1875-48-5

Basic information

• Product Name: N-AMINOPHTHALIMIDE
• Synonyms: 2-AMINOISOINDOLINE-1,3-DIONE;N,N-PHTHALOYLHYDRAZINE, UNSYM;N-AMINOPHTHALIMIDE;SPECS AQ-344/40414632;Aminophthalimidetech;N-AMINOPHTHALIMIDE, TECH., 90%;N-Aminophthalimide, 90%, tech.;2-Amino-2H-isoindole-1,3-dione
• CAS NO: 1875-48-5
• Molecular Formula: C8H6N2O2
• Molecular Weight: 162.15
• EINECS: 217-505-9
• Product Categories: N-Substituted Maleimides, Succinimides & Phthalimides;N-Substituted Phthalimides;Building Blocks;Carbonyl Compounds;Chemical Synthesis;Hydrazides;Organic Building Blocks
• Mol File: 1875-48-5.mol
• Article Data: 31

Chemical Properties

• Melting Point: 200-202 °C(lit.)
• Boiling Point: 288.82°C (rough estimate)
• Flash Point: 164.6 °C
• Appearance: /
• Density: 1.3264 (rough estimate)
• Vapor Pressure: 4.97E-05mmHg at 25°C
• Refractive Index: 1.5770 (estimate)
• Storage Temp.: 2-8°C
• Solubility: Solubility in hot methanol almost transparent.
• PKA: -1.73±0.20(Predicted)
• BRN: 383756
• CAS DataBase Reference: N-AMINOPHTHALIMIDE(CAS DataBase Reference)
• NIST Chemistry Reference: N-AMINOPHTHALIMIDE(1875-48-5)
• EPA Substance Registry System: N-AMINOPHTHALIMIDE(1875-48-5)

Safety Data

• Hazard Codes: Xn
• Statements: 36/37/38-42/43
• Safety Statements: 22-26-36/37-45
• WGK Germany: 3
• F: 9
• Hazardous Substances Data: 1875-48-5(Hazardous Substances Data)

Usage

Chemical Description

N-aminophthalimide is a nitrogen-containing heterocyclic compound that can be used as a reagent in organic synthesis.

InChI:InChI=1/C8H6N2O2/c9-10-7(11)5-3-1-2-4-6(5)8(10)12/h1-4H,9H2

Synthetic route

phthalimide (136918-14-4) → N-aminophthalamide (1875-48-5)

Conditions	Yield
With hydrazine hydrate In ethanol at 0 - 20℃; for 2h; Large scale;	99.5%
With hydrazine hydrate In ethanol; water at -20 - 20℃; for 4h;	92%
With hydrazine In ethanol at 5℃; for 2h;	75%

3t-(4-chloro-phenyl)-2-cyano-1-phthalimido-aziridine-2r-carboxylic acid methyl ester (49678-79-7) → N-aminophthalamide (1875-48-5) + methyl 2-cyano-3-(isopropylamino)-4-phenylbut-2-enoate (84118-25-2)

Conditions	Yield
With hydrazine hydrate In methanol for 2h; Ambient temperature;	A n/a B 98%

2-cyano-3-(isopropylimino)-2-(methoxycarbonyl)-4-(p-methoxyphenyl)-1-phthalimidoazetidine (72011-38-2) → N-aminophthalamide (1875-48-5) + methyl 2-cyano-3-(isopropylamino)-4-(p-methylphenyl)-but-2-enoate (84118-27-4)

Conditions	Yield
With hydrazine hydrate In methanol for 2h; Ambient temperature;	A n/a B 95%

2-cyano-2-(methoxycarbonyl)-4-(p-chlorophenyl)-1-phthalimido-3-(tert-butylimino)azetidine (72011-33-7) → N-aminophthalamide (1875-48-5) + methyl 2-cyano-3-(tert-butylamino)-4-(p-chlorophenyl)but-2-enoate (84130-26-7)

Conditions	Yield
With hydrazine hydrate In methanol for 2h; Ambient temperature;	A n/a B 95%

2-cyano-3-(isopropylimino)-2-(methoxycarbonyl)-4-(p-chlorophenyl)-1-phthalimidoazetidine (343797-05-7) → N-aminophthalamide (1875-48-5) + methyl 2-cyano-3-(isopropylamino)-4-(p-chlorophenyl)-but-2-enoate (84118-26-3)

Conditions	Yield
With hydrazine hydrate In methanol for 2h; Ambient temperature;	A n/a B 95%

potassium phtalimide (1074-82-4) → N-aminophthalamide (1875-48-5)

Conditions	Yield
With O-(diphenylphosphinyl)hydroxylamine In N,N-dimethyl-formamide at 20℃; for 4h;	92%

N-(2-hydroxyethyl)-2-phthalimidoaceto-2',6'-xylidide (75889-07-5) → N-aminophthalamide (1875-48-5) + N-(2-hydroxyethyl)-2-aminoaceto-2',6'-xylidide hydrochloride (75889-12-2)

Conditions	Yield
With hydrogenchloride; hydrazine hydrate In ethanol Heating; 1.) 2 h, 2.) 0.5 h;	A 86% B 87%

Upstream product

• 93669-06-8 2-<(1H-Imidazol-1-yl)octyl>-1H-isoindole-1,3(2H)-dione 
• 85-44-9 phthalic anhydride 
• 136918-14-4 phthalimide 
• 64-17-5 ethanol 
• 164415-13-8 o-(Aminocarbamoyl)benzamide 
• 5460-29-7 2-(3-bromopropyl)isoindole-1,3-dione 
• 72459-53-1 2-[2-(1H-imidazol-1-yl)ethyl]-isoindole-1,3(2H)-dione 
• 100327-50-2 2-[2-(1,2,4-triazol-1-yl)ethyl]isoindoline-1,3-dione 
• 1074-82-4 potassium phtalimide 
• 108-24-7 acetic anhydride 
• 80337-77-5 methyl 3-<2'-(4-phthalimidobutyl)-2,4'-bithiazole-4-carboxamido>propyl sulfide 
• 49678-79-7 3t-(4-chloro-phenyl)-2-cyano-1-phthalimido-aziridine-2r-carboxylic acid methyl ester 
• 72011-38-2 2-cyano-3-(isopropylimino)-2-(methoxycarbonyl)-4-(p-methoxyphenyl)-1-phthalimidoazetidine 
• 72011-33-7 2-cyano-2-(methoxycarbonyl)-4-(p-chlorophenyl)-1-phthalimido-3-(tert-butylimino)azetidine 

Downstream Products

• 304481-13-8 N-phthalimido-phthalamic acid 
• 32387-09-0 2-trans-cinnamylidenamino-isoindoline-1,3-dione 
• 108368-15-6 2-[5-(4-nitro-phenoxy)-pentylamino]-isoindoline-1,3-dione 
• 4388-29-8 [2,2'-biisoindoline]-1,1',3,3'-tetraone 
• 85468-44-6 (E)-2-(benzylideneamino)isoindole-1,3-dione 
• 94374-88-6 2-benzylideneamino-benzo[de]isoquinoline-1,3-dione 
• 85468-48-0 N-(p-methoxybenzylidene)aminophthalimide 
• 94374-92-2 N-(2-Hydroxy-benzylidenamino)-naphthalimid 
• 1705-04-0 4-benzoyloxy-2H-phthalazin-1-one 
• 16067-65-5 N-(1,3-dioxo-1,3-dihydroisoindol-2-yl)-benzamide 
• 19162-45-9 N-(1,3-dioxo-1H-benzo[de]isoquinolin-2(3H)-yl)benzamide 
• 57353-95-4 2-isopropylidenamino-isoindoline-1,3-dione 
• 4752-10-7 1,4-dichlorophthalazine 
• 1445-69-8 2,3-dihydrophthalazine-1,4-dione 

Relevant articles and documents

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(Chemical Equation Presented) 1,1′-Bipyrrole is synthesized in four steps from hydrazine. A colorless solid, mp 52°C, it sublimes readily at room temperature and forms X-ray quality crystals in which the rings are not coplanar but are nearly orthogonal.

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