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1H-Isoindole-1,3(2H)-dione,2-[(2R)-2-oxiranylmethyl]-
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Name

1H-Isoindole-1,3(2H)-dione,2-[(2R)-2-oxiranylmethyl]-

 EINECS 629-091-0
CAS No. 181140-34-1 Density 1.446 g/cm3
PSA 58.70000 LogP 0.84030
Solubility N/A Melting Point 101 °C
Formula C11H9NO3 Boiling Point 347.4 °C at 760 mmHg
Molecular Weight 203.197 Flash Point 163.9 °C
Transport Information N/A Appearance N/A
Safety 26-39 Risk Codes 41
Molecular Structure Molecular Structure of 181140-34-1 ((R)-(-)-GLYCIDYL PHTHALIMIDE) Hazard Symbols IrritantXi
Synonyms

1H-Isoindole-1,3(2H)-dione,2-(oxiranylmethyl)-, (R)-;(R)-2-(Oxiranylmethyl)-1H-isoindole-1,3(2H)-dione;(R)-N-(2,3-Epoxypropan-1-yl)phthalimide;N-((2R)-Oxiran-2-ylmethyl)phthalimide;N-(R)-Glycidylphthalimide;1H-Isoindole-1,3(2H)-dione, 2-[(2R)-oxiranylmethyl]-(9CI);

Article Data 12

1H-Isoindole-1,3(2H)-dione,2-[(2R)-2-oxiranylmethyl]- Synthetic route

641617-21-2

2-[(2R)-3-bromo-2-hydroxypropyl]-1H-isoindole-1,3(2H)-dione

181140-34-1

(-)-2-[(2R)-oxiran-2-ylmethyl]-1H-isoindole-1,3(2H)-dione

Conditions
ConditionsYield
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%
136918-14-4

phthalimide

51594-55-9

(R)-(-)-epichlorohydrin

181140-34-1

(-)-2-[(2R)-oxiran-2-ylmethyl]-1H-isoindole-1,3(2H)-dione

Conditions
ConditionsYield
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%
136918-14-4

phthalimide

57044-25-4

(R)-oxiranemethanol

181140-34-1

(-)-2-[(2R)-oxiran-2-ylmethyl]-1H-isoindole-1,3(2H)-dione

Conditions
ConditionsYield
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;
136918-14-4

phthalimide

67843-74-7

(S)-epichlorohydrin

A

181140-34-1

(-)-2-[(2R)-oxiran-2-ylmethyl]-1H-isoindole-1,3(2H)-dione

B

(R)-1-chloro-3-phtalimido-propan-2-ol

Conditions
ConditionsYield
With potassium fluoride on basic alumina In 2-methyltetrahydrofuran for 3h; Inert atmosphere; Reflux; stereospecific reaction;A 11%
B 85%
136918-14-4

phthalimide

67843-74-7

(S)-epichlorohydrin

181140-34-1

(-)-2-[(2R)-oxiran-2-ylmethyl]-1H-isoindole-1,3(2H)-dione

Conditions
ConditionsYield
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
19667-37-9, 34839-11-7, 148857-42-5, 148857-44-7

2-(3-chloro-2-hydroxypropyl)-1H-isoindole-1,3(2H)-dione

181140-34-1

(-)-2-[(2R)-oxiran-2-ylmethyl]-1H-isoindole-1,3(2H)-dione

Conditions
ConditionsYield
With potassium tert-butylate In isopropyl alcohol at 15℃; for 4h;75%
With potassium carbonate In toluene Reflux;n/a
67843-74-7

(S)-epichlorohydrin

1074-82-4

potassium phtalimide

181140-34-1

(-)-2-[(2R)-oxiran-2-ylmethyl]-1H-isoindole-1,3(2H)-dione

Conditions
ConditionsYield
With benzyltrimethylammonium chloride In tert-butyl alcohol at 20℃; for 24h;72%
51594-55-9

(R)-(-)-epichlorohydrin

1074-82-4

potassium phtalimide

A

181140-34-1

(-)-2-[(2R)-oxiran-2-ylmethyl]-1H-isoindole-1,3(2H)-dione

B

161596-47-0

(S)-N-glycidylphthalimide

Conditions
ConditionsYield
With benzyltrimethylammonium chloride In DMF (N,N-dimethyl-formamide) at 20℃; for 16h;
136918-14-4

phthalimide

181140-34-1

(-)-2-[(2R)-oxiran-2-ylmethyl]-1H-isoindole-1,3(2H)-dione

Conditions
ConditionsYield
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
136918-14-4

phthalimide

51594-55-9

(R)-(-)-epichlorohydrin

A

19667-37-9, 34839-11-7, 148857-42-5, 148857-44-7

2-(3-chloro-2-hydroxypropyl)-1H-isoindole-1,3(2H)-dione

B

181140-34-1

(-)-2-[(2R)-oxiran-2-ylmethyl]-1H-isoindole-1,3(2H)-dione

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

1H-Isoindole-1,3(2H)-dione,2-[(2R)-2-oxiranylmethyl]- Specification

The CAS register number of 1H-Isoindole-1,3(2H)-dione,2-[(2R)-2-oxiranylmethyl]- is 181140-34-1. It also can be called as (R)-2-(Oxiranylmethyl)-1H-isoindole-1,3(2H)-dione and the systematic name about this chemical is 2-[(2R)-oxiran-2-ylmethyl]-1H-isoindole-1,3(2H)-dione. The molecular formula about this chemical is C11H9NO3 and the molecular weight is 203.19. It belongs to the following product categories which include N-Substituted Maleimides, Succinimides & Phthalimides; N-Substituted Phthalimides; Oxiranes; Simple 3-Membered Ring Compounds and so on.

Physical properties about 1H-Isoindole-1,3(2H)-dione,2-[(2R)-2-oxiranylmethyl]- are: (1)ACD/LogP: 1.60; (2)#H bond acceptors: 4; (3)#Freely Rotating Bonds: 2; (4)Polar Surface Area: 49.91 Å2; (5)Index of Refraction: 1.648; (6)Molar Refractivity: 51.16 cm3; (7)Molar Volume: 140.4 cm3; (8)Polarizability: 20.28x10-24cm3; (9)Surface Tension: 64.5 dyne/cm; (10)Density: 1.446 g/cm3; (11)Flash Point: 163.9 °C; (12)Enthalpy of Vaporization: 59.17 kJ/mol; (13)Boiling Point: 347.4 °C at 760 mmHg; (14)Vapour Pressure: 5.38E-05 mmHg at 25 °C.

When you are using this chemical, please be cautious about it as the following:
This chemical is risk of serious damage to the eyes. If you want to use this chemical, wear eye / face protection. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.

You can still convert the following datas into molecular structure:
(1)SMILES: O=C1c3c(C(=O)N1C[C@H]2OC2)cccc3
(2)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
(3)InChIKey: DUILGEYLVHGSEE-SSDOTTSWBY
(4)Std. 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-/m1/s1
(5)Std. InChIKey: DUILGEYLVHGSEE-SSDOTTSWSA-N

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