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255122

Sigma-Aldrich

1,2-Benzodiphenylene sulfide

99%

Synonym(s):

Benzo[b]naphtho[2,1-d]thiophene

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About This Item

Empirical Formula (Hill Notation):
C16H10S
CAS Number:
239-35-0
Molecular Weight:
234.32
EC Number:
205-948-0
MDL number:
MFCD00010043
UNSPSC Code:
12352100
PubChem Substance ID:
24855289
NACRES:
NA.22

assay

99%

form

solid

mp

188-190 °C (lit.)

solubility

chloroform: soluble 2.5%, clear to very slightly hazy, colorless to faint yellow or tan

SMILES string

c1ccc2c(c1)ccc3c4ccccc4sc23

InChI

1S/C16H10S/c1-2-6-12-11(5-1)9-10-14-13-7-3-4-8-15(13)17-16(12)14/h1-10H

InChI key

YEUHHUCOSQOCIX-UHFFFAOYSA-N

General description

1,2-benzodiphenylene sulfide is a rare constituent of coal tar. Photodeoxygenation of 1,2-benzodiphenylene sulfoxide, generates an intermediate capable of oxidizing the solvent benzene to phenol[1]. Liquid-phase photolysis of 1,2-benzodiphenylene sulfide to generate atomic oxygen [O(3P)] or an equivalent active oxygen species has been reported[2].

Application

1,2-Benzodiphenylene sulfide has been used in direct screening of sediment samples for polycyclic aromatic hydrocarbons by flow manifold coupled on-line to a fluorimetric detector[3].

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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Certificates of Analysis (COA)

Lot/Batch Number
MKCS1675
MKCS1244
MKCR5753
MKCP1119
MKCM3057

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Direct automatic screening and individual determination of polycyclic aromatic hydrocarbons using supercritical fluid extraction coupled on-line with liquid chromatography and fluorimetric detection.
Zougagh M, et al.
Analytica Chimica Acta, 524(1), 279-285 (2004)
Keith B Thomas et al.
The Journal of organic chemistry, 68(5), 1886-1891 (2003-03-01)
A liquid-phase photolysis of 1,2-benzodiphenylene sulfoxide, 1, and dibenzothiophene sulfoxide, 2, was used to generate atomic oxygen [O(3P)] or an equivalent active oxygen species. The reaction for sulfoxide photodeoxygenation was similar to a microwave discharge method for generating O(3P) atoms
E Lucien et al.
The Journal of organic chemistry, 66(13), 4576-4579 (2001-06-26)
We report that the photodeoxygenation of 1,2-benzodiphenylene sulfoxide, 1, generates an intermediate capable of oxidizing the solvent benzene to phenol. The reactivity of the intermediate was probed with various substrates (2-methylbutane, chloride ion, and para-substituted aryl sulfides). The intermediate produced

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