diethyl 1H-indole-2,5-dicarboxylate

Base Information

• Chemical Name: diethyl 1H-indole-2,5-dicarboxylate
• CAS No.: 127221-02-7
• Molecular Formula: C₁₄H₁₅NO₄
• Molecular Weight: 261.277
• Hs Code.: 2933990090
• DSSTox Substance ID: DTXSID80576011
• Nikkaji Number: J803.083I
• Wikidata: Q82465519
• Mol file: 127221-02-7.mol

Synonyms:127221-02-7;diethyl 1H-indole-2,5-dicarboxylate;5-ETHOXYCARBONYLINDOLE-2-CARBOXYLIC ACID ETHYL ESTER;1H-Indole-2,5-dicarboxylic acid, 2,5-diethyl ester;1H-indole-2,5-dicarboxylic acid diethyl ester;SCHEMBL68923;DTXSID80576011;IEFLIZMMNNHRSB-UHFFFAOYSA-N;CFA22102;diethyl1H-indole-2,5-dicarboxylate;MFCD03094964;AKOS015898565;MB02637;AS-75833;CS-0151730;D82202;1H-Indole-2,5-dicarboxylicacid,2,5-diethyl ester;A805663;Z325900036;(R)-[3-oxo-1-(2,4,5-trifluoro-benzyl)-3-(3-trifluoromethyl-5,6-dihydro-8H-[1,2,4]trizolo[4,3-a]-pyrazin-7-yl)-propyl]-carbamicacidtert-butylester

Chemical Property of diethyl 1H-indole-2,5-dicarboxylate

Chemical Property:

• Boiling Point: 420.183 °C at 760 mmHg
• Flash Point: 207.92 °C
• PSA: 68.39000
• Density: 1.24 g/cm³
• LogP: 2.52130
• Storage Temp.: Sealed in dry,Room Temperature
• XLogP3: 3.4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 6
• Exact Mass: 261.10010796
• Heavy Atom Count: 19
• Complexity: 344

Purity/Quality:

97% ^*data from raw suppliers

Diethyl1H-indole-2,5-dicarboxylate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)C1=CC2=C(C=C1)NC(=C2)C(=O)OCC

Technology Process of diethyl 1H-indole-2,5-dicarboxylate

There total 3 articles about diethyl 1H-indole-2,5-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: 34.0%

2-oxo-propionic acid ethyl ester (617-35-6) + p-aminoethylbenzoate (94-09-7) → diethyl 1H-indole-2,5-dicarboxylate (127221-02-7)

Guidance literature:

With oxygen; palladium diacetate; acetic acid; In dimethyl sulfoxide; at 70 ℃; for 24h; under 760.051 Torr; Schlenk technique; Molecular sieve;

DOI:10.1021/acs.joc.8b02180

Reference yield: 24.0%

oxalyl dichloride (79-37-8) + 2-carbethoxyindole (3770-50-1,117770-52-2) + ethanol (64-17-5) → diethyl 1H-indole-2,5-dicarboxylate (127221-02-7) + diethyl 1H-indole-2,3-dicarboxylate (128942-88-1)

Guidance literature:

oxalyl dichloride; 2-carbethoxyindole; With aluminium trichloride; In dichloromethane; at 20 ℃; for 2h;

ethanol; at 20 ℃; for 4h;

Reference yield:

1H-indole-2,5-dicarboxylic acid 2-ethyl ester (138731-14-3) → diethyl 1H-indole-2,5-dicarboxylate (127221-02-7)

Guidance literature:

With hydrogenchloride;

DOI:10.1021/jo01132a001

upstream raw materials:

1H-indole-2,5-dicarboxylic acid 2-ethyl ester

oxalyl dichloride

2-carbethoxyindole

ethanol