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(S)-(+)-Glycidyl Phthalimide

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(S)-(+)-Glycidyl Phthalimide Basic information

Product Name:
(S)-(+)-Glycidyl Phthalimide
Synonyms:
  • (S)-2-OXIRANYLMETHYL-ISOINDOLE-1,3-DIONE
  • (S)-(+)-GLYCIDYL PHTHALIMIDE
  • (S)-GLYCIDYL PHTHALIMIDE
  • 2-[[(2S)-oxiran-2-yl]methyl]isoindole-1,3-dione
  • Rivaroxaban Impurity 39
  • 2-((2S)-OXIRANYLMETHYL)-1H-ISOINDOLE-1,3(2H)-DIONE
  • (S)-(+)-N-(2,3-Epoxypropyl)phthalimide
  • (S)-N-Glycidylphthalimide
CAS:
161596-47-0
MF:
C11H9NO3
MW:
203.19
EINECS:
454-720-9
Product Categories:
  • Intermediate of Rivaroxaban
  • N-Substituted Maleimides, Succinimides & Phthalimides
  • N-Substituted Phthalimides
  • Oxiranes
  • Simple 3-Membered Ring Compounds
  • bc0001
Mol File:
161596-47-0.mol
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(S)-(+)-Glycidyl Phthalimide Chemical Properties

Melting point:
102 °C
Boiling point:
347.4±15.0 °C(Predicted)
Density 
1.446±0.06 g/cm3(Predicted)
vapor pressure 
0.001-2.17Pa at 25-90.25℃
refractive index 
10 ° (C=2.2, CHCl3)
storage temp. 
under inert gas (nitrogen or Argon) at 2-8°C
solubility 
Chloroform (Slightly), Ethyl Acetate (Slightly)
pka
-2.24±0.20(Predicted)
form 
Solid
color 
White
InChI
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-/m0/s1
InChIKey
DUILGEYLVHGSEE-ZETCQYMHSA-N
SMILES
C1(=O)C2=C(C=CC=C2)C(=O)N1C[C@H]1CO1
LogP
1.2 at 40℃
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Safety Information

Hazard Codes 
Xi
Risk Statements 
41
Safety Statements 
26-39
WGK Germany 
2
HS Code 
29252900
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(S)-(+)-Glycidyl Phthalimide Usage And Synthesis

Chemical Properties

White powder

Uses

(S)-(+)-Glycidyl Phthalimide is a phthalimide derivative used as an intermediate in the preparation of the antibiotic Linezolid (L466500). It is also a key intermediate of rivaroxaban.

Synthesis

Phthalimide and (S)-1-substituent propylene oxide are used as raw materials, a reaction occurs under the action of a catalyst to generate 2-((S)-3-substituent-2-hydroxypropyl isodihydroindole-1,3-dione, and finally (S)-glycidyl phthalimide is generated by means of a ring-closure reaction.

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