5455-98-1

Basic information

• Product Name: N-(2,3-EPOXYPROPYL)PHTHALIMIDE
• Synonyms: (phthalimidomethyl)oxirane;2-(oxiranylmethyl)-1h-isoindole-1,3(2h)-dione;2-(oxiranylmethyl)-1h-isoindole-3(2h)-dione;2,3-epoxypropylphthalimide;denacolex731;n-(2,3-epoxypropyl)-phthalimid;2-(OXIRAN-2-YLMETHYL)ISOINDOLINE-1,3-DIONE;N-GLYCIDYLPHTHALIMIDE
• CAS NO: 5455-98-1
• Molecular Formula: C₁₁H₉NO₃
• Molecular Weight: 203.19
• EINECS: 226-710-2
• Product Categories: Fused Ring Systems;Others chemical reagents;Pharmaceutical Intermediates;Miscellaneous Reagents;Building Blocks;Chemical Synthesis;Epoxides;Organic Building Blocks;Oxygen Compounds
• Mol File: 5455-98-1.mol
• Article Data: 25

Chemical Properties

• Melting Point: 92-98 °C(lit.)
• Boiling Point: 341.49°C (rough estimate)
• Flash Point: 163.9 °C
• Appearance: White to pale yellow/Crystalline Powder
• Density: 1.2621 (rough estimate)
• Vapor Pressure: 5.38E-05mmHg at 25°C
• Refractive Index: 1.4950 (estimate)
• Storage Temp.: Refrigerator
• Solubility: Chloroform (Slightly), Ethyl Acetate (Slightly)
• PKA: -2.24±0.20(Predicted)
• BRN: 171277
• CAS DataBase Reference: N-(2,3-EPOXYPROPYL)PHTHALIMIDE(CAS DataBase Reference)
• NIST Chemistry Reference: N-(2,3-EPOXYPROPYL)PHTHALIMIDE(5455-98-1)
• EPA Substance Registry System: N-(2,3-EPOXYPROPYL)PHTHALIMIDE(5455-98-1)

Safety Data

• Hazard Codes: Xi
• Statements: 41
• Safety Statements: 26-39
• WGK Germany: 2
• RTECS: TI4950000
• F: 21
• Hazardous Substances Data: 5455-98-1(Hazardous Substances Data)

Usage

Description

N-(2,3-EPOXYPROPYL)PHTHALIMIDE is a white crystalline powder that serves as a versatile reagent in the chemical synthesis process. It is particularly known for its ability to facilitate the simultaneous preparation of a primary amine and secondary alcohol, making it a valuable compound in various chemical applications.

Uses

Used in Chemical Synthesis:
N-(2,3-EPOXYPROPYL)PHTHALIMIDE is used as a reagent for the simultaneous preparation of a primary amine and secondary alcohol. This dual functionality allows for the efficient synthesis of complex molecules, which can be beneficial in various chemical and pharmaceutical applications.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, N-(2,3-EPOXYPROPYL)PHTHALIMIDE is used as a key intermediate in the synthesis of various drugs and drug candidates. Its ability to produce primary amines and secondary alcohols makes it a valuable tool in the development of new medications with specific therapeutic properties.
Used in Research and Development:
N-(2,3-EPOXYPROPYL)PHTHALIMIDE is also utilized in research and development settings, where it can be employed to explore new chemical reactions and synthetic pathways. This can lead to the discovery of novel compounds with potential applications in various fields, including medicine, agriculture, and materials science.
Used in Material Science:
In the field of material science, N-(2,3-EPOXYPROPYL)PHTHALIMIDE can be used to develop new polymers and materials with specific properties. N-(2,3-EPOXYPROPYL)PHTHALIMIDE's ability to produce primary amines and secondary alcohols can be leveraged to create materials with tailored characteristics, such as improved strength, flexibility, or chemical resistance.
Overall, N-(2,3-EPOXYPROPYL)PHTHALIMIDE is a versatile and valuable compound with a wide range of applications in various industries, including chemical synthesis, pharmaceuticals, research and development, and material science. Its unique properties make it an essential tool for the development of new drugs, materials, and other products with specific and useful characteristics.

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

Synthetic route

3-phthalimido-1-propene (5428-09-1) → 2-oxiranylmethylisoindole-1,3-dione (5455-98-1)

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;

2-(3-chloro-2-hydroxypropyl)-1H-isoindole-1,3(2H)-dione (19667-37-9, 34839-11-7, 148857-42-5, 148857-44-7) → 2-oxiranylmethylisoindole-1,3-dione (5455-98-1)

Conditions	Yield
With potassium fluoride supported on Celite In acetonitrile for 0.5h; Reflux; regioselective reaction;	98%
With potassium carbonate In toluene Reflux;

potassium phtalimide (1074-82-4) + epichlorohydrin (106-89-8) → 2-oxiranylmethylisoindole-1,3-dione (5455-98-1)

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

phthalimide (136918-14-4) + epichlorohydrin (106-89-8) → 2-oxiranylmethylisoindole-1,3-dione (5455-98-1)

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%

phthalimide (136918-14-4) + epichlorohydrin (106-89-8) → 2-oxiranylmethylisoindole-1,3-dione (5455-98-1) + 2-(3-chloro-2-hydroxypropyl)-1H-isoindole-1,3(2H)-dione (19667-37-9, 34839-11-7, 148857-42-5, 148857-44-7)

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℃;

phthalimide (136918-14-4) + oxiranyl-methanol (556-52-5) → 2-oxiranylmethylisoindole-1,3-dione (5455-98-1)

Conditions	Yield
With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran Mitsunobu reaction;	75%
With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran for 18h; Ambient temperature;	72%

potassium phtalimide (1074-82-4) + 1,2-Epoxy-3-bromopropane (3132-64-7) → 2-oxiranylmethylisoindole-1,3-dione (5455-98-1)

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

potassium phtalimide (1074-82-4) → 2-oxiranylmethylisoindole-1,3-dione (5455-98-1)

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

potassium phtalimide (1074-82-4) + o-xylylene dichloride → 2-oxiranylmethylisoindole-1,3-dione (5455-98-1)

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

glycidyl p-toluenesulfonate (118712-54-2) → 2-oxiranylmethylisoindole-1,3-dione (5455-98-1)

Reaxys ID: 20826319 → 2-oxiranylmethylisoindole-1,3-dione (5455-98-1)

phthalimide (136918-14-4) → 2-oxiranylmethylisoindole-1,3-dione (5455-98-1)

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

2-oxiranylmethylisoindole-1,3-dione (5455-98-1) → 2-(3-chloro-2-hydroxypropyl)-1H-isoindole-1,3(2H)-dione (19667-37-9, 34839-11-7, 148857-42-5, 148857-44-7)

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%

2-oxiranylmethylisoindole-1,3-dione (5455-98-1) → 2-(2-hydroxy-3-iodopropyl)-1H-isoindole-1,3(2H)-dione

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

1,1,1-tri(hydroxymethyl)propane (77-99-6) + 2-oxiranylmethylisoindole-1,3-dione (5455-98-1) + oxiranyl-methanol (556-52-5) → C72H107N3O34

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%

1-(2,3-dichlorophenyl)-piperazine hydrochloride + 2-oxiranylmethylisoindole-1,3-dione (5455-98-1) → 2-[3-[4-(2,3-dichlorophenyl)piperazin-1-yl]-2-hydroxypropyl]isoindoline-1,3-dione (1220950-99-1)

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

2-oxiranylmethylisoindole-1,3-dione (5455-98-1) + N-(tert-butoxycarbonyl)-1,4-phenylenediamine (71026-66-9) → C22H25N3O5

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

2-oxiranylmethylisoindole-1,3-dione (5455-98-1) → 2-(3-bromo-2-hydroxypropyl)-1H-isoindole-1,3(2H)-dione (6284-27-1)

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;

2-oxiranylmethylisoindole-1,3-dione (5455-98-1) + benzoic acid (65-85-0) → N-<3-(benzoyloxy)-2-hydroxypropyl>phthalimide (130277-94-0)

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

piperidine (110-89-4) + carbon disulfide (75-15-0) + 2-oxiranylmethylisoindole-1,3-dione (5455-98-1) → 3-(1,3-dioxoisoindolin-2-yl)-2-hydroxypropyl piperidine-1-carbodithioate

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

carbon disulfide (75-15-0) + 2-oxiranylmethylisoindole-1,3-dione (5455-98-1) + diethylamine (109-89-7) → 3-(1,3-dioxoisoindolin-2-yl)-2-hydroxypropyl diethylcarbamodithioate

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

2-oxiranylmethylisoindole-1,3-dione (5455-98-1) → 2-(3-azido-2-hydroxypropyl)-1H-isoindole-1,3(2H)-dione (200483-38-1)

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%

2-oxiranylmethylisoindole-1,3-dione (5455-98-1) + dibenzylamine (103-49-1) → 2-(3-(dibenzylamino)-2-hydroxypropyl)isoindoline-1,3-dione (170799-33-4)

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 + 2-oxiranylmethylisoindole-1,3-dione (5455-98-1) → 1-amino-3-(4-(2,3-dichlorophenyl)piperazin-1-yl)propan-2-ol (1220950-98-0)

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%

pyrrolidine (123-75-1) + carbon disulfide (75-15-0) + 2-oxiranylmethylisoindole-1,3-dione (5455-98-1) → 3-(1,3-dioxoisoindolin-2-yl)-2-hydroxypropyl pyrrolidine-1-carbodithioate

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

carbon disulfide (75-15-0) + 2-oxiranylmethylisoindole-1,3-dione (5455-98-1) → 2-((2-thioxo-1,3-dithiolan-4-yl)methyl)isoindoline-1,3-dione

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

2-oxiranylmethylisoindole-1,3-dione (5455-98-1) → 1-hydroxy-3-phthalimidopropan-2-one (35750-04-0)

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

2-oxiranylmethylisoindole-1,3-dione (5455-98-1) + 2-(4-fluoro-benzyl-amino)-ethanol (22116-33-2) → 4-(4-fluorobenzyl)-2-aminomethylmorpholine hydrochloride

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%

morpholine (110-91-8) + carbon disulfide (75-15-0) + 2-oxiranylmethylisoindole-1,3-dione (5455-98-1) → 3-(1,3-dioxoisoindolin-2-yl)-2-hydroxypropyl morpholine-4-carbodithioate

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

2-oxiranylmethylisoindole-1,3-dione (5455-98-1) + phenyl isocyanate (103-71-9) → 3-phenyl-5-(phthalimidomethyl)oxazolidin-2-one

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

sodium cyanide (773837-37-9) + 2-oxiranylmethylisoindole-1,3-dione (5455-98-1) → 4-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-3-hydroxybutanenitrile (13635-07-9, 132155-85-2, 132203-23-7)

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

2-oxiranylmethylisoindole-1,3-dione (5455-98-1) + thiophenol (108-98-5) → 2-[2-hydroxy-3-(phenylthio)propyl]-1H-isoindole-1,3(2H)-dione (1396010-01-7)

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

2-oxiranylmethylisoindole-1,3-dione (5455-98-1) + D-phenylalanine-L-alanine methylester (80870-39-9) → 2-{2-[3-(1,3-dioxo-1,3-dihydroisoindol-2-yl)-2-hydroxypropylamino]-3-phenylpropionylamino}propionic acid methyl ester (1166862-28-7)

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

hexamethylene imine (111-49-9) + carbon disulfide (75-15-0) + 2-oxiranylmethylisoindole-1,3-dione (5455-98-1) → 3-(1,3-dioxoisoindolin-2-yl)-2-hydroxypropyl azepane-1-carbodithioate

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

2-oxiranylmethylisoindole-1,3-dione (5455-98-1) + 2-(4-fluoro-benzyl-amino)-ethanol (22116-33-2) → 4-(4-fluorobenzyl)-2-aminomethylmorpholine sulfate

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%

ortho-methylphenyl iodide (615-37-2) + 2-oxiranylmethylisoindole-1,3-dione (5455-98-1) + tris-iso-propylsilyl acetylene (89343-06-6) → 2-(2-hydroxy-3-(3-methyl-2-((triisopropylsilyl)ethynyl)phenyl)propyl)isoindoline-1,3-dione

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%

2-oxiranylmethylisoindole-1,3-dione (5455-98-1) + 2-(4-fluoro-benzyl-amino)-ethanol (22116-33-2) → C12H17FN2O4S

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%

2-oxiranylmethylisoindole-1,3-dione (5455-98-1) + 2-(4-fluoro-benzyl-amino)-ethanol (22116-33-2) → 4-(4-fluorobenzyl)-2-aminomethylmorpholine phosphate

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%

Upstream product

• 1074-82-4 potassium phtalimide 
• 106-89-8 epichlorohydrin 
• 3132-64-7 1,2-Epoxy-3-bromopropane 
• 136918-14-4 phthalimide 
• 556-52-5 oxiranyl-methanol 
• 5428-09-1 3-phthalimido-1-propene 
• 118712-54-2 glycidyl p-toluenesulfonate 
• 19667-37-9 2-(3-chloro-2-hydroxypropyl)-1H-isoindole-1,3(2H)-dione 

Downstream Products

• 6284-28-2 2-oxo-5-phthalimidomethyl-tetrahydro-furan-3-carboxylic acid ethyl ester 
• 6284-27-1 2-(3-bromo-2-hydroxypropyl)-1H-isoindole-1,3(2H)-dione 
• 61986-26-3 N-(2,3-dihydro-benzo[4,5]imidazo[2,1-b]oxazol-2-ylmethyl)-phthalimide 
• 616-29-5 1,3-Diamino-2-hydroxypropane 
• 93272-45-8 2-(2-hydroxy-3-(2-nitro-1H-imidazol-1-yl)propyl)isoindoline-1,3-dione 
• 86506-69-6 2-[2-hydroxy-3-[3-(1-piperidinylmethyl)-phenoxy]propyl]-1H-isoindole-1,3-(2H)-dione 
• 117078-38-3 2-<2-Hydroxy-3-<3-(3-methyl-1-piperidinylmethyl)phenoxy>propyl>-1H-isoindol-1,3(2H)-dion 
• 130277-94-0 N-<3-(benzoyloxy)-2-hydroxypropyl>phthalimide 
• 90503-16-5 2-(3-(benzyloxy)-2-hydroxypropyl)isoindoline-1,3-dione 
• 170799-33-4 2-(3-(dibenzylamino)-2-hydroxypropyl)isoindoline-1,3-dione 
• 1026802-84-5 Cyclohexylmethyl-[3-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-2-trimethylsilanyloxy-propyl]-phosphinic acid ethyl ester 

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