1-BOC-4-Chloroindole

Base Information

• Chemical Name: 1-BOC-4-Chloroindole
• CAS No.: 129822-46-4
• Molecular Formula: C13H14ClNO2
• Molecular Weight: 251.70900
• Hs Code.: 2933990090
• DSSTox Substance ID: DTXSID30464797
• Nikkaji Number: J416.461J
• Wikidata: Q82290292
• Mol file: 129822-46-4.mol

Synonyms:1-BOC-4-Chloroindole;129822-46-4;N-(BOC)-4-chloroindole;tert-Butyl 4-chloro-1H-indole-1-carboxylate;Tert-butyl 4-chloroindole-1-carboxylate;N-Boc-4-chloroindole;SCHEMBL2878376;DTXSID30464797;SNYOMIGRAXEOBR-UHFFFAOYSA-N;1H-Indole-1-carboxylic acid, 4-chloro-, 1,1-dimethylethyl ester;MFCD09025758;AKOS015836996;BS-20438;tert-Butyl4-chloro-1H-indole-1-carboxylate;CS-0205353;FT-0724192;F83004;4-chloro-indole-1-carboxylic acid tert-butyl ester

Chemical Property of 1-BOC-4-Chloroindole

Chemical Property:

• Vapor Pressure: 4.55E-05mmHg at 25°C
• Boiling Point: 349.9oC at 760 mmHg
• Flash Point: 165.4oC
• PSA: 31.23000
• Density: 1.19g/cm3
• LogP: 4.07790
• Storage Temp.: Room temperature.
• XLogP3: 3.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 251.0713064
• Heavy Atom Count: 17
• Complexity: 300

Purity/Quality:

98%min ^*data from raw suppliers

1-BOC-4-Chloroindole ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)N1C=CC2=C1C=CC=C2Cl

Technology Process of 1-BOC-4-Chloroindole

There total 7 articles about 1-BOC-4-Chloroindole 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%

4-chloro-1H-indole (25235-85-2) + di-tert-butyl dicarbonate (24424-99-5) → tert-butyl 4-chloro-1H-indole-1-carboxylate (129822-46-4)

Guidance literature:

With dmap; In tetrahydrofuran; at 20 ℃;

DOI:10.1039/c2cc17815j

Reference yield: 66.0%

tert-butyl carbazate (4248-19-5) + 1-bromo-2-[(E)-2-bromovinyl]-3-chlorobenzene (1243601-90-2) → tert-butyl 4-chloro-1H-indole-1-carboxylate (129822-46-4)

Guidance literature:

With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; caesium carbonate; In toluene; at 110 ℃; for 16h; Inert atmosphere;

DOI:10.1016/j.tet.2010.05.046

Reference yield: 17.0%

tert-butyl carbazate (4248-19-5) + 2-[(E)-2-bromoethenyl]-1,3-dichlorobenzene → tert-butyl 4-chloro-1H-indole-1-carboxylate (129822-46-4)

Guidance literature:

With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; caesium carbonate; DavePhos; In toluene; at 110 ℃; for 16h; Inert atmosphere;

DOI:10.1016/j.tet.2010.05.046

upstream raw materials:

4-Chloro-2-hydroxy-2,3-dihydro-indole-1-carboxylic acid tert-butyl ester

4-chloro-1H-indole

di-tert-butyl dicarbonate

3-chloro-2-methylbenzenamine

Downstream raw materials:

[1-(tert-butoxycarbonyl)-4-chloro-1H-indol-2-yl]boronic acid

4-(4-chloro-1H-indol-2-yl)-N-[2-(4-fluorophenyl)ethyl]-6-methoxy-1,3,5-triazin-2-amine

tert-butyl 4-chloro-2-(4-{[2-(4-fluorophenyl)ethyl]amino}-6-methoxy-1,3,2-triazin-2-yl)-1H-indole-1-carboxylate

Refernces

• 1、 Hua, Xiye,Masson-Makdissi, Jeanne,Sullivan, Ryan J.,Newman, Stephen G.. "Inherent vs Apparent Chemoselectivity in the Kumada-Corriu Cross-Coupling Reaction". supporting information. p. 5312 - 5315. Retrieved 2016/11/02.
• 2、 Liu, Qiang,Zhao, Qing Yong,Liu, Jie,Wu, Pan,Yi, Hong,Lei, Aiwen. "A trans diacyloxylation of indoles". supporting information; experimental part. p. 3239 - 3241. Retrieved 2012/04/10.