476004-81-6

Basic information

• Product Name: 2-(Pinacolateboryl)indole
• Synonyms: 2-Indoleboronic acid pinacol ester;Indole-2-boronic acid pinacol ester 95%;2-(((1H-indol-2-yl)boryl)oxy)-3-hydroxy-2,3-dimethylbutanoate;2-PINACOLATEBORYL INDOLE;2-((1H-Indol-2-yl)boryloxy)-3-hydroxy-2,3-dimethylbutanoic acid;2-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole;1H-Indole-2-boronic acid pinacol ester;Indole-2-boronic acid pinacol ester
• CAS NO: 476004-81-6
• Molecular Formula: C₁₄H₁₈BNO₂
• Molecular Weight: 243.11
• Product Categories: Indoles
• Mol File: 476004-81-6.mol
• Article Data: 1

Chemical Properties

• Melting Point: 84-85 °C
• Boiling Point: 396 °C
• Flash Point: 193 °C
• Appearance: /
• Density: 1.11
• Storage Temp.: Refrigerated.
• PKA: 16.76±0.30(Predicted)
• CAS DataBase Reference: 2-(Pinacolateboryl)indole(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(Pinacolateboryl)indole(476004-81-6)
• EPA Substance Registry System: 2-(Pinacolateboryl)indole(476004-81-6)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 476004-81-6(Hazardous Substances Data)

Usage

General Description

2-(Pinacolateboryl)indole is a chemical compound that consists of a boron-containing molecule attached to an indole ring. It is commonly used as a building block in organic synthesis for the formation of carbon-carbon bonds, particularly in the production of pharmaceuticals and other biologically active compounds. The pinacol boronate group is a versatile and stable functional group that can be easily manipulated and transformed into a variety of different chemical structures, making 2-(Pinacolateboryl)indole a valuable tool in the field of organic chemistry. Its reactivity and flexibility make it a widely utilized compound in the development of new and innovative chemical reactions and processes.

Upstream product

• 120-72-9 indole 
• 73183-34-3 bis(pinacol)diborane 
• 25015-63-8 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane 
• 71-43-2 benzene 

Downstream Products

• 55968-16-6 2-(2-thienyl)indole 

Relevant articles and documents

Iridium-catalyzed, silyl-directed borylation of nitrogen-containing heterocycles

Chemical Figure Presented Selective methods for the functionalization of indoles and other nitrogen heterocycles would provide access to the core structures of many natural products and pharmaceuticals. Although there are many methods and strategies for the synthesis of substituted indoles or functionalization of the azole ring, strategies for the selective functionalization of the benzo-fused portion of the indole skeleton, particularly the 7-position, are less common. We report a one-pot, iridium-catalyzed, silyl-directed C-H borylation of indoles at the 7-position. This process occurs in high yield with a variety of substituted indoles, and conversions of the 7-borylindole products to 7-aryl-, 7-cinnamyl-, and 7-haloindoles are demonstrated. The lr-catalyzed, silyl-directed C-H borylation also occurs with several other nitrogen heterocycles, including carbazole, phenothiazines, and tetrahydroquinoline. The utility of this methodology is highlighted by the one-pot synthesis of a member of the pyrrolophenanthrldone class of alkaloid natural products. Copyright