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Merck
CN

277053

(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
UNSPSC Code:
12352005
NACRES:
NA.22
PubChem Substance ID:
24856730
MDL number:
MFCD00010408
Beilstein/REAXYS Number:
3587324

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InChI

1S/C6H13NO/c1-8-5-6-3-2-4-7-6/h6-7H,2-5H2,1H3/t6-/m0/s1

SMILES string

COC[C@@H]1CCCN1

InChI key

CHPRFKYDQRKRRK-LURJTMIESA-N

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.)

functional group

ether

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

signalword

Warning

Hazard Classifications

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

target_organs

Respiratory system

Storage Class

3 - Flammable liquids

wgk

WGK 3

flash_point_f

113.0 °F - closed cup

flash_point_c

45 °C - closed cup

ppe

Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
10397KJ
08831JJ
07128LE
07413LC
14007BO

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Stereocontrolled Addition Reaction of Organometallics to Chiral a-Keto Amides.
Fujisawa T, et al.
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