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201030

Sigma-Aldrich

Osmium tetroxide

ReagentPlus®, 99.8%

Synonym(s):

Osmium(VIII)-oxide, ‘Osmic acid’

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About This Item

Linear Formula:
OsO4
CAS Number:
20816-12-0
Molecular Weight:
254.23
EC Number:
244-058-7
MDL number:
MFCD00011150
UNSPSC Code:
12352303
PubChem Substance ID:
329751973
NACRES:
NA.55

vapor density

8.8 (vs air)

Quality Level

200

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

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.
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.

Legal Information

ReagentPlus is a registered trademark of Merck KGaA, Darmstadt, Germany

Pictograms

Skull and crossbonesCorrosion
GHS06,GHS05

Signal Word

Danger

Hazard Statements

H300 + H310 + H330,H314

Hazard Classifications

Acute Tox. 1 Dermal - Acute Tox. 2 Inhalation - Acute Tox. 2 Oral - Eye Dam. 1 - Skin Corr. 1B

Storage Class Code

6.1A - Combustible acute toxic Cat. 1 and 2 / very toxic hazardous materials

WGK

WGK 1

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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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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)
Highly enantioselective dihydroxylation of olefins by osmium tetroxide with chiral diamines.
Nakajima M, et al.
Tetrahedron, 49(47), 10793-10806 (1993)
Direct Lactonization of Alkenols via Osmium Tetroxide-Mediated Oxidative Cleavage.
Schomaker JM, et al.
Organic Letters, 5(17), 3089-3092 (2003)
Hwang, K.C.
Journal of the Chemical Society. Chemical Communications, 173-173 (1995)
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)
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