Ethyl 4-nitrobenzenecarboximidate

Base Information

• Chemical Name: Ethyl 4-nitrobenzenecarboximidate
• CAS No.: 831-68-5
• Molecular Formula: C9H10N2O3
• Molecular Weight: 194.19
• DSSTox Substance ID: DTXSID801298919
• Mol file: 831-68-5.mol

Synonyms:831-68-5;benzenecarboximidic acid,4-nitro-,ethyl ester;ethyl 4-nitrobenzenecarboximidate;ethyl 4-nitro-benzimidate;SCHEMBL15599678;DTXSID801298919

Chemical Property of Ethyl 4-nitrobenzenecarboximidate

Chemical Property:

• PSA: 78.90000
• LogP: 2.57960
• XLogP3: 2.4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 194.06914219
• Heavy Atom Count: 14
• Complexity: 217

Purity/Quality:

95% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

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

Technology Process of Ethyl 4-nitrobenzenecarboximidate

There total 2 articles about Ethyl 4-nitrobenzenecarboximidate 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: 71.4%

ethanol (64-17-5) + 4-nitrobenzonitrile (619-72-7) → 4-nitro-benzimidic acid ethyl ester (831-68-5)

Guidance literature:

With hydrogenchloride; In 1,4-dioxane; at 20 ℃; for 12h;

Reference yield:

4-nitrobenzaldehdye (555-16-8) → 4-nitro-benzimidic acid ethyl ester (831-68-5)

Guidance literature:

Multi-step reaction with 2 steps

1: hydroxylamine hydrochloride / dimethyl sulfoxide / 4 h / Reflux

2: hydrogenchloride / 1,4-dioxane / 12 h / 20 °C

With hydrogenchloride; hydroxylamine hydrochloride; In 1,4-dioxane; dimethyl sulfoxide;

Reference yield: 95.0%

1-benzyl-1H-pyrrole-2,5-dione (1631-26-1) + 4-nitro-benzimidic acid ethyl ester (831-68-5) → 1'-benzyl-3-ethoxy-6-nitrospiro[isoindole-1,3'-pyrrolidine]-2',5'-dione

Guidance literature:

With carbonyl(pentamethylcyclopentadienyl)cobalt diiodide; silver trifluoromethanesulfonate; In 1,2-dichloro-ethane; at 100 ℃; for 11h; Sealed tube;

DOI:10.1021/acs.orglett.7b02266

upstream raw materials:

ethanol

4-nitrobenzonitrile

4-nitrobenzaldehdye

Downstream raw materials:

5-isopropylidene-2-(4-nitro-phenyl)-3,5-dihydro-imidazol-4-one

4-Nitrothiobenzoesaeure-O-ethylester

(E)-4-nitro-benzohydroximic acid ethyl ester

(Z)-4-nitro-benzohydroximic acid ethyl ester

Refernces

• 1、 Nandi, Rajesh,Mandal, Prakash K.,Kayet, Anirban,Bhattachariya, Tamalika,Ghosh, Sukla,Maiti, Dilip K.. "Benzimidates as gem-Diamidation and Amidoindolyzation Cascade Synthons with a Hydrated NiII Catalyst". supporting information. p. 3474 - 3478. Retrieved 2020/04/20.
• 2、 Lv, Ningning,Chen, Zhengkai,Liu, Yue,Liu, Zhanxiang,Zhang, Yuhong. "Synthesis of Functionalized Indenones via Rh-Catalyzed C-H Activation Cascade Reaction". supporting information. p. 2588 - 2591. Retrieved 2017/05/24.