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Sigma-Aldrich

Selenium dioxide

reagent grade, powder, 98%

Synonym(s):

NSC 56753, Selenium oxide

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About This Item

Linear Formula:
SeO2
CAS Number:
7446-08-4
Molecular Weight:
110.96
EC Number:
231-194-7
MDL number:
MFCD00003562
UNSPSC Code:
12352303
PubChem Substance ID:
24859512
NACRES:
NA.22

grade

reagent grade

vapor pressure

1 mmHg ( 157 °C)

assay

98%

form

powder

reaction suitability

reagent type: oxidant

color

off-white to pink

mp

315 °C (subl.) (lit.)

SMILES string

O=[Se]=O

InChI

1S/O2Se/c1-3-2

InChI key

JPJALAQPGMAKDF-UHFFFAOYSA-N

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Application

Selenium dioxide (SeO2) is mainly used to oxidize the α-methylene carbon atoms adjacent to a double bond to form allylic hydroxy derivatives.
Other applications:
  • SeO2 reacts with olefins in the presence of tert-butyl hydrogen peroxide to form allylic alcohols without the formation of rearrangement or dehydration by-products. This reagent system is also useful for the oxidation reactions of acetylenic fatty esters.
  • SeO2 can be used for the oxidation of 1,3,5-cycloheptatriene to form tropone.
  • Piperidoindole systems on oxidation with SeO2 forms either 2-acyl- or 3-acyl-indoles or fully aromatic β-carbolines, depending on the starting material.
  • SeO2 reacts with chlorotrimethylsilane to form selenium oxychloride in situ, which is an effective chlorinating reagent for alcohols. This reagent is a better alternative to thionyl chloride and other chlorinating agents.

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 2

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

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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Tropone. Selenium Dioxide Oxidation of 1, 3, 5-Cycloheptatriene.
Radlick P.
The Journal of Organic Chemistry, 29(4), 960-960 (1964)
Oxidation reactions of acetylenic fatty esters with selenium dioxide/tert-butyl hydroperoxide.
Jie M S L K, et al.
Lipids, 32(10), 1119-1123 (1997)
Selenium dioxide oxidations in the indole area. Synthesis of β-carboline alkaloids.
Cain M, et al.
Journal of the American Chemical Society, 105(4), 907-913 (1983)
Allylic oxidation of olefins by catalytic and stoichiometric selenium dioxide with tert-butyl hydroperoxide.
Umbreit M A and Sharpless K B
Journal of the American Chemical Society, 99(16), 5526-5528 (1977)
Tao Huang et al.
International journal of nanomedicine, 15, 4275-4288 (2020-07-02)
Selenium nanoparticles (Se NPs) are promising antibacterial agents to tackle the growing problem of antimicrobial resistance. The aim of this study was to fabricate Se NPs with a net positive charge to enhance their antibacterial efficacy. Se NPs were coated
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