1-methylindole-5-carboxylic Acid

Base Information

• Chemical Name: 1-methylindole-5-carboxylic Acid
• CAS No.: 186129-25-9
• Molecular Formula: C10H9NO2
• Molecular Weight: 175.187
• Hs Code.: 2933998090
• European Community (EC) Number: 676-097-4
• DSSTox Substance ID: DTXSID20426748
• Wikidata: Q72491940
• Mol file: 186129-25-9.mol

Synonyms:1-Methyl-1H-Indole-5-Carboxylic Acid;186129-25-9;1-methylindole-5-carboxylic Acid;1-Methyl-5-indolecarboxylic Acid;1H-Indole-5-carboxylic acid, 1-methyl-;MFCD03839859;1-Methyl-5-indolecarboxylicAcid;SCHEMBL103922;N-methylindol-5-carboxylic acid;DTXSID20426748;UHQAIJFIXCOBCN-UHFFFAOYSA-N;Methyl 1H-indole-5-carboxylic acid;BBL010464;STK719877;1-methyl-1H-indol-5-carboxylic acid;AKOS005174503;AB92306;FS-2252;AM803416;SY022474;A4116;BB 0259462;CS-0073862;FT-0647909;1-methylindole-5-carboxylic acid, AldrichCPR;EN300-186478;Q-102905;F2173-1246;Z1154255784;1-methyl-1H-indole-5-carboxylic acid

Chemical Property of 1-methylindole-5-carboxylic Acid

Chemical Property:

• Vapor Pressure: 9.54E-07mmHg at 25°C
• Melting Point: 221-223.5 °C
• Refractive Index: 1.612
• Boiling Point: 389 °C at 760 mmHg
• PKA: 4.44±0.30(Predicted)
• Flash Point: 189 °C
• PSA: 42.23000
• Density: 1.24 g/cm³
• LogP: 1.87650
• Storage Temp.: 2-8°C
• XLogP3: 2.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 175.063328530
• Heavy Atom Count: 13
• Complexity: 217

Purity/Quality:

98%min ^*data from raw suppliers

5-Carboxy-1-methylindole ^*data from reagent suppliers

Safty Information:

• Pictogram(s): R36/37/38:
• Hazard Codes: Xn,Xi
• Statements: 36/37/38-20/21/22-36
• Safety Statements: 26-36/37/39-22

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CN1C=CC2=C1C=CC(=C2)C(=O)O
• Uses: 5-Carboxy-1-methylindole is used in the preparation of diazaspiro ROCK inhibitors which is used for treating diseases.

Technology Process of 1-methylindole-5-carboxylic Acid

There total 14 articles about 1-methylindole-5-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: 97.0%

methyl 1-methyl-1H-indole-5-carboxylate (128742-76-7) → 1-methyl-1H-indole-5-carboxylic acid (186129-25-9)

Guidance literature:

With water; sodium hydroxide; In tetrahydrofuran; at 40 ℃; for 4h;

Reference yield: 84.0%

1H-Indole-5-carboxylic acid (1670-81-1,142396-03-0) + methyl iodide (74-88-4) → 1-methyl-1H-indole-5-carboxylic acid (186129-25-9)

Guidance literature:

1H-Indole-5-carboxylic acid; With sodium hydride; In N,N-dimethyl-formamide; at 0 ℃; for 0.5h;

methyl iodide; In N,N-dimethyl-formamide; at 20 ℃; for 12h;

DOI:10.1016/j.ejmech.2019.01.066

Reference yield: 84.0%

carbon dioxide (124-38-9,18923-20-1) + (1-methyl-1H-indol-5-yl)magnesium bromide → 1-methyl-1H-indole-5-carboxylic acid (186129-25-9)

Guidance literature:

In tetrahydrofuran; at 1 ℃; for 0.0833333h;

DOI:10.1016/j.tet.2005.09.022

upstream raw materials:

methyl 1-methyl-1H-indole-5-carboxylate

carbon dioxide

5-methoxycarbonylindole

ethyl indole-5-carboxylate

Downstream raw materials:

1-methyl-2-oxoindoline-5-carboxylic acid

1-methylindole

1-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole

Refernces

• 1、 Lillich, Felix F.,Willems, Sabine,Ni, Xiaomin,Kilu, Whitney,Borkowsky, Carmen,Brodsky, Mirko,Kramer, Jan S.,Brunst, Steffen,Hernandez-Olmos, Victor,Heering, Jan,Schierle, Simone,Kestner, Roxane-I.,Mayser, Franziska M.,Helmst?dter, Moritz,G?bel, Tamara,Weizel, Lilia,Namgaladze, Dmitry,Kaiser, Astrid,Steinhilber, Dieter,Pfeilschifter, Waltraud,Kahnt, Astrid S.,Proschak, Anna,Chaikuad, Apirat,Knapp, Stefan,Merk, Daniel,Proschak, Ewgenij. "Structure-Based Design of Dual Partial Peroxisome Proliferator-Activated Receptor γagonists/Soluble Epoxide Hydrolase Inhibitors". supporting information. p. 17259 - 17276. Retrieved 2021/12/09.
• 2、 Ashok,Shivananda,Manikandan,Chandrasekaran. "Discovery and synthesis of 2-amino-1-methyl-1H-imidazol-4(5H)-ones as GPCR ligands; an approach to develop breast cancer drugs via GPCR associated PAR1 and PI3Kinase inhibition mechanism". . p. 641 - 651. Retrieved 2019/02/26.