(2S)-1-{[5-(dimethylamino)naphthalen-1-yl]sulfonyl}pyrrolidine-2-carboxylic acid

• ChemBase ID: 102095
• Molecular Formular: C17H20N2O4S
• Molecular Mass: 348.4167
• Monoisotopic Mass: 348.11437813
• SMILES: CN(C)c1cccc2c(cccc12)S(=O)(=O)N1CCC[C@H]1C(=O)O
• Canonical SMILES: OC(=O)[C@@H]1CCCN1S(=O)(=O)c1cccc2c1cccc2N(C)C
• InChI: InChI=1S/C17H20N2O4S/c1-18(2)14-8-3-7-13-12(14)6-4-10-16(13)24(22,23)19-11-5-9-15(19)17(20)21/h3-4,6-8,10,15H,5,9,11H2,1-2H3,(H,20,21)/t15-/m0/s1
• InChIKey: ZHJIWURDCGMVQE-HNNXBMFYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-1-{[5-(dimethylamino)naphthalen-1-yl]sulfonyl}pyrrolidine-2-carboxylic acid
• IUPAC Traditional name: (2S)-1-[5-(dimethylamino)naphthalen-1-ylsulfonyl]pyrrolidine-2-carboxylic acid
• Synonyms: DANSYL-L-PROLINE CYCLOHEXYLAMMONIUM SALT; Dansyl-L-proline; 丹磺酰-L-脯氨酸

Database IDs

• CAS Number: 1239-94-7; 42808-11-7
• EC Number: 255-949-5
• MDL Number: MFCD00069514
• Beilstein Number: 497317
• PubChem SID: 162088683; 24888961
• PubChem CID: 688442

CALCULATED PROPERTIES

• Acid pKa: 3.315486
• H Acceptors: 5
• H Donor: 1
• LogD (pH = 5.5): 0.05795296
• LogD (pH = 7.4): -1.1889964
• Log P: 0.7967784
• Molar Refractivity: 92.259 cm^3
• Polarizability: 36.923283 Å^3
• Polar Surface Area: 77.92 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 111-121°C; 150-153 °C
• Optical Rotation: [α]20/D -45±2°, c = 1% in 1 M HCl

Safety Information

• Storage Condition: 0°C
• German water hazard class: 3
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥99.0% (TLC)
• Empirical Formula (Hill Notation): C17H20N2O4S

DETAILS

MP Biomedicals - 02100125

Cyclohexylammonium Salt

Sigma Aldrich - 87778

Other Notes
Derivatizing agent for HPLC; assay of enantiomeric purity of amines1