1-Methylindole-2-carboxylic acid

Base Information

• Chemical Name: 1-Methylindole-2-carboxylic acid
• CAS No.: 16136-58-6
• Molecular Formula: C10H9NO2
• Molecular Weight: 175.187
• Hs Code.: 29339980
• European Community (EC) Number: 625-083-6
• NSC Number: 68357
• DSSTox Substance ID: DTXSID60167123
• Nikkaji Number: J102.515E
• Wikidata: Q72491957
• ChEMBL ID: CHEMBL36834
• Mol file: 16136-58-6.mol

Synonyms:1-Methylindole-2-carboxylic acid;1-Methyl-1H-indole-2-carboxylic acid;16136-58-6;1H-INDOLE-2-CARBOXYLIC ACID, 1-METHYL-;1-Methyl-2-indolecarboxylic acid;Indole-2-carboxylic acid, 1-methyl-;MFCD00005801;BRN 0007274;CHEMBL36834;5-22-03-00015 (Beilstein Handbook Reference);NSC68357;N-Methylindolcarbonsaure;ChemDiv3_011259;SCHEMBL117186;MAHAMBLNIDMREX-UHFFFAOYSA-;DTXSID60167123;HMS1504P17;(N-methyl)indole-2-carboxylic acid;1-methyl-1H-indole carboxylic acid;d-asparticacid(obzl)-obzlp-tosylate;1-methyl-1H-2-indolecarboxylic acid;BBL037008;BDBM50424778;NSC 68357;NSC-68357;STK120292;1-methyl-1H-indol-2-carboxylic acid;AKOS000262610;CG-0519;CS-W007740;PB40936;IDI1_028817;1-Methylindole-2-carboxylic acid, 98%;AC-22708;LS-82730;SY050484;AM20060408;BB 0220035;EU-0015870;FT-0637326;M1519;EN300-51846;M-4050;A810257;CS-007/03901012;Z57204959;F0919-4682

Chemical Property of 1-Methylindole-2-carboxylic acid

Chemical Property:

• Appearance/Colour: Beige crystalline powder
• Vapor Pressure: 9.54E-07mmHg at 25°C
• Melting Point: 212-213 °C
• Refractive Index: 1.612
• Boiling Point: 389 °C at 760 mmHg
• PKA: 4.19±0.30(Predicted)
• Flash Point: 189 °C
• PSA: 42.23000
• Density: 1.24 g/cm³
• LogP: 1.87650
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• XLogP3: 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% ^*data from raw suppliers

1-Methylindole-2-carboxylic acid ^*data from reagent suppliers

Safty Information:

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

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CN1C2=CC=CC=C2C=C1C(=O)O
• Uses: ? ;Reactant for preparation of keto-indoles as novel indoleamine 2,3-dioxygenase (IDO) inhibitors1? ;Reactant for synthesis of fenbufen and ethacrynic acid derivatives as potential antitumor agents via amide coupling reactions2? ;Reactant for diastereoselective synthesis of vinylated heterocycles via ruthenium-catalyzed oxidative vinylation with alkenes3? ;Reactant for synthesis of 2,3-dihalo indoles via hypervalent iodine mediated decarboxylative halogenation4? ;Reactant for preparation of α-ketoamides as cathepsin S inhibitors with potential applications ag Reactant for preparation of keto-indoles as novel indoleamine 2,3-dioxygenase (IDO) inhibitorsReactant for synthesis of fenbufen and ethacrynic acid derivatives as potential antitumor agents via amide coupling reactionsReactant for diastereoselective synthesis of vinylated heterocycles via ruthenium-catalyzed oxidative vinylation with alkenesReactant for synthesis of 2,3-dihalo indoles via hypervalent iodine mediated decarboxylative halogenationReactant for preparation of α-ketoamides as cathepsin S inhibitors with potential applications against tumor invasion and angiogenesisReactant for preparation of anthranilic acid mimics as bacterial translation inhibitors

Technology Process of 1-Methylindole-2-carboxylic acid

There total 23 articles about 1-Methylindole-2-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: 100.0%

methyl 1-methyl-1H-indole-2-carboxylate (37493-34-8) → N-methyl-1H-indole-2-carboxylic acid (16136-58-6)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; for 7h; Heating;

DOI:10.1016/j.tet.2004.07.071

Reference yield: 98.0%

N-methyl-2-chloroaniline (932-32-1) + 2-oxo-propionic acid (127-17-3) → N-methyl-1H-indole-2-carboxylic acid (16136-58-6)

Guidance literature:

With potassium phosphate; magnesium sulfate; acetic acid; bis(tri-t-butylphosphine)palladium⁽⁰⁾; In N,N-dimethyl acetamide; at 140 ℃; for 14h;

DOI:10.1002/anie.200460122

Reference yield: 96.0%

carbon dioxide (124-38-9,18923-20-1) + 2,3-dibromo-1-methyl-1H-indole (128746-62-3) → N-methyl-1H-indole-2-carboxylic acid (16136-58-6)

Guidance literature:

Multistep reaction;

DOI:10.1016/S0040-4039(02)01710-0

upstream raw materials:

1-methylindole

2-(methyl-phenyl-hydrazono)-propionic acid

1-Methylnaphthalene

2-(methyl-phenyl-hydrazono)-propionic acid ethyl ester

Downstream raw materials:

1-methylindole

(1-methyl-1H-indol-2-yl)-methanol

methyl 1-methyl-1H-indole-2-carboxylate

N,N-dimethyl-1-methylindole-2-carboxamide

Refernces

• 1、 Shirley,Roussel. "-". . p. 375,377. Retrieved 1953.
• 2、 Arnhof, Heribert,Bader, Gerd,Bruchhaus, Jens,Burkard, Michelle,Ciftci, Tuncay,Dahmann, Georg,Du, Alicia,Ettmayer, Peter,Fett, Thomas N.,Garavel, Géraldine,Gerstberger, Thomas,Haering, Daniela,Harrer, Christoph,Hofbauer, Karin S.,Kessler, Dirk,Kousek, Roland,Li, Dongyang,Li, Yali,Lv, Xiaobing,Martinelli, Paola,Mayer, Moriz,McConnell, Darryl B.,Mischerikow, Nikolai,Mitzner, Sophie,Pearson, Mark,Peric-Simov, Biljana,Quant, Jens,Rinnenthal, Joerg,Rumpel, Klaus,Savarese, Fabio,Scherbantin, Yvonne,Schnitzer, Renate,Scholz, Guido,Schrenk, Andreas,Sharps, Bernadette,Sommergruber, Wolfgang,Treu, Matthias,Weinstabl, Harald,Wolkerstorfer, Bernhard,Zahn, Stephan K.,Zhang, Xuechun,Zoephel, Andreas. "Intracellular Trapping of the Selective Phosphoglycerate Dehydrogenase (PHGDH) Inhibitor BI-4924 Disrupts Serine Biosynthesis". supporting information. . Retrieved 2019/09/06.
• 3、 Mietke, Thomas,Cruchter, Thomas,Larionov, Vladimir A.,Faber, Tabea,Harms, Klaus,Meggers, Eric. "Asymmetric Nazarov Cyclizations Catalyzed by Chiral-at-Metal Complexes". supporting information. p. 2093 - 2100. Retrieved 2018/04/19.