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8.00653

Selenium dioxide

(sublimed) for synthesis

Synonym(s):

Selenium dioxide, Selenious anhydride, Selenium(IV) oxide

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About This Item

Empirical Formula (Hill Notation):
O2Se
CAS Number:
7446-08-4
Molecular Weight:
110.96
MDL number:
MFCD00003562
UNSPSC Code:
12352303
EC Index Number:
231-194-7
NACRES:
NA.22
Form:
crystals
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vapor pressure

<1 Pa ( 20 °C)

Quality Level

200

form

crystals

potency

68.1 mg/kg LD50, oral (Rat)

reaction suitability

reagent type: oxidant

pH

2 (20 °C, 10 g/L in H2O)

mp

340 °C

solubility

1353 g/L

density

3.95 g/cm3 at 20 °C

storage temp.

2-30°C

SMILES string

[Se](=O)=O

InChI

1S/O2Se/c1-3-2

InChI key

JPJALAQPGMAKDF-UHFFFAOYSA-N

Application

Selenium dioxide (SeO2) is mainly used to oxidize the activated carbon-bearing positions (α-methylene carbon atoms), particularly at allylic or propargylic sites. The more substituted end of the double bond undergoes oxidation.
It can also be used as an oxidizing reagent to synthesize:
  • Amides by oxidative amidation of aldehydes with amines.
  • Tropone from cycloheptatriene in the presence of potassium dihydrogen phosphate.
  • Acetyltetrahydrobenzofurans by oxidation of conjugated dienones.
  • 9-hydroxy-undec-10-ynoate from methyl undec-10-ynoate.

Analysis Note

Assay (iodometric): ≥ 98.0 %

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Danger

Hazard Classifications

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

wgk

WGK 2

flash_point_f

Not applicable

flash_point_c

Not applicable

Storage Class

6.1D - Non-combustible acute toxic Cat.3 / toxic hazardous materials or hazardous materials causing chronic effects

Regulatory Information

危险化学品

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Jacek Młochowski et al.
Molecules (Basel, Switzerland), 20(6), 10205-10243 (2015-06-06)
A variety of selenium compounds were proven to be useful reagents and catalysts for organic synthesis over the past several decades. The most interesting aspect, which emerged in recent years, concerns application of hydroperoxide/selenium(IV) oxide and hydroperoxide/organoselenium catalyst systems, as
M S Jie et al.
Lipids, 32(10), 1119-1123 (1997-11-14)
Reaction of methyl undec-10-ynoate (1) with selenium dioxide/tert-butyl hydroperoxide (TBHP) in aqueous dioxane gave methyl 9-oxo-undec-10-ynoate (2, 9%) and 9-hydroxy-undec-10-ynoate (3, 60%), while methyl octadec-9-ynoate (4) yielded mixtures of positional isomers of mono-keto (viz. methyl 8-oxo- and 11-oxo-octadec-9-ynoate, 5, 5%)
Selenium (IV) Oxide
Hoekstra WJ, et al.
eEROS (Encyclopedia of Reagents for Organic Synthesis) (2017)

Global Trade Item Number

SKUGTIN
800653100004022536361437
800653005004022536361413
800653000504027269276256
800653025004022536361420