6-Bromo-1-(tert-butyldimethylsilyl)indole

Base Information

• Chemical Name: 6-Bromo-1-(tert-butyldimethylsilyl)indole
• CAS No.: 184637-11-4
• Molecular Formula: C14H20BrNSi
• Molecular Weight: 310.309
• Hs Code.: 2933990090
• DSSTox Substance ID: DTXSID80441210
• Nikkaji Number: J1.856.500E
• Wikidata: Q82257872
• Mol file: 184637-11-4.mol

Synonyms:6-BROMO-1-(TERT-BUTYLDIMETHYLSILYL)INDOLE;184637-11-4;(6-bromoindol-1-yl)-tert-butyl-dimethylsilane;1-(tert-Butyldimethylsilyl)-6-bromo-1H-indole;6-Bromo-1-(tert-butyldimethylsilyl)-1H-indole;DTXSID80441210;MFCD17926506;AKOS015835899;BS-25461;EN300-178026

Chemical Property of 6-Bromo-1-(tert-butyldimethylsilyl)indole

Chemical Property:

• PSA: 4.93000
• LogP: 5.25710
• Storage Temp.: Refrigerated.
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 2
• Exact Mass: 309.05484
• Heavy Atom Count: 17
• Complexity: 284

Purity/Quality:

≥95% ^*data from raw suppliers

6-Bromo-1-(tert-butyldimethylsilyl)indole ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)[Si](C)(C)N1C=CC2=C1C=C(C=C2)Br

Technology Process of 6-Bromo-1-(tert-butyldimethylsilyl)indole

There total 1 articles about 6-Bromo-1-(tert-butyldimethylsilyl)indole 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%

6-bromo-1H-indole (52415-29-9) + tert-butyldimethylsilyl chloride (18162-48-6) → 6-bromo-1-(tert-butyldimethylsilyl)-1H-indole (184637-11-4)

Guidance literature:

6-bromo-1H-indole; With sodium hydride; In N,N-dimethyl-formamide; mineral oil; at 0 - 20 ℃; for 0.5h;

tert-butyldimethylsilyl chloride; In N,N-dimethyl-formamide; mineral oil; at 0 - 20 ℃; for 1h;

DOI:10.3762/bjoc.14.102

Reference yield: 75.0%

1-acetoxy-1,2-benziodoxol-3-one (1829-26-1) + 6-bromo-1-(tert-butyldimethylsilyl)-1H-indole (184637-11-4) → 1-(6-bromo-1-methyl-1H-indol-3-yl)-1H-1λ3-benzo[b]iodo-3(2H)-one

Guidance literature:

With scandium tris(trifluoromethanesulfonate); In dichloromethane; at 20 ℃;

DOI:10.3762/bjoc.14.102

Reference yield:

6-bromo-1-(tert-butyldimethylsilyl)-1H-indole (184637-11-4) → 6-Bromo-1-(tert-butyl-dimethyl-silanyl)-3-phenyl-1H-indole

Guidance literature:

Multi-step reaction with 2 steps

1: 98 percent / N-bromosuccinimide / tetrahydrofuran / 4 h / -78 °C

2: 1.) tert-BuLi, 2.) trimethoxyborane, 3.) H₂O, 4.) tetrakis(triphenylphosphine)palladium, 2 M aq. Na₂CO₃

With N-Bromosuccinimide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; Trimethyl borate; water; tert.-butyl lithium; sodium carbonate; In tetrahydrofuran;

DOI:10.1248/cpb.44.1831

upstream raw materials:

6-bromo-1H-indole

tert-butyldimethylsilyl chloride

Downstream raw materials:

6-indolylboronic acid

Refernces

• 1、 Perrotta, Daniele,Wang, Ming-Ming,Waser, Jér?me. "Lewis Acid Catalyzed Enantioselective Desymmetrization of Donor–Acceptor meso-Diaminocyclopropanes". supporting information. p. 5120 - 5123. Retrieved 2018/03/27.
• 2、 Kawasaki, Ikuo,Yamashita, Masayuki,Ohta, Shunsaku. "Total synthesis of nortopsentins A-D, marine alkaloids". . p. 1831 - 1839. Retrieved 2007/10/03.