N-(Z-amino)phthalimide

Base Information

• Chemical Name: N-(Z-amino)phthalimide
• CAS No.: 287728-91-0
• Molecular Formula: C16H12 N2 O4
• Molecular Weight: 296.282
• DSSTox Substance ID: DTXSID60403235
• Nikkaji Number: J2.044.269G
• Wikidata: Q82206854
• Mol file: 287728-91-0.mol

Synonyms:N-(Z-amino)phthalimide;287728-91-0;Benzyl N-(1,3-dioxoisoindol-2-yl)carbamate;N-(Benzyloxycarbonylamino)phthalimide;SCHEMBL5638173;DTXSID60403235;AKOS015903040;J-017256;N-(1,3-dioxo-2,3-dihydro-1H-isoindol-2-yl)(benzyloxy)formamide

Chemical Property of N-(Z-amino)phthalimide

Chemical Property:

• Melting Point: 132-137 °C
• PKA: 7.28±0.20(Predicted)
• PSA: 75.71000
• Density: 1.42±0.1 g/cm3(Predicted)
• LogP: 2.45280
• XLogP3: 2.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 296.07970687
• Heavy Atom Count: 22
• Complexity: 435

Purity/Quality:

N-(Z-AMINO)PHTHALIMIDE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)COC(=O)NN2C(=O)C3=CC=CC=C3C2=O

Technology Process of N-(Z-amino)phthalimide

There total 5 articles about N-(Z-amino)phthalimide 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: 92.0%

phthalic anhydride (85-44-9) + N-benzyloxycarbonyl-hydrazine (5331-43-1) → N-benzyloxycarbonylaminophthalimide (287728-91-0)

Guidance literature:

In toluene; for 3h; Heating;

DOI:10.1002/ejoc.200300445

Reference yield:

phthalic anhydride (85-44-9) → N-benzyloxycarbonylaminophthalimide (287728-91-0)

Guidance literature:

Multi-step reaction with 3 steps

1: tetrahydrofuran / 0.08 h / 20 °C

2: 1,3-dicyclohexylcarbodiimide / tetrahydrofuran / 1 h

3: acetic acid; triethylamine / tetrahydrofuran / 1 h / Heating

With acetic acid; triethylamine; dicyclohexyl-carbodiimide; In tetrahydrofuran; 1: Acylation / 2: Cyclization / 3: Isomerization;

DOI:10.1021/jo000225s

Reference yield:

N'-(3-oxo-3H-isobenzofuran-1-ylidene)-hydrazinecarboxylic acid benzyl ester → N-benzyloxycarbonylaminophthalimide (287728-91-0)

Guidance literature:

With acetic acid; triethylamine; In tetrahydrofuran; for 1h; Heating;

DOI:10.1021/jo000225s

upstream raw materials:

phthalic anhydride

N-benzyloxycarbonyl-hydrazine

Downstream raw materials:

2-[benzyloxycarbonyl-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-amino]-3-methyl-pentanoic acid methyl ester

(S)-α-(N-benzyloxycarbonylaminophthalimido)-γ-butyrolactone

1-benzyl-1-benzyloxycarbonylhydrazine

Refernces

• 1、 Brosse, Nicolas,Pinto, Maria-Fatima,Jamart-Gregoire, Brigitte. "New Synthesis of 1,1-Substituted Hydrazines by Alkylation of N-Acyl- or N-alkyloxycarbonylaminophthalimide Using the Mitsunobu Protocol". . p. 4370 - 4374. Retrieved 2007/10/03.