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N-(2,3-Epoxypropyl)phthalimide

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Name

N-(2,3-Epoxypropyl)phthalimide

EINECS 226-710-2
CAS No. 5455-98-1 Density 1.446 g/cm3
PSA 49.91000 LogP 0.61930
Solubility N/A Melting Point 92-98 °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 white crystalline powder
Safety 26-39 Risk Codes 41
Molecular Structure Molecular Structure of 5455-98-1 (N-(2,3-EPOXYPROPYL)PHTHALIMIDE) Hazard Symbols IrritantXi
Synonyms

1H-Isoindole-1,3(2H)-dione,2-(oxiranylmethyl)- (9CI);Phthalimide, N-(2,3-epoxypropyl)- (8CI);(Phthalimidomethyl)oxirane;2,3-Epoxypropylphthalimide;2-(Phthalimidomethyl)oxirane;2-[(Oxiranyl)methyl]isoindole-1,3-dione;DenacolEX 731;N-(2,3-Epoxypropan-1-yl)phthalimide;N-(2,3-Epoxypropyl)phthalimide;N-Glycidylphthalimide;N-Oxiranylmethylphthalimide;NSC 7244;N-(2,3-Epoxypropyl) phthalmide;

Article Data 29

N-(2,3-Epoxypropyl)phthalimide Synthetic route

5428-09-1

3-phthalimido-1-propene

5455-98-1

2-oxiranylmethylisoindole-1,3-dione

Conditions
ConditionsYield
With 3-chloro-benzenecarboperoxoic acid In dichloromethane99%
With 3-chloro-benzenecarboperoxoic acid In dichloromethane for 72h;92%
With 3-chloro-benzenecarboperoxoic acid In dichloromethane at 20℃; for 16h;
19667-37-9, 34839-11-7, 148857-42-5, 148857-44-7

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

5455-98-1

2-oxiranylmethylisoindole-1,3-dione

Conditions
ConditionsYield
With potassium fluoride supported on Celite In acetonitrile for 0.5h; Reflux; regioselective reaction;98%
With potassium carbonate In toluene Reflux;
1074-82-4

potassium phtalimide

106-89-8

epichlorohydrin

5455-98-1

2-oxiranylmethylisoindole-1,3-dione

Conditions
ConditionsYield
for 8h; Reflux;95%
In N,N-dimethyl-formamide at 20℃; for 10h;90%
at 120℃; for 5h;80%
136918-14-4

phthalimide

106-89-8

epichlorohydrin

5455-98-1

2-oxiranylmethylisoindole-1,3-dione

Conditions
ConditionsYield
With potassium carbonate at 120℃; for 5h;89%
With potassium fluoride; 3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate at 85℃; for 6h;87%
Stage #1: phthalimide With potassium hydroxide In ethanol; water at 75 - 85℃;
Stage #2: epichlorohydrin at 120℃;
68.54%
With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran at 0 - 15℃; for 12h; Inert atmosphere;36.6%
136918-14-4

phthalimide

106-89-8

epichlorohydrin

A

5455-98-1

2-oxiranylmethylisoindole-1,3-dione

B

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

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

Conditions
ConditionsYield
With potassium fluoride on basic alumina In 2-methyltetrahydrofuran for 3h; Inert atmosphere; Reflux; chemoselective reaction;A 12%
B 86%
With aluminum oxide In 1-methyl-pyrrolidin-2-one at 64 - 68℃;
136918-14-4

phthalimide

556-52-5

oxiranyl-methanol

5455-98-1

2-oxiranylmethylisoindole-1,3-dione

Conditions
ConditionsYield
With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran Mitsunobu reaction;75%
With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran for 18h; Ambient temperature;72%
1074-82-4

potassium phtalimide

3132-64-7

1,2-Epoxy-3-bromopropane

5455-98-1

2-oxiranylmethylisoindole-1,3-dione

Conditions
ConditionsYield
In 1,2-dimethoxyethane at 120℃; for 3h;51%
1074-82-4

potassium phtalimide

5455-98-1

2-oxiranylmethylisoindole-1,3-dione

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 80.2 percent / dimethylformamide / 50 °C
2: 92 percent / m-chloroperbenzoic acid / CH2Cl2 / 72 h
View Scheme
Multi-step reaction with 2 steps
1: N,N-dimethyl-formamide / 16 h / 80 °C
2: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 16 h / 20 °C
View Scheme
1074-82-4

potassium phtalimide

o-xylylene dichloride

o-xylylene dichloride

5455-98-1

2-oxiranylmethylisoindole-1,3-dione

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 82 percent / 18-crown-6 / toluene
2: 99 percent / mCPBA / CH2Cl2
View Scheme
118712-54-2

glycidyl p-toluenesulfonate

5455-98-1

2-oxiranylmethylisoindole-1,3-dione

N-(2,3-Epoxypropyl)phthalimide Consensus Reports

Reported in EPA TSCA Inventory.

N-(2,3-Epoxypropyl)phthalimide Specification

The IUPAC name of N-(2,3-Epoxypropyl)phthalimide is 2-(oxiran-2-ylmethyl)isoindole-1,3-dione. With the CAS registry number 5455-98-1, it is also named as (Phthalimidomethyl)oxirane. The product's categories are Fused Ring Systems; Others Chemical Reagents, and the other registry number is 142176-79-2. Besides, it is white crystalline powder, which should be sealed in a dark, ventilated and dry place at 0-6 °C. In addition, its molecular formula is C11H9NO3 and molecular weight is 203.19.

The other characteristics of this product can be summarized as: (1)EINECS: 226-710-2; (2)ACD/LogP: 1.60; (3)# of Rule of 5 Violations: 0; (4)ACD/LogD (pH 5.5): 1.6; (5)ACD/LogD (pH 7.4): 1.6; (6)ACD/BCF (pH 5.5): 9.76; (7)ACD/BCF (pH 7.4): 9.76; (8)ACD/KOC (pH 5.5): 177.71; (9)ACD/KOC (pH 7.4): 177.71; (10)#H bond acceptors: 4; (11)#H bond donors: 0; (12)#Freely Rotating Bonds: 2; (13)Index of Refraction: 1.648; (14)Molar Refractivity: 51.16 cm3; (15)Molar Volume: 140.4 cm3; (16)Surface Tension: 64.5 dyne/cm; (17)Density: 1.446 g/cm3; (18)Flash Point: 163.9 °C; (19)Melting Point: 92-98 °C; (20)Enthalpy of Vaporization: 59.17 kJ/mol; (21)Boiling Point: 347.4 °C at 760 mmHg; (22)Vapour Pressure: 5.38E-05 mmHg at 25 °C.

Preparation of N-(2,3-Epoxypropyl)phthalimide: this chemical can be prepared by chloromethyl-oxirane and phthalimide; potassium salt.



This reaction needs dimethylformamide at temperature of 20 °C. The reaction time is 10 hours. The yield is 90 %.

Uses of N-(2,3-Epoxypropyl)phthalimide: it can react with 2-nitro-1H-imidazole to get 2-[2-hydroxy-3-(2-nitro-imidazol-1-yl)-propyl]-isoindole-1,3-dione.



This reaction needs K2CO3 and ethanol by heating for 6 hours. The yield is 59 %.

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

People can use the following data to convert to the molecule structure.
(1)Canonical SMILES: C1C(O1)CN2C(=O)C3=CC=CC=C3C2=O
(2)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
(3)InChIKey: DUILGEYLVHGSEE-UHFFFAOYSA-N 

The toxicity data is as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
rat LCLo inhalation 4400mg/m3/4H (4400mg/m3) SENSE ORGANS AND SPECIAL SENSES: OTHER CHANGES: OLFACTION

LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES
Journal of the American College of Toxicology. Vol. 4(1), Pg. 219, 1985.
rat LD50 oral 4700mg/kg (4700mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

BEHAVIORAL: ATAXIA

GASTROINTESTINAL: CHANGES IN STRUCTURE OR FUNCTION OF SALIVARY GLANDS
Toxicology and Applied Pharmacology. Vol. 51, Pg. 197, 1979.

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