(1-(tert-Butyldimethylsilyl)-1H-indol-5-yl)boronic acid

Base Information

• Chemical Name: (1-(tert-Butyldimethylsilyl)-1H-indol-5-yl)boronic acid
• CAS No.: 913835-68-4
• Molecular Formula: C₁₄H₂₂BNO₂Si
• Molecular Weight: 275.231
• Hs Code.: 2933990090
• European Community (EC) Number: 689-370-8
• DSSTox Substance ID: DTXSID10402531
• Wikidata: Q82205951
• Mol file: 913835-68-4.mol

Synonyms:913835-68-4;(1-(tert-Butyldimethylsilyl)-1H-indol-5-yl)boronic acid;1-(TERT-BUTYLDIMETHYLSILYL)-1H-INDOL-5-YLBORONIC ACID;1-TBDMS-indole-5-boronic acid;[1-[tert-butyl(dimethyl)silyl]indol-5-yl]boronic acid;[1-(tert-butyldimethylsilyl)-1H-indol-5-yl]boronic acid;1-(tert-Butyldimethylsilyl)-1H-indol-5-yl-5-boronic acid;1-TBDMS-5-indoleboronic acid;DTXSID10402531;MFCD03095156;AKOS015894148;BS-24819;1-(Tert-Butyldimethylsilyl)Indole-5-Boronic;CS-0175365;F87610;1-(tert-Butyldimethylsilyl)indole-5-boronic acid;J-503669;(1-(tert-Butyldimethylsilyl)-1H-indol-5-yl)boronicacid;{1-[tert-Butyl(dimethyl)silyl]-1H-indol-5-yl}boronic acid

Chemical Property of (1-(tert-Butyldimethylsilyl)-1H-indol-5-yl)boronic acid

Chemical Property:

• Vapor Pressure: 1.46E-05mmHg at 25°C
• Melting Point: 248-250°C
• Refractive Index: 1.51
• Boiling Point: 352.1 °C at 760 mmHg
• PKA: 8.98±0.30(Predicted)
• Flash Point: 166.7 °C
• PSA: 45.39000
• Density: 1.01g/cm³
• LogP: 2.17440
• Storage Temp.: Keep Cold
• 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%,99%, ^*data from raw suppliers

1-[(tert-Butyl)dimethylsilyl]-1H-indole-5-boronic acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: B(C1=CC2=C(C=C1)N(C=C2)[Si](C)(C)C(C)(C)C)(O)O
• Uses: [1-(tert-Butyldimethylsilyl)-1H-indol-5-yl]boronic Acid is used in preparation of 1H-Pyrazolo[3,4-d]pyrimidine, 7H-Pyrrolo[2,3-d]pyrimidine, and Pyrrolo[2,1-f][1,2,4]triazine derivatives which are selective Brk kinase inhibitors for prevention or treatment of cancers.

Technology Process of (1-(tert-Butyldimethylsilyl)-1H-indol-5-yl)boronic acid

There total 3 articles about (1-(tert-Butyldimethylsilyl)-1H-indol-5-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: 69.0%

Triisopropyl borate (5419-55-6) + 5-bromo-1-(tert-butyldimethylsilyl)-1H-indole (331432-91-8) → (1-(tert-butyldimethylsilyl)-1H-indol-5-yl)boronic acid (913835-68-4)

Guidance literature:

5-bromo-1-(tert-butyldimethylsilyl)-1H-indole; With n-butyllithium; In tetrahydrofuran; at -78 ℃; for 0.5h;

Triisopropyl borate; In tetrahydrofuran; at -78 - 20 ℃; for 3.75h;

DOI:10.1002/cmdc.202100283

Reference yield:

5-bromo-1H-indole (10075-50-0) → (1-(tert-butyldimethylsilyl)-1H-indol-5-yl)boronic acid (913835-68-4)

Guidance literature:

Multi-step reaction with 2 steps

1.1: sodium hydride / 0.25 h / 0 °C

1.2: 16 h / 0 - 20 °C

2.1: n-butyllithium / tetrahydrofuran / 0.5 h / -78 °C

2.2: 3.75 h / -78 - 20 °C

With n-butyllithium; sodium hydride; In tetrahydrofuran;

DOI:10.1002/cmdc.202100283

Reference yield:

tert-butyldimethylsilyl chloride (18162-48-6) → (1-(tert-butyldimethylsilyl)-1H-indol-5-yl)boronic acid (913835-68-4)

Guidance literature:

Multi-step reaction with 2 steps

1.1: sodium hydride / 0.25 h / 0 °C

1.2: 16 h / 0 - 20 °C

2.1: n-butyllithium / tetrahydrofuran / 0.5 h / -78 °C

2.2: 3.75 h / -78 - 20 °C

With n-butyllithium; sodium hydride; In tetrahydrofuran;

DOI:10.1002/cmdc.202100283

upstream raw materials:

Triisopropyl borate

5-bromo-1-(tert-butyldimethylsilyl)-1H-indole

5-bromo-1H-indole

tert-butyldimethylsilyl chloride

Refernces