dimethyl 1H-indole-2,6-dicarboxylate

Base Information

• Chemical Name: dimethyl 1H-indole-2,6-dicarboxylate
• CAS No.: 881040-29-5
• Molecular Formula: C₁₂H₁₁NO₄
• Molecular Weight: 233.224
• DSSTox Substance ID: DTXSID30405847
• Nikkaji Number: J2.671.722A
• Wikidata: Q72470691
• Mol file: 881040-29-5.mol

Synonyms:dimethyl 1H-indole-2,6-dicarboxylate;881040-29-5;DIMETHYL INDOLE-2,6-DICARBOXYLATE;dimethyl1H-indole-2,6-dicarboxylate;1H-INDOLE-2,6-DICARBOXYLIC ACID, 2,6-DIMETHYL ESTER;2,6-dimethyl 1H-indole-2,6-dicarboxylate;SCHEMBL6421763;1H-INDOLE-2,6-DICARBOXYLIC ACID DIMETHYL ESTER;DTXSID30405847;AMY36656;MFCD06653349;AKOS001476664;dimethyl 1H-indole-2?6-dicarboxylate;AC-22710;BS-49591;CS-0054389;FT-0682465;methyl 6-methoxycarbonylindole-2-carboxylate;EN300-1086719;J-504694

Chemical Property of dimethyl 1H-indole-2,6-dicarboxylate

Chemical Property:

• Vapor Pressure: 1.3E-06mmHg at 25°C
• Refractive Index: 1.615
• Boiling Point: 400.1 °C at 760 mmHg
• Flash Point: 195.8 °C
• PSA: 68.39000
• Density: 1.312 g/cm³
• LogP: 1.74110
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• XLogP3: 2.3
• 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-2,6-dicarboxylate 95% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC(=O)C1=CC2=C(C=C1)C=C(N2)C(=O)OC

Technology Process of dimethyl 1H-indole-2,6-dicarboxylate

There total 5 articles about dimethyl 1H-indole-2,6-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: 89.0%

(Z)-methyl 3-amino-4-(2-bromo-3-methoxy-3-oxoprop-1-enyl)benzoate (1586740-60-4) → dimethyl 1H-indole-2,6-dicarboxylate (881040-29-5)

Guidance literature:

With 1,4-diaza-bicyclo[2.2.2]octane; copper(l) iodide; potassium carbonate; In 1,4-dioxane; for 5h; Schlenk technique; Inert atmosphere; Reflux;

DOI:10.1016/j.tetlet.2013.10.048

Reference yield: 73.0%

3-amino-4-(2,2-dibromovinyl)-benzoic acid methyl ester (863870-44-4) + methanol (67-56-1) + carbon monoxide (201230-82-2) → dimethyl 1H-indole-2,6-dicarboxylate (881040-29-5)

Guidance literature:

With bis-triphenylphosphine-palladium(II) chloride; N-ethyl-N,N-diisopropylamine; triphenylphosphine; In tetrahydrofuran; at 110 ℃; for 20h; under 7600.51 Torr; Autoclave;

DOI:10.1021/ol801985q

Reference yield: 65.0%

methanol (67-56-1) + carbon monoxide (201230-82-2) + C8H6Br3N (1072943-54-4) → dimethyl 1H-indole-2,6-dicarboxylate (881040-29-5)

Guidance literature:

With bis-triphenylphosphine-palladium(II) chloride; N-ethyl-N,N-diisopropylamine; triphenylphosphine; In tetrahydrofuran; at 110 ℃; for 24h; under 7600.51 Torr; Autoclave;

DOI:10.1021/ol801985q

upstream raw materials:

3-amino-4-(2,2-dibromovinyl)-benzoic acid methyl ester

methanol

carbon monoxide

C₈H₆Br₃N

Refernces

• 1、 Vieira, Tiago O.,Meaney, Laura A.,Shi, Yong-Ling,Alper, Howard. "Tandem palladium-catalyzed N,C-coupling/carbonylation sequence for the synthesis of 2-carboxyindoles". supporting information; experimental part. p. 4899 - 4901. Retrieved 2009/05/31.