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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)

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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)
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)
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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