Dimethyl 1H-indole-2,3-dicarboxylate

Base Information

• Chemical Name: Dimethyl 1H-indole-2,3-dicarboxylate
• CAS No.: 54781-93-0
• Molecular Formula: C12H11 N O4
• Molecular Weight: 233.224
• Hs Code.: 29339980
• DSSTox Substance ID: DTXSID40203255
• Nikkaji Number: J291.458A
• Mol file: 54781-93-0.mol

Synonyms:Dimethyl 1H-indole-2,3-dicarboxylate;54781-93-0;Dimethyl indole-2,3-dicarboxylate;DIMETHYLINDOLE-2,3-DICARBOXYLATE;Dimethyl 2,3-indoledicarboxylate;Indole-2,3-dicarboxylic acid, dimethyl(ester);2,3-dicarbomethoxyindole;Maybridge1_006201;1H-indole-2,3-dicarboxylic acid dimethyl ester;Oprea1_099063;SCHEMBL3275502;HMS559B19;DTXSID40203255;MFCD00082731;AKOS015898309;CCG-248588;CS-W010344;SDCCGMLS-0066201.P001;Dimethyl 2,3-indoledicarboxylate, 98%;Dimethyl 1H-indole-2,3-dicarboxylate #;DS-17351;FT-0609499;C75571;D-1850

Chemical Property of Dimethyl 1H-indole-2,3-dicarboxylate

Chemical Property:

• Appearance/Colour: yellow powder
• Vapor Pressure: 1.46E-05mmHg at 25°C
• Melting Point: 113-114 °C(lit.)
• Refractive Index: 1.5560 (estimate)
• Boiling Point: 366.5°C at 760 mmHg
• PKA: 13.39±0.30(Predicted)
• Flash Point: 175.5°C
• PSA: 68.39000
• Density: 1.312g/cm³
• LogP: 1.74110
• Storage Temp.: Sealed in dry,Room Temperature
• XLogP3: 2.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 4
• Exact Mass: 233.06880783
• Heavy Atom Count: 17
• Complexity: 318

Purity/Quality:

99% ^*data from raw suppliers

Dimethyl 1H-indole-2,3-dicarboxylate 95.0% ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC(=O)C1=C(NC2=CC=CC=C21)C(=O)OC
• Uses: Reactant for preparation of:Indole-indolone scaffoldsChemiluminescent agentsAntihypertensive agentsInhibitors of blood platelet aggregation and inotropic agents

Technology Process of Dimethyl 1H-indole-2,3-dicarboxylate

There total 6 articles about Dimethyl 1H-indole-2,3-dicarboxylate 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: 70.0%

C21H18N2O6 → 1-methyl-1H-indole-2,3-dione (2058-74-4) + 1H-indole-2,3-dicarboxylic acid dimethyl ester (54781-93-0)

Guidance literature:

With water; In toluene; at 80 ℃; for 12h;

DOI:10.1016/j.tet.2013.03.062

Reference yield: 70.0%

C21H18N2O6 → 1-methyl-1H-indole-2,3-dione (2058-74-4) + 1H-indole-2,3-dicarboxylic acid dimethyl ester (54781-93-0) + C18H16N2O3

Guidance literature:

With water; silica gel; In toluene; at 80 ℃; for 12h;

DOI:10.1016/j.tet.2013.03.062

Reference yield: 58.0%

dimethyl 2-(3,4-methoxyphenyl)quinoline-3,4-dicarboxylate 1-oxide (88344-52-9) → methyl 3,4-dimethoxybenzoate (2150-38-1) + 1H-indole-2,3-dicarboxylic acid dimethyl ester (54781-93-0) + methyl 2-(3,4-dimethoxyphenyl)indole-3-carboxylate (88344-57-4) + dimethyl 1-(3,4-dimethoxyphenyl)-2-oxo-1,2-dihydroquinoline-3,4-dicarboxylate (88344-55-2)

Guidance literature:

In methanol; chloroform; Further byproducts given; a) irradiation, 24 h, b) in the dark, 90 h;

upstream raw materials:

tetrachloromethane

(N,N'-diphenyl-hydrazino)-butenedioic acid dimethyl ester

dimethyl 2-(3,4-methoxyphenyl)quinoline-3,4-dicarboxylate 1-oxide

1-(4-benzyloxyphenyl)-2-phenylhydrazine

Downstream raw materials:

1,4-dioxo-1,2,3,4-tetrahydro-5H-pyridazino<4,5-b>indole

1-(3-cyano-benzyl)-1H-indole-2,3-dicarboxylic acid dimethyl ester

methyl 2-(((benzyloxy)carbonyl)amino)-1-methyl-1H-indole-3-carboxylate

methyl 2-amino-1-methylindole-3-carboxylate

Refernces

• 1、 Miki, Yasuyoshi,Matsushita, Ko-Ichi,Hibino, Hajime,Shirokoshi, Hideaki. "Synthesis and reaction of dimethyl 7-bromoindole-2,3-dicarboxylates". . p. 1585 - 1596. Retrieved 2007/10/03.