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

• ChemBase ID: 77290
• Molecular Formular: C6H13NO
• Molecular Mass: 115.17352
• Monoisotopic Mass: 115.09971404
• SMILES: N1(CCC[C@H]1CO)C
• Canonical SMILES: OC[C@@H]1CCCN1C
• InChI: InChI=1S/C6H13NO/c1-7-4-2-3-6(7)5-8/h6,8H,2-5H2,1H3/t6-/m0/s1
• InChIKey: VCOJPHPOVDIRJK-LURJTMIESA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: [(2S)-1-methylpyrrolidin-2-yl]methanol
• IUPAC Traditional name: [(2S)-1-methylpyrrolidin-2-yl]methanol
• Synonyms: (S)-(+)-2-(Hydroxymethyl)-1-methylpyrrolidine; (S)-2-Hydroxymethyl-1-methylpyrrolidine; N-Methyl-L-prolinol; (S)-(-)-1-Methyl-2-pyrrolidinemethanol; (S)-(-)-1-Methyl-2-pyrrolidinemethanol; N-Methyl-L-prolinol; [(2S)-1-methylpyrrolidin-2-yl]methanol; (S)-2-羟甲基-1-甲基吡咯烷; N-甲基-L-脯氨醇; (S)-(-)-1-甲基-2-吡咯烷甲醇; N-甲基-L-脯氨醇

Database IDs

• CAS Number: 34381-71-0
• EC Number: 251-981-9
• MDL Number: MFCD00011727
• Beilstein Number: 79851
• PubChem SID: 24858272; 24885858; 162042163
• PubChem CID: 643492

CALCULATED PROPERTIES

• Acid pKa: 15.113259
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): -3.4511359
• LogD (pH = 7.4): -2.2805235
• Log P: -0.03436801
• Molar Refractivity: 33.4916 cm^3
• Polarizability: 13.196873 Å^3
• Polar Surface Area: 23.47 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Boiling Point: 67-69 °C/12 mmHg(lit.)
• Flash Point: 145.4 °F; 63 °C
• Density: 0.968 g/mL at 25 °C(lit.)
• Refractive Index: n20/D 1.469; n20/D 1.469(lit.)
• Optical Rotation: [α]19/D -49.5°, c = 5 in methanol; [α]20/D -51±1°, c = 5% in methanol
• Hydrophobicity(logP): 0.237

Safety Information

• Storage Warning: Irritant
• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter; Eyeshields, Gloves, half-mask respirator (US), multi-purpose combination respirator cartridge (US)
• Storage Temperature: -20°C

Product Information

• Purity: ≥99.0% (sum of enantiomers, GC); 95%; 95+%; 96%
• Grade: purum
• Empirical Formula (Hill Notation): C6H13NO

DETAILS

Sigma Aldrich - 302767

Packaging
5, 25 g in glass bottle
Application
Precursor to phosphine ligands for catalytic asymmetric Grignard cross-coupling reactions.1

Sigma Aldrich - 68890

Other Notes
Chiral ligand used in the enantioface conjugate addition of cuprates to enones1,2; Used as starting material for the preparation of (S)-2-cyanomethyl-1-methylpyrrolidine without loss of optical purity3; Intermediate in an optically active alkaloid synthesis4; Preparation of (S)-prophos5