401816-16-8

Basic information

• Product Name: 2,6-Difluoropyridine-4-boronic acid
• Synonyms: 2,6-DIFLUORO-4-PYRIDYLBORONIC ACID;(2,6-DIFLUOROPYRIDIN-4-YL)BORONIC ACID;2,6-DIFLUOROPYRIDINE-4-BORONIC ACID;Boronic acid, (2,6-difluoro-4-pyridinyl)- (9CI);B-(2,6-difluoro-4-pyridinyl)-Boronic acid;B-(2,6-Difluoro-pyridin-4-yl)boronic acid
• CAS NO: 401816-16-8
• Molecular Formula: C₅H₄BF₂NO₂
• Molecular Weight: 158.9
• Product Categories: HALIDE;BORONICACID;Boronic acid;Organoborons;Pyridine;Pyridines
• Mol File: 401816-16-8.mol
• Article Data: 2

Chemical Properties

• Boiling Point: 334 °C at 760 mmHg
• Flash Point: 155.8 °C
• Appearance: /
• Density: 1.44g/cm³
• Storage Temp.: Inert atmosphere,Store in freezer, under -20°C
• PKA: 5.46±0.11(Predicted)
• CAS DataBase Reference: 2,6-Difluoropyridine-4-boronic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 2,6-Difluoropyridine-4-boronic acid(401816-16-8)
• EPA Substance Registry System: 2,6-Difluoropyridine-4-boronic acid(401816-16-8)

Safety Data

• Hazard Codes: Xi
• Statements: 37/38-41
• Safety Statements: 26-39
• Hazardous Substances Data: 401816-16-8(Hazardous Substances Data)

Usage

General Description

2,6-Difluoropyridine-4-boronic acid is a chemical compound with the formula C5H4B F2NO2. It is a boronic acid derivative used in organic synthesis and medicinal chemistry. This chemical is a key building block in the construction of various bioactive molecules and pharmaceuticals. It is commonly used as a reagent in the Suzuki-Miyaura cross-coupling reaction to form carbon-carbon bonds. Additionally, 2,6-Difluoropyridine-4-boronic acid has potential applications in the development of new drugs and agrochemicals due to its versatile reactivity and functional group compatibility.

Upstream product

• 903513-58-6 4‐bromo‐2,6‐difluoropyridine 
• 5419-55-6 Triisopropyl borate 
• 685517-71-9 2,6-difluoro-4-iodopyridine 
• 121-43-7 Trimethyl borate 
• 108-18-9 diisopropylamine 

Downstream Products

• 1555700-88-3 4-(2,6-difluoropyridin-4-yl)-7-methoxy-3,3-dimethyl-1-(2-nitrophenyl)indoline 
• 1555700-90-7 2-(4-(2,6-difluoropyridin-4-yl)-7-methoxy-3,3-dimethylindolin-1-yl)aniline 
• 1555700-93-0 1-(2-(4-(2,6-difluoropyridin-4-yl)-7-methoxy-3,3-dimethylindolin-1-yl)phenyl)-3-(4-(trifluoromethoxy)phenyl)urea 
• 1555695-20-9 1-(2-(4-(2,6-difluoropyridin-4-yl)-7-hydroxy-3,3-dimethylindolin-1-yl)phenyl)-3-(4-(trifluoromethoxy)phenyl)urea trifluoroacetate 
• 1800398-38-2 N-(3-(2-(2-hydroxyethoxy)-6-morpholinopyridin-4-yl)-4-methylphenyl)-2-(trifluoromethyl)isonicotinamide 

Relevant articles and documents

Substituted pyridines

A class of 2,4-; 2,3,4-; 2,4,6-; 2,3,4,5,6-substituted pyridines is provided which include novel compounds. The substitutions are achieved according to methods disclosed herein in which a metallated pyridine is reacted with an electrophile. Suitable electrophiles include CO2, SO2, dialkylcarbonates, ureas, formamides, amides, carboxylic acid esters, mono- and dihaloalkyls, halogens such as chlorine, fluorine, bromine, and iodine, metallic salts, sulfones, sulfonyls, aldehydes, ketones, anhydrides, nitrites, and electrophilic boron compounds including, but not limited to, boron trialkoxides and boron trihalides. The subject invention more specifically discloses a process for the synthesis of 2,6-difluoropyridin-4-ylboronic acid which comprises: (1) reacting 2,4,6-trifluoropyridine with hydrazine monohydrate to produce 2,6-difluoro-4-hydrazinopyridine, (2) reacting the 2,6-difluoro-4-hydrazinopyridine with elemental bromine to produce 4-bromo-2,6-difluoropyridine, and (3) reacting the 4-bromo-2,6-difluoropyridine with an organolithium compound and a borate at a temperature of less than about 0° C. to produce the 2,6-difluoropyridin-4-ylboronic acid, wherein said process is conducted in an organic solvent.