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Merck

201030

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
NACRES:
NA.55
PubChem Substance ID:
329751973
UNSPSC Code:
12352303
EC Number:
244-058-7
MDL number:
MFCD00011150
Assay:
99.8%
Form:
crystalline, powder

Key Documents

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InChI key

VUVGYHUDAICLFK-UHFFFAOYSA-N

InChI

1S/4O.Os

SMILES string

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

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

Quality Level

200

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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

signalword

Danger

Hazard Classifications

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

Storage Class

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

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Certificates of Analysis (COA)

Lot/Batch Number
BCCN6483
BCCN1963
BCCN5511
BCCN1962
BCCN1961

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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)
Osmium tetroxide catalyzed hydroxylation of hindered olefins.
Ray R and Matteson DS.
Tetrahedron Letters, 21(5), 449-450 (1980)
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