Methyl 1H-indole-2-carboxylate

Base Information

• Chemical Name: Methyl 1H-indole-2-carboxylate
• CAS No.: 1202-04-6
• Molecular Formula: C10H9NO2
• Molecular Weight: 175.187
• Hs Code.: 29339900
• European Community (EC) Number: 214-861-7
• NSC Number: 78006
• DSSTox Substance ID: DTXSID10152726
• Nikkaji Number: J47.057K
• Wikidata: Q63398093
• ChEMBL ID: CHEMBL4467578
• Mol file: 1202-04-6.mol

Synonyms:Methyl 1H-indole-2-carboxylate;1202-04-6;Methyl Indole-2-carboxylate;Indole-2-carboxylic Acid Methyl Ester;Methyl 2-indolecarboxylate;1H-Indole-2-carboxylic acid, methyl ester;MFCD00460779;1H-INDOLE-2-CARBOXYLIC ACID METHYL ESTER;EINECS 214-861-7;Ethyl-indole-2-caboxylate;NSC78006;2-Methoxycarbonylindole;Methylindole-2-carboxylate;TimTec1_000020;SCHEMBL519591;CHEMBL4467578;DTXSID10152726;HMS1534A20;AMY10022;BCP27180;CS-M2632;STR04421;1H-Indole-2-carboxylic acid methyl;2-indolecarboxylic acid methyl ester;NSC 78006;NSC-78006;STK759197;AKOS000265415;AB06098;AT15691;AC-12173;SY021058;FT-0612649;M1749;Methyl 1H-indole-2-carboxylate, AldrichCPR;4P-019;EN300-176613;I-2500;AH-357/03497008;SR-01000522291;SR-01000522291-1;BRD-K59513633-001-01-0;Q63398093;Z17755623

Chemical Property of Methyl 1H-indole-2-carboxylate

Chemical Property:

• Appearance/Colour: off white crystals
• Vapor Pressure: 0.000153mmHg at 25°C
• Melting Point: 151- 153 °C
• Refractive Index: 1.639
• Boiling Point: 331.7 °C at 760 mmHg
• PKA: 14.97±0.30(Predicted)
• Flash Point: 154.4 °C
• PSA: 42.09000
• Density: 1.253 g/cm³
• LogP: 1.95450
• Storage Temp.: Sealed in dry,Room Temperature
• Water Solubility.: 470 mg/L (25 ºC)
• XLogP3: 2.5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 175.063328530
• Heavy Atom Count: 13
• Complexity: 205

Purity/Quality:

99%, ^*data from raw suppliers

Methyl indole-2-carboxylate ^*data from reagent suppliers

Safty Information:

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

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC(=O)C1=CC2=CC=CC=C2N1

Technology Process of Methyl 1H-indole-2-carboxylate

There total 108 articles about Methyl 1H-indole-2-carboxylate 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%

methanol (67-56-1) + Indole-2-carboxylic acid (1477-50-5,1228050-17-6) → indole-2-carboxylic acid methyl ester (1202-04-6)

Guidance literature:

With hydrogenchloride; for 24h; Heating;

DOI:10.1055/s-2002-33921

Reference yield: 100.0%

indoline-2-carboxylic acid methyl ester (59040-84-5,130791-93-4,141410-06-2) → indole-2-carboxylic acid methyl ester (1202-04-6)

Guidance literature:

With Diphenyliodonium triflate; In 2,2,2-trifluoroethanol; at 75 ℃;

DOI:10.1055/s-0034-1379885

Reference yield: 100.0%

methyl 1-methylsulfonylindole-2-carboxylate → indole-2-carboxylic acid methyl ester (1202-04-6)

Guidance literature:

With 1,3-dimethyl-2-(2-hydroxy-1-naphthyl)benzimidazoline; In dichloromethane; for 0.5h; Inert atmosphere; Irradiation;

DOI:10.1016/j.tet.2015.06.071

upstream raw materials:

diazomethane

Indole-2-carboxylic acid

methanol

methyl 2-(phenylhydrazono)propionate

Downstream raw materials:

methyl N-(2-dibenzylaminoethyl)indole-2-carboxylate

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

methyl 2-(2-cyanophenyl)acetate

2,3-Dihydro-1H-indol-2-ylmethanol

Refernces

A β-carboline-1-one mimic of the anticancer Amaryllidaceae constituent pancratistatin: Synthesis and biological evaluation

10.1002/anie.200460218

The research focuses on the synthesis and biological evaluation of a b-carboline-1-one mimic of the anticancer Amaryllidaceae constituent pancratistatin. The purpose of the study was to develop a more soluble analogue of pancratistatin, which has shown activity against various cancer cell lines but has poor bioavailability. The researchers hypothesized that the potency of pancratistatin and related compounds might be due to the hydrogen-bonding donor-acceptor pairing of the b-ketoamide motifs present in these compounds. They synthesized compound 5, a b-carboline-1-one analogue of pancratistatin, to test this hypothesis and evaluated its activity against a series of cancer cell lines. The synthesis involved several interesting transformations and used chemicals such as vinylaziridine, methyl indole-2-carboxylate, tosylamide, and various reagents for hydrolysis, iodolactonization, and detosylation steps. The biological evaluation showed that compound 5 had borderline activity in a murine P388 lymphocytic leukemia assay, while some intermediates in the synthesis process showed promising activities against certain cancer cell lines. The study concluded that the presence of both oxygen atoms in the methylenedioxy bridge of pancratistatin is essential for high activity, and that future analogues could be structured around different scaffolds based on the activity of intermediates like iodolactone 11. The synthesis of compound 5, with nine steps, is the shortest existing preparation of pancratistatin analogues containing the aminoinositol motif, and the researchers plan to focus on heteroatom alterations in the aromatic portion of pancratistatin for future analogues.

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