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Sigma-Aldrich

Benzeneseleninic acid anhydride

70%

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Linear Formula:
C6H5SeOOSeOC6H5
CAS Number:
17697-12-0
Molecular Weight:
360.13
Beilstein:
2332406
MDL number:
MFCD00001991
UNSPSC Code:
12352100
PubChem Substance ID:
24852763

Assay

70%

form

powder

impurities

<30% benzeneseleninic acid

mp

165-170 °C (lit.)

SMILES string

O=[Se](O[Se](=O)c1ccccc1)c2ccccc2

InChI

1S/C12H10O3Se2/c13-16(11-7-3-1-4-8-11)15-17(14)12-9-5-2-6-10-12/h1-10H

InChI key

FHPZOWOEILXXBD-UHFFFAOYSA-N

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General description

Oxidation of phenols by benzeneseleninic acid anhydride yields ortho-quinones. Benzeneseleninic anhydride acts as a mild oxidant for the conversion of benzylic hydrocarbons into aldehydes or ketones.

Application

Benzeneseleninic acid anhydride was used to oxidize hydrazines to afford azo-compounds.

Signal Word

Danger

Hazard Statements

H301 + H331,H373,H410

Hazard Classifications

Acute Tox. 3 Inhalation - Acute Tox. 3 Oral - Aquatic Acute 1 - Aquatic Chronic 1 - STOT RE 2

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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Comparative oxidation of phenols with benzeneseleninic anhydride and with benzeneseleninic acid.
Barton DHR, et al.
Tetrahedron, 44(20), 6397-6406 (1988)
Preparation of aldehydes and ketones by oxidation of benzylic hydrocarbons with benzeneseleninic anhydride.
Barton DHR, et al.
Tetrahedron Letters, 20(35), 3331-3334 (1979)
Dehydrogenation of hydrazines and of 4-azacholestan-3-one with benzeneseleninic acid and benzeneseleninic anhydride.
Back TG.
Journal of the Chemical Society. Chemical Communications, 6, 278-279 (1978)
Naotoshi Toki et al.
Chemical & pharmaceutical bulletin, 52(8), 1009-1012 (2004-08-12)
Benzeneseleninic anhydride in the presence of tert-butyl hydroperoxide in chlorobenzene at about 70 degrees C is an effective oxidizing agent for the selective oxidation of alcohols at the benzylic position.
T Iida et al.
Journal of lipid research, 29(8), 1097-1101 (1988-08-01)
A facile one-step conversion of stereoisomeric methyl 3-hydroxycholanoates to 1,4-dien-3-one, by treatment in boiling toluene with iodoxybenzene catalyzed by benzeneselenic anhydride, is described. The direct oxidation-dehydrogenation at C-3 is applicable to other cholanoates (hyodeoxycholic, chenodeoxycholic, ursodeoxycholic, deoxycholic, and cholic) when
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