1-Methylindole-3-carboxylic acid

Base Information

• Chemical Name: 1-Methylindole-3-carboxylic acid
• CAS No.: 32387-21-6
• Molecular Formula: C10H9NO2
• Molecular Weight: 175.187
• Hs Code.: 29339900
• European Community (EC) Number: 628-244-9
• DSSTox Substance ID: DTXSID70357533
• Nikkaji Number: J1.089.399B
• Wikidata: Q50318274
• ChEMBL ID: CHEMBL1650259
• Mol file: 32387-21-6.mol

Synonyms:32387-21-6;1-Methylindole-3-carboxylic acid;1-Methyl-1H-Indole-3-Carboxylic Acid;1-Methyl-3-indolecarboxylic acid;1H-Indole-3-carboxylic acid, 1-methyl-;1-Methylindole-3-carboxylicacid;N-methylindole-3-carboxylic acid;MFCD01321244;Bionet2_001079;SCHEMBL535878;CHEMBL1650259;1-methylindole-3-carboxilic acid;DTXSID70357533;1-methyl-3-indolylcarboxylic acid;HVRCLXXJIQTXHC-UHFFFAOYSA-N;HMS1367B01;BCP26624;STK721128;AKOS000262942;AC-2857;CS-W017453;1-methyl-1-H-indole-3-carboxylic acid;1-Methylindole-3-carboxylic acid, 97%;SY003132;A5810;AM20050442;FT-0639019;EN300-13334;M-4052;7T-1500;Q50318274;Z90124414

Chemical Property of 1-Methylindole-3-carboxylic acid

Chemical Property:

• Vapor Pressure: 9.54E-07mmHg at 25°C
• Melting Point: 197-200 °C (dec.)
• Refractive Index: 1.612
• Boiling Point: 389 °C at 760 mmHg
• PKA: 4.01±0.10(Predicted)
• Flash Point: 189 °C
• PSA: 42.23000
• Density: 1.24 g/cm³
• LogP: 1.87650
• Storage Temp.: Sealed in dry,Room Temperature
• XLogP3: 1.8
• 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:

99.9% ^*data from raw suppliers

1-Methylindole-3-Carboxylic Acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CN1C=C(C2=CC=CC=C21)C(=O)O
• Uses: Reactant for preparation of bisindolyl pyrimidinones analogs of PKC inhibitor LY333531Reactant for preparation of (heteroaryl)(carboxamido)arylpyrrole derivatives as Cdc7 kinase inhibitors, antitumor and antiproliferative agentsReactant for preparation of (pyrrolidinylmethoxy)cyclohexanecarboxylic acids as antigen-4 (VLA-4) antagonistsReactant for preparation of EphB3 receptor tyrosine kinase inhibitorsReactant for preparation of pyrazolodiazepine derivatives as human P2X7 receptor antagonistsReactant for preparation of potent nonpeptidic urotensin II receptor agonistsReactant for preparation of pyrrolizidine esters, amides, and ureas as 5-HT4 receptor ligands

Technology Process of 1-Methylindole-3-carboxylic acid

There total 6 articles about 1-Methylindole-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: 39.0%

tert.-butylhydroperoxide (75-91-2) + 1H-indole-3-carboxylic acid (771-50-6) → 1-methyl-3-indolecarboxylic acid (32387-21-6) + 3-methoxycarbonylindole (942-24-5) + methyl 1-methyl-1H-indole-3-carboxylate (108438-43-3)

Guidance literature:

With copper quinolate; In water; dimethyl sulfoxide; at 120 ℃; for 24h;

DOI:10.1021/jo4016387

Reference yield: 12.0%

carbon dioxide (124-38-9,18923-20-1) + 1-methyl-5-phenyl-1H-indole → 1-methyl-3-indolecarboxylic acid (32387-21-6) + 1-methyl-5-phenyl-1H-indole-3-carboxylic acid

Guidance literature:

With dimethylaluminum chloride; In hexane; toluene; at 20 ℃; for 3h;

DOI:10.1016/j.tet.2015.12.028

Reference yield:

1-methylindole-3-carboxamidine E-oxime (390799-61-8,125818-00-0,131012-60-7) → 1-methyl-3-indolecarboxylic acid (32387-21-6) + 1-Methylindole-3-carboxylic acid amide (118959-44-7) + 1-methyl-1H-indole-3-carbonitrile (24662-37-1) + 1-methylindole-3-carboxamidine Z-oxime

Guidance literature:

With bromine; dinitrogen monoxide; In phosphate buffer; pH=7.36; Further Variations:; pH-values; concentration, dose rate; Product distribution; Radiolysis;

upstream raw materials:

1-methylindole-3-carboxamidine E-oxime

tert.-butylhydroperoxide

1H-indole-3-carboxylic acid

1-methylindole

Downstream raw materials:

2-(3-methyl-but-2-enyl)-2-(1-methyl-indol-3-yl)-4-phenyl-2H-oxazol-5-one

1,2-dimethyl-1H-indole-3-carboxylic acid

3-chlorocarbonyl-1-methylindole

N₂-[(4R)-4-hydroxy-1-(1-methyl-1H-indol-3-yl)carbonyl-L-prolyl]-N-methyl-N-phenylmethyl-3-(2-naphthyl)-L-alaninamide

Refernces

• 1、 Suga, Takuya,Mizuno, Hajime,Takaya, Jun,Iwasawa, Nobuharu. "Direct carboxylation of simple arenes with CO2 through a rhodium-catalyzed C-H bond activation". supporting information. p. 14360 - 14363. Retrieved 2015/02/19.
• 2、 Everett, Steven A.,Naylor, Matthew A.,Stratford, Michael R.L.,Patel, Kantilal B.,Ford, Eleonora,Mortensen, Alan,Ferguson, Amanda C.,Vojnovic, Borivoj,Wardman, Peter. "Iminoxyl radicals and stable products from the one-electron oxidation of 1-methylindole-3-carbaldehyde oximes". . p. 1989 - 1997. Retrieved 2007/10/03.