N-[(2S)-pyrrolidin-2-ylmethyl]aniline

• ChemBase ID: 144800
• Molecular Formular: C11H16N2
• Molecular Mass: 176.25814
• Monoisotopic Mass: 176.13134852
• SMILES: c1ccc(cc1)NC[C@@H]1CCCN1
• Canonical SMILES: C1CN[C@@H](C1)CNc1ccccc1
• InChI: InChI=1S/C11H16N2/c1-2-5-10(6-3-1)13-9-11-7-4-8-12-11/h1-3,5-6,11-13H,4,7-9H2/t11-/m0/s1
• InChIKey: MCHWKJRTMPIHRA-NSHDSACASA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: N-[(2S)-pyrrolidin-2-ylmethyl]aniline
• IUPAC Traditional name: N-[(2S)-pyrrolidin-2-ylmethyl]aniline
• Synonyms: (S)-(+)-2-(Anilinomethyl)pyrrolidine; (S)-2-(Anilinomethyl)pyrrolidine; (S)-(+)-2-(苯胺甲基)吡咯烷; (S)-2-(苯氨基甲基)吡咯烷

Database IDs

• CAS Number: 64030-44-0
• MDL Number: MFCD00015890
• Beilstein Number: 472065
• PubChem SID: 162239012; 24863349
• PubChem CID: 6950385

CALCULATED PROPERTIES

• H Acceptors: 2
• H Donor: 2
• LogD (pH = 5.5): -1.6896728
• LogD (pH = 7.4): -1.3862232
• Log P: 1.5471851
• Molar Refractivity: 56.1874 cm^3
• Polarizability: 21.506163 Å^3
• Polar Surface Area: 24.06 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Boiling Point: 111-112 °C/0.55 mmHg(lit.); 120-122 °C/2 mmHg; 120-122°C/2mm
• Flash Point: >110°C(230°F); 113 °C; 235.4 °F
• Density: 1.046; 1.046 g/mL at 25 °C(lit.)
• Refractive Index: 1.5750; n20/D 1.575
• Optical Rotation: [α]20/D +19±1°, c = 1% in ethanol; [α]20/D +19°, c = 1 in ethanol; +20 (c=1 in ethanol)

Safety Information

• Storage Warning: Air Sensitive
• European Hazard Symbols: Corrosive (C)
• UN Number: 3267; UN2735
• German water hazard class: 3
• Hazard Class: 8
• Packing Group: 2; III
• Risk Statements: 34
• Safety Statements: 26-36/37/39-45
• TSCA Listed: 否
• GHS Pictograms: GHS05
• GHS Signal Word: Danger
• GHS Hazard statements: H314; H314-H318
• GHS Precautionary statements: P280-P305 + P351 + P338-P310; P280-P305+P351+P338-P309-P310
• Personal Protective Equipment: Faceshields, full-face respirator (US), Gloves, Goggles, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter
• RID/ADR: UN 3267 8/PG 2

Product Information

• Purity: ≥97.0% (NT); 96%; 98%
• Grade: purum
• Empirical Formula (Hill Notation): C11H16N2

DETAILS

Sigma Aldrich - 374911

Packaging
1 g in glass bottle

Sigma Aldrich - 10418

Other Notes
Chiral auxiliary used in asymmetric Grignard and related reactions1,2; Preparation of a modified auxiliary useful for similar reactions3,4