25-9 3-methyl-5-phenylthiophene-2-carboxylic acid 
• 116016-64-9 2-bromo-3-methyl-5-phenylthiophene 
• 7065-27-2 2-methyl-2-(2-phenylethynyl)oxirane 
• 7783-06-4 hydrogen sulfide 
• 7732-18-5 water 
• 616-44-4 3-Methylthiophene 
• 591-50-4 iodobenzene 
• 108-86-1 bromobenzene 
• 14282-78-1 4-methylthiophene-2-carboxylic acid 
• 122-57-6 1-Phenylbut-1-en-3-one 
• 1565-86-2 3-Methyl-1-phenyl-1-butanol 
• 32094-37-4 1-methyl-4-(3-methylbut-1-en-1-yl)benzene 

Downstream Products

• 126953-99-9 2-(α-Carbomethoxy-α-trifluoroacetamidotrifluoroethyl)-3-methyl-5-phenylthiophene 
• 116016-64-9 2-bromo-3-methyl-5-phenylthiophene 
• 354528-32-8 1,2-bis-(3-methyl-5-phenyl-2-thienyl)perfluorocyclopentene 
• 874823-48-0 1-(2-methyl-5-phenyl-3-thienyl)-2-(3-methyl-5-phenyl-2-thienyl)-3,3,4,4,5,5-hexafluorocyclopent-1-ene 
• 23806-25-9 3-methyl-5-phenylthiophene-2-carboxylic acid 
• 116016-65-0 2-bromo-5-phenylthiophene-3-carbaldehyde 
• 116016-67-2 3-(2-bromo-5-phenyl-3-thienyl)acrolein 
• 116016-66-1 3-(2-bromo-5-phenyl-3-thienyl)acrylic acid 
• 1628556-78-4 2-[3,3,4,4,5,5-Hexafluoro-2-(2-methyl-1-naphthalenyl)-1-cyclopenten-1-yl]-3-methyl-5-phenylthiophene 

Relevant articles and documents

Transition-Metal-Free Sulfuration/Annulation of Alkenes: Economical Access to Thiophenes Enabled by the Cleavage of Multiple C-H Bonds

A novel, atom economical, and transition-metal-free strategy for the synthesis of thiophenes from substituted buta-1-enes with potassium sulfide has been presented. The reaction achieves double C-S bond formations via cleavage of multiple C-H bonds and provides an efficient approach to access various functionalized thiophenes. Moreover, the strategy can also be used for the synthesis of thiophenes from 1,4-diaryl-1,3-dienes. Mechanistically, DMSO plays a role of oxidant and S3?- in situ generated from K2S is involved.

Unexpected intermolecular Pd-catalyzed cross-coupling reaction employing heteroaromatic carboxylic acids as coupling partners

Aryl-substituted five-membered heteroaromatics have attracted great interest over the past years due to their presence in a large number of pharmaceuticals and natural products. Recently, an advance in the preparation of these scaffolds was achieved by employing a C-H functionalization strategy. This method allows easy access to these biaryl motifs by precluding the necessity of preparing specific coupling partners, although poor regioselectivity is sometimes observed when more than one reactive C-H is present on the substrate. In an effort to circumvent this liability, we envisioned the use of a carboxylic acid moiety as a blocking group that could be later functionalized or removed. Remarkably, the coupling was found to occur exclusively at the position previously occupied by the acid, even in the presence of a reactive C-H group. This selective transformation was also found to proceed with other heteroaromatic carboxylic acids, allowing for the preparation of a variety of aryl-substituted heteroaromatics that would be difficult to obtain via other methods. Copyright

1-(2-Methyl-5-phenyl-3-thienyl)-2-(3-methyl-5-phenyl-2-thienyl)-3,3,4,4,5, 5-hexafluorocyclopent-1-ene: A novel photochromic hybrid diarylethene

The title compound, C27H18F6S2, a novel photochromic hybrid diarylethene derivative containing 2- and 3-thienyl substituents, is one of the most promising photochromic candidates with shorter wavelength for optical storage and other optoelectronic devices. In the crystal structure, the molecule adopts a photoactive antiparallel conformation. The distance between the two reactive C atoms, i.e. the ring C atoms to which the methyl groups are attached, is 3.430 (4) A. The dihedral angles between the thienyl and adjacent phenyl rings are 26.8 (2) and 33.98 (9)°.

Substituent effect on the photochromic reactivity of bis(2-thienyl)perfluorocyclopentenes

Substituent effect on the photochromic reactivity of bis(2-thienyl)perfluorocyclopentenes was examined. Introduction of phenyl groups having electron-donating substituents on the para-position of the phenyl ring to the 5-position of the thiophene rings shifted the absorption bands of the open-ring isomers to longer wavelengths and reduced the quantum yield of the cyclization reactions. The substitution with p-(N,N-diethylamino)phenyl groups prohibited the cyclization reaction. The absorption spectra of the closed-ring isomers were not influenced by the substitution.

Synthesis of Unsymmetrical Arylthiophenes and Bithienyls via Oxidative Cyclization of 1,3-Butadiene-1-thiols

Oxidative cyclization of 2-mercapto-5-aryl-2,4-pentanedienoic acids with iodine produced the respective 5-aryl-2-thenoic acids.The method was also suitable for the synthesis of unsymmetrical substituted 2,2,-bithienyls, and 2,3'-bithienyls.The synthesis o