Benzo[c]thiophene

Base Information

• Chemical Name: Benzo[c]thiophene
• CAS No.: 270-82-6
• Molecular Formula: C₈H₆S
• Molecular Weight: 134.202
• UNII: P5T9LN69TC
• DSSTox Substance ID: DTXSID00181489
• Nikkaji Number: J247.739D
• Wikipedia: Benzo(c)thiophene
• Wikidata: Q4117655
• Metabolomics Workbench ID: 55508
• Mol file: 270-82-6.mol

Synonyms:Benzo[c]thiophene;2-Benzothiophene;270-82-6;Benzo(c)thiophene;isobenzothiophene;P5T9LN69TC;Isothianaphtene;isothianaphthene;CHEBI:36953;2-Benzothiophene #;UNII-P5T9LN69TC;2-THIA-2H-INDENE;SCHEMBL51694;2-THIA-2H-ISOINDENE;DTXSID00181489;FT-0715850;Q4117655

Chemical Property of Benzo[c]thiophene

Chemical Property:

• Vapor Pressure: 0.0959mmHg at 25°C
• Melting Point: 58-60℃
• Boiling Point: 231.2°Cat760mmHg
• Flash Point: 66.8°C
• PSA: 28.24000
• Density: 1.187g/cm³
• LogP: 2.90130
• XLogP3: 2.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 134.01902136
• Heavy Atom Count: 9
• Complexity: 88.7

Purity/Quality:

98%,99%, ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC2=CSC=C2C=C1

Technology Process of Benzo[c]thiophene

There total 9 articles about Benzo[c]thiophene 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: 86.0%

syn- and anti-cis-8-thiabicyclo<4.3.0>non-3-ene 8-oxide (3533-72-0) → benzo[c]thiophene (270-82-6)

Guidance literature:

With aluminum oxide; at 130 ℃; for 2h; under 25 Torr;

DOI:10.1002/asia.201200698

Reference yield: 77.0%

1,3-Dihydro-2-methoxybenzothiophenium-trifluoromethansulfonat (131193-77-6) → benzo[c]thiophene (270-82-6)

Guidance literature:

With triethylamine; In dichloromethane; for 10h; Ambient temperature;

Reference yield:

α,α'-dibromo-o-xylene (91-13-4) → benzo[c]thiophene (270-82-6)

Guidance literature:

Multi-step reaction with 4 steps

1: 69 percent / Na₂S*9H₂O / Triethylhexadecylammonium-bromid / toluene; H₂O / 24 h / Ambient temperature

2: 81 percent / 60percent H₂O₂, HOAc / 4 h / 0 °C

3: 40 percent / CH₂Cl₂ / 7 h / Ambient temperature

4: 77 percent / NEt₃ / CH₂Cl₂ / 10 h / Ambient temperature

With sodium sulfide; dihydrogen peroxide; acetic acid; triethylamine; cetyltriethylammonium bromide; In dichloromethane; water; toluene;

upstream raw materials:

syn- and anti-cis-8-thiabicyclo<4.3.0>non-3-ene 8-oxide

1,3-Dihydro-2-methoxybenzothiophenium-trifluoromethansulfonat

1,3-Dihydrobenzothiophen

o-xylene

Downstream raw materials:

9,10-diphenyl-9,10-dihydro-9,10-episulfido-anthracene

Refernces

• 1、 Yu, Craig P.,Kimura, Ryoya,Kurosawa, Tadanori,Fukuzaki, Eiji,Watanabe, Tetsuya,Ishii, Hiroyuki,Kumagai, Shohei,Yano, Masafumi,Takeya, Jun,Okamoto, Toshihiro. "Air-Stable Benzo[ c]thiophene Diimide n-Type π-Electron Core". . p. 4448 - 4453. Retrieved 2019.
• 2、 -. "HETEROARYL COMPOUNDS AND METHODS OF USE THEREOF". Page/Page column 72. . Retrieved 2013/08/28.