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161596-47-0

Basic Information
CAS No.: 161596-47-0
Name: (S)-(+)-GLYCIDYL PHTHALIMIDE
Article Data: 31
Molecular Structure:
Molecular Structure of 161596-47-0 ((S)-(+)-GLYCIDYL PHTHALIMIDE)
Formula: C11H9NO3
Molecular Weight: 203.197
Synonyms: 1H-Isoindole-1,3(2H)-dione,2-(oxiranylmethyl)-, (S)-;1H-Isoindole-1,3(2H)-dione, 2-[(2S)-oxiranylmethyl]-(9CI);(S)-2-(Oxiran-2-ylmethyl)-1H-isoindole-1,3(2H)-dione;(S)-N-(2,3-Epoxypropan-1-yl)phthalimide;N-((2S)-Oxiran-2-ylmethyl)phthalimide;N-(S)-Glycidylphthalimide;
EINECS: 1308068-626-2
Density: 1.446 g/cm3
Melting Point: 102 °C
Boiling Point: 347.4 °C at 760 mmHg
Flash Point: 163.9 °C
Hazard Symbols: IrritantXi
Risk Codes: 41
Safety: 26-39
PSA: 49.91000
LogP: 0.61930
Synthetic route
148857-42-5

2-((S)-3-chloro-2-hydroxypropyl)isoindoline-1,3-dione

161596-47-0

(S)-N-glycidylphthalimide

Conditions
ConditionsYield
With sodium carbonate In 5,5-dimethyl-1,3-cyclohexadiene for 4h; Reflux; Green chemistry;94%
With sodium carbonate In 5,5-dimethyl-1,3-cyclohexadiene for 4h; Reflux;89%
With potassium phosphate In 1,2-dichloro-ethane at 80℃; for 14h; Product distribution / selectivity;n/a
40137-25-5

1H-isoindole-1,3(2H)-dione, 2-[[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]methyl]

161596-47-0

(S)-N-glycidylphthalimide

Conditions
ConditionsYield
Stage #1: 1H-isoindole-1,3(2H)-dione, 2-[[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]methyl] With hydrogen bromide In 1,2-dichloro-ethane at 10 - 15℃; for 4h;
Stage #2: With sodium methylate In methanol at 0 - 15℃; for 3h;
93.6%
Multi-step reaction with 4 steps
1: hydrogenchloride / water / 2 h / 60 - 67 °C / Industrial scale
2: pyridinium p-toluenesulfonate / toluene / 0.25 h / 30 - 50 °C / Industrial scale
3: chloro-trimethyl-silane / toluene / 2.5 h / 30 °C
4: sodium methylate / methanol / 20 h / 30 °C
View Scheme
Multi-step reaction with 4 steps
1: hydrogenchloride / water / 2 h / 60 - 67 °C / Industrial scale
2: pyridinium p-toluenesulfonate / toluene / 3 h / Dean-Stark; Reflux; Industrial scale
3: N-Bromosuccinimide / 1,2-dichloro-ethane / 1.33 h / 12 - 22 °C / Industrial scale
4: sodium methylate / toluene; methanol / 5.17 h / 9 - 22 °C / Industrial scale
View Scheme
136918-14-4

phthalimide

60456-23-7

(S)-oxiranemethanol

161596-47-0

(S)-N-glycidylphthalimide

Conditions
ConditionsYield
With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran at 0 - 20℃;91%
With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran at 0 - 20℃;91%
With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran at 20 - 25℃; for 18h;80%
136918-14-4

phthalimide

51594-55-9

(R)-(-)-epichlorohydrin

161596-47-0

(S)-N-glycidylphthalimide

Conditions
ConditionsYield
With benzyltrimethylammonium chloride In isopropyl alcohol at 40℃; for 22h;90%
With potassium tert-butylate; benzyltrimethylammonium chloride; sodium carbonate In tetrahydrofuran at 50℃; for 39h;81%
With benzyltrimethylammonium chloride; sodium hydrogencarbonate In isopropyl alcohol at 20℃; for 25h;80%

C15H17NO4

161596-47-0

(S)-N-glycidylphthalimide

Conditions
ConditionsYield
Stage #1: C15H17NO4 With hydrogenchloride In dichloromethane; water at 10 - 15℃; for 4h;
Stage #2: With sodium methylate In methanol at 0 - 15℃; for 3h; Reagent/catalyst;
89.7%

C17H21NO4

161596-47-0

(S)-N-glycidylphthalimide

Conditions
ConditionsYield
Stage #1: C17H21NO4 With hydrogen iodide In chloroform at 10 - 15℃; for 4h;
Stage #2: With sodium ethanolate In ethanol at 0 - 15℃; for 3h;
85.9%
51594-55-9

(R)-(-)-epichlorohydrin

1074-82-4

potassium phtalimide

161596-47-0

(S)-N-glycidylphthalimide

Conditions
ConditionsYield
With benzyltrimethylammonium chloride In isopropyl alcohol at 10℃; for 46h;83%
With benzyltrimethylammonium chloride In tetrahydrofuran at 50℃; for 44h;74%
With benzyltrimethylammonium chloride In methanol at 20℃; for 15h;68%
136918-14-4

phthalimide

51594-55-9

(R)-(-)-epichlorohydrin

A

161596-47-0

(S)-N-glycidylphthalimide

B

148857-42-5

2-((S)-3-chloro-2-hydroxypropyl)isoindoline-1,3-dione

Conditions
ConditionsYield
With potassium fluoride on basic alumina In 2-methyltetrahydrofuran for 3h; Inert atmosphere; Reflux; stereospecific reaction;A 10%
B 83%
67843-74-7

(S)-epichlorohydrin

1074-82-4

potassium phtalimide

161596-47-0

(S)-N-glycidylphthalimide

Conditions
ConditionsYield
at 70℃; for 1h; Temperature;83%
With N-benzyl-N,N,N-triethylammonium chloride; potassium iodide In isopropyl alcohol at 28℃; for 72h; Reagent/catalyst; Temperature; Solvent;88.1 g

1H-isoindole-1,3(2H)-dione, 2-[2-(benzoyloxy)-3-bromopropyl]

161596-47-0

(S)-N-glycidylphthalimide

Conditions
ConditionsYield
With sodium methylate In methanol; toluene at 9 - 22℃; for 5.16667h; Industrial scale;80.8%
Downstream Products
446292-07-5
168828-89-5
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    Product name (S)-(+)-N-(2,3-Epoxypropyl)phthalimide CAS NO.: 161596-47-0 MolecularFormua C11H9NO3 MolecularWeight 203.19 Melting point 102℃

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    Appearance:White powder Storage:ln stock Package:25kg/Barrel Application:Rivaroxaban intermediate Transportation:Express/Sea/Air Port:Any port in china

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  • (S)-(+)-GLYCIDYL PHTHALIMIDE CAS NO 161596-47-0

  • Casno:

    161596-47-0

    (S)-(+)-GLYCIDYL PHTHALIMIDE CAS NO 161596-47-0

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Specification

The (S)-2-Oxiranylmethyl-isoindole-1,3-dione is an organic compound with the formula C11H9NO3. The systematic name of this chemical is 2-(oxiran-2-ylmethyl)-1H-isoindole-1,3(2H)-dione . With the CAS registry number 161596-47-0, it is also named as 1H-Isoindole-1,3(2H)-dione, 2-(oxiranylmethyl)-. The product's categories are N-Substituted Maleimides, Succinimides & Phthalimides; N-Substituted Phthalimides; Oxiranes; Simple 3-Membered Ring Compounds.

Physical properties about (S)-2-Oxiranylmethyl-isoindole-1,3-dione are: (1)ACD/LogP: 1.60; (2)ACD/LogD (pH 5.5): 1.6; (3)ACD/LogD (pH 7.4): 1.6; (4)ACD/BCF (pH 5.5): 9.76; (5)ACD/BCF (pH 7.4): 9.76; (6)ACD/KOC (pH 5.5): 177.71; (7)ACD/KOC (pH 7.4): 177.71; (8)#H bond acceptors: 4; (9)#Freely Rotating Bonds: 2; (10)Polar Surface Area: 49.91 Å2; (11)Index of Refraction: 1.648; (12)Molar Refractivity: 51.16 cm3; (13)Molar Volume: 140.4 cm3; (14)Polarizability: 20.28×10-24cm3; (15)Surface Tension: 64.5 dyne/cm; (16)Density: 1.446 g/cm3; (17)Flash Point: 163.9 °C; (18)Enthalpy of Vaporization: 59.17 kJ/mol; (19)Boiling Point: 347.4 °C at 760 mmHg; (20)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 eyes. When you are using it, 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)N1CC2OC2)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
(3)InChIKey: DUILGEYLVHGSEE-UHFFFAOYAO
(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
(5)Std. InChIKey: DUILGEYLVHGSEE-UHFFFAOYSA-N

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