N,N-dimethylmethanesulfonamide

• ChemBase ID: 8437
• Molecular Formular: C3H9NO2S
• Molecular Mass: 123.17406
• Monoisotopic Mass: 123.03539953
• SMILES: N(S(=O)(=O)C)(C)C
• Canonical SMILES: CN(S(=O)(=O)C)C
• InChI: InChI=1S/C3H9NO2S/c1-4(2)7(3,5)6/h1-3H3
• InChIKey: WCFDSGHAIGTEKL-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: N,N-dimethylmethanesulfonamide
• IUPAC Traditional name: N,N-dimethylmethanesulfonamide
• Synonyms: N,N-Dimethyl methanesulfonamide; N,N-Dimethylmethanesulfonamide; N,N-二甲基甲磺酰胺

Database IDs

• CAS Number: 918-05-8
• EC Number: 213-039-5
• MDL Number: MFCD00014740
• Beilstein Number: 1747409
• PubChem SID: 160971744
• PubChem CID: 70191

CALCULATED PROPERTIES

• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): -1.0878974
• LogD (pH = 7.4): -1.0878974
• Log P: -1.0878974
• Molar Refractivity: 27.8603 cm^3
• Polarizability: 11.6424 Å^3
• Polar Surface Area: 37.38 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 46-50°C; 49-50°C
• Boiling Point: 119-120°C/17mm

Safety Information

• Storage Warning: IRRITANT
• TSCA Listed: false; 否

Product Information

• Purity: 98+%

REFERENCES

• Lithiation, followed by acylation with esters and reductive cleavage of the C-S bond of the acylsulfonamide with sodium amalgam, provides a route to methyl ketones: J. Am. Chem. Soc., 87, 1345 (1965).
• Quaternization with a powerful alkylating agent leads to a methanesulfonyl trialkylammonium salt, suitable for the mesylation of sensitive substrates: J. Am. Chem. Soc., 97, 2566 (1975).