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Merck

208868

Osmium tetroxide solution

2.5 wt. % in tert-butanol

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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:
329752049
UNSPSC Code:
12352303
MDL number:
MFCD00011150
form:
liquid

Product Name

Osmium tetroxide solution, 2.5 wt. % in tert-butanol

InChI

1S/4O.Os

SMILES string

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

InChI key

VUVGYHUDAICLFK-UHFFFAOYSA-N

vapor pressure

5.42 psi ( 20 °C)
6.76 psi ( 55 °C)

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

Quality Level

100

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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.

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.

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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

Storage Class

3 - Flammable liquids

wgk

WGK 2

flash_point_f

39.2 °F - closed cup

flash_point_c

4 °C - closed cup

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Certificates of Analysis (COA)

Lot/Batch Number
MKCX2588
MKCX8098
MKCR6297
MKCN6416
MKCJ8385

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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)
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
Manuel Marx et al.
Nature protocols, 7(2), 394-407 (2012-02-04)
In this report, we describe a reliable protocol for biocytin labeling of neuronal tissue and diaminobenzidine (DAB)-based processing of brain slices. We describe how to embed tissues in different media and how to subsequently histochemically label the tissues for light
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