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

Base Information

• Chemical Name: 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole
• CAS No.: 388116-27-6
• Molecular Formula: C14H18BNO2
• Molecular Weight: 243.113
• Hs Code.: 2933990090
• European Community (EC) Number: 695-961-1
• DSSTox Substance ID: DTXSID20462343
• Nikkaji Number: J1.635.712J
• Wikidata: Q72482942
• Mol file: 388116-27-6.mol

Synonyms:388116-27-6;Indole-4-boronic acid pinacol ester;4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole;Indole-4-boronic acid, pinacol ester;4-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole;MFCD08689896;1H-Indole-4-boronic acid, pinacol ester;4-(4,4,5,5-tetramethyl(1,3,2]dioxaborolan-2-yl)-1H-indole;4-(4,4,5,5-tetramethyl[1,3,2]dioxaborolan-2-yl)-1H-indole;1H-INDOLE, 4-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)-;(1H-INDOL-4-YL)BORONIC ACID PINACOL ESTER;SCHEMBL476853;DTXSID20462343;QDCIXBBEUHMLDN-UHFFFAOYSA-N;Indol-4-boronic acid pinacol ester;4-indole boronic acid pinacol ester;RB2036;AKOS000283818;CS-W019752;PB34318;SY012840;Indole-4-boronic acid pinacol ester, 95%;AM20040345;FT-0684797;EN300-6480642;A824286;J-513434;Z2037316489;4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)1H-indole;4-(4,4,5,5tetramethyl[1,3,2]-dioxaborolan-2-yl)-1H-indole;4-(4,4,5 ,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-indole;4-(4,4,5,5,-tetramethyl-[1,3,2]dioxaborolane-2-yl)-1H-indole;4-(4,4,5,5-tetra-methyl-[1,3,2]dioxaborolan-2-yl)-1H-indole;4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl) 1H-indole;4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-indole;4-(4,4,5,5-tetramethyl[1,3,2]-dioxaborolan-2-yl)-1H-indole;4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole, AldrichCPR

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

Chemical Property:

• Vapor Pressure: 4.03E-06mmHg at 25°C
• Melting Point: 120-125 °C(lit.)
• Refractive Index: 1.562
• Boiling Point: 395.997 °C at 760 mmHg
• PKA: 16.83±0.30(Predicted)
• Flash Point: 193.292 °C
• PSA: 34.25000
• Density: 1.112 g/cm³
• LogP: 2.46710
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 243.1430590
• Heavy Atom Count: 18
• Complexity: 316

Purity/Quality:

99% ^*data from raw suppliers

Indole-4-boronic acid pinacol ester ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38-36
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: B1(OC(C(O1)(C)C)(C)C)C2=C3C=CNC3=CC=C2
• Uses: Indole-4-boronic acid, pinacol ester

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

There total 1 articles about 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-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: 66.0%

4-bromo-1H-indole (52488-36-5) + bis(pinacol)diborane (73183-34-3) → indole (120-72-9) + indole-4-boronic acid pinacol ester (388116-27-6)

Guidance literature:

With potassium acetate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In dichloromethane; dimethyl sulfoxide; at 80 ℃; for 22h;

Reference yield: 100.0%

6-(benzyloxy)-5-bromo-N-phenylpyridin-3-amine + indole-4-boronic acid pinacol ester (388116-27-6) → 6-(benzyloxy)-5-(1H-indol-4-yl)-N-phenylpyridin-3-amine

Guidance literature:

With bis-triphenylphosphine-palladium(II) chloride; sodium carbonate; In 1,4-dioxane; water; for 16h; Inert atmosphere; Reflux;

DOI:10.1016/j.ejmech.2019.111917

Reference yield: 99.0%

6-(benzyloxy)-5-bromo-N-(3-fluorophenyl)pyridin-3-amine + indole-4-boronic acid pinacol ester (388116-27-6) → 6-(benzyloxy)-N-(3-fluorophenyl)-5-(1H-indol-4-yl)pyridin-3-amine

Guidance literature:

With bis-triphenylphosphine-palladium(II) chloride; sodium carbonate; In 1,4-dioxane; water; for 16h; Inert atmosphere; Reflux;

DOI:10.1016/j.ejmech.2021.113748

upstream raw materials:

4-bromo-1H-indole

bis(pinacol)diborane

Downstream raw materials:

4-(3-fluoro-phenyl)-1H-indole

2-[3-(1H-Indol₄-yl)-phenoxy]-ethanol

[3-(1H-indol-4-yl)-phenyl]-acetic acid

4-(4-bromo-phenyl)-1H-indole

Refernces