METHYL 5-NITRO-1H-INDOLE-2-CARBOXYLATE

Base Information

• Chemical Name: METHYL 5-NITRO-1H-INDOLE-2-CARBOXYLATE
• CAS No.: 157649-56-4
• Molecular Formula: C10H8 N2 O4
• Molecular Weight: 220.18
• Hs Code.: 2933990090
• Mol file: 157649-56-4.mol

Synonyms:METHYL 5-NITRO-1H-INDOLE-2-CARBOXYLATE;5-NITRO-2-INDOLECARBOXYLIC ACID

Chemical Property of METHYL 5-NITRO-1H-INDOLE-2-CARBOXYLATE

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.761
• Boiling Point: 520.834°C at 760 mmHg
• PKA: 13.22±0.30(Predicted)
• Flash Point: 268.791°C
• PSA: 87.91000
• Density: 1.633g/cm³
• LogP: 2.38590
• Storage Temp.: 2-8°C

Purity/Quality:

98%min ^*data from raw suppliers

Methyl 5-nitro-1H-indole-2-carboxylate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of METHYL 5-NITRO-1H-INDOLE-2-CARBOXYLATE

There total 11 articles about METHYL 5-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: 86.0%

methyl 2-azido-3-(3-nitrophenyl)acrylate (98092-65-0) → 5-nitro-1H-indole-2-carboxylic acid methyl ester (157649-56-4)

Guidance literature:

In toluene; at 200 ℃; for 0.166667h; Microwave irradiation;

DOI:10.1016/j.bmcl.2013.01.066

Reference yield: 78.0%

methyl 5-nitroindoline-2-carboxylate (428861-45-4) → 5-nitro-1H-indole-2-carboxylic acid methyl ester (157649-56-4)

Guidance literature:

With manganese(IV) oxide; In toluene; for 1h; Heating;

DOI:10.1055/s-2002-20043

Reference yield: 10.0%

(Z)-2-benzyloxycarbonylamino-3-(2-chloro-5-nitro-phenyl)-acrylic acid methyl ester → 5-nitro-indole-1,2-dicarboxylic acid 1-benzyl ester 2-methyl ester + 5-nitro-1H-indole-2-carboxylic acid methyl ester (157649-56-4)

Guidance literature:

With potassium carbonate; L-proline; copper(l) iodide; In 1,4-dioxane; at 100 ℃; for 24h;

DOI:10.1016/j.tetlet.2005.10.077

upstream raw materials:

methyl 5-nitroindoline-2-carboxylate

methanol

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

2-chloro-5-nitrobenzaldehyde

Downstream raw materials:

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

methyl 5-aminoindole-2-carboxylate

Refernces

• 1、 Ranasinghe, Nadeesha,Jones, Graham B.. "Extending the versatility of the Hemetsberger-Knittel indole synthesis through microwave and flow chemistry". . p. 1740 - 1742. Retrieved 2013/04/10.
• 2、 Nazaré, Marc,Will, David W.,Matter, Hans,Schreuder, Herman,Ritter, Kurt,Urmann, Matthias,Essrich, Melanie,Bauer, Armin,Wagner, Michael,Czech, J?rg,Lorenz, Martin,Laux, Volker,Wehner, Volkmar. "Probing the subpockets of factor Xa reveals two binding modes for inhibitors based on a 2-carboxyindole scaffold: A study combining structure-activity relationship and X-ray crystallography". . p. 4511 - 4525. Retrieved 2007/10/03.