1192037-87-8

Basic information

• Product Name: 5-Bromo-1-methyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1h-indole
• Synonyms: 5-Bromo-1-methyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1h-indole;5-Bromo-1-methylindole-2-boronic acid, pinacol ester
• CAS NO: 1192037-87-8
• Molecular Formula: C15H19BBrNO2
• Molecular Weight: 336.03186
• Mol File: 1192037-87-8.mol
• Article Data: 4

Chemical Properties

• Appearance: /
• Storage Temp.: Sealed in dry,Store in freezer, under -20°C
• CAS DataBase Reference: 5-Bromo-1-methyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1h-indole(CAS DataBase Reference)
• NIST Chemistry Reference: 5-Bromo-1-methyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1h-indole(1192037-87-8)
• EPA Substance Registry System: 5-Bromo-1-methyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1h-indole(1192037-87-8)

Safety Data

• Hazardous Substances Data: 1192037-87-8(Hazardous Substances Data)

Usage

Uses

5-Bromo-1-methylindole-2-boronic Acid, Pinacol Ester is used in iridium N-heterocyclic carbene-catalyzed carbon-hydrogen borylation of arenes by diisopropylaminoborane.

Upstream product

• 73183-34-3 bis(pinacol)diborane 
• 10075-52-2 5-bromo-1-methyl-H-indole 
• 25015-63-8 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane 
• 76-09-5 2,3-dimethyl-2,3-butane diol 
• 22092-92-8 diisopropopylaminoborane 

Relevant articles and documents

Boron(III)-Catalyzed C2-Selective C?H Borylation of Heteroarenes

A BF3?Et2O-catalyzed C2-selective C?H borylation of indoles with bis(pinacolato)diboron was developed to afford indole-2-boronic acid pinacol esters. A variety of functional groups were tolerated, and other heteroarenes like pyrrole and benzo[b]thiophene were also suitable substrates. An electrophilic substitution mechanism was proposed based on the preliminary mechanistic studies. This novel transformation utilizes simple and cheap BF3?Et2O as catalyst and exhibits unusual C2 regioselectivity, providing a significant non-transition-metal-catalyzed C?H borylation and an efficient method towards the synthesis of C2-functionalized heteroarenes.

Benzoic Acid-Promoted C2-H Borylation of Indoles with Pinacolborane

A benzoic acid-promoted C2-H borylation of indoles with pinacolborane to afford C2-borylated indoles is developed. Preliminary mechanistic studies indicate BH3-related borane species formed via the decomposition of pinacolborane to be the probable catalyst. This transformation provides a prompt route toward the synthesis of diverse C2-functionalized indoles.