(2S)-N-(3,5-dimethylphenyl)-3-methyl-2-(N-methylformamido)butanamide

• ChemBase ID: 141651
• Molecular Formular: C15H22N2O2
• Molecular Mass: 262.34738
• Monoisotopic Mass: 262.16812795
• SMILES: Cc1cc(cc(c1)NC(=O)[C@H](C(C)C)N(C)C=O)C
• Canonical SMILES: O=CN([C@H](C(=O)Nc1cc(C)cc(c1)C)C(C)C)C
• InChI: InChI=1S/C15H22N2O2/c1-10(2)14(17(5)9-18)15(19)16-13-7-11(3)6-12(4)8-13/h6-10,14H,1-5H3,(H,16,19)/t14-/m0/s1
• InChIKey: WWUZCRRIJZUXEZ-AWEZNQCLSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-N-(3,5-dimethylphenyl)-3-methyl-2-(N-methylformamido)butanamide
• IUPAC Traditional name: (2S)-N-(3,5-dimethylphenyl)-3-methyl-2-(N-methylformamido)butanamide
• Synonyms: Kenamide; (S)-N-(3,5-Dimethylphenyl)-3-methyl-2-(N-formyl-N-methylamino)butanamide; (S)-N-(3,5-二甲基苯基)-3-甲基-2-(N-甲酰基-N-甲氨基)丁酰胺

Database IDs

• CAS Number: 731797-86-7
• MDL Number: MFCD10565636
• PubChem SID: 162235885
• PubChem CID: 11402790

CALCULATED PROPERTIES

• Acid pKa: 13.355023
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): 2.763752
• LogD (pH = 7.4): 2.763752
• Log P: 2.7637525
• Molar Refractivity: 77.7026 cm^3
• Polarizability: 29.15121 Å^3
• Polar Surface Area: 49.41 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 97-104 °C
• Optical Rotation: [α]22/D -229°, c = 1 in chloroform

Safety Information

• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 22
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H302
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• Storage Temperature: 2-8°C

Product Information

• Purity: 97%
• Empirical Formula (Hill Notation): C15H22N2O2

DETAILS

Sigma Aldrich - 693561

Application
Used in the asymmetric reduction of prochiral N-aryl ketimines with trichlorosilane.1†2
Packaging
50, 100 mg in glass bottle