tert-Butyl 6-bromo-1H-indole-1-carboxylate

Base Information

• Chemical Name: tert-Butyl 6-bromo-1H-indole-1-carboxylate
• CAS No.: 147621-26-9
• Molecular Formula: C13H14BrNO2
• Molecular Weight: 296.164
• Hs Code.: 2933990090
• DSSTox Substance ID: DTXSID60466289
• Nikkaji Number: J2.104.612D
• Wikidata: Q82292822
• Mol file: 147621-26-9.mol

Synonyms:147621-26-9;tert-Butyl 6-bromo-1H-indole-1-carboxylate;1-BOC-6-Bromoindole;Tert-butyl 6-bromoindole-1-carboxylate;tert-Butyl6-bromo-1H-indole-1-carboxylate;MFCD09954826;1H-INDOLE-1-CARBOXYLIC ACID, 6-BROMO-, 1,1-DIMETHYLETHYL ESTER;6-Bromo-1-Boc-1H-indole;SCHEMBL4150745;6-BROMO-INDOLE-1-CARBOXYLIC ACID TERT-BUTYL ESTER;DTXSID60466289;OUOWFTDOMYJYKB-UHFFFAOYSA-N;1-tert-butoxycarbonyl-6-bromoindole;XFA62126;AKOS015841302;AS-2785;MB08284;SY317118;CS-0187681;FT-0685683;1,1-Dimethylethyl 6-bromo-1H-indole-1-carboxylate;W-205663;6-Bromo-1H-indole-1-carboxylic acid 1,1-dimethylethyl ester

Chemical Property of tert-Butyl 6-bromo-1H-indole-1-carboxylate

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 102-103℃
• Boiling Point: 367.855°C at 760 mmHg
• Flash Point: 176.272°C
• PSA: 31.23000
• Density: 1.379g/cm³
• LogP: 4.18700
• Storage Temp.: Room temperature.
• 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-6-Bromoindole ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T
• Hazard Codes: T
• Statements: 25
• Safety Statements: 45

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)N1C=CC2=C1C=C(C=C2)Br

Technology Process of tert-Butyl 6-bromo-1H-indole-1-carboxylate

There total 4 articles about tert-Butyl 6-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: 99.0%

6-bromo-1H-indole (52415-29-9) + di-tert-butyl dicarbonate (24424-99-5) → 6-bromoindole-1-carboxylic acid tert-butyl ester (147621-26-9)

Guidance literature:

With dmap; In tetrahydrofuran; at 20 ℃; for 4h;

DOI:10.1021/ja016863p

Reference yield: 76.0%

tert-butyl 6-(((trifluoromethyl)sulfonyl)oxy)-1H-indole-1-carboxylate (1247868-61-6) → 6-bromoindole-1-carboxylic acid tert-butyl ester (147621-26-9)

Guidance literature:

With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; t-BuBrettPhos; triisobutylaluminum; butanone; potassium bromide; In toluene; at 100 ℃; for 24h; Inert atmosphere;

DOI:10.1021/ja107481a

Reference yield:

6-bromo-1H-indole (52415-29-9) + tert-butyldicarbonate (34619-03-9) → 6-bromoindole-1-carboxylic acid tert-butyl ester (147621-26-9)

Guidance literature:

With dmap; triethylamine; In N,N-dimethyl-formamide; at 0 - 20 ℃; for 1h;

DOI:10.1016/j.bmcl.2011.01.035

upstream raw materials:

6-bromo-1H-indole

di-tert-butyl dicarbonate

4-bromo-2-nitrotoluene

tert-butyl 6-(((trifluoromethyl)sulfonyl)oxy)-1H-indole-1-carboxylate

Downstream raw materials:

1-tert-butoxycarbonyl-6-(4-methoxyphenyl)indole

1-(tert-butoxycarbonyl)-6-(4-cyanophenyl)-1H-indole

C₂₂H₁₈N₄

C₂₂H₂₄N₄