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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:
Molecular Weight:
95.12
Beilstein:
1740835
EC Number:
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
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

Signal Word

Warning

Hazard Statements

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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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)
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)
Sevgi Karakuş et al.
European journal of medicinal chemistry, 44(9), 3591-3595 (2009-03-28)
Due to a continuing effort to develop new antiviral agents, a series of 1-[4-(methanesulfonamido)-3-phenoxyphenyl]-3-alkyl/aryl thioureas 3a-i have been synthesized by the reaction of alkyl/aryl isothiocyanates with 4-amino-2-phenoxymethanesulfonanilide. These derivatives were structurally characterized by the use of spectral techniques and evaluated

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