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

Base Information

• Chemical Name: 5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole
• CAS No.: 269410-24-4
• Molecular Formula: C14H18 B N O2
• Molecular Weight: 243.113
• Hs Code.: 29349990
• European Community (EC) Number: 625-804-4
• DSSTox Substance ID: DTXSID40370496
• Nikkaji Number: J2.422.743J
• Wikidata: Q72482939
• Mol file: 269410-24-4.mol

Synonyms:269410-24-4;5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole;5-Indoleboronic acid pinacol ester;Indole-5-boronic acid pinacol ester;1H-Indole-5-boronic acid pinacol ester;5-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole;INDOLE-5-BORONIC ACID, PINACOL ESTER;MFCD03789263;1H-Indole, 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-;5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-indole;(1H-INDOL-5-YL)BORONIC ACID PINACOL ESTER;INDOLYL-5-BORONIC ACID PINACOL ESTER;5-Indolylboronic acid, pinacol ester;SCHEMBL9918;DTXSID40370496;FATPQDPUKVVCLT-UHFFFAOYSA-N;5-indole boronic acid pinacol ester;BCP10037;AKOS000283817;AM62764;GS-6535;PB14363;5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1h- indole (5-Indoleboronic acid pinacol ester);5-Indoleboronic acid pinacol ester, 97%;SY021939;A5278;CS-0041510;FT-0644223;FT-0687416;I0590;EN300-212557;J-016625;J-516197;Z1741960625;2-(1H-Indole-5-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane;5-(4,4,5,5,-tetramethyl-1,3,2-dioxaborolan-2-yl)-1h-indole;3-hydroxy-2,3-dimethylbutan-2-yl hydrogen 1H-indol-5-ylboronate

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

Chemical Property:

• Appearance/Colour: Pale yellow to brownish crystalline powder
• Vapor Pressure: 4.03E-06mmHg at 25°C
• Melting Point: 120-125 ºC
• Boiling Point: 396°Cat760mmHg
• PKA: 17.01±0.30(Predicted)
• Flash Point: 193.3°C
• PSA: 34.25000
• Density: 1.11g/cm³
• LogP: 2.46710
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• Water Solubility.: Insoluble
• 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:

98% ^*data from raw suppliers

Indole-5-boronicacid,pinacolester ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xi,Xn
• Statements: 36/37/38-22
• Safety Statements: 26-36-36/37/39

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: B1(OC(C(O1)(C)C)(C)C)C2=CC3=C(C=C2)NC=C3
• Uses: Indole-5-boronic acid, pinacol ester

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

There total 2 articles about 5-(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: 40.0%

5-chloro-1H-indole (17422-32-1) + bis(pinacol)diborane (73183-34-3) → indole (120-72-9) + 5-(4,4,5,5,-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole (269410-24-4)

Guidance literature:

With bis(1,3-dimesityl-1H-imidazol-2(3H)-ylidene)nickel⁽⁰⁾; potassium methanolate; In hexane; at 25 ℃; for 6h; Inert atmosphere; Irradiation;

DOI:10.1021/jacs.0c08834

Reference yield: 16.0%

2-bromoanisole (578-57-4) + 1,1-dimethylethyl 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole-1-carboxylate (777061-36-6) → 5-(4,4,5,5,-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole (269410-24-4) + tert-butyl 5-(2-methoxyphenyl)-1H-indole-1-carboxylate

Guidance literature:

With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium phosphate; In 1,4-dioxane; at 100 ℃; for 72h;

DOI:10.1021/jo0491612

Reference yield: 97.0%

methyldiphenylsilane (776-76-1) + 5-(4,4,5,5,-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole (269410-24-4) → 1-(methyldiphenylsilyl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole (1343516-72-2)

Guidance literature:

With pyridine; zinc trifluoromethanesulfonate; In propiononitrile; at 90 ℃; for 15h; Inert atmosphere;

DOI:10.1002/chem.201200651

upstream raw materials:

2-bromoanisole

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

5-chloro-1H-indole

bis(pinacol)diborane

Downstream raw materials:

3-(2-cyano-phenyl)-3-(1H-indol-5-yl)-propionic acid methyl ester

C₂₆H₁₉N₅O

methyl 3-amino-4-(1H-indol-5-yl)-5-phenylthiophene-2-carboxylate

3-(1H-indol-5-yl)-cyclohex-2-enone

Refernces

• 1、 Prieto, Monica,Zurita, Esther,Rosa, Esmeralda,Munoz, Lourdes,Lloyd-Williams, Paul,Giralt, Ernest. "Arylboronic acids and arylpinacolboronate esters in suzuki coupling reactions involving indoles. Partner role swapping and heterocycle protection". . p. 6812 - 6820. Retrieved 2007/10/03.