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Merck
CN

671711

(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

Key Documents

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Assay

≥99.0% (GC)

form

solid

optical activity

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

mp

100-102 °C

functional group

ether
imide

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

Signal Word

Danger

Hazard Statements

H318

Precautionary Statements

P280 - P305 + P351 + P338

Hazard Classifications

Eye Dam. 1

Storage Class Code

11 - Combustible Solids

WGK

WGK 2

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
BCCD3771
BCCB3252
BCBM8279V
BCBG2053V
BCBB9881

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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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