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671711

Sigma-Aldrich

(R)-(−)-N-(2,3-Epoxypropyl)phthalimide

≥99.0% (GC)

Synonym(s):

(R)-N-Glycidylphthalimide

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About This Item

Empirical Formula (Hill Notation):
C11H9NO3
CAS Number:
181140-34-1
Molecular Weight:
203.19
MDL number:
MFCD04973349
UNSPSC Code:
12352005
PubChem Substance ID:
24885103
NACRES:
NA.22

assay

≥99.0% (GC)

form

solid

optical activity

[α]/D -7 to -13°, c = 2.2 in chloroform

mp

100-102 °C

SMILES string

O=C1N(C[C@@H]2CO2)C(=O)c3ccccc13

InChI

1S/C11H9NO3/c13-10-8-3-1-2-4-9(8)11(14)12(10)5-7-6-15-7/h1-4,7H,5-6H2/t7-/m1/s1

InChI key

DUILGEYLVHGSEE-SSDOTTSWSA-N

Application

(R)-(-)-N-(2,3-Epoxypropyl)phthalimide may be used in the preparation of the following potential chiral solvating agents:
  • 2-[(2R)-2-hydroxy-3-[[(1R)-2-hydroxy-1-phenyl-ethyl]amino]propyl] isoindoline-1,3-dione
  • 2-[(2R)-2-hydroxy-3-[[(1R,2S)-2-hydroxyindan-1-yl]amino]propyl]isoindoline-1,3-dione
  • 2-[(2R)-2-hydroxy-3-[[(1R)-1-(hydroxymethyl)-propyl]amino]propyl] isoindoline-1,3-dione
  • 2-[(2R)-2-hydroxy-3-[[(1S)-1-phenylethyl]-amino]propyl]isoindoline-1,3-dione
It may also be used in the synthesis of 2-((5R)-2-oxo-5-oxazolidinyl) methyl)-1H-isoindole-1,3 (2H)-dione.

pictograms

Corrosion
GHS05

signalword

Danger

hcodes

H318

Hazard Classifications

Eye Dam. 1

Storage Class

11 - Combustible Solids

wgk_germany

WGK 2

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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A facile synthesis of 2-((5R)-2-oxo-5-oxazolidinyl) methyl)-1H-isoindole-1, 3 (2H)-dione.
Madhusudhan G, et al.
Indian J. Chem. B, 45, 1264-1268 (2006)
Amino alcohol based chiral solvating agents: synthesis and applications in the NMR enantiodiscrimination of carboxylic acids.
Bozkurt S, et al.
Tetrahedron Asymmetry, 22(5), 541-549 (2011)

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