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Merck

208868

Sigma-Aldrich

Osmium tetroxide solution

2.5 wt. % in tert-butanol

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About This Item

Fórmula lineal:
OsO4
Número de CAS:
Peso molecular:
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.

signalword

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_germany

WGK 2

flash_point_f

39.2 °F - closed cup

flash_point_c

4 °C - closed cup


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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
Carsten Købler et al.
Analytical and bioanalytical chemistry, 406(16), 3863-3873 (2014-01-23)
Ultrastructural characterisation is important for understanding carbon nanotube (CNT) toxicity and how the CNTs interact with cells and tissues. The standard method for this involves using transmission electron microscopy (TEM). However, in particular, the sample preparation, using a microtome to

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