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64275

Sigma-Aldrich

Methanesulfonamide

≥97.0% (CHN)

Synonym(s):

Mesylamide, Methanesulfonic amide, Methanesulphonamide

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About This Item

Linear Formula:
CH3SO2NH2
CAS Number:
3144-09-0
Molecular Weight:
95.12
Beilstein:
1740835
EC Number:
221-553-6
MDL number:
MFCD00007940
UNSPSC Code:
12352100
PubChem Substance ID:
57651977
NACRES:
NA.22

Assay

≥97.0% (CHN)

form

solid

mp

85-89 °C (lit.)

SMILES string

CS(N)(=O)=O

InChI

1S/CH5NO2S/c1-5(2,3)4/h1H3,(H2,2,3,4)

InChI key

HNQIVZYLYMDVSB-UHFFFAOYSA-N

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Application

  • Methanesulfonamide is used in the synthesis of important organic reagents such as N-(2-methylthio-1-p-toluenesufonyl)methanesulfonamide and tert-butyl ((2-(trimethylsilyl)ethyl)sulfonyl)carbamate.
  • It can be used as a source of nitrogen in the conversion of carboxylic acids to corresponding nitriles.
  • It is widely used as a reagent in the synthesis of medicinally important compounds such as derivatives of indole-N-acetamide, methanesulfonamide pyrimidine-substituted 3,5-dihydroxy-6-heptenoates and repertaxin.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2

Storage Class Code

11 - Combustible Solids

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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2-Arylpropionic CXC chemokine receptor 1 (CXCR1) ligands as novel noncompetitive CXCL8 inhibitors.
Allegretti M, et al.
Journal of Medicinal Chemistry, 48(13), 4312-4331 (2005)
Synthesis and biological activity of methanesulfonamide pyrimidine-and N-methanesulfonyl pyrrole-substituted 3, 5-dihydroxy-6-heptenoates, a novel series of HMG-CoA reductase inhibitors.
Watanabe M, et al.
Bioorganic & Medicinal Chemistry, 5(2), 437-444 (1997)
Development and preliminary optimization of indole-N-acetamide inhibitors of hepatitis C virus NS5B polymerase.
Harper S, et al.
Journal of Medicinal Chemistry, 48(5), 1314-1317 (2005)
A Convenient Synthesis of Chloronitrobenzonitrile Isomers and Homologs.
Grivsky E M
Bull. Soc. Chim. Belg., 80(3?4), 245-252 (1971)
T H Maren et al.
The Journal of biological chemistry, 268(35), 26233-26239 (1993-12-15)
Aliphatic sulfonamides, as CH3SO2NH2, are very weak inhibitors of the carbonic anhydrases (KI congruent to 10(-4) M) and are extremely weak acids (Ka congruent to 10(-10.5) M). We now find CF3SO2NH2 a very potent inhibitor of carbonic anhydrase II (KI
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