162101-25-9

Basic information

• Product Name: 2,6-Difluorophenylboronic acid
• Synonyms: 2,6-Difluorophenylboronic acid 98%;2,6-DIFLUOROPHENYLBORONIC ACID;2,6-DIFLUOROBENZENEBORONIC ACID;Boronic acid, (2,6-difluorophenyl)- (9CI);2,6-Difluorophenylboronic;2,6-Difluorobenzeneboronic acid 98%;2,6-Difluorobenzeneboronicacid98%;2,6-Difluoropenylboronic acid
• CAS NO: 162101-25-9
• Molecular Formula: C₆H₅BF₂O₂
• Molecular Weight: 157.91
• EINECS: -0
• Product Categories: Organometallic Reagents;Boronate Ester;Potassium Trifluoroborate;Pyridines;HALIDE;blocks;BoronicAcids;FluoroCompounds;Substituted Boronic Acids;Fluorobenzene;Boronic Acid;Aryl;Halogenated;Organoborons;B (Classes of Boron Compounds);Boronic Acids;Boronic Acids;Boronic Acids and Derivatives;Aryl Boronic Acids;Boronic Acids and Derivatives;Chemical Synthesis;Disubstituted Aryl Boronic Acids
• Mol File: 162101-25-9.mol
• Article Data: 8

Chemical Properties

• Melting Point: 147-149 °C(lit.)
• Boiling Point: 260.1 °C at 760 mmHg
• Flash Point: 111.1 °C
• Appearance: /solid
• Density: 1.35 g/cm³
• Vapor Pressure: 0.297mmHg at 25°C
• Refractive Index: 1.51
• Storage Temp.: 0-6°C
• Solubility: Soluble in methanol.
• PKA: 8.12±0.58(Predicted)
• BRN: 8545931
• CAS DataBase Reference: 2,6-Difluorophenylboronic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 2,6-Difluorophenylboronic acid(162101-25-9)
• EPA Substance Registry System: 2,6-Difluorophenylboronic acid(162101-25-9)

Safety Data

• Hazard Codes: Xi,Xn
• Statements: 36/37/38-22
• Safety Statements: 26-36-37/39
• WGK Germany: 3
• HazardClass: IRRITANT
• Hazardous Substances Data: 162101-25-9(Hazardous Substances Data)

Usage

Description

2,6-Difluorophenylboronic acid is a white to off-white crystalline powder that serves as a versatile chemical intermediate and reagent in the field of organic synthesis. It is characterized by the presence of two fluorine atoms at the 2nd and 6th positions of the phenyl ring, which imparts unique chemical properties to the molecule.

Uses

Used in Suzuki Reaction:
2,6-Difluorophenylboronic acid is used as a substrate in the model reaction of Suzuki–Miyaura coupling with 4-chloro-3-methylanisole. This reaction is a widely employed method for the formation of carbon-carbon bonds, particularly in the synthesis of complex organic molecules.
Used in Organic Semiconductors:
2,6-Difluorophenylboronic acid is used as a starting material to prepare 4-bromo-2,3′,5′,6-tetrafluorobiphenyl, a key intermediate for the synthesis of 2,6-difluorinated oligophenyls. These oligophenyls are applicable in the development of organic semiconductors, which are essential components in various electronic devices such as solar cells, light-emitting diodes (LEDs), and field-effect transistors (FETs).
Used in Pharmaceutical Industry:
2,6-Difluorophenylboronic acid is used as a key intermediate for the synthesis of ethyl 4-(2,6-difluorophenyl)nicotinate, which is a key intermediate for the synthesis of 4-phenyl pyridine based potent TGR5 agonists. TGR5 agonists have potential therapeutic applications in the treatment of various metabolic disorders, including obesity, type 2 diabetes, and non-alcoholic fatty liver disease.
Used in Intermediates of Liquid Crystals:
2,6-Difluorophenylboronic acid is also utilized in the synthesis of intermediates for liquid crystals, which are widely used in display technologies such as liquid crystal displays (LCDs) found in televisions, computer monitors, and smartphones. The unique properties of 2,6-difluorophenylboronic acid make it an essential component in the development of advanced liquid crystal materials with improved performance characteristics.

InChI:InChI=1/C8H9FO/c1-6(10)7-4-2-3-5-8(7)9/h2-6,10H,1H3

Upstream product

• 64248-56-2 1-bromo-2,6-difluorobenzene 
• 372-18-9 1,3-Difluorobenzene 
• 121-43-7 Trimethyl borate 
• 7732-18-5 water 
• 1338809-69-0 2,6-difluorophenylboronic acid catechol ester 
• 1239569-27-7 2-(2,6-difluorophenyl)-5,5-dimethyl-1,3,2-dioxaborinane 
• 863868-37-5 2-(2,6-difluorophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 

Downstream Products

• 28177-48-2 2,6-difluorophenol 
• 100325-47-1 4-(2,6-difluorophenyl)pyridine 
• 929194-29-6 7-(2,6-difluoro-phenyl)-5-methyl-benzo[1,2,4]triazin-3-ylamine 
• 684287-35-2 9-benzhydryloxy-5-(2,6-difluoro-phenyl)-7-(4-fluoro-benzyl)-6,7-dihydro-pyrrolo[3,4-g]quinolin-8-one 
• 852121-85-8 (+/-)-{[7-(2,6-difluorophenyl)-5-fluoro-2,3-dihydro-1-benzofuran-2-yl]methyl}amine 
• 505082-79-1 2',6'-difluorobiphenyl-4-carboxylic acid 
• 255050-58-9 4-(2-thiomethyl-6-fluorophenyl)pyridine 
• 255050-60-3 4-(2-methylsulfinyl-6-fluorophenyl)piperidine 
• 104197-13-9 4-bromo-2,6-difluorophenol 
• 464206-35-7 (2,6-difluoro-4-bromophenol) 4-fluorobenzoate 
• 464206-37-9 (2,6-difluoro-4-bromophenol) 3,4-difluorobenzoate 
• 464206-39-1 (2,6-difluoro-4-bromophenol) 3,4,5-trifluorobenzoate 

Relevant articles and documents

Protodeboronation of (Hetero)Arylboronic Esters: Direct versus Prehydrolytic Pathways and Self-/Auto-Catalysis

The kinetics and mechanism of the base-catalyzed hydrolysis (ArB(OR)2→ ArB(OH)2) and protodeboronation (ArB(OR)2→ ArH) of a series of boronic esters, encompassing eight different polyols and 10 polyfluoroaryl and heteroaryl moieties, have been investigated by in situ and stopped-flow NMR spectroscopy (19F,1H, and11B), pH-rate dependence, isotope entrainment,2H KIEs, and KS-DFT computations. The study reveals the phenomenological stability of boronic esters under basic aqueous-organic conditions to be highly nuanced. In contrast to common assumption, esterification does not necessarily impart greater stability compared to the corresponding boronic acid. Moreover, hydrolysis of the ester to the boronic acid can be a dominant component of the overall protodeboronation process, augmented by self-, auto-, and oxidative (phenolic) catalysis when the pH is close to the pKaof the boronic acid/ester.

1-cyclopropyl-4-oxo-7-fluoro-8-methoxy -1,4-dihydro-quinoline-3-carboxylic acid synthesizing method

The invention discloses a synthesis method of 1-cyclopropyl-4-oxo-7-fluoro-8-methoxy-1,4-dihydroquinolyl-3-carboxylic acid. The synthesis method comprises the following reaction steps: reacting m-difluorophenyl with an organolithium reagent, reacting an obtained aryllithium intermediate with borate, quenching to obtain 2,6-difluorophenylboronic acid and 2,6-difluorophenylborate, reacting 2,6-difluorophenol obtained through oxidation with a methylating reagent, reacting the obtained 2,6-difluorophenylmethyl ether with the organolithium reagent, reacting the obtained corresponding aryllithium intermediate with carbon dioxide, reacting the obtained product with an acylchlorinating reagent to obtain 2,4-difluoro-3-methoxy benzoyl chloride, and performing cyclization, hydrolysis and the like to obtain the 1-cyclopropyl-4-oxo-7-fluoro-8-methoxy-1,4-dihydroquinolyl-3-carboxylic acid. The synthesis method has the advantages as follows: raw materials are easy to obtain; the yield in each step is high; the atom economy is high; the synthesis method is suitable for industrial application.

Polyfluoroorganoboron-oxygen compounds. 1: Polyfluorinated aryl(dihydroxy)boranes and tri(aryl)boroxins

A general preparative procedure for polyfluorinated aryl(dihydroxy)boranes C6H5-nFnB(OH)2 (n = 3 - 5) is described. Polyfluorinated aryl(dihydroxy)boranes are easily dehydrated to the corresponding tri(aryl)boroxins (C6H5-nFnBO)3 by thermal or chemical treatment. The property of the acids C6H5-nFnB(OH)2 to condensate depends on the number and on the position of the fluorine atoms in the aryl group. Examples of both classes of boron compounds were isolated as pure individuals and characterized by multinuclear NMR spectroscopy.