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277053 Sigma-Aldrich

(S)-(+)-2-(Methoxymethyl)pyrrolidine

99%

Synonym: O-Methyl-L-prolinol, SMP

  • CAS Number 63126-47-6

  • Empirical Formula (Hill Notation) C6H13NO

  • Molecular Weight 115.17

  •  Beilstein/REAXYS Number 3587324

  •  MDL number MFCD00010408

  •  PubChem Substance ID 24856730

  •  NACRES NA.22

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Properties

Related Categories Asymmetric Synthesis, Chemical Synthesis, Chiral Catalysts, Ligands, and Reagents, Proline-Based Organocatalysts
assay   99%
optical activity   [α]20/D +2.4°, c = 2 in benzene
refractive index   n20/D 1.4457 (lit.)
bp   62 °C/40 mmHg (lit.)
density   0.933 g/mL at 25 °C (lit.)
SMILES string   COC[C@@H]1CCCN1
InChI   1S/C6H13NO/c1-8-5-6-3-2-4-7-6/h6-7H,2-5H2,1H3/t6-/m0/s1
InChI key   CHPRFKYDQRKRRK-LURJTMIESA-N

Description

Application

(S)-(+)-2-(Methoxymethyl)pyrrolidine may be used to prepare planar chiral 2-phospha[3]ferrocenophanes. It may also be used as an organocatalyst in the cross-aldol reaction of dihydroxyacetone with p-nitrobenzaldehyde to form the corresponding polyol. SMP reacts with benzoylformic acid to form (S)-N-benzoylformyl-2-(methoxymethyl)-pyrrolidine.

Chiral auxiliary for asymmetric synthesis of propargyl alcohols and 4-nitrocyclohexanones, and for asymmetric Michael additions to enones.

Packaging

5 g in glass bottle

500 mg in amber glass bottle

Safety & Documentation

Safety Information

Symbol 
Signal word 
Warning
Hazard statements 
Precautionary statements 
Target organs 
Respiratory system
RIDADR 
UN 1993C 3 / PGIII
WGK Germany 
WGK 3
Flash Point(F) 
113.0 °F - closed cup
Flash Point(C) 
45 °C - closed cup
Protocols & Articles
Peer-Reviewed Papers
15

References

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