Methyl indole-5-carboxylate

Base Information

• Chemical Name: Methyl indole-5-carboxylate
• CAS No.: 1011-65-0
• Molecular Formula: C10H9NO2
• Molecular Weight: 175.187
• Hs Code.: 29339900
• European Community (EC) Number: 627-947-8
• DSSTox Substance ID: DTXSID00372193
• Nikkaji Number: J258.258I
• Wikidata: Q72491915
• ChEMBL ID: CHEMBL109238
• Mol file: 1011-65-0.mol

Synonyms:Methyl indole-5-carboxylate;1011-65-0;methyl 1H-indole-5-carboxylate;Indole-5-carboxylic Acid Methyl Ester;MFCD00153023;1H-Indole-5-carboxylic acid, methyl ester;1H-Indole-5-carboxylic acid methyl ester;methyl 5-indolecarboxylate;Indole-5-carboxylate;5-methoxycarbonylindole;5-methloxycarbonylindole;5-(methoxycarbonyl)indole;methylindole-5-carboxylate;5-(methloxycarbonyl)indole;methyl 5-indole carboxylate;methyl 5-indole-carboxylate;methyl-5-indole carboxylate;Methyl-indole-5-carboxylate;5-Methoxycarbonyl-1H-indole;MLS001250153;SCHEMBL103794;CHEMBL109238;ISUPSL100238;Mehtyl 1H-indole-5-carboxylate;5-Indolecarboxylicacidmethylester;BDBM93019;DTXSID00372193;CHEBI:194927;DRYBMFJLYYEOBZ-UHFFFAOYSA-N;HMS2220E16;HMS3330O22;Methyl indole-5-carboxylate, 99%;BCP27016;CS-D1099;5-Indolecarboxylic acid methyl ester;BBL104415;STK503886;AKOS000265192;AC-3031;AM81120;PB29029;SB10354;SS-6027;SMR000686020;SY003617;SY282727;BB 0253734;FT-0620502;I0545;Indole-5-carboxylic acid methyl ester, 98%;EN300-154351;I-2515;A800341;Z1153206326;InChI=1/C10H9NO2/c1-13-10(12)8-2-3-9-7(6-8)4-5-11-9/h2-6,11H,1H

Chemical Property of Methyl indole-5-carboxylate

Chemical Property:

• Appearance/Colour: off-white to light brown crystalline powder
• Vapor Pressure: 0.000153mmHg at 25°C
• Melting Point: 126-128 °C
• Refractive Index: 1.639
• Boiling Point: 331.7 °C at 760 mmHg
• PKA: 16.09±0.30(Predicted)
• Flash Point: 154.4 °C
• PSA: 42.09000
• Density: 1.253 g/cm³
• LogP: 1.95450
• Storage Temp.: Refrigerator
• Water Solubility.: Insoluble in water.
• XLogP3: 2.6
• 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:

98% ^*data from raw suppliers

Methyl indole-5-carboxylate ^*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

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: COC(=O)C1=CC2=C(C=C1)NC=C2
• Uses: Methyl indole-5-carboxylate may be used as a reactant in the following processes:biosynthesis of inhibitors of protein kinasesmetal-free Friedel-Crafts alkylationpreparation of diphenylsulfonium ylides from Martin′s sulfuranecross dehydrogenative coupling reactionssynthesis of indirubin derivativespreparation of aminoindolylacetates

Technology Process of Methyl indole-5-carboxylate

There total 42 articles about Methyl indole-5-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%

Indole-6-carboxylic acid (1670-82-2,261352-47-0) + diethylazodicarboxylate (1972-28-7,218603-74-8) → 5-methoxycarbonylindole (1011-65-0)

Guidance literature:

With triphenylphosphine; In tetrahydrofuran; methanol; dichloromethane;

Reference yield: 98.0%

1H-Indole-5-carboxylic acid (1670-81-1,142396-03-0) + methyl iodide (74-88-4) → 5-methoxycarbonylindole (1011-65-0)

Guidance literature:

With sodium hydrogencarbonate; In N,N-dimethyl-formamide; for 72h;

DOI:10.1021/ol060039u

Reference yield: 92.0%

2,3-dihydro-1H-indole-5-carboxylic acid methyl ester (141452-01-9) → 5-methoxycarbonylindole (1011-65-0)

Guidance literature:

With dichloro[1,3-bis(2-methylphenyl)-2-imidazolidinylidene](benzylidene) (tricyclohexylphosphine) ruthenium(II); oxygen; In ethyl acetate; at 70 ℃; for 46h; under 760.051 Torr; Sealed tube;

DOI:10.1002/chem.202001961

upstream raw materials:

1H-Indole-5-carboxylic acid

methyl iodide

ethene

3-bromo-4-nitrobenzoate methyl ester

Downstream raw materials:

methyl 3‐formyl‐1H‐indole‐5‐carboxylate

Methyl 3-[[4-(2-phenylethyl)amino]-1-cyclohexen-1-yl]-1H-indole-5-carboxylate

methyl 3-((R)-1-(3,4,5-trimethoxyphenylamino)-2,2,2-trifluoroethyl)-1H-indole-5-carboxylate

(R)-methyl 3-(2,2,2-trifluoro-1-hydroxy-1-phenylethyl)-1H-indole-5-carboxylate

Refernces

• 1、 Jagadeesh, Rajenahally V.,Junge, Henrik,Pohl, Marga-Martina,Radnik, Joerg,Brueckner, Angelika,Beller, Matthias. "Selective oxidation of alcohols to esters using heterogeneous Co 3O4-N@C catalysts under mild conditions". . p. 10776 - 10782. Retrieved 2013.
• 2、 Mane, Rajendra Shivaji,Sasaki, Takehiko,Bhanage, Bhalchandra Mahadeo. "Silica supported palladium-phosphine as a reusable catalyst for alkoxycarbonylation and aminocarbonylation of aryl and heteroaryl iodides". . p. 94776 - 94785. Retrieved 2015.
• 3、 Ye, Ying,Suo, Yourui,Yang, Fang,Yang, Yongjing,Han, Lijuan. "Microwave-assisted synthesis and molecular recognition properties of novel indole acylhydrazone receptors". . p. 296 - 299. Retrieved 2015.
• 4、 -. "A method of synthesis of indole derivatives". Paragraph 0018-0021. . Retrieved 2022/01/10.