(2S)-2-(methoxymethyl)pyrrolidin-1-amine

• ChemBase ID: 151210
• Molecular Formular: C6H14N2O
• Molecular Mass: 130.18816
• Monoisotopic Mass: 130.11061308
• SMILES: COC[C@@H]1CCCN1N
• Canonical SMILES: COC[C@@H]1CCCN1N
• InChI: InChI=1S/C6H14N2O/c1-9-5-6-3-2-4-8(6)7/h6H,2-5,7H2,1H3/t6-/m0/s1
• InChIKey: BWSIKGOGLDNQBZ-LURJTMIESA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-(methoxymethyl)pyrrolidin-1-amine
• IUPAC Traditional name: (2S)-2-(methoxymethyl)pyrrolidin-1-amine
• Synonyms: SAMP; (S)-(-)-1-Amino-2-(methoxymethyl)pyrrolidine; (2S)-2-(Methoxymethyl)-1-pyrrolidinamine; (S)-1-Amino-2-(methoxymethyl)pyrrolidine; [(2S)-2-(Methoxymethyl)pyrrolidin-1-yl]amine; (S)-(-)-1-Amino-2-(methoxymethyl)pyrrolidine; (S)-(-)-1-氨基-2-(甲氧基甲基)吡咯烷

Database IDs

• CAS Number: 59983-39-0
• MDL Number: MFCD00064485
• Beilstein Number: 1523794
• PubChem SID: 24846168; 24856982; 162245367
• PubChem CID: 7156993

CALCULATED PROPERTIES

• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): -1.1626784
• LogD (pH = 7.4): -0.47170112
• Log P: -0.44943118
• Molar Refractivity: 37.4322 cm^3
• Polarizability: 14.598005 Å^3
• Polar Surface Area: 38.49 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Boiling Point: 42 °C/1.8 mmHg(lit.)
• Flash Point: 161.6 °F; 72 °C
• Density: 0.97 g/mL at 25 °C(lit.)
• Refractive Index: n20/D 1.465; n20/D 1.465(lit.)
• Optical Rotation: [α]20/D -79°, neat; [α]20/D -82±2°, neat

Safety Information

• 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
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥95.0% (sum of enantiomers, GC); 95%
• Grade: purum
• Optical Purity: ee: 97% (GLC)
• Empirical Formula (Hill Notation): C6H14N2O

DETAILS

Sigma Aldrich - 281573

Packaging
1 g in ampule
Application
Undergoes condensation reactions with carbonyl compounds to produce hydrazones which are useful synthons in highly enantioselective syntheses.1,2,3

Toronto Research Chemicals - A611925

(S)-(-)-1-Amino-2-(methoxymethyl)pyrrolidine is a disubstituted pyrrolidine. (S)-(-)-1-Amino-2-(methoxymethyl)pyrrolidine undergoes condensation reactions with carbonyl compounds to produce hydrazones which are useful for highly enantioselective synthesis

REFERENCES

• Enders, D. et al.: Tetrahed. Lett., 2, 191 (1977)
• Zakharova, V. et al.: Zeitsch. Naturforsch. B Chem. Sci., 61, 464 ·2006);