tert-Butyl 3-iodo-1H-indole-1-carboxylate

Base Information

• Chemical Name: tert-Butyl 3-iodo-1H-indole-1-carboxylate
• CAS No.: 192189-07-4
• Molecular Formula: C13H14INO2
• Molecular Weight: 343.164
• Hs Code.: 2933990090
• DSSTox Substance ID: DTXSID60440903
• Nikkaji Number: J993.650E
• Wikidata: Q72510248
• Mol file: 192189-07-4.mol

Synonyms:192189-07-4;tert-Butyl 3-iodo-1H-indole-1-carboxylate;1-Boc-3-iodoindole;Tert-butyl 3-iodoindole-1-carboxylate;1-(TERT-BUTOXYCARBONYL)-3-IODO-1H-INDOLE;3-IODOINDOLE-1-CARBOXYLIC ACID TERT-BUTYL ESTER;1H-Indole-1-carboxylic acid, 3-iodo-, 1,1-dimethylethyl ester;MFCD05864781;N-(boc)-3-iodoindole;1-BOC-3-iodo-1h-indole;1-Boc-3-iodoindole,95%;SCHEMBL10819499;DTXSID60440903;AMY39181;AB8726;AKOS015912193;BS-2029;SB15145;SY012341;tert-Butyl3-iodo-1H-indole-1-carboxylate;CS-0040991;FT-0755177;A880337;3-Iodoindole-1-carboxylic acid tert-butyl ester;1-Boc-3-iodoindole, 95%

Chemical Property of tert-Butyl 3-iodo-1H-indole-1-carboxylate

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 36-40℃
• Refractive Index: 1.61
• Boiling Point: 388.372 °C at 760 mmHg
• Flash Point: 188.681 °C
• PSA: 31.23000
• Density: 1.561 g/cm³
• LogP: 4.02910
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• Sensitive.: Light Sensitive
• Water Solubility.: Insoluble in water.
• XLogP3: 3.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 343.00693
• Heavy Atom Count: 17
• Complexity: 300

Purity/Quality:

99.3% ^*data from raw suppliers

tert-Butyl3-Iodo-1H-indole-1-carboxylate ^*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=C(C2=CC=CC=C21)I
• Uses: 1-Boc-3-iodoindole is used as a pharmaceutical intermediate and also used in ceramic manufacturing industry.

Technology Process of tert-Butyl 3-iodo-1H-indole-1-carboxylate

There total 8 articles about tert-Butyl 3-iodo-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: 96.0%

3-Iodo-1H-indole (26340-47-6) + di-tert-butyl dicarbonate (24424-99-5) → tert-butyl 3-iodo-1H-indol-1-carboxylate (192189-07-4)

Guidance literature:

With dmap; triethylamine; In dichloromethane; at 20 ℃; for 1h;

DOI:10.1021/acs.orglett.8b00521

Reference yield: 92.11%

3-Iodo-1H-indole (26340-47-6) + tert-Butoxycarbonylpivalat (39982-01-9) → tert-butyl 3-iodo-1H-indol-1-carboxylate (192189-07-4)

Guidance literature:

With dmap; triethylamine; In dichloromethane; at 20 ℃; for 1h;

Reference yield: 92.0%

indole (120-72-9) + di-tert-butyl dicarbonate (24424-99-5) → tert-butyl 3-iodo-1H-indol-1-carboxylate (192189-07-4)

Guidance literature:

indole; With potassium hydroxide; In N,N-dimethyl-formamide; at 20 ℃; for 0.166667h;

With iodine; In N,N-dimethyl-formamide; at 20 ℃; for 1h;

di-tert-butyl dicarbonate; With dmap; triethylamine; In dichloromethane; at 20 ℃; for 1h;

DOI:10.1002/jccs.201900278

upstream raw materials:

3-Iodo-1H-indole

di-tert-butyl dicarbonate

indole-1-carboxylic acid tert-butyl ester

3-(Dimethylaminomethyl)indole

Downstream raw materials:

3-(1-benzyl-1H-1,2,3-triazol-4-yl)-1H-indole

C₂₂H₂₂N₄O₂

benzhydrylidene aza-N-Boc-3-indolylpropargylglycinyl-D-phenylalanine tert-butyl ester

(2'R,4Z)-1-((diphenylmethylene)amino)-3-(tert-butyl-3'-phenyl-2'-propanoate)-4-(N'-Boc-3'-indoylmethylene)imidazolidin-2-one

Refernces

• 1、 Wang, Ruei-Yu,Kao, Wei-Ting,Shih, Tzenge-Lien. "Synthesis of selenium-containing biindolyls and their Diels–Alder reaction toward the synthesis of heteroannulated [a]- and [c]-carbazoles". . p. 829 - 837. Retrieved 2020.
• 2、 Garrison, Michelle A.,Mahoney, Andrew R.,Wuest, William M.. "Tricepyridinium-inspired QACs yield potent antimicrobials and provide insight into QAC resistance". supporting information. p. 463 - 466. Retrieved 2020/10/19.