181140-34-1

Basic information

• Product Name: (R)-(-)-GLYCIDYL PHTHALIMIDE
• Synonyms: (R)-(-)-N-(2,3-Epoxypropyl)phthaliMide, ee: 98%;1H-Isoindole-1,3(2H)-dione,2-[(2R)-2-oxiranylMethyl]-;(R)-(-)-N-(2,3-Epoxypropyl)phthaliMide >=99.0% (GC);2-[(2R)-oxiran-2-ylmethyl]-1H-isoindol-1,3(2H)-dione;2-((2R)-OXIRANYLMETHYL)-1H-ISOINDOLE-1,3(2H)-DIONE;(R)-2-OXIRANYLMETHYL-ISOINDOLE-1,3-DIONE;(R)-(-)-GLYCIDYL PHTHALIMIDE;(R)-GLYCIDYL PHTHALIMIDE
• CAS NO: 181140-34-1
• Molecular Formula: C₁₁H₉NO₃
• Molecular Weight: 203.19
• EINECS: 1592732-453-0
• Product Categories: N-Substituted Maleimides, Succinimides & Phthalimides;N-Substituted Phthalimides;Oxiranes;Simple 3-Membered Ring Compounds
• Mol File: 181140-34-1.mol
• Article Data: 12

Chemical Properties

• Melting Point: 101 °C
• Boiling Point: 347.4 °C at 760 mmHg
• Flash Point: 163.9 °C
• Appearance: /
• Density: 1.446±0.06 g/cm3 (20 ºC 760 Torr)
• Vapor Pressure: 5.38E-05mmHg at 25°C
• Refractive Index: -10 ° (C=2.2, CHCl3)
• Storage Temp.: Inert atmosphere,Room Temperature
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• PKA: -2.24±0.20(Predicted)
• CAS DataBase Reference: (R)-(-)-GLYCIDYL PHTHALIMIDE(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-(-)-GLYCIDYL PHTHALIMIDE(181140-34-1)
• EPA Substance Registry System: (R)-(-)-GLYCIDYL PHTHALIMIDE(181140-34-1)

Safety Data

• Hazard Codes: Xi
• Statements: 41
• Safety Statements: 26-39
• WGK Germany: 2
• Hazardous Substances Data: 181140-34-1(Hazardous Substances Data)

Usage

Chemical Properties

White solid

Uses

Different sources of media describe the Uses of 181140-34-1 differently. You can refer to the following data:
1. (R)-N-Glycidylphthalimide is a reagent used for the simultaneous preparation of amino alcohol solvating agents as well as preparation of orally available anticoagulants.
2. (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-dione2-[(2R)-2-hydroxy-3-[[(1R,2S)-2-hydroxyindan-1-yl]amino]propyl]isoindoline-1,3-dione2-[(2R)-2-hydroxy-3-[[(1R)-1-(hydroxymethyl)-propyl]amino]propyl] isoindoline-1,3-dione2-[(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.

InChI:InChI=1/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

Synthetic route

2-[(2R)-3-bromo-2-hydroxypropyl]-1H-isoindole-1,3(2H)-dione (641617-21-2) → (-)-2-[(2R)-oxiran-2-ylmethyl]-1H-isoindole-1,3(2H)-dione (181140-34-1)

Conditions	Yield
With sodium hydride In tetrahydrofuran for 18h; Product distribution / selectivity;	90.6%
With sodium methylate In methanol; toluene at 20℃; for 1.5h; Product distribution / selectivity;	56.7%

phthalimide (136918-14-4) + (R)-(-)-epichlorohydrin (51594-55-9) → (-)-2-[(2R)-oxiran-2-ylmethyl]-1H-isoindole-1,3(2H)-dione (181140-34-1)

Conditions	Yield
Stage #1: phthalimide; (R)-(-)-epichlorohydrin With benzyltrimethylammonium chloride In isopropyl alcohol at 40℃; for 24h; Stage #2: With potassium tert-butylate In isopropyl alcohol at 20℃; for 3h;	89%

phthalimide (136918-14-4) + (R)-oxiranemethanol (57044-25-4) → (-)-2-[(2R)-oxiran-2-ylmethyl]-1H-isoindole-1,3(2H)-dione (181140-34-1)

Conditions	Yield
With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran at 20 - 25℃; for 18h;	86%
With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran at 20℃; Mitsunobu reaction;	75%
With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran Mitsunobu reaction;
With di-tert-butyl-diazodicarboxylate; triphenylphosphine In dichloromethane at 20℃; Mitsunobu reaction;
With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran at 0 - 20℃; Molecular sieve;

phthalimide (136918-14-4) + (S)-epichlorohydrin (67843-74-7) → (-)-2-[(2R)-oxiran-2-ylmethyl]-1H-isoindole-1,3(2H)-dione (181140-34-1) + (R)-1-chloro-3-phtalimido-propan-2-ol

Conditions	Yield
With potassium fluoride on basic alumina In 2-methyltetrahydrofuran for 3h; Inert atmosphere; Reflux; stereospecific reaction;	A 11% B 85%

phthalimide (136918-14-4) + (S)-epichlorohydrin (67843-74-7) → (-)-2-[(2R)-oxiran-2-ylmethyl]-1H-isoindole-1,3(2H)-dione (181140-34-1)

Conditions	Yield
With benzyltrimethylammonium chloride; sodium carbonate In tert-butyl alcohol at 20℃; for 23h;	84%
With benzyltrimethylammonium chloride In Isopropyl acetate at 20℃; for 72h;	1.1 g

2-(3-chloro-2-hydroxypropyl)-1H-isoindole-1,3(2H)-dione (19667-37-9, 34839-11-7, 148857-42-5, 148857-44-7) → (-)-2-[(2R)-oxiran-2-ylmethyl]-1H-isoindole-1,3(2H)-dione (181140-34-1)

Conditions	Yield
With potassium tert-butylate In isopropyl alcohol at 15℃; for 4h;	75%
With potassium carbonate In toluene Reflux;	n/a

(S)-epichlorohydrin (67843-74-7) + potassium phtalimide (1074-82-4) → (-)-2-[(2R)-oxiran-2-ylmethyl]-1H-isoindole-1,3(2H)-dione (181140-34-1)

Conditions	Yield
With benzyltrimethylammonium chloride In tert-butyl alcohol at 20℃; for 24h;	72%

(R)-(-)-epichlorohydrin (51594-55-9) + potassium phtalimide (1074-82-4) → (-)-2-[(2R)-oxiran-2-ylmethyl]-1H-isoindole-1,3(2H)-dione (181140-34-1) + (S)-N-glycidylphthalimide (161596-47-0)

Conditions	Yield
With benzyltrimethylammonium chloride In DMF (N,N-dimethyl-formamide) at 20℃; for 16h;

phthalimide (136918-14-4) → (-)-2-[(2R)-oxiran-2-ylmethyl]-1H-isoindole-1,3(2H)-dione (181140-34-1)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: aluminum oxide / 1-methyl-pyrrolidin-2-one / 64 - 68 °C 1.2: 0.5 h 2.1: potassium carbonate / toluene / Reflux View Scheme
Multi-step reaction with 2 steps 1.1: aluminum oxide / 1-methyl-pyrrolidin-2-one / 64 - 68 °C 1.2: 0.5 h 2.1: potassium carbonate / toluene / Reflux View Scheme
Multi-step reaction with 2 steps 1.1: aluminum oxide / 1-methyl-pyrrolidin-2-one / 64 - 68 °C 1.2: 0.5 h 2.1: potassium carbonate / toluene / Reflux View Scheme

phthalimide (136918-14-4) + (R)-(-)-epichlorohydrin (51594-55-9) → 2-(3-chloro-2-hydroxypropyl)-1H-isoindole-1,3(2H)-dione (19667-37-9, 34839-11-7, 148857-42-5, 148857-44-7) + (-)-2-[(2R)-oxiran-2-ylmethyl]-1H-isoindole-1,3(2H)-dione (181140-34-1)

Conditions	Yield
With aluminum oxide In 1-methyl-pyrrolidin-2-one at 64 - 68℃;

2-oxiranylmethylisoindole-1,3-dione (5455-98-1) → (-)-2-[(2R)-oxiran-2-ylmethyl]-1H-isoindole-1,3(2H)-dione (181140-34-1) + (S)-N-glycidylphthalimide (161596-47-0)

Conditions	Yield
With Cu metal organic framework based on (R)-3,3′-bis(6-carboxy-2-naphthyl)-2,2′-dihydroxy-1,1′-binaphthyl*silica packed stainless steel column (10 cm long × 4.0 mm i.d.) In ethanol; hexane at 25℃; Resolution of racemate;

(-)-2-[(2R)-oxiran-2-ylmethyl]-1H-isoindole-1,3(2H)-dione (181140-34-1) → 2-[(2R)-3-bromo-2-hydroxypropyl]-1H-isoindole-1,3(2H)-dione (641617-21-2)

Conditions	Yield
With hydrogen bromide In chloroform; water at 0℃; for 0.5h;	96%
Stage #1: (-)-2-[(2R)-oxiran-2-ylmethyl]-1H-isoindole-1,3(2H)-dione With iodobromomethane In 2-methyltetrahydrofuran at -78℃; for 0.0333333h; Stage #2: With methyllithium In 2-methyltetrahydrofuran; diethyl ether at -78℃; for 1h; enantioselective reaction;	87%

(1R,2S)-1-Amino-2-indanol (136030-00-7) + (-)-2-[(2R)-oxiran-2-ylmethyl]-1H-isoindole-1,3(2H)-dione (181140-34-1) → 2-[(2R)-2-hydroxy-3-[[(1R,2S)-2-hydroxyindan-1-yl]amino]propyl] isoindoline-1,3-dione (1309774-74-0)

Conditions	Yield
In isopropyl alcohol at 0℃; for 9h; Reflux;	93%

(S)-1-phenyl-ethylamine (2627-86-3) + (-)-2-[(2R)-oxiran-2-ylmethyl]-1H-isoindole-1,3(2H)-dione (181140-34-1) → 2-[(2R)-2-hydroxy-3-[[(1S)-1-phenylethyl]amino]propyl]isoindoline-1,3-dione (1309774-76-2)

Conditions	Yield
In isopropyl alcohol at 0℃; for 9h; Reflux;	91%

4-di[(2-hydroxyethyl)amino]-aniline (19298-14-7) + (-)-2-[(2R)-oxiran-2-ylmethyl]-1H-isoindole-1,3(2H)-dione (181140-34-1) → C19H21N3O4

Conditions	Yield
In ethanol at 75 - 85℃; for 24h;	90%

(-)-2-[(2R)-oxiran-2-ylmethyl]-1H-isoindole-1,3(2H)-dione (181140-34-1) → (R)-1-chloro-3-phtalimido-propan-2-ol

Conditions	Yield
Stage #1: (-)-2-[(2R)-oxiran-2-ylmethyl]-1H-isoindole-1,3(2H)-dione With Chloroiodomethane In 2-methyltetrahydrofuran at -78℃; for 0.0333333h; Stage #2: With methyllithium In 2-methyltetrahydrofuran; diethyl ether at -78℃; for 1h; enantioselective reaction;	90%

(-)-2-[(2R)-oxiran-2-ylmethyl]-1H-isoindole-1,3(2H)-dione (181140-34-1) → C11H10INO3

Conditions	Yield
Stage #1: (-)-2-[(2R)-oxiran-2-ylmethyl]-1H-isoindole-1,3(2H)-dione With diiodomethane In 2-methyltetrahydrofuran at -78℃; for 0.0333333h; Stage #2: With methyllithium In 2-methyltetrahydrofuran; diethyl ether at -78℃; for 1h; enantioselective reaction;	89%

4-Chloroguaiacol (16766-30-6) + (-)-2-[(2R)-oxiran-2-ylmethyl]-1H-isoindole-1,3(2H)-dione (181140-34-1) → (R)-1-(4-chloro-2-methoxyphenoxy)-3-phthalimido-2-propanol (874113-26-5)

Conditions	Yield
With cesium fluoride In DMF (N,N-dimethyl-formamide) at 80℃; for 38h;	87%
With potassium carbonate In DMF (N,N-dimethyl-formamide) at 80℃; for 46h;	59%

7-fluoro-1-(piperazin-1-yl)isoquinoline + (-)-2-[(2R)-oxiran-2-ylmethyl]-1H-isoindole-1,3(2H)-dione (181140-34-1) → 2-[(2S)-3-[4-(7-fluoroisoquinolin-1-yl)piperazin-1-yl]-2-hydroxypropyl]-2,3-dihydro-1H-isoindole-1,3-dione

Conditions	Yield
In acetonitrile at 70℃; for 6h;	84%

1-(2-Methoxyphenyl)piperazine (35386-24-4) + (-)-2-[(2R)-oxiran-2-ylmethyl]-1H-isoindole-1,3(2H)-dione (181140-34-1) → (S)-(-)-1-phthaloylamino-3-[4-(2-methoxyphenyl)piperazin-1-yl]propan-2-ol (180959-07-3)

Conditions	Yield
In tetrahydrofuran for 72h; Heating;	83%

(R)-Phenylglycinol (56613-80-0) + (-)-2-[(2R)-oxiran-2-ylmethyl]-1H-isoindole-1,3(2H)-dione (181140-34-1) → 2-[(2R)-2-hydroxy-3-[[(1R)-2-hydroxy-1-phenyl-ethyl]amino]propyl] isoindoline-1,3-dione (1309774-73-9)

Conditions	Yield
In isopropyl alcohol at 0℃; for 9h; Reflux;	83%

2-(2-(4-aminophenylamino)ethoxy)acetic acid + (-)-2-[(2R)-oxiran-2-ylmethyl]-1H-isoindole-1,3(2H)-dione (181140-34-1) → C21H23N3O6

Conditions	Yield
In ethanol at 75 - 85℃; for 24h;	80%

(S)-N-benzyl-α-cyclohexylethylamine (141396-54-5) + (-)-2-[(2R)-oxiran-2-ylmethyl]-1H-isoindole-1,3(2H)-dione (181140-34-1) → 2-[(2S)-2-hydroxy-3-[N-benzyl-[(1S)-α-cyclohexylethyl]amino]propyl]isoindoline-1,3-dione

Conditions	Yield
In isopropyl alcohol for 13h; Cooling with ice; Reflux; regioselective reaction;	77.66%

(S)-1-phenyl-ethylamine (2627-86-3) + (-)-2-[(2R)-oxiran-2-ylmethyl]-1H-isoindole-1,3(2H)-dione (181140-34-1) → 2-[(2S)-2-hydroxy-3-[[(1S)-α-phenylethyl]amino]propyl]isoindoline-1,3-dione

Conditions	Yield
In isopropyl alcohol for 13h; Cooling with ice; Reflux; regioselective reaction;	76.69%

(-)-2-[(2R)-oxiran-2-ylmethyl]-1H-isoindole-1,3(2H)-dione (181140-34-1) → (S)-2-(thiiran-2-ylmethyl)isoindoline-1,3-dione

Conditions	Yield
With thiourea In methanol at 20℃; for 22h;	74%

[(1S)-1-cyclohexylethyl]amine (17430-98-7) + (-)-2-[(2R)-oxiran-2-ylmethyl]-1H-isoindole-1,3(2H)-dione (181140-34-1) → 2-[(2S)-2-hydroxy-3-[[(1S)-α-cyclohexylethyl]amino]propyl]isoindoline-1,3-dione

Conditions	Yield
In isopropyl alcohol for 13h; Cooling with ice; Reflux; regioselective reaction;	73.07%

(2R)-2-aminobutan-1-ol (5856-63-3) + (-)-2-[(2R)-oxiran-2-ylmethyl]-1H-isoindole-1,3(2H)-dione (181140-34-1) → 2-[(2R)-2-hydroxy-3-[[(1R)-1-(hydroxymethyl)propyl]amino]propyl] isoindoline-1,3-dione (1309774-75-1)

Conditions	Yield
In isopropyl alcohol at 0℃; for 9h; Reflux;	73%

carbon dioxide (124-38-9) + (-)-2-[(2R)-oxiran-2-ylmethyl]-1H-isoindole-1,3(2H)-dione (181140-34-1) → C12H9NO5

Conditions	Yield
With C25H22OP(1+)*Br(1-) In chlorobenzene at 120℃; under 760.051 Torr; for 12h;	73%

3,6-dibromo-9H-carbazole (6825-20-3) + (-)-2-[(2R)-oxiran-2-ylmethyl]-1H-isoindole-1,3(2H)-dione (181140-34-1) → 2-[(S)-3-(3,6-dibromocarbazol-9-yl)-2-hydroxypropyl]isoindole-1,3-dione

Conditions	Yield
Stage #1: 3,6-dibromo-9H-carbazole With caesium carbonate In N,N-dimethyl-formamide at 30℃; for 1h; Stage #2: (-)-2-[(2R)-oxiran-2-ylmethyl]-1H-isoindole-1,3(2H)-dione In N,N-dimethyl-formamide at 30℃; for 15h;	72%

(S)-1-(1-Naphthyl)ethylamine (10420-89-0) + (-)-2-[(2R)-oxiran-2-ylmethyl]-1H-isoindole-1,3(2H)-dione (181140-34-1) → 2-[(2S)-2-hydroxy-3-[[(1S)-1-naphthylethyl]amino]propyl]isoindoline-1,3-dione

Conditions	Yield
In isopropyl alcohol for 13h; Cooling with ice; Reflux; regioselective reaction;	72%

(-)-2-[(2R)-oxiran-2-ylmethyl]-1H-isoindole-1,3(2H)-dione (181140-34-1) → (R)2-(oxiran-2-ylmethyl)isoindolin-1-one (1344708-81-1)

Conditions	Yield
With tetrabutyl ammonium fluoride In tetrahydrofuran at 25℃; Inert atmosphere;	70%

(1R,2R)-N,N'-dibenzylcyclohexane-1,2-diamine (65838-10-0, 135613-88-6, 143443-23-6) + (-)-2-[(2R)-oxiran-2-ylmethyl]-1H-isoindole-1,3(2H)-dione (181140-34-1) → N,N'-dibenzyl-N,N'-bis[(S)-2-hydroxy-3-phtalimido]-(1R,2R)-1,2-diaminocyclohexane

Conditions	Yield
In isopropyl alcohol for 13h; Cooling with ice; Reflux; regioselective reaction;	70%

[(1R)-1-cyclohexylethyl]amine (5913-13-3) + (-)-2-[(2R)-oxiran-2-ylmethyl]-1H-isoindole-1,3(2H)-dione (181140-34-1) → 2-[(2S)-2-hydroxy-3-[[(1R)-α-cyclohexylethyl]amino]propyl]isoindoline-1,3-dione

Conditions	Yield
In isopropyl alcohol for 13h; Cooling with ice; Reflux; regioselective reaction;	68%

(-)-2-[(2R)-oxiran-2-ylmethyl]-1H-isoindole-1,3(2H)-dione (181140-34-1) + 4-(4-aminophenyl)morpholin-3-one (438056-69-0) → 2,2'-((2R,2'R)-((4-(3-oxomorpholino)phenyl)azadiyl)bis(2-hydroxypropane-3,1-diyl))bis(isoindoline-1,3-dione)

Conditions	Yield
In ethanol for 24h; Reflux;	60%

Upstream product

• 136918-14-4 phthalimide 
• 67843-74-7 (S)-epichlorohydrin 
• 19667-37-9 2-(3-chloro-2-hydroxypropyl)-1H-isoindole-1,3(2H)-dione 
• 51594-55-9 (R)-(-)-epichlorohydrin 
• 5455-98-1 2-oxiranylmethylisoindole-1,3-dione 
• 641617-21-2 2-[(2R)-3-bromo-2-hydroxypropyl]-1H-isoindole-1,3(2H)-dione 
• 1074-82-4 potassium phtalimide 
• 57044-25-4 (R)-oxiranemethanol 

Downstream Products

• 878799-13-4 2-chloro-N-[(2R)-3-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-2-hydroxypropyl]-4-fluorobenzenesulfonamide 
• 6284-28-2 2-oxo-5-phthalimidomethyl-tetrahydro-furan-3-carboxylic acid ethyl ester 
• 1643354-27-1 2,2'-((2R,2'R)-((4-(3-oxomorpholino)phenyl)azadiyl)bis(2-hydroxypropane-3,1-diyl))bis(isoindoline-1,3-dione) 

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