1218790-39-6

Basic information

• Product Name: 5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-2-(trifluoromethyl)pyridine
• Synonyms: 2-Trifluoromethylpyridine-5-boronic acid pinacol ester;Pyridine, 2-(trifluoroMethyl)-5-(4,4,5,5-tetraMethyl-1,3,2-dioxaborolan-2-yl)-;2-(trifluoroMethyl)-5-(4,4,5,5-tetraMethyl-1,3,2-dioxaborolan-2-yl)pyridine;(6-(TRIFLUOROMETHYL)PYRIDIN-3-YL)BORONIC ACID PINACOL ESTER
• CAS NO: 1218790-39-6
• Molecular Formula: C₁₂H₁₅BF₃NO₂
• Molecular Weight: 273.0592096
• Mol File: 1218790-39-6.mol
• Article Data: 6

Chemical Properties

• Appearance: /
• Density: 1.18
• Storage Temp.: Refrigerated.
• CAS DataBase Reference: 5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-2-(trifluoromethyl)pyridine(CAS DataBase Reference)
• NIST Chemistry Reference: 5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-2-(trifluoromethyl)pyridine(1218790-39-6)
• EPA Substance Registry System: 5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-2-(trifluoromethyl)pyridine(1218790-39-6)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 1218790-39-6(Hazardous Substances Data)

Usage

General Description

5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-2-(trifluoromethyl)pyridine is a chemical compound that contains a pyridine ring with a trifluoromethyl group and a boron-containing heterocycle. It is commonly used as a reagent in organic synthesis, particularly in the formation of carbon-carbon bonds and for the introduction of the trifluoromethyl group into organic molecules. The boron atom in the compound makes it useful for Suzuki-Miyaura coupling reactions, a widely used method for the synthesis of biaryls and other organic compounds. Its unique structure and reactivity make it an important tool for the development of new pharmaceuticals, agrochemicals, and materials.

InChI:InChI=1S/C12H15BF3NO2/c1-10(2)11(3,4)19-13(18-10)8-5-6-9(17-7-8)12(14,15)16/h5-7H,1-4H3

Upstream product

• 61676-62-8 2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 436799-32-5 5-bromo-2(trifluoromethyl)pyridine 
• 368-48-9 2-(trifluoromethyl)pyridine 
• 73183-34-3 bis(pinacol)diborane 

Downstream Products

• 1450666-86-0 (4-(5-amino-6-(6-(trifluoromethyl)pyridin-3-yl)pyrazin-2-yl)phenyl)(4-methyl-1,4-diazepan-1-yl)methanone 
• 1590398-10-9 3-fluoro-5-(6-trifluoromethyl-pyridin-3-yl)benzylamine 
• 1590397-44-6 2-[(4-fluorobenzenesulfonyl)(isopropyl)amino]-N-[3-fluoro-5-(6-trifluoromethylpyridin-3-yl)benzyl]acetamide 
• 1450666-98-4 (4-(5-amino-6-(6-(trifluoromethyl)pyridin-3-yl)pyrazin-2-yl)phenyl)(4-(tertbutyl)piperazin-1-yl)methanone 
• 1450667-04-5 (4-(5-amino-6-(6-(trifluoromethyl)pyridin-3-yl)pyrazin-2-yl)phenyl)(3-hydroxypyrrolidin-1-yl)methanone 
• 1450667-02-3 (4-(5-amino-6-(6-(trifluoromethyl)pyridin-3-yl)pyrazin-2-yl)phenyl)(3-aminopyrrolidin-1-yl)methanone 
• 1450667-05-6 (4-(5-amino-6-(6-(trifluoromethyl)pyridin-3-yl)pyrazin-2-yl)phenyl)(4-aminopiperidin-1-yl)methanone 
• 1450666-96-2 (4-(5-amino-6-(6-(trifluoromethyl)pyridin-3-yl)pyrazin-2-yl)phenyl)(4-hydroxypiperidin-1-yl)methanone 
• 1450666-76-8 (4-(5-amino-6-(6-(trifluoromethyl)pyridin-3-yl)pyrazin-2-yl)phenyl)(4-methylpiperazin-1-yl)methanone 
• 1450666-82-6 C₂₆H₂₇F₃N₆O₃ 
• 1214370-35-0 5-phenyl-2-(trifluoromethyl)pyridine 

Relevant articles and documents

Anthracene-containing dimer skeleton ligand and preparation method thereof, and application in metal catalytic reaction

The invention provides an anthracene dimer derivative phosphine-containing ligand as shown in the following formula I, wherein the anthracene dimer derivative phosphine-containing ligand can be used for a series of transition metal catalyzed coupling reac

A Monophosphine Ligand Derived from Anthracene Photodimer: Synthetic Applications for Palladium-Catalyzed Coupling Reactions

Herein, we present an air-stable dianthracenyl monophosphine ligand (diAnthPhos) which can be prepared in two steps from commercially available anthracene derivatives. The ligand exhibits excellent efficiency for palladium-catalyzed coupling reactions. In particular, Miyaura borylation of heterocycle-containing electrophiles can be facilitated employing the diAnthPhos ligand with a broad substrate scope and low catalyst loading. The valuable synthetic utility of the new ligand is further demonstrated by a one-pot Miyaura borylation/Suzuki coupling protocol for heteroaryl-containing substrates.

Iridium-catalyzed C-H borylation of pyridines

The iridium-catalysed C-H borylation is a valuable and attractive method for the preparation of aryl and heteroaryl boronates. However, application of this methodology for the preparation of pyridyl and related azinyl boronates can be challenged by low reactivity and propensity for rapid protodeborylation, particularly for a boronate ester ortho to the azinyl nitrogen. Competition experiments have revealed that the low reactivity is due to inhibition of the active catalyst through coordination of the azinyl nitrogen lone pair at the vacant site on the iridium. This effect can be overcome through the incorporation of a substituent at C-2. Moreover, when this is sufficiently electron-withdrawing protodeborylation is sufficiently slowed to permit isolation and purification of the C-6 boronate ester. Following functionalization, reduction of the directing C-2 substituent provides the product arising from formal ortho borylation of an unhindered pyridine ring. This journal is the Partner Organisations 2014.