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269190

Sigma-Aldrich

Methanesulfonic anhydride

97%

Synonym(s):

Mesyl anhydride, Mesylic anhydride, Methanesulfonyl anhydride, Methylsulfonyl methanesulfonate

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About This Item

Linear Formula:
(CH3SO2)2O
CAS Number:
7143-01-3
Molecular Weight:
174.20
Beilstein:
972316
EC Number:
230-442-1
MDL number:
MFCD00007556
UNSPSC Code:
12352100
PubChem Substance ID:
24856315
NACRES:
NA.22

vapor density

3.3 (vs air)

Quality Level

200

Assay

97%

form

solid

bp

125 °C/4 mmHg (lit.)

mp

64-67 °C (lit.)

functional group

sulfonic acid

SMILES string

CS(=O)(=O)OS(C)(=O)=O

InChI

1S/C2H6O5S2/c1-8(3,4)7-9(2,5)6/h1-2H3

InChI key

IZDROVVXIHRYMH-UHFFFAOYSA-N

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General description

Methanesulfonic anhydride is an organic compound that is commonly used as a reagent for the preparation of methyl sulfonates (mesylates). It is also used in the synthesis of methanesulfonamides using various amine precursors. Additionally, the mixture of methanesulfonic anhydride and dimethyl sulfoxide can be used as an oxidizing agent for the oxidation of primary and secondary alcohols to aldehydes and ketones.

Pictograms

Corrosion
GHS05

Signal Word

Danger

Hazard Statements

H314

Hazard Classifications

Skin Corr. 1A

Supplementary Hazards

EUH014

Storage Class Code

8A - Combustible corrosive hazardous materials

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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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Mark C Wilkinson
Organic letters, 13(9), 2232-2235 (2011-03-29)
The utility of methanesulfonic anhydride for promoting the Friedel-Crafts acylation reaction of aryl and alkyl carboxylic acids is disclosed. This reagent allows the preparation of aryl ketones in good yield with minimal waste containing no metallic or halogenated components, clearly
Keith Smith et al.
Organic & biomolecular chemistry, 2(21), 3150-3154 (2004-10-27)
Regioselective methanesulfonylation of simple aromatics using methanesulfonic anhydride can be achieved over zeolite catalysts. For example, methanesulfonylation of toluene over various cation-exchanged zeolite beta catalysts affords higher para-selectivity in the synthesis of methyl tolyl sulfone than standard Friedel-Crafts methanesulfonylation utilising
Mohammad Hasani et al.
The journal of physical chemistry. B, 123(8), 1815-1821 (2019-02-20)
Protic ionic liquids (PILs) are made by proton transfer from a Brønsted acid to a base and are of interest for their solvent and electrolyte properties such as high ionic conductivity. Unfortunately, many PILs have been misnamed, because their ionic

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