[(2S)-1-benzylpyrrolidin-2-yl]methanol

• ChemBase ID: 144885
• Molecular Formular: C12H17NO
• Molecular Mass: 191.26948
• Monoisotopic Mass: 191.13101417
• SMILES: c1ccc(cc1)CN1CCC[C@H]1CO
• Canonical SMILES: OC[C@@H]1CCCN1Cc1ccccc1
• InChI: InChI=1S/C12H17NO/c14-10-12-7-4-8-13(12)9-11-5-2-1-3-6-11/h1-3,5-6,12,14H,4,7-10H2/t12-/m0/s1
• InChIKey: ZAIQBJPTOXDDKA-LBPRGKRZSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: [(2S)-1-benzylpyrrolidin-2-yl]methanol
• IUPAC Traditional name: [(2S)-1-benzylpyrrolidin-2-yl]methanol
• Synonyms: (S)-(-)-1-Benzylpyrrolidine-2-methanol; N-Benzyl-L-prolinol; (S)-1-N-Benzyl-prolinol; (S)-(-)-1-苄基吡咯烷-2-甲醇; N-苄基-L-脯氨醇

Database IDs

• CAS Number: 53912-80-4
• MDL Number: MFCD00011728
• Beilstein Number: 3663640
• PubChem SID: 24848355; 24858233; 162239097
• PubChem CID: 719760

CALCULATED PROPERTIES

• Acid pKa: 15.11204
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): -1.6743542
• LogD (pH = 7.4): -0.3316241
• Log P: 1.6901051
• Molar Refractivity: 58.1042 cm^3
• Polarizability: 22.808998 Å^3
• Polar Surface Area: 23.47 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Boiling Point: 115-120 °C/0.5 mmHg(lit.)
• Flash Point: 110 °C; 230 °F
• Density: 1.08 g/mL at 25 °C(lit.)
• Refractive Index: n20/D 1.541; n20/D 1.541(lit.)
• Optical Rotation: [α]20/D -72.7°, neat; [α]20/D -74±2°, neat

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: Eyeshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥98.0% (sum of enantiomers, GC); 98%; 99%
• Grade: purum
• Empirical Formula (Hill Notation): C12H17NO

DETAILS

Sigma Aldrich - 302112

Application
Precursor in the synthesis of proline-derived homochiral amine oxides.1 Starting material for enantiomerically pure 3-hydroxypiperidine, a structural feature present in many natural products.2
Packaging
5, 25 g in glass bottle

Sigma Aldrich - 13839

Caution
may discolor to yellow on storage
Other Notes
Chiral auxiliary1