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208868

Sigma-Aldrich

Osmium tetroxide solution

2.5 wt. % in tert-butanol

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Linear Formula:
OsO4
CAS Number:
Molecular Weight:
254.23
MDL number:
UNSPSC Code:
12352303
PubChem Substance ID:
NACRES:
NA.55

vapor pressure

5.42 psi ( 20 °C)
6.76 psi ( 55 °C)

Quality Level

form

liquid

contains

tert-butyl hydroperoxide as stabilizer

reaction suitability

reagent type: oxidant

concentration

2.5 wt. % in tert-butanol

density

1.0 g/mL at 20 °C
0.811 g/mL at 25 °C

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 solution (OsO4) is commonly used as a catalyst in various organic reactions. OsO4 is a strong oxidizing agent and can be used to break carbon-carbon bonds. Additionally, it can be used in the cis dihydroxylation of alkenes, diastereoselective and asymmetric dihydroxylation, osmylation and oxyamination of alkenes.

Application

Osmium tetroxide solution is used as catalyst in the:
  • Cis dihydroxylation of alkenes to form cis-1,2-diols.
  • Direct oxidation of 1,4-dienes to yield carboxylic acids using oxone as a co-oxidant.

Osmium tetroxide can also be used:
  • In the stereoselective synthesis of (+)-norrisolide.

Signal Word

Danger

Hazard Classifications

Acute Tox. 3 Dermal - Acute Tox. 3 Inhalation - Acute Tox. 4 Oral - Eye Dam. 1 - Flam. Liq. 2 - Muta. 2 - Skin Irrit. 2 - Skin Sens. 1 - STOT SE 3

Target Organs

Respiratory system

WGK

WGK 2

Flash Point(F)

39.2 °F

Flash Point(C)

4 °C


Certificates of Analysis (COA)

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Asymmetric induction in the reaction of osmium tetroxide with olefins.
Hentges SG and Barry Sharpless K.
Journal of the American Chemical Society, 102(12), 4263-4265 (1980)
On stereochemistry of osmium tetroxide oxidation of allylic alcohol systems: empirical rule.
Cha JK, et al.
Tetrahedron Letters, 24(37), 3943-3946 (1983)
Kinetics of Oxidation of Some Fluoroquinolones by Hexacyanoferrate (III) in Alkaline Medium.
Diab N, et al.
International Journal of Chemistry (Canadian Center of Science and Education), 34(2), 1388-1388 (2013)
F Wyss et al.
Veterinary pathology, 52(6), 1235-1242 (2015-01-27)
Pododermatitis is frequent in captive flamingos worldwide, but little is known about the associated histopathologic lesions. Involvement of a papillomavirus or herpesvirus has been suspected. Histopathologic evaluation and viral assessment of biopsies from 19 live and 10 dead captive greater
Yukihiko Sugita et al.
The Journal of general virology, 92(Pt 11), 2485-2493 (2011-07-29)
Negatively stained influenza virions sometimes show irregular morphology and are often referred to as pleomorphic. However, this irregular morphology has not been visualized when ultrathin-section transmission and scanning electron microscopies are used. This study focused on the effects of ultracentrifugation

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