Benzothiophene

Base Information

• Chemical Name: Benzothiophene
• CAS No.: 95-15-8
• Deprecated CAS: 11095-43-5
• Molecular Formula: C8H6S
• Molecular Weight: 134.202
• Hs Code.: 29349990
• European Community (EC) Number: 202-395-7
• NSC Number: 47196
• UNII: 073790YQ2G
• DSSTox Substance ID: DTXSID2052736
• Nikkaji Number: J3.019.265F,J4.710D
• Wikipedia: Benzothiophene
• Wikidata: Q419709
• Metabolomics Workbench ID: 55217
• ChEMBL ID: CHEMBL87112
• Mol file: 95-15-8.mol

Synonyms:benzo(b)thiophene;benzothiophene;thianaphthene

Chemical Property of Benzothiophene

Chemical Property:

• Appearance/Colour: white to red crystalline low melting solid
• Vapor Pressure: 0.163mmHg at 25°C
• Melting Point: 30-33 °C
• Refractive Index: 1.675
• Boiling Point: 221 °C at 760 mmHg
• PKA: 32.4
• Flash Point: 62 °C
• PSA: 28.24000
• Density: 1.187 g/cm³
• LogP: 2.90130
• Storage Temp.: Room temperature.
• Solubility.: 0.13g/l
• Water Solubility.: insoluble
• XLogP3: 3.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 134.01902136
• Heavy Atom Count: 9
• Complexity: 101

Purity/Quality:

99% ^*data from raw suppliers

Benzo[b]thiophene ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn,Xi
• Hazard Codes: Xn,Xi,N
• Statements: 22-36/37/38-20/21/22-51/53
• Safety Statements: 22-24/25-36-26-61

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Other Classes -> Thiophenes
• Canonical SMILES: C1=CC=C2C(=C1)C=CS2
• Uses: Benzo[b]thiophene has application in organic as well as pharmaceutical industry as a component in the synthesis of Raloxifene, a breast cancer therapeutic, or hydrodesulfurization reactions. manufacture of pharmaceuticals, thioindigo. Benzo[b]thiophene is used in the preparation of 2-thianapthenylphenyllithium, via metalation by n-butyllithium. It is used in organic as well as pharmaceutical industry as a component in the synthesis of raloxifene, a breast cancer therapeutic, or hydrodesulfurization reactions. Thianaphthene may be used in the preparation of 2-thianapthenylphenyllithium, via metalation by n-butyllithium.

Technology Process of Benzothiophene

There total 217 articles about Benzothiophene which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 72.0%

phenylmercaptoacetaldehyde dimethyl acetal (99172-76-6) → diphenyldisulfane (882-33-7) + Benzo[b]thiophene (95-15-8,11095-43-5)

Guidance literature:

K₁₀-ZnCl₂; In gas; at 300 ℃;

DOI:10.1021/jo00112a010

Reference yield: 68.0%

bis (2-chloroethyl) sulphide (505-60-2) + acetylene (74-86-2,25067-58-7) → thiophene (188290-36-0,8014-23-1,25233-34-5) + carbon disulfide (75-15-0,12122-00-8) + Benzo[b]thiophene (95-15-8,11095-43-5) + benzene (71-43-2,26181-88-4,54682-86-9,13967-78-7,174973-66-1)

Guidance literature:

With disulfide oil; at 650 ℃; for 1.75h; Further byproducts given;

DOI:10.1007/s11178-005-0260-5

Reference yield: 50.0%

benzothiaferrole (12086-84-9) → iron pentacarbonyl (13463-40-6,37220-42-1) + Benzo[b]thiophene (95-15-8,11095-43-5)

Guidance literature:

With CO; In hexane; loading an autoclave cup with Fe-compound in hexane and CO (500 psig, 25°C), heating (160°C, 700 psig, 19 h); cooling, transferring of soln. to a Schlenk flask (N2), GC and IR;

DOI:10.1021/om00095a024

upstream raw materials:

piperidine

3-Bromothianaphthene

styrene

3-hydroxybenzothiophene

Downstream raw materials:

2-(2-nitrophenyl)-benzo[b]thiophene

2-(p-methoxycarbonylphenyl)benzothiophene

dimethyl(o-tolyl)(benzothien-2-yl)silane

3-(2'-formylthiophenyl)-2-methylpropenal

Refernces

• 1、 Yuan, Tao,Zheng, Meifang,Antonietti, Markus,Wang, Xinchen. "Ceramic boron carbonitrides for unlocking organic halides with visible light". . p. 6323 - 6332. Retrieved 2021/05/19.
• 2、 Hu, Fangdong,Jia, Jie,Li, Ximing,Xia, Ying. "Enantioselective hydroarylation or hydroalkenylation of benzo[b]thiophene 1,1-dioxides with organoboranes". supporting information. p. 896 - 901. Retrieved 2021/02/01.