(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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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