(2R,5R)-2,5-dimethylpyrrolidine

• ChemBase ID: 152094
• Molecular Formular: C6H13N
• Molecular Mass: 99.17412
• Monoisotopic Mass: 99.10479942
• SMILES: C[C@@H]1CC[C@H](N1)C
• Canonical SMILES: C[C@@H]1CC[C@H](N1)C
• InChI: InChI=1S/C6H13N/c1-5-3-4-6(2)7-5/h5-7H,3-4H2,1-2H3/t5-,6-/m1/s1
• InChIKey: ZEBFPAXSQXIPNF-PHDIDXHHSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,5R)-2,5-dimethylpyrrolidine
• IUPAC Traditional name: (2R,5R)-2,5-dimethylpyrrolidine
• Synonyms: (2R,5R)-(-)-trans-2,5-Dimethylpyrrolidine; (2R,5R)-(-)-反-2,5-二甲基吡咯烷

Database IDs

• CAS Number: 62617-70-3
• MDL Number: MFCD01863020
• Beilstein Number: 4652641
• PubChem SID: 24866019; 162246239
• PubChem CID: 641767

CALCULATED PROPERTIES

• H Acceptors: 1
• H Donor: 1
• LogD (pH = 5.5): -2.195254
• LogD (pH = 7.4): -2.143705
• Log P: 1.046069
• Molar Refractivity: 31.072 cm^3
• Polarizability: 12.598926 Å^3
• Polar Surface Area: 12.03 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Flash Point: 44.6 °F; 7 °C
• Density: 0.852 g/mL at 20 °C(lit.)
• Refractive Index: n20/D 1.431
• Optical Rotation: [α]20/D -19.0±1.5°, c = 2% in methylene chloride

Safety Information

• European Hazard Symbols: Corrosive (C); Flammable (F)
• UN Number: 2924
• German water hazard class: 3
• Hazard Class: 3
• Packing Group: 2
• Risk Statements: 11-22-34
• Safety Statements: 26-36/37/39-45
• GHS Pictograms: GHS02; GHS05; GHS07
• GHS Signal Word: Danger
• GHS Hazard statements: H225-H302-H314
• GHS Precautionary statements: P210-P280-P305 + P351 + P338-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 2924 3/PG 2
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥97.0% (GC)
• Empirical Formula (Hill Notation): C6H13N

DETAILS

Sigma Aldrich - 41566

Other Notes
Important chiral auxiliary with a pseudo C2 axis; diastereoselective alkylation of ketone enamines 1; Highly stereoselective addition reactions of the enamine of β-keto esters (vinylogous urethanes) 2; Radical reactions of unsaturated amides3
Packaging
50, 250 mg in glass bottle