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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

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

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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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