N-aminophthalimide

Base Information

• Chemical Name: N-aminophthalimide
• CAS No.: 1875-48-5
• Molecular Formula: C9H10O4
• Molecular Weight: 162.148
• Hs Code.: 29251900
• European Community (EC) Number: 217-505-9
• NSC Number: 407982,91685
• DSSTox Substance ID: DTXSID70172061
• Nikkaji Number: J126.330G
• Wikidata: Q83042207
• Mol file: 1875-48-5.mol

Synonyms:N-aminophthalimide

Chemical Property of N-aminophthalimide

Chemical Property:

• Appearance/Colour: white to off-white crystalline powder
• Vapor Pressure: 4.97E-05mmHg at 25°C
• Melting Point: 200-202 °C
• Refractive Index: 1.67
• Boiling Point: 348.6 °C at 760 mmHg
• PKA: -1.73±0.20(Predicted)
• Flash Point: 164.6 °C
• PSA: 63.40000
• Density: 1.472 g/cm³
• LogP: 0.79450
• Storage Temp.: 2-8°C
• Solubility.: Solubility in hot methanol almost transparent.
• XLogP3: 0.6
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 0
• Exact Mass: 162.042927438
• Heavy Atom Count: 12
• Complexity: 215

Purity/Quality:

99% ^*data from raw suppliers

2-Aminoisoindoline-1,3-dione ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 36/37/38-42/43
• Safety Statements: 22-26-36/37-45

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Nitrogen Compounds -> Hydrazides
• Canonical SMILES: C1=CC=C2C(=C1)C(=O)N(C2=O)N
• Uses: It is employed in the aziridination of chiral N-enoyl sultams. It is also used in the synthesis of n-phthalimidoaziridines N-Aminophthalimide was employed in the aziridination of chiral N-enoyl sultams. It was also used in the synthesis of n-phthalimidoaziridines.

Technology Process of N-aminophthalimide

There total 71 articles about N-aminophthalimide which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 99.5%

phthalimide (136918-14-4,85-41-6) → N-aminophthalamide (1875-48-5)

Guidance literature:

With hydrazine hydrate; In ethanol; at 0 - 20 ℃; for 2h; Large scale;

Reference yield: 98.0%

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)

Guidance literature:

With hydrazine hydrate; In methanol; for 2h; Ambient temperature;

DOI:10.1021/jo00152a014

Reference yield: 95.0%

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)

Guidance literature:

With hydrazine hydrate; In methanol; for 2h; Ambient temperature;

DOI:10.1021/jo00152a014

upstream raw materials:

2-<(1H-Imidazol-1-yl)octyl>-1H-isoindole-1,3(2H)-dione

phthalic anhydride

phthalimide

ethanol

Downstream raw materials:

N-phthalimido-phthalamic acid

2-trans-cinnamylidenamino-isoindoline-1,3-dione

2-[5-(4-nitro-phenoxy)-pentylamino]-isoindoline-1,3-dione

[2,2'-biisoindoline]-1,1',3,3'-tetraone

Refernces

Intramolecular cycloaddition of N-phthalimidoaziridines to double and triple carbon-carbon bonds

10.1016/j.tetlet.2009.08.015

The research investigates the intramolecular cycloaddition of N-phthalimidoaziridines to carbon–carbon double and triple bonds. The purpose is to explore the potential of this reaction to produce complex nitrogen-containing heterocyclic compounds, which have applications in various fields including natural product synthesis and pharmaceuticals. The study synthesized N-phthalimidoaziridines with unsaturated side chains from salicylic aldehyde and used oxidative aminoaziridination procedures. Key chemicals involved include salicylic aldehyde, ortho-(allyloxy)- and ortho-(propargyloxy)cinnamic acids, benzylidenemalonic acid derivatives, and N-aminophthalimide. The results showed that thermolysis of these aziridines led to the formation of condensed N-phthalimidopyrrolidines, N-phthalimidopyrrolines, or their subsequent transformations, with yields and product configurations influenced by the nature of the substituents and the type of unsaturated bond. The study concludes that the reaction is a general process for the described compounds, with the rate-determining step likely being the cleavage of the aziridine to form the azomethine ylide. The configuration of the products aligns with a mechanism involving thermally allowed conrotatory ring-opening followed by a concerted 1,3-dipolar cycloaddition.