N-(2,3-Epoxypropyl)phthalimide supplier

Name
N-(2,3-EPOXYPROPYL)PHTHALIMIDE
EINECS 226-710-2
CAS No. 5455-98-1
Article Data29
CAS DataBase
Density 1.446 g/cm³
Solubility
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
Appearance white crystalline powder
Safety 26-39
Risk Codes 41
Molecular Structure
Hazard Symbols Xi
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;
PSA 49.91000
LogP 0.61930

Synthetic route

: 5428-09-1
3-phthalimido-1-propene

: 5455-98-1
2-oxiranylmethylisoindole-1,3-dione

Conditions

Conditions	Yield
With 3-chloro-benzenecarboperoxoic acid In dichloromethane	99%
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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℃;

...Expand

: 136918-14-4
phthalimide

: 556-52-5
oxiranyl-methanol

: 5455-98-1
2-oxiranylmethylisoindole-1,3-dione

Conditions

Conditions	Yield
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

Conditions	Yield
In 1,2-dimethoxyethane at 120℃; for 3h;	51%

: 1074-82-4
potassium phtalimide

: 5455-98-1
2-oxiranylmethylisoindole-1,3-dione

Conditions

Conditions	Yield
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

Conditions	Yield
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

Reaxys ID: 20826319: Reaxys ID: 20826319

: 5455-98-1
2-oxiranylmethylisoindole-1,3-dione

: 136918-14-4
phthalimide

: 5455-98-1
2-oxiranylmethylisoindole-1,3-dione

Conditions

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

: 5455-98-1
2-oxiranylmethylisoindole-1,3-dione

: 19667-37-9, 34839-11-7, 148857-42-5, 148857-44-7
2-(3-chloro-2-hydroxypropyl)-1H-isoindole-1,3(2H)-dione

Conditions

Conditions	Yield
With hydrogenchloride In chloroform; water at 0℃; for 0.5h;	100%
With hydrogenchloride In chloroform; water at 0℃; for 0.5h;	100%
With hydrogenchloride; water In chloroform at 0℃; for 0.5h; regioselective reaction;	100%

: 5455-98-1
2-oxiranylmethylisoindole-1,3-dione

: 2-(2-hydroxy-3-iodopropyl)-1H-isoindole-1,3(2H)-dione

Conditions

Conditions	Yield
With water; hydrogen iodide In chloroform at 0℃; for 1h; regioselective reaction;	100%
Stage #1: 2-oxiranylmethylisoindole-1,3-dione With diiodomethane In 2-methyltetrahydrofuran at -78℃; for 0.0333333h; Stage #2: With methyllithium In 2-methyltetrahydrofuran; diethyl ether at -78℃; for 1h; Reagent/catalyst;	91%
With chloroform; hydrogen iodide
With water; hydrogen iodide

: 77-99-6
1,1,1-tri(hydroxymethyl)propane

: 5455-98-1
2-oxiranylmethylisoindole-1,3-dione

: 556-52-5
oxiranyl-methanol

: C72H107N3O34

Conditions

Conditions	Yield
Stage #1: 1,1,1-tri(hydroxymethyl)propane With potassium tert-butylate In tetrahydrofuran at 120℃; for 18h; Inert atmosphere; Stage #2: oxiranyl-methanol In tetrahydrofuran at 120℃; for 0.5h; Inert atmosphere; Stage #3: 2-oxiranylmethylisoindole-1,3-dione In tetrahydrofuran at 120℃; Inert atmosphere;	100%

...Expand

: 1-(2,3-dichlorophenyl)-piperazine hydrochloride

: 5455-98-1
2-oxiranylmethylisoindole-1,3-dione

: 1220950-99-1
2-[3-[4-(2,3-dichlorophenyl)piperazin-1-yl]-2-hydroxypropyl]isoindoline-1,3-dione

Conditions

Conditions	Yield
With triethylamine In isopropyl alcohol at 100℃; for 1.5h; Microwave irradiation;	99%
With triethylamine In tetrahydrofuran at 20 - 80℃; Inert atmosphere;
With triethylamine In tetrahydrofuran at 80℃; Inert atmosphere;
With triethylamine In tetrahydrofuran at 20 - 80℃; Inert atmosphere;	13 g

: 5455-98-1
2-oxiranylmethylisoindole-1,3-dione

: 71026-66-9
N-(tert-butoxycarbonyl)-1,4-phenylenediamine

: C22H25N3O5

Conditions

Conditions	Yield
In isopropyl alcohol for 5h; Reflux;	99%

: 5455-98-1
2-oxiranylmethylisoindole-1,3-dione

: 6284-27-1
2-(3-bromo-2-hydroxypropyl)-1H-isoindole-1,3(2H)-dione

Conditions

Conditions	Yield
With water; hydrogen bromide In chloroform at 0℃; for 0.5h; regioselective reaction;	98%
Stage #1: 2-oxiranylmethylisoindole-1,3-dione With iodobromomethane In 2-methyltetrahydrofuran at -78℃; for 0.0333333h; Stage #2: With methyllithium In 2-methyltetrahydrofuran; diethyl ether at -78℃; for 1h;	89%
With chloroform; hydrogen bromide
With water; hydrogen bromide
With hydrogen bromide In chloroform at 0℃; for 16h;

: 5455-98-1
2-oxiranylmethylisoindole-1,3-dione

: 65-85-0
benzoic acid

: 130277-94-0
N-<3-(benzoyloxy)-2-hydroxypropyl>phthalimide

Conditions

Conditions	Yield
With sodium benzoate In N,N-dimethyl-formamide for 3h; Heating;	98%

: 110-89-4
piperidine

: 75-15-0
carbon disulfide

: 5455-98-1
2-oxiranylmethylisoindole-1,3-dione

: 3-(1,3-dioxoisoindolin-2-yl)-2-hydroxypropyl piperidine-1-carbodithioate

Conditions

Conditions	Yield
In water at 20℃; for 8h; regioselective reaction;	98%

...Expand

: 75-15-0
carbon disulfide

: 5455-98-1
2-oxiranylmethylisoindole-1,3-dione

: 109-89-7
diethylamine

: 3-(1,3-dioxoisoindolin-2-yl)-2-hydroxypropyl diethylcarbamodithioate

Conditions

Conditions	Yield
In water at 20℃; for 8h; regioselective reaction;	98%

...Expand

: 5455-98-1
2-oxiranylmethylisoindole-1,3-dione

: 200483-38-1
2-(3-azido-2-hydroxypropyl)-1H-isoindole-1,3(2H)-dione

Conditions

Conditions	Yield
With sodium azide; water; acetic acid at 0 - 30℃; for 6h; regioselective reaction;	97%
With lithium azidohydridodiisobutylaluminate In tetrahydrofuran for 2h; Ambient temperature;	76%
With sodium azide; ammonium chloride In ethanol; water at 0 - 20℃;	74.2%

: 5455-98-1
2-oxiranylmethylisoindole-1,3-dione

: 103-49-1
dibenzylamine

: 170799-33-4
2-(3-(dibenzylamino)-2-hydroxypropyl)isoindoline-1,3-dione

Conditions

Conditions	Yield
at 80℃; for 20h;	95%
Stage #1: 2-oxiranylmethylisoindole-1,3-dione; dibenzylamine at 80℃; Stage #2: With ethanol at 20℃;	4.5 g

: 1-(2,3-dichlorophenyl)-piperazine hydrochloride

: 5455-98-1
2-oxiranylmethylisoindole-1,3-dione

: 1220950-98-0
1-amino-3-(4-(2,3-dichlorophenyl)piperazin-1-yl)propan-2-ol

Conditions

Conditions	Yield
Stage #1: 1-(2,3-dichlorophenyl)-piperazine hydrochloride; 2-oxiranylmethylisoindole-1,3-dione With triethylamine In tetrahydrofuran at 80℃; Stage #2: With water In tetrahydrofuran Stage #3: With hydrazine hydrate In ethanol at 80℃; for 2h;	95%

: 123-75-1
pyrrolidine

: 75-15-0
carbon disulfide

: 5455-98-1
2-oxiranylmethylisoindole-1,3-dione

: 3-(1,3-dioxoisoindolin-2-yl)-2-hydroxypropyl pyrrolidine-1-carbodithioate

Conditions

Conditions	Yield
In water at 20℃; for 8h; regioselective reaction;	95%

...Expand

: 75-15-0
carbon disulfide

: 5455-98-1
2-oxiranylmethylisoindole-1,3-dione

: 2-((2-thioxo-1,3-dithiolan-4-yl)methyl)isoindoline-1,3-dione

Conditions

Conditions	Yield
With 1-n-butyl-3-methylimidazolim bromide; potassium hydroxide; lithium bromide In neat (no solvent) at 70℃; for 24h; chemoselective reaction;	95%

: 5455-98-1
2-oxiranylmethylisoindole-1,3-dione

: 35750-04-0
1-hydroxy-3-phthalimidopropan-2-one

Conditions

Conditions	Yield
With ammonium heptamolybdate; dihydrogen peroxide In tetrahydrofuran at 20℃; for 0.75h; Oxidation;	94%

: 5455-98-1
2-oxiranylmethylisoindole-1,3-dione

: 22116-33-2
2-(4-fluoro-benzyl-amino)-ethanol

: 4-(4-fluorobenzyl)-2-aminomethylmorpholine hydrochloride

Conditions

Conditions	Yield
Stage #1: 2-oxiranylmethylisoindole-1,3-dione; 2-(4-fluoro-benzyl-amino)-ethanol at 70 - 80℃; for 3h; Stage #2: With sulfuric acid at 70 - 145℃; for 2.5h; Stage #3: With hydrogenchloride In ethanol; water for 1.5h;	92.7%

: 110-91-8
morpholine

: 75-15-0
carbon disulfide

: 5455-98-1
2-oxiranylmethylisoindole-1,3-dione

: 3-(1,3-dioxoisoindolin-2-yl)-2-hydroxypropyl morpholine-4-carbodithioate

Conditions

Conditions	Yield
In water at 20℃; for 8h; regioselective reaction;	92%

...Expand

: 5455-98-1
2-oxiranylmethylisoindole-1,3-dione

: 103-71-9
phenyl isocyanate

: 3-phenyl-5-(phthalimidomethyl)oxazolidin-2-one

Conditions

Conditions	Yield
With triethylammonium iodide In neat (no solvent) at 100℃; for 1h; Green chemistry;	92%

: 773837-37-9
sodium cyanide

: 5455-98-1
2-oxiranylmethylisoindole-1,3-dione

: 13635-07-9, 132155-85-2, 132203-23-7
4-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-3-hydroxybutanenitrile

Conditions

Conditions	Yield
With water; acetic acid In ethanol at 0 - 20℃; for 5h; regioselective reaction;	91%

: 5455-98-1
2-oxiranylmethylisoindole-1,3-dione

: 108-98-5
thiophenol

: 1396010-01-7
2-[2-hydroxy-3-(phenylthio)propyl]-1H-isoindole-1,3(2H)-dione

Conditions

Conditions	Yield
With zinc perchlorate In chloroform at 20℃; for 6h; regioselective reaction;	91%

: 5455-98-1
2-oxiranylmethylisoindole-1,3-dione

: 80870-39-9
D-phenylalanine-L-alanine methylester

: 1166862-28-7
2-{2-[3-(1,3-dioxo-1,3-dihydroisoindol-2-yl)-2-hydroxypropylamino]-3-phenylpropionylamino}propionic acid methyl ester

Conditions

Conditions	Yield
In trifluoroethanol for 3.5h; Reflux;	90%

: 111-49-9
hexamethylene imine

: 75-15-0
carbon disulfide

: 5455-98-1
2-oxiranylmethylisoindole-1,3-dione

: 3-(1,3-dioxoisoindolin-2-yl)-2-hydroxypropyl azepane-1-carbodithioate

Conditions

Conditions	Yield
In water at 20℃; for 8h; regioselective reaction;	90%

...Expand

: 5455-98-1
2-oxiranylmethylisoindole-1,3-dione

: 22116-33-2
2-(4-fluoro-benzyl-amino)-ethanol

: 4-(4-fluorobenzyl)-2-aminomethylmorpholine sulfate

Conditions

Conditions	Yield
Stage #1: 2-oxiranylmethylisoindole-1,3-dione; 2-(4-fluoro-benzyl-amino)-ethanol at 70 - 80℃; for 3h; Stage #2: With sulfuric acid at 70 - 145℃; for 2.5h; Stage #3: With sulfuric acid In ethanol for 2h;	89.88%

: 615-37-2
ortho-methylphenyl iodide

: 5455-98-1
2-oxiranylmethylisoindole-1,3-dione

: 89343-06-6
tris-iso-propylsilyl acetylene

: 2-(2-hydroxy-3-(3-methyl-2-((triisopropylsilyl)ethynyl)phenyl)propyl)isoindoline-1,3-dione

Conditions

Conditions	Yield
With 1-methyl-pyrrolidin-2-one; norborn-2-ene; potassium acetate; palladium diacetate; XPhos at 60℃; for 24h; Glovebox; Inert atmosphere; Sealed tube; regioselective reaction;	89%

...Expand

: 5455-98-1
2-oxiranylmethylisoindole-1,3-dione

: 22116-33-2
2-(4-fluoro-benzyl-amino)-ethanol

: C12H17FN2O4S

Conditions

Conditions	Yield
Stage #1: 2-oxiranylmethylisoindole-1,3-dione; 2-(4-fluoro-benzyl-amino)-ethanol at 70 - 80℃; for 3h; Stage #2: With sulfuric acid at 70 - 145℃; for 2.5h; Stage #3: With sulfuric acid In ethanol for 1.5h;	88.53%

: 5455-98-1
2-oxiranylmethylisoindole-1,3-dione

: 22116-33-2
2-(4-fluoro-benzyl-amino)-ethanol

: 4-(4-fluorobenzyl)-2-aminomethylmorpholine phosphate

Conditions

Conditions	Yield
Stage #1: 2-oxiranylmethylisoindole-1,3-dione; 2-(4-fluoro-benzyl-amino)-ethanol at 70 - 80℃; for 3h; Stage #2: With sulfuric acid at 70 - 145℃; for 2.5h; Stage #3: With phosphoric acid In ethanol for 1.5h;	88.27%

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 C₁₁H₉NO₃and 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 K₂CO₃and 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.

Product Name

N-(2,3-EPOXYPROPYL)PHTHALIMIDE

Synthetic route

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

N-(2,3-Epoxypropyl)phthalimide Specification

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