1-tert-Butyl 2-methyl 1H-indole-1,2-dicarboxylate

Base Information

• Chemical Name: 1-tert-Butyl 2-methyl 1H-indole-1,2-dicarboxylate
• CAS No.: 163229-48-9
• Molecular Formula: C15H17NO4
• Molecular Weight: 275.304
• Hs Code.: 2933990090
• DSSTox Substance ID: DTXSID70383695
• Nikkaji Number: J1.279.119D
• Wikidata: Q82175485
• Mol file: 163229-48-9.mol

Synonyms:163229-48-9;1-(tert-Butyl) 2-methyl 1H-indole-1,2-dicarboxylate;1-tert-Butyl 2-methyl 1H-indole-1,2-dicarboxylate;1-O-tert-butyl 2-O-methyl indole-1,2-dicarboxylate;tert-butyl methyl 1h-indole-1,2-dicarboxylate;SCHEMBL18537881;DTXSID70383695;AB6742;MFCD05865115;AKOS015912278;Methyl 1-boc-1H-indole-2-carboxylate;AS-44799;CS-0154779;FT-0747340;1-tert-Butyl2-methyl1H-indole-1,2-dicarboxylate;Methyl 1H-indole-2-carboxylate, N-BOC protected;W-205920;1-(tert-Butyl)-2-methyl-1H-indole-1,2-dicarboxylate;1-(tert-butyl)2-methyl 1h-indole-1,2-dicarboxylate;1-(TERT-BUTYL)2-METHYL1H-INDOLE-1,2-DICARBOXYLATE;1H-Indole-1,2-dicarboxylic acid 1-tert-butyl 2-methyl ester;1H-Indole-1,2-dicarboxylic acid, 1-(1,1-dimethylethyl) 2-methyl ester

Chemical Property of 1-tert-Butyl 2-methyl 1H-indole-1,2-dicarboxylate

Chemical Property:

• Vapor Pressure: 3.34E-06mmHg at 25°C
• Melting Point: 66 °C
• Refractive Index: 1.543
• Boiling Point: 387.3 °C at 760 mmHg
• Flash Point: 188 °C
• PSA: 57.53000
• Density: 1.16g/cm³
• LogP: 3.21110
• Storage Temp.: Sealed in dry,Room Temperature
• XLogP3: 3.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 4
• Exact Mass: 275.11575802
• Heavy Atom Count: 20
• Complexity: 388

Purity/Quality:

98%min ^*data from raw suppliers

Methyl 1H-indole-2-carboxylate, N-Boc protected 97% ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T
• Hazard Codes: T

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)N1C2=CC=CC=C2C=C1C(=O)OC

Technology Process of 1-tert-Butyl 2-methyl 1H-indole-1,2-dicarboxylate

There total 12 articles about 1-tert-Butyl 2-methyl 1H-indole-1,2-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: 99.5%

indole-2-carboxylic acid methyl ester (1202-04-6) + di-tert-butyl dicarbonate (24424-99-5) → 1-(1,1-dimethylethyl)-1H-indole-1,2-dicarboxylic acid 2-methyl ester (163229-48-9)

Guidance literature:

With dmap; In tetrahydrofuran; at 20 ℃; for 1h;

DOI:10.1246/bcsj.77.1021

Reference yield:

Indole-2-carboxylic acid (1477-50-5,1228050-17-6) → 1-(1,1-dimethylethyl)-1H-indole-1,2-dicarboxylic acid 2-methyl ester (163229-48-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 93 percent / thionyl chloride / 18 h / 20 °C

2: 98 percent / DMAP / acetonitrile / 1 h / 20 °C

With dmap; thionyl chloride; In acetonitrile; 1: Esterification / 2: Substitution;

DOI:10.1021/ja001271c

Reference yield:

1-(tert-butoxycarbonyl)-1H-indole-2-carboxylic acid (136382-33-7) + methyl iodide (74-88-4) → 1-(1,1-dimethylethyl)-1H-indole-1,2-dicarboxylic acid 2-methyl ester (163229-48-9)

Guidance literature:

at 35 ℃; for 2h;

DOI:10.1016/j.chempr.2020.08.022

upstream raw materials:

indole-2-carboxylic acid methyl ester

di-tert-butyl dicarbonate

2-carbethoxyindole

methyl2-<(E)-phenylhydrazono>propionate

Downstream raw materials:

methyl (2S,3aS,7aS)-N-(benzyloxycarbonyl)-2-methyloctahydroindole-2-carboxylate

methyl N-(tert-butoxycarbonyl)-4,5,6,7-tetrahydroindole-2-carboxylate

methyl (+/-)-1-t-butoxycarbonyl-indoline-2-carboxylate