16587-47-6

Basic information

• Product Name: 6-METHYLBENZOTHIOPHENE
• Synonyms: 6-Methyl-1-benzothiophene;6-Methylbenzo[b]thiophene;6-Methylthianaphthene;Benzo[b]thiophene, 6-methyl-;Benzothiophene, 6-methyl;6-METHYLBENZOTHIOPHENE
• CAS NO: 16587-47-6
• Molecular Formula: C₉H₈S
• Molecular Weight: 148.22
• EINECS: 250-609-2
• Mol File: 16587-47-6.mol

Chemical Properties

• Melting Point: 42.0-42.5 °C
• Boiling Point: 243 °C at 760 mmHg
• Flash Point: 72.4 °C
• Appearance: /
• Density: 1.146 g/cm³
• Vapor Pressure: 0.0514mmHg at 25°C
• Refractive Index: 1.652
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• CAS DataBase Reference: 6-METHYLBENZOTHIOPHENE(CAS DataBase Reference)
• NIST Chemistry Reference: 6-METHYLBENZOTHIOPHENE(16587-47-6)
• EPA Substance Registry System: 6-METHYLBENZOTHIOPHENE(16587-47-6)

Safety Data

• Hazardous Substances Data: 16587-47-6(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
6-METHYLBENZOTHIOPHENE is used as a chemical intermediate for the synthesis of various pharmaceutical drugs, leveraging its unique structure to contribute to the development of new medicinal compounds.
Used in Organic Synthesis:
6-METHYLBENZOTHIOPHENE is used as a key building block in organic synthesis, facilitating the creation of a wide range of organic compounds for diverse applications.
Used in Environmental Analysis:
6-METHYLBENZOTHIOPHENE is used as a marker compound for the detection and analysis of hydrocarbons in environmental samples, helping to assess the presence of pollutants and monitor environmental health.
Used in Crude Oil Composition:
6-METHYLBENZOTHIOPHENE is found in crude oil, where it contributes to the overall chemical makeup of the substance, playing a role in the refining process and the production of various petroleum products.

InChI:InChI=1/C9H8S/c1-7-2-3-8-4-5-10-9(8)6-7/h2-6H,1H3

Upstream product

• 57860-49-8 3-methyl-1-(2,2-dimethoxy-ethyl-sulfanyl)-benzene 
• 3996-30-3 2-[(3-methylphenyl)thio]acetic acid 
• 6007-83-6 2,3-thiophenedicarboxylic acid anhydride 
• 542-92-7 cyclopenta-1,3-diene 
• 51830-51-4 m-tolylsulfanyl-acetaldehyde diethylacetal 
• 86119-84-8 phosphoric acid 
• 70260-86-5 4-(S)-oxiranylmethoxy-1H-indole 
• 574706-08-4 1-(1H-indol-4-yloxy)-3-[4-(4-methyl-benzo[b]thiophen-2-yl)-piperidin-1-yl]-propan-2-ol 
• 68670-98-4 2,3-dihydro-6-methylbenzo[b]thiophen-3-one 
• 2728-05-4 N,N-Diethyl-p-toluamid 
• 596805-23-1 N,N-diethyl-2-methylsulfanyl-4-methylbenzamide 
• 17347-32-9 6-bromobenzothiophene 
• 13061-96-6 dihydroxy-methyl-borane 

Downstream Products

• 89816-56-8 2-allyl-6-methylbenzothiophene 
• 22720-97-4 2-(4-methyl)phenyl-6-methylbenzothiophene 
• 22721-01-3 5-methyl-2-p-tolylbenzothiophen 
• 27047-29-6 6-methyl-2-phenylbenzothiophen 
• 82787-84-6 6-methylbenzothiophene-3-carboxylic acid 
• 82787-85-7 6-methylbenzothiophene-3-carboxylic acid methyl ester 
• 6386-80-7 benzo[b]thiophene-6-carbaldehyde 
• 10133-25-2 benzo[b]thiophene-4-carboxaldehyde 
• 820240-91-3 6-methylbenzothiophene boronic acid 
• 82787-72-2 6-methylbenzothiophene-2-carboxylic acid methyl ester 

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.

Application of directed metalation in synthesis. Part 4: Expedient synthesis of substituted benzo[b]thiophene and naphthothiophene

A short, simple and inexpensive synthesis of several diversely substituted benzo[b]thiophenes and one naphthothiophene is described. The method involves introduction of methylsulfanyl group ortho- to the amide function of readily available N,N-diethylamides of aryl carboxylic acid by directed metalation. Thioindoxyls, obtained in high yields through side-chain deprotonation and cyclisation in one pot, are reduced to benzo[b]thiophene or napthothiophene.

Advances toward new antidepressants beyond SSRIs: 1-aryloxy-3-piperidinylpropan-2-ols with dual 5-HT1A receptor antagonism/SSRI activities. Part 1

A series of 1-aryloxy-3-piperidinylpropan-2-ols possessing potent dual 5-HT1A receptor antagonism and serotonin reuptake inhibition was discovered. 1-(1H-Indol-4-yloxy)-3-(4-benzo[b]thiophen-2-ylpiperidinyl)propan-2-ols exhibited selective and high affinity at the 5-HT1A receptor and serotonin reuptake inhibition at nanomolar concentrations for dual activities.

N-ALKOXYALKYL-N,N-DIALKYLAMINE DERIVATIVES OR SALTS THEREOF, AND REMEDIES FOR NERVE DEGENERATION DISEASES CONTAINING THE SAME

An N-alkoxyalkyl-N,N-dialkylamine derivative represented by the following general formula [1]: wherein the ring D represents a 5- or 6-membered heterocyclic ring or hydrocarbon ring; R3 and R4, which are the same or different, represent an unsubstituted or substituted alkyl, cycloalkyl or aralkyl group; and R1, R2, R5, R6, R7, R8, m and n are as defined in the specification, or a salt thereof has an anti-hypoxic activity, a nerve-protecting activity and a nerve regeneration promoting activity and is useful for the treatment of neurodegenerative diseases.

Evolution of products in the combustion of scrap tires in a horizontal, laboratory scale reactor

A horizontal laboratory reactor was used to study the evolution of byproducts from the combustion of scrap tires at five nominal temperatures (ranging from 650 to 1050 °C) and different oxygen:sample ratios A model was used to calculate the bulk air ratio (λ), and the oxygen consumption was discussed considering this ratio λ. More than 100 volatile and semivolatile compounds were identified and quantified by gas chromatography mass spectrometry, plotting their yields vs the bulk air ratio and temperature. Five different behaviors considering the bulk air ratio and the temperature were identified.

SUBSTITUTED SULFONIC ACID N-[(AMINOIMINOMETHYL)PHENYLALKYL]-AZAHETEROCYCLAMIDE COMPOUNDS

The compounds of formula I exhibit useful pharmacological activity and accordingly are incorporated into pharmaceutical compositions and used in the treatment of patients suffering from certain medical disorders. More specifically, they are inhibitors of the activity of Factor Xa. The present invention is directed to compounds of formula I, compositions containing compounds of formula I, and their use, which are for treating a patient suffering from, or subject to, physiological condition which can be ameliorated by the administration of an inhibitor of the activity of Factor Xa.

An improved synthesis of benzo[b]thiophene and its derivatives using modified montmorillonite clay catalysts

Methods for the preparation of benzothiophene (3) and its derivatives by cyclization of phenylthioacetals (1) over ZnCl2-promoted montmorillonite clay are described. Reactions in solution resulted in only moderate (ca. 50%) yields of 3 and the formation of diphenyl disulfide (4) and uncharacterized products. The production of 4 was explained by coordination of 1 via its oxygen atom to active sites of the catalyst and subsequent bimolecular processes. Good to excellent yields (67-98%) of 3 and its derivatives were obtained using vapor phase techniques at 200-300°C to promote the desired intramolecular cyclizations.

ALKYLATION OF THIOPHENES AND PREPARATION OF BENZOTHIOPHENES USING MODIFIED MONTMORILLONITE CLAY CATALYSTS

Regioselective benzylation of thiophene and benzothiophene using benzyl chloride and a ZnCl2-promoted montmorillonite catalysts is described.An improved process for the cyclization of (arylthio)acetaldehyde dialkyl acetals to benzothiophenes using the same catalyst is also documented.

Thermolysis of Thiophenedicarboxylic Acid Anhydrides as a Route to Five-Membered Hetarynes

Flow vacuum thermolysis (FVT) of the anhydrides of thiophene-2,3- (5) and -3,4-dicarboxylic acid (6) and of thianaphthene-2,3-dicarboxylic acid (7) in the presence of thiophene, 1,3-cyclohexadiene, or benzene gave thianthrene (15a), presumably by aromatization of an intermadiate Diels-Alder adduct of the diene traps and the aryne 2,3-didehydrothiophene (8).A similar rationale explains the formation of dibenzothiophene from 7 and thiophene, the four monomethylthianaphthenes 22-25 from 5 and cyclopentadiene, 5,6-dimethylthianaphthene (15f) from 5 and 2,3-dimethylbutadiene, and a mixture of hydroxythianaphthenes (15d) from 5 and furan.The latter reaction also produces a mixture of isomeric cyclopentanothiophenes (19) which probably arise by decarbonylation of 15d.An FVT reaction of 5 with propyne as the trap gave a mixture of allenyl-(28) and propynylthiophenes 29 which probably arise by an ene reaction of the trap and the aryne 8.Decomposition of the anhydrides 5 and 6 in molten anthracene led only to Friedel-Crafts products such as thienylanthracenes 33 and quinones 34 from 5 and 39 and 40 from 6.The diene reactivity of thiophene 13a in the gas phase was demonstrated by the formation of naphthalene from its reaction with benzyne generated from the thermolysis of indanetrione and by the formation of indene from 13a plus cyclopentadiene.Possible, but improbable, interpretations of the FVT results without invoking a five-membered hetaryne intermediate are considered.