Tert-butyl 3-bromo-1h-indole-1-carboxylate

Base Information

• Chemical Name: Tert-butyl 3-bromo-1h-indole-1-carboxylate
• CAS No.: 143259-56-7
• Molecular Formula: C₁₃H₁₄BrNO₂
• Molecular Weight: 296.164
• Hs Code.: 2933990090
• European Community (EC) Number: 674-763-9
• DSSTox Substance ID: DTXSID10602357
• Nikkaji Number: J2.694.762F
• Wikidata: Q82499370
• Mol file: 143259-56-7.mol

Synonyms:1-Boc-3-Bromoindole;143259-56-7;tert-butyl 3-bromo-1h-indole-1-carboxylate;3-bromoindole-1-carboxylic acid tert-butyl ester;tert-butyl 3-bromoindole-1-carboxylate;MFCD05864772;n-boc-3-bromoindole;1H-Indole-1-carboxylic acid, 3-bromo-, 1,1-dimethylethyl ester;3-Bromo-indole-1-carboxylic acid tert-Butyl ester;SCHEMBL1055676;AMY7550;DTXSID10602357;DMNYMGSBBRRGOW-UHFFFAOYSA-N;AKOS015838295;AC-7383;CS-W003256;MB03667;PS-7153;SY005985;t-butyl 3-bromo-1h-indole-1-carboxylate;tert-butyl3-bromo-1h-indole-1-carboxylate;DB-011841;A808046;J-007783

Chemical Property of Tert-butyl 3-bromo-1h-indole-1-carboxylate

Chemical Property:

• Vapor Pressure: 1.33E-05mmHg at 25°C
• Refractive Index: 1.576
• Boiling Point: 367.855 °C at 760 mmHg
• Flash Point: 176.272 °C
• PSA: 31.23000
• Density: 1.379 g/cm³
• LogP: 4.18700
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• XLogP3: 4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 295.02079
• Heavy Atom Count: 17
• Complexity: 300

Purity/Quality:

97% ^*data from raw suppliers

1-Boc-3-bromoindole ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)N1C=C(C2=CC=CC=C21)Br

Technology Process of Tert-butyl 3-bromo-1h-indole-1-carboxylate

There total 4 articles about Tert-butyl 3-bromo-1h-indole-1-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-1-carboxylic acid tert-butyl ester (75400-67-8) → 3-bromoindole-1-carboxylic acid tert-butyl ester (143259-56-7)

Guidance literature:

With N-Bromosuccinimide; In tetrahydrofuran; at 20 ℃; for 18h;

DOI:10.1016/j.bmcl.2014.07.062

Reference yield:

3-bromoindole (1484-27-1) + di-tert-butyl dicarbonate (24424-99-5) → 3-bromoindole-1-carboxylic acid tert-butyl ester (143259-56-7)

Guidance literature:

With dmap; triethylamine; In dichloromethane; at 20 ℃; for 3h; Inert atmosphere;

DOI:10.1021/jo4028177

Reference yield:

indole (120-72-9) → 3-bromoindole-1-carboxylic acid tert-butyl ester (143259-56-7)

Guidance literature:

Multi-step reaction with 2 steps

1: bromine / N,N-dimethyl-formamide / 0.5 h / 0 °C / Inert atmosphere

2: triethylamine; dmap / dichloromethane / 3 h / 20 °C / Inert atmosphere

With dmap; bromine; triethylamine; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jo4028177

upstream raw materials:

indole-1-carboxylic acid tert-butyl ester

3-bromoindole

di-tert-butyl dicarbonate

indole

Downstream raw materials:

tert-butyl 3-(3-(4-methoxyphenyl)(1-¹³C)prop-2-ynoyl)-1H-indole-1-carboxylate

tert-butyl 3-(3-(4-methoxyphenyl)prop-2-ynoyl)-1H-indole-1-carboxylate

tert-butyl 3-benzoyl-1H-indole-1-carboxylate

(1-(tert-butoxycarbonyl)-1H-indol-3-yl)boronic acid