Ethyl 7-nitro-1H-indole-2-carboxylate

Base Information

• Chemical Name: Ethyl 7-nitro-1H-indole-2-carboxylate
• CAS No.: 6960-46-9
• Molecular Formula: C11H10N2O4
• Molecular Weight: 234.211
• Hs Code.: 29339980
• European Community (EC) Number: 674-195-1
• NSC Number: 69878
• DSSTox Substance ID: DTXSID30290598
• Nikkaji Number: J1.412.477B
• Wikidata: Q72476357
• Mol file: 6960-46-9.mol

Synonyms:6960-46-9;Ethyl 7-nitro-1H-indole-2-carboxylate;ethyl 7-nitroindole-2-carboxylate;7-nitroindole-2-carboxylic acid ethyl ester;1h-indole-2-carboxylic acid, 7-nitro-, ethyl ester;NSC 69878;Ethyl-7-nitro-1H-indole-2-carboxylate;NSC69878;Oprea1_376503;SCHEMBL1016404;DTXSID30290598;ethyl 7-nitro-2-indolecarboxylate;MFCD00216475;NSC-69878;AKOS005135916;AM10039;CCG-236914;PS-3452;Ethyl 7-nitro-1H-indole-2-carboxylate #;CS-0041751;FT-0636316;N-3305;A836560;Indole-2-carboxylic acid, 7-nitro-, ethyl ester;SR-01000512230;SR-01000512230-1;7-Chloro-3-ethyl-2H-benzo[e][1,2,4]thiadiazine 1,1-dioxide

Chemical Property of Ethyl 7-nitro-1H-indole-2-carboxylate

Chemical Property:

• Appearance/Colour: yellow to brown powder
• Vapor Pressure: 1.4E-07mmHg at 25°C
• Melting Point: 90-96 °C
• Refractive Index: 1.652
• Boiling Point: 429.5 °C at 760 mmHg
• PKA: 11.98±0.30(Predicted)
• Flash Point: 213.5 °C
• PSA: 87.91000
• Density: 1.393 g/cm³
• LogP: 2.77600
• Storage Temp.: 2-8°C
• Water Solubility.: Negligible
• XLogP3: 3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 234.06405680
• Heavy Atom Count: 17
• Complexity: 315

Purity/Quality:

99% ^*data from raw suppliers

7-Nitroindole-2-carboxylicacidethylester 98% ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)C1=CC2=C(N1)C(=CC=C2)[N+](=O)[O-]
• Uses: Ethyl 7-Nitroindole-2-carboxylate is used to prepare aryl(indolyl)oxadiazoles via Fischer indole synthesis of pyruvate nitrophenylhydrazones. It is also used to synthesize p38 Inhibitors.

Technology Process of Ethyl 7-nitro-1H-indole-2-carboxylate

There total 3 articles about Ethyl 7-nitro-1H-indole-2-carboxylate 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: 80.0%

2-oxo-propionic acid ethyl ester (617-35-6) + o-nitrophenylhydrazine hydrochloride (6293-87-4) → ethyl 7-nitroindole-2-carboxylate (6960-46-9)

Guidance literature:

With bismuth(III) nitrate; PPA; In methanol; for 2.5h; Reflux;

DOI:10.1080/00397910802656059

Reference yield:

o-nitrophenylhydrazine hydrochloride (6293-87-4) → ethyl 7-nitroindole-2-carboxylate (6960-46-9)

Guidance literature:

Multi-step reaction with 2 steps

1: ethanol / 0.17 h / 20 °C

2: PPA / 7 h / 50 - 80 °C

With PPA; In ethanol;

DOI:10.1016/j.bmc.2014.01.047

Reference yield:

(Z)-ethyl α-azido-β-(m-nitrophenyl)acrylate → ethyl 7-nitroindole-2-carboxylate (6960-46-9) + 5-nitro-indole-2-carboxylic acid ethyl ester (16732-57-3)

Guidance literature:

In 1,2-dichloro-benzene; at 150 ℃; for 0.5h; Overall yield = 62 %; Overall yield = 0.553 g; regioselective reaction;

DOI:10.1039/c3ra42296h

upstream raw materials:

2-oxo-propionic acid ethyl ester

o-nitrophenylhydrazine hydrochloride

Downstream raw materials:

7-nitro-1H-indole-2-carboxylic acid

7-nitro-1H-indole

2-[5-(4-fluorophenyl)-1,3,4-oxadiazol-2-yl]-7-nitro-1H-indole

2-[5-(4-methylphenyl)-1,3,4-oxadiazol-2-yl]-7-nitro-1H-indole