Dibenzothiophene

Base Information

• Chemical Name: Dibenzothiophene
• CAS No.: 132-65-0
• Molecular Formula: C12H8S
• Molecular Weight: 184.262
• Hs Code.: 29349990
• European Community (EC) Number: 205-072-9
• NSC Number: 756732,2843
• UNII: Z3D4AJ1R48
• DSSTox Substance ID: DTXSID0047741
• Nikkaji Number: J2.523B
• Wikipedia: Dibenzothiophene
• Wikidata: Q544767
• NCI Thesaurus Code: C47484
• Metabolomics Workbench ID: 53911
• ChEMBL ID: CHEMBL219828
• Mol file: 132-65-0.mol

Synonyms:dibenzothiophene

Chemical Property of Dibenzothiophene

Chemical Property:

• Appearance/Colour: White to light yellow crystal powder
• Vapor Pressure: 0.000281mmHg at 25°C
• Melting Point: 97-100 °C(lit.)
• Refractive Index: 1.756
• Boiling Point: 332.5 °C at 760 mmHg
• Flash Point: 114.806 °C
• PSA: 28.24000
• Density: 1.252 g/cm³
• LogP: 4.05450
• Storage Temp.: Store below +30°C.
• Solubility.: 0.0015g/l (Lit.)
• Water Solubility.: SOLUBLE
• XLogP3: 4.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 184.03467143
• Heavy Atom Count: 13
• Complexity: 170

Purity/Quality:

99% ^*data from raw suppliers

Dibenzothiophene ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn,N
• Statements: 22-20/21/22-50/53
• Safety Statements: 36-61-60

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Other Classes -> Other Organic Compounds
• Canonical SMILES: C1=CC=C2C(=C1)C3=CC=CC=C3S2
• Description: Dibenzothiophene (DBT) is an organosulfur compound found in crude oil and petroleum. It is a colourless solid that is chemically somewhat similar to anthracene. Dibenzothiophene is used as a chemical intermediate in cosmetics and pharmaceuticals (NLM, 2006).It is used to investigate the effect of sulfur compounds in gasoline range during the fluid catalytic cracking (FCC) process.
• Uses: Dibenzothiophene (DBT) can be used as:A starting material for the synthesis of corresponding sulfoxide and sulfone by oxidative desulfurization using various catalysts.A template for the synthesis of surface molecular imprinted polymer (SMIP). SMIP is applicable for the removal of dibenzothiophene during desulfurization of the gasoline.A precursor for the synthesis of DBT based π-conjugating polymers. Dibenzothiophene is used to investigate the effect of sulfur compounds in gasoline range during the fluid catalytic cracking (FCC) process.

Technology Process of Dibenzothiophene

There total 266 articles about Dibenzothiophene 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: 98.0%

2-(5-benzyloxy-pentylsulfanyl)-2'-iodo-biphenyl → dibenzothiophene (132-65-0) + ((pentyloxy)methyl)benzene (6382-14-5)

Guidance literature:

With triethyl borane; tri-n-butyl-tin hydride; In dichloromethane; at -78 ℃; for 0.5h;

DOI:10.1002/1615-4169(20010226)343:2<166::AID-ADSC166>3.0.CO;2-O

Reference yield: 50.0%

4'-nitrobiphenyl-2-sulphenanilide (110228-47-2) → dibenzothiophene (132-65-0) + 1-phenyl-2-[(2-phenylphenyl)disulfanyl]benzene (19813-97-9) + 4-nitro-aniline (100-01-6,104810-17-5) + 2-(biphenyl-2-ylthio)-4-nitroaniline (110228-55-2)

Guidance literature:

In benzene; at 150 ℃; for 20h;

Reference yield:

→ dibenzothiophene (132-65-0) + 3-phenyldibenzo[b,d]thiophene (98251-30-0) + 2-dibenzothiophenethiol (68560-31-6) + benzene-1,4-dithiol (624-39-5) + diphenyl sulfide (139-66-2) + 1,4-bis(phenylthio)benzene (3459-94-7) + 2-(phenylthio)-dibenzothiophene + 4-phenylmercaptothiophenol (52872-99-8) + [1,1'-biphenyl]-4-yl(phenyl)sulfane (59090-57-2) + thiophenol (108-98-5)

Guidance literature:

at 650 ℃; Inert atmosphere; Pyrolysis;

DOI:10.1021/ma902118s

upstream raw materials:

2-bromo-2’-fluoro-1,1’-biphenyl

o-fluorophenylboronic acid

1,2,3,4-tetrahydrodibenzothiophene

dibenzothiophene sulfone

Downstream raw materials:

β-(dibenzothiophene-2-carbonyl)propionic acid

4-Butyldibenzothiophen

4-benzylthiodibenzothiophene

dibenzo[b,d]-thiophene-4-ylmethanol

Refernces

• 1、 Klochkova et al.. "-". . . Retrieved 1977.
• 2、 Pandya, Vrajesh B.,Jain, Mukul R.,Chaugule, Balaji V.,Patel, Jigar S.,Parmar, Bhavesh M.,Joshi, Jignesh K.,Patel, Pankaj R.. "Efficient synthesis of unsymmetrical dibenzothiophenes by acid-mediated intramolecular cyclization of biaryl methyl sulfoxides". . p. 497 - 505. Retrieved 2012.
• 3、 Shaykhutdinova, Polina,Kemper, Sebastian,Oestreich, Martin. "Refinement of the Catalyst Backbone of Chiral Intramolecular Silicon–Sulfur Lewis Pairs: Improved Enantioselectivity in the Diels–Alder Reaction of Cyclohexa-1,3-diene and Chalcone Derivatives". . p. 2896 - 2901. Retrieved 2018.
• 4、 Shimizu, Masaki,Ogawa, Mai,Tamagawa, Tomokazu,Shigitani, Ryosuke,Nakatani, Masaki,Nakano, Yoshiki. "Copper-Catalyzed Double S-Arylation of Potassium Thioacetate with Dibenziodolium Triflates: Facile Synthesis of Unsymmetrical Dibenzothiophenes". . p. 2785 - 2788. Retrieved 2016.
• 5、 Kabe, Toshiaki,Ishihara, Atsushi,Nomura, Masatoshi,Itoh, Tetsuro,Qi, Pingyen. "Effects of Solvents in Deep Desulfurization of Benzothiophene and Dibenzothiophene". . p. 2233 - 2236. Retrieved 1991.
• 6、 Ashby et al.. "-". . p. 1251. Retrieved 1971.
• 7、 Morofuji, Tatsuya,Yoshida, Tatsuki,Tsutsumi, Ryosuke,Yamanaka, Masahiro,Kano, Naokazu. "Arylation of aryllithiums with: S-arylphenothiazinium ions for biaryl synthesis". . p. 13995 - 13998. Retrieved 2020.
• 8、 Depew, M. Catherine,Zhongli, Liu,Wan, Jeffrey K. S.. "Chemically Induced Dynamic Electron Polarization (CIDEP) of Some Sulfur-Containing Cation Radicals: Evidence of the Charge-Transfer Processes between Quinone Cation Radicals and Sulfur Heterocyclic Compounds". . p. 2480 - 2481. Retrieved 1983.
• 9、 Nagata, Toshiyuki,Yoshimura, Toshiaki,Fujimori, Ken,Oae, Shigeru. "REDUCTION OF SULFOXIDES AND SULFILIMINES CATALYZED BY METALLOPORPHINS". . p. 341 - 344. Retrieved 1984.
• 10、 Campaigne et al.. "-". . p. 4111. Retrieved 1962.