1964-45-0

Basic information

• Product Name: 3,5-DIMETHYLTHIANAPHTHENE
• Synonyms: 3,5-DIMETHYLTHIANAPHTHENE;3,5-DIMETHYLBENZO[B]THIOPHENE;3,5-DIMETHYLBENZOTHIOPHENE;3,5-dimethylthianapthene;3,5-DIMETHYLBENZO[B]THIOPHENE,97%;3,5-DIMETHYLTHIANAPH;3,5-Dimethyl-1-benzothiophene, 3,5-Dimethylthianaphthene
• CAS NO: 1964-45-0
• Molecular Formula: C10H10S
• Molecular Weight: 162.25
• Product Categories: Heterocycle-oher series
• Mol File: 1964-45-0.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 62-64°C 0,1mm
• Flash Point: 62-64°C/0.1mm
• Appearance: /
• Density: 1.114 g/cm³
• Vapor Pressure: 0.0191mmHg at 25°C
• Refractive Index: 1.635
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 3,5-DIMETHYLTHIANAPHTHENE(CAS DataBase Reference)
• NIST Chemistry Reference: 3,5-DIMETHYLTHIANAPHTHENE(1964-45-0)
• EPA Substance Registry System: 3,5-DIMETHYLTHIANAPHTHENE(1964-45-0)

Safety Data

• Statements: 36/37/38
• Safety Statements: 26-36/37/39
• Hazardous Substances Data: 1964-45-0(Hazardous Substances Data)

Usage

Synthesis Reference(s)

Journal of Heterocyclic Chemistry, 25, p. 1271, 1988 DOI: 10.1002/jhet.5570250445

InChI:InChI=1/C10H10S/c1-7-3-4-10-9(5-7)8(2)6-11-10/h3-6H,1-2H3

Upstream product

• 4923-87-9 5-bromobenzo[b]thiophene 
• 1423-62-7 3,5-dibromobenzothiophene 
• 13061-96-6 dihydroxy-methyl-borane 
• 958301-36-5 4-methyl-2-(1-methylethenyl)-1-(1-phenylethylthio)benzene 
• 106-45-6 para-thiocresol 
• 17067-25-3 1-(2-mercapto-5-methyl-phenyl)-ethanone 
• 1964-27-8 1-(5-methyl-2-methylsulfanyl-phenyl)-ethanone 
• 17067-18-4 (2-acetyl-4-methyl-phenylsulfanyl)-acetic acid 
• 1200-13-1 1-(p-tolylsulfanyl)propan-2-one 
• 6179-20-0 3,5-dimethyl-benzo[b]thiophene-2-carboxylic acid 
• 917-64-6 methyl magnesium iodide 
• 65520-23-2 5-methyl-benzo[b]thiophen-3-ol 

Downstream Products

• 1964-40-5 3,5-dimethylbenzo[b]thiophene 1,1-dioxide 
• 1365719-31-8 3,5-dimethyl-N-[3-(1H-tetrazol-5-yl)phenyl]-1-benzothiophene-2-sulfonamide 

Relevant articles and documents

Enantioselective hydroarylation or hydroalkenylation of benzo[b]thiophene 1,1-dioxides with organoboranes

An efficient protocol for the asymmetric hydroarylation and hydroalkenylation of benzo[b]thiophene 1,1-dioxides with organoboranes has been developed. The combination of a rhodium(I) precatalyst and a chiral diene ligand constitutes the catalytic system, which enables the facile synthesis of 2,3-dihydrobenzo[b]thiophene 1,1-dioxides in good yields with high enantioselectivities. The merging of this asymmetric hydroarylation with the downstream alkylations delivers 2,3-dihydrobenzo[b]thiophene 1,1-dioxides that contain two continuous quaternary stereocenters with high enantioselectivities in a diastereodivergent manner.

Preparation and pharmacological evaluation of a novel series of 2-(phenylthio)benzo[b]thiophenes as selective MT2 receptor ligands

A series of N-(2-(5-fluoro-2-(4-fluorophenylthio)benzo[b]thiophen-3-yl) ethyl)acylamides was synthesized and evaluated for binding affinity and intrinsic activity at melatonin receptors. The affinity of each compound for the melatonin receptors was determined by binding studies on cloned human MT 1 and MT2 receptors expressed in CHO cells. Agonist and antagonist potency was measured on the [35S]GTPγS binding assay for the most interesting compounds. The new derivatives 8-14 showed modest to high selectivity (between 4 and 220) for MT2 receptors. The most selective compound, N-(2-(5-fluoro-2-(4-fluorophenylthio)benzo[b]thiophen-3-yl) ethyl)but-3-enamide (14), an MT2 ligand with affinity for the MT 2 receptor similar to that of melatonin and a 220-fold preference over MT1 receptors, acts as a partial agonist. In addition, N-(2-(5-fluoro-2-(4-fluorophenylthio)benzo[b]thiophen-3-yl)ethyl)propionamide (9), a nanomolar MT2 ligand with a good selectivity ratio (MT 1/MT2 = 51) shows antagonist activity on both melatonin receptors.

Synthesis of Substituted Benzothiophenes by Acid-Catalyzed Cyclization of Thiophenylacetals and Ketones

Benzothiophenes substituted at the 3 position with methyl or carboxymethyl and at the 5 position with methyl, methoxy, chloro, bromo and nitro were prepared by cyclization of thiophenyl-acetals and ketones using a suspension of polyphosphoric acid in refluxing chlorobenzene.The overall efficiency of this method is superior to literature procedures because of the lower temperature and the limited amount of PPA used.