(2S)-2-(methoxymethyl)pyrrolidine

• ChemBase ID: 149379
• Molecular Formular: C6H13NO
• Molecular Mass: 115.17352
• Monoisotopic Mass: 115.09971404
• SMILES: COC[C@@H]1CCCN1
• Canonical SMILES: COC[C@@H]1CCCN1
• InChI: InChI=1S/C6H13NO/c1-8-5-6-3-2-4-7-6/h6-7H,2-5H2,1H3/t6-/m0/s1
• InChIKey: CHPRFKYDQRKRRK-LURJTMIESA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-(methoxymethyl)pyrrolidine
• IUPAC Traditional name: (2S)-2-(methoxymethyl)pyrrolidine
• Synonyms: SMP; O-Methyl-L-prolinol; (S)-(+)-2-(Methoxymethyl)pyrrolidine; (S)-2-(Methoxymethyl)pyrrolidine; O-甲基-L-脯氨醇; (S)-(+)-2-(甲氧基甲基)吡咯烷; (S)-(+)-2-(甲氧甲基)吡咯烷

Database IDs

• CAS Number: 63126-47-6
• MDL Number: MFCD00010408
• Beilstein Number: 3587324
• PubChem SID: 24883791; 24856730; 162243545
• PubChem CID: 671217

CALCULATED PROPERTIES

• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): -3.0112984
• LogD (pH = 7.4): -2.732641
• Log P: 0.22571056
• Molar Refractivity: 32.9481 cm^3
• Polarizability: 13.269628 Å^3
• Polar Surface Area: 21.26 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Boiling Point: 61-62°C/40mm; 62 °C/40 mmHg(lit.)
• Flash Point: 113 °F; 45 °C; 45°C(113°F)
• Density: 0.932 g/mL at 20 °C(lit.); 0.933; 0.933 g/mL at 25 °C(lit.)
• Refractive Index: 1.4457; n20/D 1.4457(lit.); n20/D 1.446
• Optical Rotation: [α]20/D +2.4±0.3°, c = 2% in benzene; [α]20/D +2.4°, c = 2 in benzene; +2.2 (c=2 in benzene)

Safety Information

• Storage Warning: Air Sensitive
• European Hazard Symbols: Irritant (Xi)
• UN Number: 1993; UN1993
• German water hazard class: 3
• Hazard Class: 3
• Packing Group: 3; III
• Risk Statements: 10-36/37/38
• Safety Statements: 26-36; 26-37
• TSCA Listed: 否
• GHS Pictograms: GHS02; GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H226-H315-H319-H335
• GHS Precautionary statements: P210-P241-P303+P361+P353-P305+P351+P338-P405-P501A; P261-P305 + P351 + P338
• Personal Protective Equipment: Eyeshields, Faceshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter
• RID/ADR: UN 1993 3/PG 3

Product Information

• Purity: ≥98.0% (sum of enantiomers, GC); 98%; 99%
• Grade: purum
• Empirical Formula (Hill Notation): C6H13NO

DETAILS

Sigma Aldrich - 277053

Packaging
5 g in glass bottle
500 mg in glass bottle
Application
Chiral auxiliary for asymmetric synthesis of propargyl alcohols1 and 4-nitrocyclohexanones,2 and for asymmetric Michael additions to enones.3

Sigma Aldrich - 65090

Other Notes
Chiral auxiliary with a broad range of different applications, review1