1-(4-aminophenyl)-N-methylmethanesulfonamide

• ChemBase ID: 84796
• Molecular Formular: C8H12N2O2S
• Molecular Mass: 200.25808
• Monoisotopic Mass: 200.06194863
• SMILES: S(=O)(=O)(Cc1ccc(cc1)N)NC
• Canonical SMILES: CNS(=O)(=O)Cc1ccc(cc1)N
• InChI: InChI=1S/C8H12N2O2S/c1-10-13(11,12)6-7-2-4-8(9)5-3-7/h2-5,10H,6,9H2,1H3
• InChIKey: CIWNHTXCBHTWRV-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-(4-aminophenyl)-N-methylmethanesulfonamide
• IUPAC Traditional name: 1-(4-aminophenyl)-N-methylmethanesulfonamide
• Synonyms: 4-Amino-N-methylβenzenemethanesulfonamide; 1-(4-Aminophenyl)-N-methylmethanesulfonamide; 4-(((Methylamino)sulfonyl)methyl)aniline; 4-Amino-N-methyl-α-toluenesulfonamide; (4-Aminophenyl)-N-methylmethanesulphonamide; 4-Amino-N-methylbenzenemethanesulfonamide; 4-Amino-N-methyl-α-toluenesulfonamide; 4-Amino-N-methylbenzenemethanesulfonamide; 4-Amino-N-methylbenzylsulfonamide; 4-Amino-N-methyl-alpha-toluenesulfonamide; 4-氨基-N-甲基苯甲磺酰胺; 4-氨基-N-甲基-α-甲苯磺酰胺; 4-氨基-N-甲基-alpha-甲苯磺胺

Database IDs

• CAS Number: 109903-35-7
• EC Number: 000-000-0
• MDL Number: MFCD00671697
• Beilstein Number: 5865321
• PubChem SID: 162071912; 24883513
• PubChem CID: 2778131

CALCULATED PROPERTIES

• Acid pKa: 11.459515
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): -0.28228763
• LogD (pH = 7.4): -0.26410788
• Log P: -0.26383707
• Molar Refractivity: 52.4004 cm^3
• Polarizability: 20.478249 Å^3
• Polar Surface Area: 72.19 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 140-142 °C(lit.); 140-142°C

Safety Information

• Storage Warning: Irritant
• European Hazard Symbols: Nature polluting (N); Irritant (Xi); Harmful (Xn)
• UN Number: 2811; UN3077
• German water hazard class: 3
• Hazard Class: 6.1; 9
• Packing Group: 3; III
• Risk Statements: 22-43; 36/37/38-43-51/53
• Safety Statements: 24-26-37-57; 36/37
• TSCA Listed: 否
• GHS Pictograms: GHS06; GHS07; GHS09
• GHS Signal Word: Danger
• GHS Hazard statements: H301-H317; H315-H319-H317-H335-H411-H401
• GHS Precautionary statements: P261-P305+P351+P338-P302+P352-P321-P405-P501A; P280-P301 + P310
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Faceshields, Gloves
• RID/ADR: UN 2811 6.1/PG 3

Product Information

• Purity: 97%
• Empirical Formula (Hill Notation): C8H12N2O2S

DETAILS

Sigma Aldrich - 647179

Packaging
5, 25 g in glass bottle

Toronto Research Chemicals - A618100

4-Amino-N-methyl-α-toluenesulfonamide is an intermediate used in the synthesis of Sumatriptan (S810000).

REFERENCES

• Prasad, A., et al.: Eur. J. Med. Chem., 24, 199 (1989)
• Abdou, N., et al.: J. Pharm. Sci., 6, 25 (1989)
• Tasaka, A., et al.: Chem. Pharma. Bull., 41, 1035 (1989)
• Starting material for an efficient Fischer indole synthesis of the 5-HT_1D receptor agonist avitriptan: J. Org. Chem., 62, 9192 (1997).