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201030

Sigma-Aldrich

Osmium tetroxide

ReagentPlus®, 99.8%

Synonym(s):

Osmium(VIII)-oxide, ‘Osmic acid’

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100 MG
€63.80
250 MG
€99.50
500 MG
€198.00
1 G
€357.00

About This Item

Linear Formula:
OsO4
CAS Number:
Molecular Weight:
254.23
EC Number:
MDL number:
UNSPSC Code:
12352303
PubChem Substance ID:
NACRES:
NA.55
Assay:
99.8%
form:
crystalline
powder

€63.80


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vapor density

8.8 (vs air)

Quality Level

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.[1] Stereochemical aspects of the OsO4 assisted oxidation of allylic alcohols and their derivatives have been reported.[2] Its reaction with olefins has been investigated.[3] It participates as a catalyst for oxidizing fluoroquinolones, via reaction with potassium hexacyanoferrate(III) in alkaline medium. Kinetics of this oxidation reaction was studied.[1]

Application

Osmium tetroxide may be employed as a catalyst for the hydroxylation of sterically hindered olefins.[4]
Osmium tetroxide may be used in the following processes:
  • To promote the lactonization of alkenols to lactones.[5]
  • To mediate the selective oxidative cleavage of olefins by oxone to form the corresponding ketones or carboxylic acids.[6]
  • Dihydroxylation of mono-trans-di, and trisubstituted olefins to form 1,2-diols with high enantioselectivity in the presence of chiral amines.[7]
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.[8]

Legal Information

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

Pictograms

Skull and crossbonesCorrosion

Signal Word

Danger

Hazard Statements

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


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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)
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)
Highly enantioselective dihydroxylation of olefins by osmium tetroxide with chiral diamines.
Nakajima M, et al.
Tetrahedron, 49(47), 10793-10806 (1993)
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)

Questions

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  1. How can I determine the shelf life / expiration / retest date of this product?

    1 answer
    1. If this product has an expiration or retest date, it will be shown on the Certificate of Analysis (COA, CofA). If there is no retest or expiration date listed on the product's COA, we do not have suitable stability data to determine a shelf life. For these products, the only date on the COA will be the release date; a retest, expiration, or use-by-date will not be displayed.
      For all products, we recommend handling per defined conditions as printed in our product literature and website product descriptions. We recommend that products should be routinely inspected by customers to ensure they perform as expected.
      For products without retest or expiration dates, our standard warranty of 1 year from the date of shipment is applicable.
      For more information, please refer to the Product Dating Information document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/449/386/product-dating-information-mk.pdf

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  2. How is shipping temperature determined? And how is it related to the product storage temperature?

    1 answer
    1. Products may be shipped at a different temperature than the recommended long-term storage temperature. If the product quality is sensitive to short-term exposure to conditions other than the recommended long-term storage, it will be shipped on wet or dry-ice. If the product quality is NOT affected by short-term exposure to conditions other than the recommended long-term storage, it will be shipped at ambient temperature. As shipping routes are configured for minimum transit times, shipping at ambient temperature helps control shipping costs for our customers. For more information, please refer to the Storage and Transport Conditions document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/316/622/storage-transport-conditions-mk.pdf

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