디벤조시오펜

다이벤조싸이오펜 · 디벤조시오펜 · 다이벤조티오펜 · 디벤조티오펜 · Dibenzo[b,d]thiophene · Dibenzothiophe · DIBENZTHIOPHENE · AKOS 298

식별자 및 물리적 특성

CAS No.	132-65-0
분자식	C12H8S
평균 분자량	184.26 g/mol
단동위원소 질량	184.03467126 g/mol
SMILES	c1ccc2c(c1)sc1ccccc12
InChIKey	IYYZUPMFVPLQIF-UHFFFAOYSA-N
PubChem CID	3023
ChEMBL	CHEMBL219828
ChEBI	CHEBI:23681
EC No.	205-072-9
DTXSID	DTXSID0047741
현지명	디벤조시오펜

화학 및 물리적 성질

XLogP	4.4
극성 표면적	28.2
수소 결합 공여자 수	0
수소 결합 수용자 수	1
회전 가능 결합 수	0
무거운 원자 수	13
형식 전하	0
복잡도	170
물질 분류	Other Classes -> Other Organic Compounds
화장품	Antioxidant
SpringerMaterials Properties	Raman spectroscopy
LogP(분배 계수)	log Kow = 4.38
Color/Form	Colorless crystals
용해도	Very soluble in ethanol and benzene. Soluble in chloroform, and methanolIn water, 1.47 mg/L water at 25 °C0.0015g/l(약)
끓는 점	332.5 °C332-333 °C (lit.)
Decomposition	When heated to decomposition it emits toxic vapors of /sulfur oxide/.
녹는점	99.5 °C97-100 °C (lit.)
증기압	0.000205 [mmHg]2.05X10-4 mm Hg at 25 °C /extrapolated/
Physical Description	Colorless solid[Hawley] White crystalline powder with a stench[MSDSonline]
Collision Cross Section	130.2 Å² [M]+ [CCS Type: DTBuffer gas: N2Ionization: APCI+Dataset: TOXCASTSource Identifier: DTXSID0047741]153.42 Å² [M+K]+ [CCS Type: TWMethod: calibrated with polyalanine and drug standards]
밀도	1.1410 (rough estimate)
굴절률	1.6500 (estimate)
인화점	170 °C
저장 조건	Store below +30°C.
물리적 상태	결정질 분말 및/또는 덩어리
색상	하얀색
pH	7 (50g/l, H2O, 20℃)(slurry)
용해도	녹는
BRN	121101
헨리 상수	2.9×10-1 mol/(m3Pa) at 25℃, Duchowicz et al. (2020)
화장품 원료 기능	항산화제
InChI	1S/C12H8S/c1-3-7-11-9(5-1)10-6-2-4-8-12(10)13-11/h1-8H
InChIKey	IYYZUPMFVPLQIF-UHFFFAOYSA-N
SMILES	c1ccc2c(c1)sc3ccccc23
LogP(분배 계수)	4.380
NIST	Dibenzothiophene(132-65-0)
EPA	Dibenzothiophene (132-65-0)

화학적 성질

Dibenzothiophene is a yellow-green, crystalline solid with an mp of 99.5°C and a bp of 332.5°C. It is soluble in ethanol, benzene, chloroform, and methanol but insoluble in water. Its dipole moment is 0.83 D. It is quite stable under normal temperature and pressure.

안전 및 규제

GHS 분류	This chemical does not meet GHS hazard criteria for 4.3% (3 of 69) of reports.DangerH302 (92.8%): Harmful if swallowed [Warning Acute toxicity, oral]P261, P262, P264, P270, P271, P273, P280, P301+P317, P302+P352, P304+P340, P316, P317, P321, P330, P332+P317, P361+P364, P362+P364, P391, P403+P233, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 69 reports by companies from 8 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
규제 정보	Chemical: DibenzothiopheneDibenzothiophene: Does not have an individual approval but may be used under an appropriate group standard
유해성 요약	There is no data available on cancer in humans. There is inadequate evidence of carcinogenicity in experimental animals. Dibenzothiophene is not classifiable as to its carcinogenicity in humans. [IARC, Vol. 103, 2013] Classified as a heterocyclic aromatic compound[HSDB] Effects in lethal-dose animal studies include general anesthesia, coma, and fatty liver degeneration[RTECS] See POLYCYCLIC AROMATIC HYDROCARBONS.
FDA 요건	Drug products containing certain active ingredients offered over-the-counter (OTC) for certain uses. A number of active ingredients have been present in OTC drug products for various uses, as described below. However, based on evidence currently available, there are inadequate data to establish general recognition of the safety and effectiveness of these ingredients for the specified uses: dibenzothiophene is included in topical acne drug products.
History and Incidents	Thiophenes, a class of polycyclic aromatic compound (PAC), which contain a sulfur in one of the rings, are components of petroleum. The Erika oil spill (December 1999) impacted 400 km of Atlantic French coast. The Erika fuel is an heavy fuel containing 3-4% sulfur and sulfur compounds such as thiophenes. It has been reported that water and sediments were contaminated by dibenzothiophene (DBT). Analysis of DNA adducts in fish liver and mussel digestive gland, living in sites impacted by Erika oil spill, has revealed DNA adduct pattern different from a classical PAH contamination. Few studies report biological activities of thiophenes in the environment .... The Exxon Valdez spilled over 77 metric tons of dibenzothiophene and methyldibenzothiophenes into the environment.

용도

개요

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.

역사

Dibenzothiophene was first synthesized in 1870 by Stemhouse by heating biphenyl with iron scrap, but the assigned incorrect structure was corrected by Graebe. The natural dibenzothiophene was isolated from coal tar by Kruber. Besides this, various alkylated dibenzothiophenes have also been isolated from the crude oil, but it was difficult to desulfurize them catalytically. The presence of sulfur in the fuel produces sulfur dioxide when burnt and causes air pollution. Dibenzothiophene is a thermally stable compound and resistant to mild oxidizing agents. Depending on the nature of the oxidizing agent it is oxidized to corresponding sulfoxide and sulfone. There are numerous protocols for the construction of dibenzothiophene but some of them are limited to the synthesis of specific compounds due to noncompatibility of functional groups.

용도

Dibenzothiophene is used to investigate the effect of sulfur compounds in the gasoline range during the fluid catalytic cracking (FCC) process. It can also 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.

일반 설명

Dibenzothiophene is an important representative of polycyclic aromatic hydrocarbons (PAHs). Kinetics of hydrodesulfurization of dibenzothiophene on presulflded molybdenaalumina catalyst has been studied in a high-pressure-flow microreactor. Biodesulfurization of dibenzothiophene by selective cleavage of carbon sulphur bonds by a thermophilic bacterium Bacillus subtilis WU-S2B has been reported.

제조 및 합성 방법

제조 방법

Dibenzothiophene is prepared by the reaction of biphenyl with sulfur dichloride in the presence of aluminium chloride. The parent dibenzothiophene has been synthesized by heating a mixture of biphenyl with sulfur at 120°C for 24 h in the presence of anhydrous AlCl3 in 79% yields. This methodology is useful for the synthesis of substituted dibenzothiophenes. An alternative new protocol has been developed for the synthesis of dibenzothiophene and bridged dibenzothiophene by heating diphenyl and phenanthrene separately with H2S in the presence of mixed metal oxides (Al2O3, Cr2O3, and MgO) at 650°C.