1-(tert-Butoxycarbonyl)-5-chloroindole

Base Information

• Chemical Name: 1-(tert-Butoxycarbonyl)-5-chloroindole
• CAS No.: 129822-48-6
• Molecular Formula: C13H14ClNO2
• Molecular Weight: 251.713
• Hs Code.: 2933990090
• European Community (EC) Number: 623-941-4
• DSSTox Substance ID: DTXSID80466589
• Nikkaji Number: J416.462H
• Wikidata: Q72510092
• Mol file: 129822-48-6.mol

Synonyms:129822-48-6;1-(tert-Butoxycarbonyl)-5-chloroindole;tert-butyl 5-chloro-1H-indole-1-carboxylate;1-Boc-5-chloroindole;N-Boc-5-chloroindole;Tert-butyl 5-chloroindole-1-carboxylate;1H-Indole-1-carboxylic acid, 5-chloro-, 1,1-dimethylethyl ester;MFCD05865201;tert-Butyl5-chloro-1H-indole-1-carboxylate;1-Boc-5-chloro-1H-indole;SCHEMBL2006239;DTXSID80466589;GBBULIKZPZSTLA-UHFFFAOYSA-N;BCP27201;AB8604;AKOS015838310;BP-12655;BS-20437;SY110366;FT-0687181;1-(tert-Butoxycarbonyl)-5-chloroindole, 97%;A15189;5-chloro-indole-1-carboxylic acid tert-butyl ester;J-503649

Chemical Property of 1-(tert-Butoxycarbonyl)-5-chloroindole

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 45-50 °C(lit.)
• Refractive Index: 1.557
• Boiling Point: 349.934 °C at 760 mmHg
• Flash Point: 165.434 °C
• PSA: 31.23000
• Density: 1.19 g/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:

99% ^*data from raw suppliers

tert-Butyl5-Chloro-1H-indole-1-carboxylate ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T
• Hazard Codes: T
• Statements: 25-43
• Safety Statements: 36/37-45

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

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

Technology Process of 1-(tert-Butoxycarbonyl)-5-chloroindole

There total 6 articles about 1-(tert-Butoxycarbonyl)-5-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: 96.0%

di-tert-butyl dicarbonate (24424-99-5) + 5-chloro-1H-indole (17422-32-1) → tert-butyl 5-chloro-1H-indole-1-carboxylate (129822-48-6)

Guidance literature:

With dmap; In dichloromethane; at 25 ℃;

Reference yield: 69.0%

tert-butyl carbazate (4248-19-5) + 1-bromo-2-[2-bromovinyl]-4-chlorobenzene → tert-butyl 5-chloro-1H-indole-1-carboxylate (129822-48-6)

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:

5-Chloro-2-hydroxy-2,3-dihydro-indole-1-carboxylic acid tert-butyl ester (138343-86-9) → tert-butyl 5-chloro-1H-indole-1-carboxylate (129822-48-6)

Guidance literature:

With hydrogenchloride; In tetrahydrofuran; Yield given; Ambient temperature;

DOI:10.1055/s-1991-26597

upstream raw materials:

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

di-tert-butyl dicarbonate

5-chloro-1H-indole

(4-chloro-2-methyl-phenyl)-carbamic acid tert-butyl ester

Downstream raw materials:

1-(tert-butoxycarbonyl)-5-chloroindoline

tert-butyl 5-chloro-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolane-2-yl)-1H-indole-1-carboxylate

N-(4-methoxyphenyl)-3-(quinolin-6-yl)butanamide

1,1-dimethylethyl 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole-1-carboxylate

Refernces

• 1、 Brown, M. Kevin,Crook, Phillip F.,Kuniyil, Rositha,Liu, Peng,Trammel, Grace L.. "Nickel-Catalyzed Dearomative Arylboration of Indoles: Regioselective Synthesis of C2- And C3-Borylated Indolines". supporting information. p. 16502 - 16511. Retrieved 2021/10/20.
• 2、 -. "SUBSTITUTED BENZOFURAN COMPOUNDS AND METHODS OF USE THEREOF FOR THE TREATMENT OF VIRAL DISEASES". Page/Page column 89; 90. . Retrieved 2013/03/26.