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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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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)
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)
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
Katarzyna Nowak et al.
Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy, 70(4), 805-810 (2007-11-23)
The excited state (S1) dipole moment of m-AMSA (1), an acridine derivative with antitumor activity, was determined from solvatochromic shifts of the lowest energy absorption band in several organic solvents. The effect of the solute shape and the values of
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