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370142

Sigma-Aldrich

(S)-(−)-2-Hydroxy-N-methylsuccinimide

97%

Synonym(s):

(S)-(−)-3-Hydroxy-1-methyl-2,5-pyrrolidinedione

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About This Item

Empirical Formula (Hill Notation):
C5H7NO3
CAS Number:
Molecular Weight:
129.11
Beilstein/REAXYS Number:
4350458
MDL number:
UNSPSC Code:
12352005
PubChem Substance ID:

Quality Level

assay

97%

form

solid

optical activity

[α]20/D −75°, c = 3.5 in ethanol

mp

82-87 °C (lit.)

SMILES string

CN1C(=O)C[C@H](O)C1=O

InChI

1S/C5H7NO3/c1-6-4(8)2-3(7)5(6)9/h3,7H,2H2,1H3/t3-/m0/s1

InChI key

NLKACWKSCREJEL-VKHMYHEASA-N

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Application

(S)-(-)-2-Hydroxy-N-methylsuccinimide may be used as a chiral auxiliary to enhance the diastereomeric excess of the Diels-Alder adducts formed in asymmetric Diels-Alder reactions.

pictograms

Exclamation mark

signalword

Warning

Hazard Classifications

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

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves


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Novel Potassium-Channel Openers: Preparation and Pharmacological Evaluation of Racemic and Optically Active N-(6-Amino-3-pyridyl)-N'-bicycloalkyl-N''-cyanoguanidine Derivatives
Eda M, et al.
Journal of Medicinal Chemistry, 37(13), 1983-1990 (1994)
Asymmetric Diels-Alder addition of cyclopentadiene to chiral naphthoquinones.
Brimble MA, et al.
Tetrahedron Asymmetry, 9(7), 1239-1255 (1998)

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