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277053

Sigma-Aldrich

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

99%

Synonym(s):

O-Methyl-L-prolinol, SMP

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About This Item

Empirical Formula (Hill Notation):
C6H13NO
CAS Number:
63126-47-6
Molecular Weight:
115.17
Beilstein:
3587324
MDL number:
MFCD00010408
UNSPSC Code:
12352005
PubChem Substance ID:
24856730
NACRES:
NA.22

Assay

99%

form

liquid

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

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.

Pictograms

FlameExclamation mark
GHS02,GHS07

Signal Word

Warning

Hazard Statements

H226,H315,H319,H335

Hazard Classifications

Eye Irrit. 2 - Flam. Liq. 3 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

3 - Flammable liquids

WGK

WGK 3

Flash Point(F)

113.0 °F - closed cup

Flash Point(C)

45 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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