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:
Molecular Weight:
115.17
Beilstein:
3587324
MDL number:
UNSPSC Code:
12352005
PubChem Substance ID:
NACRES:
NA.22
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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
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.
Signal Word
Warning
Hazard Statements
Precautionary Statements
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
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Lian Xia et al.
Journal of chromatography. A, 1500, 24-31 (2017-04-15)
A magnetic, mesoporous core/shell structured Fe
Direct organocatalytic aldol reactions in buffered aqueous media.
Cordova A, et al.
Chemical Communications (Cambridge, England), 24, 3024-3025 (2002)
Jingyu Wang et al.
Polymers, 11(4) (2019-04-10)
Conventional endovascular embolization of intracranial (or brain) aneurysms using helical detachable platinum coils can be time-consuming and occasionally requires retreatment due to incomplete coil packing. These shortcomings create a need for new biomedical devices and methods of achieving brain aneurysm
2-Phospha [3] ferrocenophanes with planar chirality: synthesis and use in enantioselective organocatalytic [3+ 2] cyclizations.
Journal of the American Chemical Society, 130(43), 14030-14031 (2008)
Roberta Fraioli et al.
Scientific reports, 7(1), 16363-16363 (2017-11-29)
Engineering the interface between biomaterials and tissues is important to increase implant lifetime and avoid failures and revision surgeries. Permanent devices should enhance attachment and differentiation of stem cells, responsible for injured tissue repair, and simultaneously discourage bacterial colonization; this
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