201030

Sigma-Aldrich

Osmium tetroxide

ReagentPlus®, 99.8%

Synonym(s):
Osmium(VIII)-oxide, ‘Osmic acid’
Linear Formula:
OsO4
CAS Number:
Molecular Weight:
254.23
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.55

Quality Level

vapor density

8.8 (vs air)

vapor pressure

7 mmHg ( 20 °C)

product line

ReagentPlus®

assay

99.8%

form

crystalline
powder

reaction suitability

reagent type: oxidant

bp

130 °C (lit.)

mp

39.5-41 °C (lit.)

storage temp.

2-8°C

SMILES string

O=[Os](=O)(=O)=O

InChI

1S/4O.Os

InChI key

VUVGYHUDAICLFK-UHFFFAOYSA-N

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General description

Osmium tetroxide (OsO4) is widely employed as a catalyst in various organic reactions. Stereochemical aspects of the OsO4 assisted oxidation of allylic alcohols and their derivatives have been reported. Its reaction with olefins has been investigated. It participates as a catalyst for oxidizing fluoroquinolones, via reaction with potassium hexacyanoferrate(III) in alkaline medium. Kinetics of this oxidation reaction was studied.

Application

Widely used oxidizer for visualizing cells in microscopy. Promotes oxidative cleavage of graphene layers in carbon nanotubes creating the possibility of opening ′windows′ in fullerene cages.
Osmium tetroxide may be employed as a catalyst for the hydroxylation of sterically hindered olefins.
Osmium tetroxide may be used in the following processes:
  • To promote the lactonization of alkenols to lactones.
  • To mediate the selective oxidative cleavage of olefins by oxone to form the corresponding ketones or carboxylic acids.
  • Dihydroxylation of mono-trans-di, and trisubstituted olefins to form 1,2-diols with high enantioselectivity in the presence of chiral amines.

Packaging

250, 500 mg in ampule
1 g in ampule

Legal Information

ReagentPlus is a registered trademark of Sigma-Aldrich Co. LLC

Pictograms

CorrosionSkull and crossbones

Signal Word

Danger

Hazard Statements

RIDADR

UN 2471 6.1 / PGI

WGK Germany

WGK 1

Certificate of Analysis

Certificate of Origin

Highly enantioselective dihydroxylation of olefins by osmium tetroxide with chiral diamines.
Nakajima M, et al.
Tetrahedron, 49(47), 10793-10806 (1993)
Hwang, K.C.
Journal of the Chemical Society. Chemical Communications, 173-173 (1995)
Osmium tetroxide-promoted catalytic oxidative cleavage of olefins: an organometallic ozonolysis.
Travis BR, et al.
Journal of the American Chemical Society, 124(15), 3824-3825 (2002)
Direct Lactonization of Alkenols via Osmium Tetroxide-Mediated Oxidative Cleavage.
Schomaker JM, et al.
Organic Letters, 5(17), 3089-3092 (2003)
Osmium tetroxide catalyzed hydroxylation of hindered olefins.
Ray R and Matteson DS.
Tetrahedron Letters, 21(5), 449-450 (1980)

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