4-Nitro-N-carboethoxyphthalimide

Base Information

• Chemical Name: 4-Nitro-N-carboethoxyphthalimide
• CAS No.: 190910-88-4
• Molecular Formula: C₁₁H₈N₂O₆
• Molecular Weight: 264.194
• Hs Code.: 2925190090
• DSSTox Substance ID: DTXSID00445139
• Wikidata: Q82263476
• Mol file: 190910-88-4.mol

Synonyms:4-Nitro-N-carboethoxyphthalimide;190910-88-4;ethyl 4-nitro-1,3-dioxoisoindoline-2-carboxylate;ethyl 4-nitro-1,3-dioxoisoindole-2-carboxylate;Ethyl 4-nitro-1,3-dioxo-1,3-dihydro-2H-isoindole-2-carboxylate;SCHEMBL2283350;DTXSID00445139;NUJJHSPYMWDZSJ-UHFFFAOYSA-N;4-nitro-1,3-dioxo-1,3-dihydro-isoindole-2-carboxylic acid ethyl ester;SB66188;A13905;ethyl4-nitro-1,3-dioxoisoindoline-2-carboxylate

Chemical Property of 4-Nitro-N-carboethoxyphthalimide

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.627
• Boiling Point: 449.4°Cat760mmHg
• Flash Point: 225.6°C
• PSA: 109.50000
• Density: 1.567g/cm³
• LogP: 1.80840
• XLogP3: 1.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 2
• Exact Mass: 264.03823598
• Heavy Atom Count: 19
• Complexity: 443

Purity/Quality:

97% ^*data from raw suppliers

Ethyl4-nitro-1,3-dioxoisoindoline-2-carboxylate 97% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)N1C(=O)C2=C(C1=O)C(=CC=C2)[N+](=O)[O-]

Technology Process of 4-Nitro-N-carboethoxyphthalimide

There total 4 articles about 4-Nitro-N-carboethoxyphthalimide 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: 75.0%

4-nitro-1H-isoindole-1,3(2H)-dione (603-62-3) + chloroformic acid ethyl ester (541-41-3) → ethyl 4-nitro-1,3-dioxoisoindoline-2-carboxylate (190910-88-4)

Guidance literature:

With triethylamine; In N,N-dimethyl-formamide; at 0 - 20 ℃; for 4h;

Reference yield:

N,N'-(3-nitro-phthaloyl)-bis-carbamic acid diethyl ester → ethyl 4-nitro-1,3-dioxoisoindoline-2-carboxylate (190910-88-4)

Guidance literature:

With benzene;

Reference yield:

3-Nitrophthaloyl dichloride (24564-71-4) → ethyl 4-nitro-1,3-dioxoisoindoline-2-carboxylate (190910-88-4)

Guidance literature:

Multi-step reaction with 2 steps

1: pyridine; benzene

2: benzene

With pyridine; benzene;

upstream raw materials:

benzene

4-nitro-1H-isoindole-1,3(2H)-dione

chloroformic acid ethyl ester

3-Nitrophthaloyl dichloride

Downstream raw materials:

(S)-(-)-4-amino-2-(2,6-dioxopiperidin-3-yl)-1H-isoindole-1,3-dione

(R)-(+)-4-amino-2-(2,6-dioxopiperidin-3-yl)-1H-isoindole-1,3-dione

Refernces

• 1、 -. "Processes for the preparation of 4-amino-2-(2,6-dioxopiperidin-3-yl)isoindoline-1,3-dione compounds". Page/Page column 12. . Retrieved 2008/06/13.
• 2、 Muller, George W.,Chen, Roger,Huang, Shaei-Yun,Corral, Laura G.,Wong, Lu Min,Patterson, Rebecca T.,Chen, Yuxi,Kaplan, Gilla,Stirling, David I.. "Amino-substituted thalidomide analogs: Potent inhibitors of TNF-α production". . p. 1625 - 1630. Retrieved 2007/10/03.