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(R)-N-Glycidylphthalimide

Product Name
(R)-N-Glycidylphthalimide
CAS No.
181140-34-1
Chemical Name
(R)-N-Glycidylphthalimide
Synonyms
Rivaroxaban Impurity M;Rivaroxaban Impurity 84;(R)-GLYCIDYL PHTHALIMIDE;(R)-N-Glycidylphthalimide;N-(R)-Glycidyl Phthalimide;(R)-(-)-GLYCIDYL PHTHALIMIDE;(R)-N-Glycidylphthalimide>Rivaroxaban Impurity 7(R-isomer);(R)-(-)-N-(2,3-Epoxypropyl)pthalaMide;N-((2R)-Oxiran-2-ylmethyl)phthalimide
CBNumber
CB9462849
Molecular Formula
C11H9NO3
Formula Weight
203.19
MOL File
181140-34-1.mol
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(R)-N-Glycidylphthalimide Property

Melting point:
101 °C
Boiling point:
347.4±15.0 °C(Predicted)
Density 
1.446±0.06 g/cm3 (20 ºC 760 Torr)
refractive index 
-10 ° (C=2.2, CHCl3)
storage temp. 
Inert atmosphere,Room Temperature
solubility 
Chloroform (Slightly), Methanol (Slightly)
form 
Solid
pka
-2.24±0.20(Predicted)
color 
White
optical activity
[α]/D -7 to -13°, c =2.2 in chloroform
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Safety

Hazard Codes 
Xi
Risk Statements 
41
Safety Statements 
26-39
WGK Germany 
2
HS Code 
29251900
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Danger
Hazard statements

H318Causes serious eye damage

Precautionary statements

P280Wear protective gloves/protective clothing/eye protection/face protection.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
671711
Product name
(R)-(?)-N-(2,3-Epoxypropyl)phthalimide
Purity
≥99.0% (GC)
Packaging
1g
Price
$40
Updated
2023/06/20
Sigma-Aldrich
Product number
671711
Product name
(R)-(?)-N-(2,3-Epoxypropyl)phthalimide
Purity
≥99.0% (GC)
Packaging
5g
Price
$44
Updated
2023/06/20
TCI Chemical
Product number
G0327
Product name
(R)-N-Glycidylphthalimide
Purity
>99.0%(GC)
Packaging
5g
Price
$60
Updated
2025/07/31
TCI Chemical
Product number
G0327
Product name
(R)-N-Glycidylphthalimide
Purity
>99.0%(GC)
Packaging
25g
Price
$181
Updated
2025/07/31
TRC
Product number
G616005
Product name
N-(R)-GlycidylPhthalimide
Packaging
10g
Price
$145
Updated
2021/12/16
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(R)-N-Glycidylphthalimide Chemical Properties,Usage,Production

Chemical Properties

White solid

Uses

(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.

Uses

(R)-N-Glycidylphthalimide is a reagent used for the simultaneous preparation of amino alcohol solvating agents as well as preparation of orally available anticoagulants.

Synthesis

136918-14-4

57044-25-4

181140-34-1

General procedure for the synthesis of (R)-N-(2,3-epoxypropyl)phthalimide from 3-hydroxy-1H-isoindol-1-one and (R)-epoxyethylene-2-methanol: To a solution of tetrahydrofuran (THF, 220 mL) containing phthalimide (6.6 g, 45.0 mmol), triphenylphosphine (PPh3, 17.7 g, 67.5 mmol), diethyl azodicarboxylate (DEAD, 11.7 mL, 67.5 mmol), and (R)-(+)-condensate were sequentially added. 67.5 mmol), diethyl azodicarboxylate (DEAD, 11.7 mL, 67.5 mmol) and (R)-(+)-glycidol (4.0 g, 54.0 mmol). The reaction mixture was stirred at room temperature overnight. Upon completion of the reaction, the THF solvent was removed by distillation under reduced pressure and the residue was purified by silica gel fast column chromatography (Biotage system, eluent: 5%-20% ethyl acetate/hexane) to afford the target product (R)-N-(2,3-epoxypropyl)phthalimide (5.8 g, 75% yield).

References

[1] Tetrahedron Asymmetry, 1996, vol. 7, # 6, p. 1641 - 1648
[2] Patent: WO2006/29210, 2006, A2. Location in patent: Page/Page column 112-113
[3] Heterocycles, 2006, vol. 67, # 2, p. 561 - 566
[4] Tetrahedron, 2004, vol. 60, # 35, p. 7679 - 7692
[5] Patent: US2006/14701, 2006, A1. Location in patent: Page/Page column 23

(R)-N-Glycidylphthalimide Preparation Products And Raw materials

Raw materials

Preparation Products

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(R)-N-Glycidylphthalimide Suppliers

Americas 1 Canada 1 China 115 Europe 1 Germany 2 India 6 Japan 6 South Korea 1 Switzerland 1 United Kingdom 2 United States 20 Global 156
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View Lastest Price from (R)-N-Glycidylphthalimide manufacturers

Henan Aochuang Chemical Co.,Ltd.
Product
(R)-N-Glycidylphthalimide 181140-34-1
Price
US $0.00-0.00/KG
Min. Order
1KG
Purity
98%
Supply Ability
1ton
Release date
2022-10-19
Zhuozhou Wenxi import and Export Co., Ltd
Product
(R)-()-N-(2,3-Epoxypropyl)phthalimide 181140-34-1
Price
US $15.00-10.00/KG
Min. Order
1KG
Purity
99%+ HPLC
Supply Ability
Monthly supply of 1 ton
Release date
2021-06-27
Career Henan Chemical Co
Product
(R)-N-Glycidylphthalimide 181140-34-1
Price
US $1.00/KG
Min. Order
1KG
Purity
99%
Supply Ability
200kgs
Release date
2020-01-29

181140-34-1, (R)-N-GlycidylphthalimideRelated Search:

3-Morpholinone, 4-(2,4-diaMinophenyl)- 4-(3-AMino-phenyl)-Morpholin-3-one (R)-5-chloro-N-(4-(3-oxomorpholino)phenyl)-N- ((2-oxooxazolidin-5-yl)methyl)thiophene-2-carboxamide (S)-2-(3-chloro-2-hydroxypropyl)isoindoline-1,3-dione Rivaroxaban Impurity 93 4-(2-nitrophenyl)Morpholin-3-one Benzoic acid, 2-[[[[(5S)-2-oxo-3-[4-(3-oxo-4-Morpholinyl)phenyl]-5-oxazolidinyl]Methyl]aMino]carbonyl]- 4,5-DICHLOROTHIOPHENE-2-CARBOXYLIC ACID 4-(4-NITROPHENYL)MORPHOLIN-3-ONE (S)-4-(4-(5-(Aminomethyl)-2-oxooxazolidin-3-yl)phenyl)morpholin-3-one.HCl 5-Chloro-2-thiophenecarboxylic Acid 2-Thiophenecarboxylic acid 2-[(2R)-2-Hydroxy-3-[[4-(3-oxo-4-Morpho linyl)phenyl]aMino]propyl]-1H-isoindole-1 ,3(2H)-dione (S)-(+)-Glycidyl Phthalimide (R)-N-Glycidylphthalimide N-(2,3-EPOXYPROPYL)PHTHALIMIDE O-Phthalimide Glycidyl phthalimide

  • (R)-(-)-N-(2,3-Epoxypropyl)phthaliMide, ee: 98%
  • 2-[(2R)-oxiran-2-ylmethyl]-1H-isoindol-1,3(2H)-dione
  • 1H-Isoindole-1,3(2H)-dione,2-[(2R)-2-oxiranylMethyl]-
  • (R)-(-)-N-(2,3-Epoxypropyl)phthaliMide >=99.0% (GC)
  • (R)-2-OXIRANYLMETHYL-ISOINDOLE-1,3-DIONE
  • (R)-(-)-GLYCIDYL PHTHALIMIDE
  • (R)-GLYCIDYL PHTHALIMIDE
  • (R)-(-)-N-(2,3-Epoxypropyl)phthalimide
  • (R)-N-Glycidylphthalimide
  • 2-[(2R)-2-OxiranylMethyl]-1H-isoindol-1,3(2H)-dione
  • (R)-2-(oxiran-2-ylMethyl)isoindoline-1,3-dione
  • 1H-Isoindole-1,3(2H)-dione, 2-[(2R)-oxiranylMethyl]-
  • (R)-2-(Oxiranylmethyl)-1H-isoindole-1,3(2H)-dione
  • (R)-N-(2,3-Epoxypropan-1-yl)phthalimide
  • N-(R)-Glycidyl Phthalimide
  • (R)-(-)-N-(2,3-Epoxypropyl)pthalaMide
  • Rivaroxaban Impurity 7(R-isomer)
  • 2-((2R)-OXIRANYLMETHYL)-1H-ISOINDOLE-1,3(2H)-DIONE
  • Rivaroxaban Impurity M
  • (R)-(-)-N-(2,3-Epoxypropyl)phthalimide, 99%, ee: 98%
  • Rivaroxaban Impurity 84
  • (R)-N-Glycidylphthalimide&gt
  • 2-[[(2R)-oxiran-2-yl]methyl]isoindole-1,3-dione
  • N-((2R)-Oxiran-2-ylmethyl)phthalimide
  • (R)-4-(OXIRAN-2-YLMETHYL)ISOINDOLINE-1,3-DIONE
  • (<i>R</i>)-(?)-<i>N</i>-(2,3-Epoxypropyl)phthalimide
  • 181140-34-1
  • N-Substituted Maleimides, Succinimides & Phthalimides
  • N-Substituted Phthalimides
  • Oxiranes
  • Simple 3-Membered Ring Compounds