benzyl (2S)-pyrrolidine-2-carboxylate hydrochloride

• ChemBase ID: 131318
• Molecular Formular: C12H16ClNO2
• Molecular Mass: 241.71394
• Monoisotopic Mass: 241.08695644
• SMILES: c1ccc(cc1)COC(=O)[C@@H]1CCCN1.Cl
• Canonical SMILES: O=C([C@@H]1CCCN1)OCc1ccccc1.Cl
• InChI: InChI=1S/C12H15NO2.ClH/c14-12(11-7-4-8-13-11)15-9-10-5-2-1-3-6-10;/h1-3,5-6,11,13H,4,7-9H2;1H/t11-;/m0./s1
• InChIKey: NEDMOHHWRPHBAL-MERQFXBCSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: benzyl (2S)-pyrrolidine-2-carboxylate hydrochloride
• IUPAC Traditional name: benzyl (2S)-pyrrolidine-2-carboxylate hydrochloride
• Synonyms: L-Proline benzyl ester hydrochloride; H-Pro-OBzl.HCl; L-脯氨酸苄酯 盐酸盐; L-脯氨酸苄酯盐酸盐

Database IDs

• CAS Number: 16652-71-4
• EC Number: 240-700-5
• MDL Number: MFCD00039002
• Beilstein Number: 3598081
• PubChem SID: 162225596; 24862432
• PubChem CID: 2733413

CALCULATED PROPERTIES

• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): -0.16295876
• LogD (pH = 7.4): 1.4450895
• Log P: 1.7732258
• Molar Refractivity: 57.446 cm^3
• Polarizability: 22.933678 Å^3
• Polar Surface Area: 38.33 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 146-148°C; 148-151 °C(lit.)
• Optical Rotation: [α]20/D -48°, c = 1 in H2O; -44 (c=1 in methanol)

Safety Information

• Storage Warning: Hygroscopic
• German water hazard class: 3
• TSCA Listed: 否
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: -20°C

Product Information

• Purity: 98%
• Empirical Formula (Hill Notation): C12H15NO2 · HCl

DETAILS

Sigma Aldrich - 364460

Packaging
5 g in glass bottle
Application
Extensive applications in peptide chemistry and used as a chiral auxiliary in the asymmetric Diels-Alder reaction.1