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325473

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.

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

Storage Class Code

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

WGK

WGK 2

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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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Selenium dioxide catalyzed conversion of alcohols to alkyl chlorides by chlorotrimethylsilane.
Lee J G and Kang K K
The Journal of Organic Chemistry, 53(15), 3634-3637 (1988)
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)
Tropone. Selenium Dioxide Oxidation of 1, 3, 5-Cycloheptatriene.
Radlick P.
The Journal of Organic Chemistry, 29(4), 960-960 (1964)
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)
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