2-METHYL-7-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)-1H-INDOLE

Base Information

• Chemical Name: 2-METHYL-7-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)-1H-INDOLE
• CAS No.: 919119-59-8
• Molecular Formula: C15H20BNO2
• Molecular Weight: 257.13600
• Mol file: 919119-59-8.mol

Synonyms:2-methyl-7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-indole;1H-Indole,2-methyl-7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl);2-METHYL-1H-INDOL-7-YLBORONIC ACID PINACOL ESTER;

Chemical Property of 2-METHYL-7-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)-1H-INDOLE

Chemical Property:

• PSA: 34.25000
• LogP: 2.77550

Purity/Quality:

97% ^*data from raw suppliers

2-Methyl-7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole 98% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 2-METHYL-7-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)-1H-INDOLE

There total 3 articles about 2-METHYL-7-(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: 83.0%

2-methyl-1H-indole (95-20-5) + bis(pinacol)diborane (73183-34-3) + 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane (25015-63-8) → 2-methyl-7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole (919119-59-8)

Guidance literature:

With Co⁽⁰⁾ coordinated to phosphine of porous metal organic framework formed by Zr(IV)-(tris[1,1'-biphenyl]phosphine); In n-heptane; at 110 ℃; for 48h; Inert atmosphere; Schlenk technique; Glovebox;

DOI:10.1002/ejic.202101019

Reference yield: 78.0%

2-methyl-1H-indole (95-20-5) + 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane (25015-63-8) → 2-methyl-7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole (919119-59-8)

Guidance literature:

With (1,5-cyclooctadiene)(methoxy)iridium(I) dimer; d^tbpy; In hexane; at 60 ℃; for 4h;

DOI:10.1021/ja0631652

Reference yield: 67.0%

2-methyl-1H-indole (95-20-5) + bis(pinacol)diborane (73183-34-3) → 2-methyl-7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole (919119-59-8)

Guidance literature:

With (1,5-cyclooctadiene)(methoxy)iridium(I) dimer; 4,4'-di-tert-butyl-2,2'-bipyridine; In tetrahydrofuran; at 60 ℃; for 4h; Inert atmosphere; Sealed tube;

DOI:10.1039/c9cc09807k

upstream raw materials:

2-methyl-1H-indole

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

bis(pinacol)diborane

Downstream raw materials:

2-methylindol-7-ol

Refernces

• 1、 Anderson, Kirsty,Eastabrook, Andrew S.,Sperry, Jonathan. "One-pot oxidative hydrolysis-oxidative cleavage of 7-borylindoles enables access to: O -amidophenols and 4-acylbenzoxazoles". supporting information. p. 3559 - 3562. Retrieved 2020/04/09.
• 2、 Wang, Guanghui,Xu, Liang,Li, Pengfei. "Double N,B-Type Bidentate Boryl Ligands Enabling a Highly Active Iridium Catalyst for C-H Borylation". supporting information. p. 8058 - 8061. Retrieved 2015/07/15.