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

Base Information

• Chemical Name: 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-(triisopropylsilyl)-1H-indole
• CAS No.: 690631-97-1
• Molecular Formula: C₂₃H₃₈BNO₂Si
• Molecular Weight: 399.457
• Hs Code.: 2933998090
• DSSTox Substance ID: DTXSID90383298
• Nikkaji Number: J2.334.419J
• Wikidata: Q82174966
• Mol file: 690631-97-1.mol

Synonyms:690631-97-1;5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-(triisopropylsilyl)-1H-indole;tri(propan-2-yl)-[5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)indol-1-yl]silane;SCHEMBL13394543;DTXSID90383298;MFCD05865113;AKOS025293747;AB22931;FT-0755320;1-(Triisopropylsilyl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolane-2-yl)-1H-indole;5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1-[tri(propan-2-yl)silyl]-1H-indole;5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-[tris(propan-2-yl)silyl]-1H-indole;5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-(triisopropylsilyl)-1H-indole, AldrichCPR

Chemical Property of 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-(triisopropylsilyl)-1H-indole

Chemical Property:

• Vapor Pressure: 1.01E-07mmHg at 25°C
• Melting Point: 107 °C
• Refractive Index: 1.505
• Boiling Point: 433.7°C at 760 mmHg
• Flash Point: 216.1°C
• PSA: 23.39000
• Density: 0.98g/cm³
• LogP: 5.96410
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 5
• Exact Mass: 399.2764862
• Heavy Atom Count: 28
• Complexity: 525

Purity/Quality:

98%min ^*data from raw suppliers

5-[4- ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: B1(OC(C(O1)(C)C)(C)C)C2=CC3=C(C=C2)N(C=C3)[Si](C(C)C)(C(C)C)C(C)C

Technology Process of 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-(triisopropylsilyl)-1H-indole

There total 4 articles about 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-(triisopropylsilyl)-1H-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: 99.0%

triisopropylsilyl chloride (13154-24-0) + 5-(4,4,5,5,-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole (269410-24-4) → 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-[tris(1-methylethyl)silyl]-1H-indole (690631-97-1)

Guidance literature:

With lithium hexamethyldisilazane; In tetrahydrofuran; at -78 - 0 ℃; for 1.16667h;

DOI:10.1002/cmdc.201800067

Reference yield: 82.0%

5-bromo-1-triisopropylsilyl-1H-indole (128564-66-9) + 4,4,5,5-tetramethyl-1,3,2-dioxaborolane → 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-[tris(1-methylethyl)silyl]-1H-indole (690631-97-1) + 1-(triisopropylsilyl)-1H-indole (123191-00-4)

Guidance literature:

With triethylamine; palladium diacetate; CyJohnPhos; In 1,4-dioxane; at 80 ℃; for 2h;

DOI:10.1002/hlca.200690097

Reference yield: 82.0%

5-bromo-1-triisopropylsilyl-1H-indole (128564-66-9) + 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane (25015-63-8) → 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-[tris(1-methylethyl)silyl]-1H-indole (690631-97-1)

Guidance literature:

With palladium diacetate; triethylamine; In 1,4-dioxane; byproducts: 1-[tris(1-methylethyl)silyl]-1H-indole; under Ar atm.; Schlenk flask charged with Pd(CH3COO)2 and P(C6H11)2(C6H4C6H5); evapd.; filled (Ar); 1,4-dioxane added; stirred for 30 min at room temp.; Et3N added; soln. of bromoindole in dioxane added; neat pinacolborane added; stirred at 80°C; cooled to room temp.; Celite and activated charcoal added; stirred for 15 min; filtered; solvent removed (vac.); residue diluted (cyclohexane); filtered through a short pad of neutral alumina; purified by column chromy (SiO2, hexane as eluent);

DOI:10.1002/hlca.200690097

upstream raw materials:

5-bromo-1-triisopropylsilyl-1H-indole

4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane

triisopropylsilyl chloride

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