5-Methoxy-1H-indole-3-carboxylic acid

Base Information

• Chemical Name: 5-Methoxy-1H-indole-3-carboxylic acid
• CAS No.: 10242-01-0
• Molecular Formula: C10H9NO3
• Molecular Weight: 191.186
• Hs Code.: 2933990090
• European Community (EC) Number: 676-180-5
• NSC Number: 88877
• DSSTox Substance ID: DTXSID40293353
• Nikkaji Number: J1.914.257D
• Wikidata: Q72490081
• Mol file: 10242-01-0.mol

Synonyms:5-Methoxy-1H-indole-3-carboxylic acid;10242-01-0;5-Methoxyindole-3-carboxylic acid;5-methoxy-3-indolecarboxylic acid;MFCD03265451;NSC 88877;5-methoxy-3-carboxyindole;1H-INDOLE-3-CARBOXYLIC ACID, 5-METHOXY-;NSC88877;SCHEMBL592889;5-Methoxyindole-3-carboxylicacid;AMY2895;DTXSID40293353;NSC-88877;STK642188;AKOS000302731;AB13930;AC-6602;CS-W000793;FS-2267;FT-0630300;M2438;EN300-71417;5-methoxyindole-3-carboxylic acid, AldrichCPR;Q-101968;Z385370196

Chemical Property of 5-Methoxy-1H-indole-3-carboxylic acid

Chemical Property:

• Vapor Pressure: 8.54E-09mmHg at 25°C
• Melting Point: 172-175 °C
• Refractive Index: 1.677
• Boiling Point: 447.6 °C at 760 mmHg
• PKA: 3.95±0.30(Predicted)
• Flash Point: 224.5 °C
• PSA: 62.32000
• Density: 1.381 g/cm³
• LogP: 1.87470
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• XLogP3: 2
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 191.058243149
• Heavy Atom Count: 14
• Complexity: 231

Purity/Quality:

99% ^*data from raw suppliers

5-Methoxyindole-3-carboxylicacid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi,Xn
• Statements: 22

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=CC2=C(C=C1)NC=C2C(=O)O
• Uses: 5-Methoxyindole-3-carboxylic Acid can be used in the synthesis of benzoheterocycle derivatives as vascular endothelial growth factor receptor-2 tyrosine kinase inhibitors and in the synthesis of indoleamine 2,3-dioxygenase 1 inhibitors with potential antitumor activity.

Technology Process of 5-Methoxy-1H-indole-3-carboxylic acid

There total 7 articles about 5-Methoxy-1H-indole-3-carboxylic 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: 99.0%

2,2,2-trifluoro-1-(5-methoxy-1H-indol-3-yl)ethan- 1- one (1051967-68-0) → 5-Methoxyindole-3-carboxylic acid (10242-01-0)

Guidance literature:

With water; potassium hydroxide; Reflux;

DOI:10.1021/jm500588w

Reference yield: 92.0%

5-methoxylindole (1006-94-6) + carbon dioxide (124-38-9,18923-20-1) → 5-Methoxyindole-3-carboxylic acid (10242-01-0)

Guidance literature:

With lithium tert-butoxide; In N,N-dimethyl-formamide; at 100 ℃; for 24h; under 760.051 Torr;

DOI:10.3987/COM-14-S(K)94

Reference yield: 83.0%

C11H12N2O3 → 5-Methoxyindole-3-carboxylic acid (10242-01-0)

Guidance literature:

With tert.-butylnitrite; water; at 29 ℃; for 0.583333h;

DOI:10.1021/acs.joc.7b00570

upstream raw materials:

5-methoxylindole

2,2,2-trifluoro-1-(5-methoxy-1H-indol-3-yl)ethan- 1- one

carbon dioxide

methyl 5-methoxy-1H-indole-3-carboxylate

Downstream raw materials:

methyl 5-methoxy-1H-indole-3-carboxylate

5-methoxylindole

indole

Refernces

• 1、 Yoo, Woo-Jin,Capdevila, Montse Guiteras,Du, Xiangwei,Kobayashi, Shu. "Base-mediated carboxylation of unprotected indole derivatives with carbon dioxide". . p. 5326 - 5329,4. Retrieved 2012.
• 2、 -. "INDOLE COMPOUNDS AND THEIR USE". Paragraph 00191; 00194; 00196. . Retrieved 2019/06/05.