[(2S)-5-oxopyrrolidin-2-yl]methyl 4-methylbenzene-1-sulfonate

• ChemBase ID: 145393
• Molecular Formular: C12H15NO4S
• Molecular Mass: 269.3168
• Monoisotopic Mass: 269.07217897
• SMILES: Cc1ccc(cc1)S(=O)(=O)OC[C@@H]1CCC(=O)N1
• Canonical SMILES: O=C1CC[C@H](N1)COS(=O)(=O)c1ccc(cc1)C
• InChI: InChI=1S/C12H15NO4S/c1-9-2-5-11(6-3-9)18(15,16)17-8-10-4-7-12(14)13-10/h2-3,5-6,10H,4,7-8H2,1H3,(H,13,14)/t10-/m0/s1
• InChIKey: AMZNHHZJURKRFX-JTQLQIEISA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: [(2S)-5-oxopyrrolidin-2-yl]methyl 4-methylbenzene-1-sulfonate
• IUPAC Traditional name: [(2S)-5-oxopyrrolidin-2-yl]methyl 4-methylbenzenesulfonate
• Synonyms: (S)-(+)-5-(Hydroxymethyl)-2-pyrrolidinone p-toluenesulfonate; (S)-(+)-5-羟甲基-2-吡咯烷酮对甲苯磺酸酯

Database IDs

• CAS Number: 51693-17-5
• MDL Number: MFCD00274229
• PubChem SID: 24868128; 162239599
• PubChem CID: 2734055

CALCULATED PROPERTIES

• Acid pKa: 13.430007
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): 1.3541673
• LogD (pH = 7.4): 1.3541671
• Log P: 1.3541675
• Molar Refractivity: 66.1631 cm^3
• Polarizability: 26.66392 Å^3
• Polar Surface Area: 72.47 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 124-128 °C(lit.)
• Optical Rotation: [α]20/D +8.5°, c = 1 in ethanol

Safety Information

• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-36
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves

Product Information

• Purity: 95%
• Empirical Formula (Hill Notation): C12H15NO4S

DETAILS

Sigma Aldrich - 444537

Packaging
5 g in glass bottle
Application
Serves as a building block in the synthesis of (R)- and (S)-diaminovaleric acids1 and of 5-azasemicorrin bidentate nitrogen ligands for enantioselective catalysis.2