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213004

Sigma-Aldrich

Benzeneseleninic acid

99%

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About This Item

Linear Formula:
C6H5SeO2H
CAS Number:
6996-92-5
Molecular Weight:
189.07
Beilstein/REAXYS Number:
1929765
EC Number:
230-271-2
MDL number:
MFCD00002100
UNSPSC Code:
12352100
PubChem Substance ID:
24852762
NACRES:
NA.22

Quality Level

100

assay

99%

form

solid

mp

121-124 °C (lit.)

SMILES string

O[Se](=O)c1ccccc1

InChI

1S/C6H6O2Se/c7-9(8)6-4-2-1-3-5-6/h1-5H,(H,7,8)

InChI key

WIHKGDVGLJJAMC-UHFFFAOYSA-N

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General description

Benzeneseleninic acid oxidizes hydrazine or 1,2-disubstituted derivatives to corresponding diazenes.

Application

Benzeneseleninic acid was used as catalyst during the oxidation of sulfides to sulfoxides via ligand coupling on the iodine atom. It was also used in the preparation of 3-methoxy-17a-oxa-D-homoestra-l,3,5(10)-trien-17-one.

signalword

Danger

Hazard Classifications

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

Storage Class

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Facile oxidation of sulfides to sulfoxides using iodosobenzene and benzeneseleninic acid as a catalyst.
Roh KR, et al.
Tetrahedron Letters, 32(6), 793-796 (1991)
Oxidation of hydrazines with benzeneseleninic acid and anhydride.
Back TG, et al.
The Journal of Organic Chemistry, 46(8), 1564-1570 (1981)
1, 2-Hydrogen shifts in thermal and photic Bamford-Stevens reactions of cyclohexanones. Activation by an endocyclic oxygen.
Olmstead KK and Nickon A.
Tetrahedron, 54(40), 12161-12172 (1998)
Craig A Bayse
Journal of inorganic biochemistry, 104(1), 1-8 (2009-10-30)
The toxicity of selenium is a major barrier to its application to the prevention of cancer, cardiovascular disease, and other chronic ailments. Organic seleninic acids, as well as other reducible selenium compounds, have been shown to react with biological sulfhydryls
S Zheng et al.
Hua xi yi ke da xue xue bao = Journal of West China University of Medical Sciences = Huaxi yike daxue xuebao, 26(4), 371-374 (1995-12-01)
In view of the negative relationship between selenium and cancer, we designed and synthesized eleven substituted benzeneselenic acids (IVa-k) The antineoplastic activity of the title compounds was evaluated via the tests of inhibition of acetylcholinesterase, HL-60 and K562 in vitro

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