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Merck
CN

269190

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
UNSPSC Code:
12352100
NACRES:
NA.22
PubChem Substance ID:
24856315
EC Number:
230-442-1
Beilstein/REAXYS Number:
972316
MDL number:
MFCD00007556

Key Documents

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Product Name

Methanesulfonic anhydride, 97%

InChI key

IZDROVVXIHRYMH-UHFFFAOYSA-N

InChI

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

SMILES string

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

vapor density

3.3 (vs air)

assay

97%

form

solid

bp

125 °C/4 mmHg (lit.)

mp

64-67 °C (lit.)

functional group

sulfonic acid

Quality Level

200

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Application

Methanesulfonic anhydride can be used as an amine base to synthesize glycosyl mesylates in situ from the corresponding free hemiacetals under mild conditions.

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

signalword

Danger

hcodes

H314

Hazard Classifications

Skin Corr. 1A

supp_hazards

EUH014

Storage Class

8A - Combustible corrosive hazardous materials

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges

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Certificates of Analysis (COA)

Lot/Batch Number
BCCM9671
BCCK2389
BCCH3828
BCCC0957
BCCB9004

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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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