(1-(tert-Butyldimethylsilyl)-1H-indol-3-yl)boronic acid

Base Information

• Chemical Name: (1-(tert-Butyldimethylsilyl)-1H-indol-3-yl)boronic acid
• CAS No.: 159590-02-0
• Molecular Formula: C14H22 B N O2 Si
• Molecular Weight: 275.23
• Hs Code.: 2933990090
• DSSTox Substance ID: DTXSID60451014
• Nikkaji Number: J1.877.083K
• Wikidata: Q82270865
• Mol file: 159590-02-0.mol

Synonyms:159590-02-0;(1-(tert-Butyldimethylsilyl)-1H-indol-3-yl)boronic acid;(1-[TERT-BUTYL(DIMETHYL)SILYL]-1H-INDOL-3-YL)BORONIC ACID;[1-[tert-butyl(dimethyl)silyl]indol-3-yl]boronic acid;1-(Tert-butyldimethylsilyl)-1H-indol-3-ylboronic acid;{1-[tert-butyl(dimethyl)silyl]-1H-indol-3-yl}boronic acid;1-[TERT-BUTYL(DIMETHYL)SILYL]-1H-INDOL-3-YL-BORONIC ACID;SCHEMBL3450325;(1-(tert-Butyldimethylsilyl)-1H-indol-3-yl)boronicacid;DTXSID60451014;GSNHHLNDEKIFIZ-UHFFFAOYSA-N;MFCD03093099;AKOS004116478;AB13206;CS-0175361;1-tert-Butyldimethylsilyl-1H-indol-3-ylboronic acid;1-(tert-Butyldimethylsilyl)-1H-indole-3-ylboronic acid;1-(TERT-BUTYLDIMETHYLSILYL)INDOL-3-YLBORONIC ACID;[1-(tert-butyl-dimethyl-silanyl)-1H-indol-3-yl]-boronic acid

Chemical Property of (1-(tert-Butyldimethylsilyl)-1H-indol-3-yl)boronic acid

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.51
• Boiling Point: 342.549°C at 760 mmHg
• PKA: 9.30±0.30(Predicted)
• Flash Point: 160.968°C
• PSA: 45.39000
• Density: 1.014g/cm³
• LogP: 2.17440
• Storage Temp.: 2-8°C
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 3
• Exact Mass: 275.1512856
• Heavy Atom Count: 19
• Complexity: 330

Purity/Quality:

98%min ^*data from raw suppliers

(1-(tert-Butyldimethylsilyl)-1H-indol-3-yl)boronicacid 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: B(C1=CN(C2=CC=CC=C12)[Si](C)(C)C(C)(C)C)(O)O

Technology Process of (1-(tert-Butyldimethylsilyl)-1H-indol-3-yl)boronic acid

There total 3 articles about (1-(tert-Butyldimethylsilyl)-1H-indol-3-yl)boronic acid 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:

3-bromo-1-(tert-butyl-dimethyl-silanyl)-1H-indole (153942-69-9) → N-(tert-butyldimethylsilyl)indol-3-ylboronic acid (159590-02-0)

Guidance literature:

3-bromo-1-(tert-butyl-dimethyl-silanyl)-1H-indole; With tert.-butyl lithium; In tetrahydrofuran;

With Trimethyl borate; In tetrahydrofuran;

DOI:10.3987/COM-02-S64

Reference yield:

C16H26BNO2Si → N-(tert-butyldimethylsilyl)indol-3-ylboronic acid (159590-02-0)

Guidance literature:

With water; In methanol; at 20 ℃; for 1h;

Reference yield:

N-tert-butyldimethylsilylindole (40899-73-8) → N-(tert-butyldimethylsilyl)indol-3-ylboronic acid (159590-02-0)

Guidance literature:

Multi-step reaction with 2 steps

1.1: NBS / tetrahydrofuran / 6 h / -78 °C

2.1: t-BuLi / tetrahydrofuran / 0.33 h / -78 °C

2.2: B(OEt)3 / tetrahydrofuran / 2 h

With N-Bromosuccinimide; tert.-butyl lithium; In tetrahydrofuran;

DOI:10.1021/jo026450m

upstream raw materials:

3-bromo-1-(tert-butyl-dimethyl-silanyl)-1H-indole

N-tert-butyldimethylsilylindole

Downstream raw materials:

N-tert-butyldimethylsilylindole

1-(tert-butyldimethylsilyl)-3-(2-thienyl)indole

Topsentin

1-(tert-Butyl-dimethyl-silanyl)-3-[2-phenylsulfanyl-3-(2-trimethylsilanyl-ethoxymethyl)-3H-imidazol-4-yl]-1H-indole

Refernces

• 1、 Yang, Cai-Guang,Liu, Gang,Jiang, Biao. "Preparing functional bis(indole) pyrazine by stepwise cross-coupling reactions: An efficient method to construct the skeleton of dragmacidin D". . p. 9392 - 9396. Retrieved 2007/10/03.