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CAS No.: | 181140-34-1 |
---|---|
Name: | (R)-(-)-GLYCIDYL PHTHALIMIDE |
Article Data: | 12 |
Molecular Structure: | |
Formula: | C11H9NO3 |
Molecular Weight: | 203.197 |
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); |
EINECS: | 629-091-0 |
Density: | 1.446 g/cm3 |
Melting Point: | 101 °C |
Boiling Point: | 347.4 °C at 760 mmHg |
Flash Point: | 163.9 °C |
Hazard Symbols: | Xi |
Risk Codes: | 41 |
Safety: | 26-39 |
PSA: | 58.70000 |
LogP: | 0.84030 |
2-[(2R)-3-bromo-2-hydroxypropyl]-1H-isoindole-1,3(2H)-dione
(-)-2-[(2R)-oxiran-2-ylmethyl]-1H-isoindole-1,3(2H)-dione
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
(R)-(-)-epichlorohydrin
(-)-2-[(2R)-oxiran-2-ylmethyl]-1H-isoindole-1,3(2H)-dione
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
(R)-oxiranemethanol
(-)-2-[(2R)-oxiran-2-ylmethyl]-1H-isoindole-1,3(2H)-dione
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
(S)-epichlorohydrin
A
(-)-2-[(2R)-oxiran-2-ylmethyl]-1H-isoindole-1,3(2H)-dione
Conditions | Yield |
---|---|
With potassium fluoride on basic alumina In 2-methyltetrahydrofuran for 3h; Inert atmosphere; Reflux; stereospecific reaction; | A 11% B 85% |
phthalimide
(S)-epichlorohydrin
(-)-2-[(2R)-oxiran-2-ylmethyl]-1H-isoindole-1,3(2H)-dione
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
(-)-2-[(2R)-oxiran-2-ylmethyl]-1H-isoindole-1,3(2H)-dione
Conditions | Yield |
---|---|
With potassium tert-butylate In isopropyl alcohol at 15℃; for 4h; | 75% |
With potassium carbonate In toluene Reflux; | n/a |
(S)-epichlorohydrin
potassium phtalimide
(-)-2-[(2R)-oxiran-2-ylmethyl]-1H-isoindole-1,3(2H)-dione
Conditions | Yield |
---|---|
With benzyltrimethylammonium chloride In tert-butyl alcohol at 20℃; for 24h; | 72% |
(R)-(-)-epichlorohydrin
potassium phtalimide
A
(-)-2-[(2R)-oxiran-2-ylmethyl]-1H-isoindole-1,3(2H)-dione
B
(S)-N-glycidylphthalimide
Conditions | Yield |
---|---|
With benzyltrimethylammonium chloride In DMF (N,N-dimethyl-formamide) at 20℃; for 16h; |
phthalimide
(-)-2-[(2R)-oxiran-2-ylmethyl]-1H-isoindole-1,3(2H)-dione
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
(R)-(-)-epichlorohydrin
A
2-(3-chloro-2-hydroxypropyl)-1H-isoindole-1,3(2H)-dione
B
(-)-2-[(2R)-oxiran-2-ylmethyl]-1H-isoindole-1,3(2H)-dione
Conditions | Yield |
---|---|
With aluminum oxide In 1-methyl-pyrrolidin-2-one at 64 - 68℃; |
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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