1H-indole-2,5-dicarboxylic Acid

Base Information

• Chemical Name: 1H-indole-2,5-dicarboxylic Acid
• CAS No.: 117140-77-9
• Molecular Formula: C10H7 N O4
• Molecular Weight: 205.17
• DSSTox Substance ID: DTXSID00401790
• Nikkaji Number: J803.082K
• Wikidata: Q72482994
• Mol file: 117140-77-9.mol

Synonyms:1H-indole-2,5-dicarboxylic Acid;117140-77-9;Indole-2,5-dicarboxylic acid;5-CARBOXYINDOLE-2-CARBOXYLIC ACID;MFCD02664447;1H-Indole-2,5-dicarboxylicacid;1H-Indole-2,5-dicarboxylic acid (5-Carboxyindole-2-carboxylic acid);SCHEMBL1842307;DTXSID00401790;MUABQYJAPOQWCH-UHFFFAOYSA-N;AKOS002664593;DS-8044;SY110958;FT-0601332;A803720;J-521530

Chemical Property of 1H-indole-2,5-dicarboxylic Acid

Chemical Property:

• Melting Point: 284-287 °C
• Boiling Point: 578.5±30.0 °C(Predicted)
• PKA: 4.21±0.30(Predicted)
• PSA: 90.39000
• Density: 1.616±0.06 g/cm3(Predicted)
• LogP: 1.56430
• Storage Temp.: 2-8°C
• XLogP3: 1.8
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 2
• Exact Mass: 205.03750770
• Heavy Atom Count: 15
• Complexity: 291

Purity/Quality:

98%min ^*data from raw suppliers

Indole-2,5-dicarboxylicAcid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC2=C(C=C1C(=O)O)C=C(N2)C(=O)O

Technology Process of 1H-indole-2,5-dicarboxylic Acid

There total 5 articles about 1H-indole-2,5-dicarboxylic Acid 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%

1H-indole-2,5-dicarboxylic acid 2-ethyl ester (138731-14-3) → 1H-indole-2,5-dicarboxylic acid (117140-77-9)

Guidance literature:

With potassium hydroxide; In ethanol;

Reference yield:

5-acetyl-1H-indole-2-carboxylic acid ethyl ester (31380-56-0) → 1H-indole-2,5-dicarboxylic acid (117140-77-9)

Guidance literature:

With sodium hydroxide; In ethanol;

DOI:10.1016/j.bmcl.2009.01.023

Reference yield:

4-Hydrazinobenzoic acid (619-67-0) → 1H-indole-2,5-dicarboxylic acid (117140-77-9)

Guidance literature:

Multi-step reaction with 3 steps

1: 89 percent / aq. AcOH / 1 h / 20 °C

2: ZnCl₂ / Heating

3: 80 percent / aq. KOH / ethanol

With potassium hydroxide; acetic acid; zinc(II) chloride; In ethanol; 1: Condensation / 2: cyclocondensation / 3: Hydrolysis;

upstream raw materials:

1H-indole-2,5-dicarboxylic acid 2-ethyl ester

4-Hydrazinobenzoic acid

ethyl pyruvate 4-carboxyphenylhydrazone

5-acetyl-1H-indole-2-carboxylic acid ethyl ester

Downstream raw materials:

1-(2-(4-(4-fluorobenzyl)piperazin-1-carbonyl)-1H-indol-3-yl)ethanone

1-(2-(4-(4-fluorobenzyl)piperazin-1-carbonyl)-1H-indol-5-yl)ethanone

Refernces

• 1、 -. "Novel aromatic compounds and poly(oxyalkylene) containing aromatic compounds possessing antibacterial, antifungal or antitumor activity". . . Retrieved 2008/06/13.
• 2、 Khalaf, Abedawn I.,Pitt, Andrew R.,Suckling, Colin J.,Scobie, Martin,Urwin, John,Waigh, Roger D.,Fishleigh, Robert V.,Young, Stephen C.. "Synthesis of Novel DNA Binding Agents: Indole-Containing Analogues of Bis-Netropsin". . p. 751 - 770. Retrieved 2007/10/03.