156545-07-2

Basic information

• Product Name: 3,5-Difluorophenylboronic acid
• Synonyms: 3,5-DIFLUOROBENZENEBORONIC ACID;3,5-DIFLUOROPHENYLBORONIC ACID;AKOS BRN-0091;RARECHEM AH PB 0167;Boronic acid, (3,5-difluorophenyl)- (9CI);3,5-Difluorobenzeneboronic acid 98%;3,5-Difluorobenzeneboronicacid98%;3,5-DIFLUOROPHENYLBORONIC ACID 98%
• CAS NO: 156545-07-2
• Molecular Formula: C₆H₅BF₂O₂
• Molecular Weight: 157.91
• EINECS: 1312995-182-4
• Product Categories: Fluorin-contained phenyl boronic acid series;HALIDE;blocks;BoronicAcids;FluoroCompounds;Substituted Boronic Acids;Boronic Acid;Aryl;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;Organometallic Reagents;Liquid crystal intermediates
• Mol File: 156545-07-2.mol

Chemical Properties

• Melting Point: 210-217 °C(lit.)
• Boiling Point: 266.9 °C at 760 mmHg
• Flash Point: 115.2 °C
• Appearance: White to beige-yellowish powder
• Density: 1.35 g/cm³
• Vapor Pressure: 1.04E-07mmHg at 25°C
• Refractive Index: 1.562
• Storage Temp.: 0-6°C
• PKA: 6.46±0.10(Predicted)
• BRN: 6800882
• CAS DataBase Reference: 3,5-Difluorophenylboronic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 3,5-Difluorophenylboronic acid(156545-07-2)
• EPA Substance Registry System: 3,5-Difluorophenylboronic acid(156545-07-2)

Safety Data

• Hazard Codes: Xi,Xn,F
• Statements: 36/37/38-20-19-11-22
• Safety Statements: 26-36-33-16-37/39
• WGK Germany: 3
• HazardClass: IRRITANT
• Hazardous Substances Data: 156545-07-2(Hazardous Substances Data)

Usage

Uses

1. Used in Pharmaceutical Synthesis:
3,5-DifluoroPhenylboronic acid is used as a reactant for the synthesis of honokiol analogs, which are known as angiogenesis inhibitors. These analogs have potential applications in the treatment of various diseases, including cancer, by inhibiting the formation of new blood vessels that supply tumors with nutrients.
2. Used in Homo-coupling Reactions:
In this application, 3,5-DifluoroPhenylboronic acid serves as a reactant in homo-coupling reactions, which involve the formation of a bond between two identical molecules. This process is essential in the synthesis of various organic compounds and materials.
3. Used in Suzuki-Miyaura Cross-coupling Reactions:
3,5-DifluoroPhenylboronic acid is used as a reactant in Suzuki-Miyaura cross-coupling reactions, a widely used method for the formation of carbon-carbon bonds in organic chemistry. This reaction is crucial in the synthesis of complex organic molecules, including pharmaceuticals and natural products.
4. Used in Enantioselective Borane Reduction:
3,5-DifluoroPhenylboronic acid is used as a reactant in the enantioselective borane reduction of trifluoroacetophenone. This reaction is essential in the synthesis of chiral compounds, which have different spatial arrangements of atoms and are crucial in the development of pharmaceuticals with specific biological activities.
5. Used in the Synthesis of N-thiazol-2-yl-benzamides:
3,5-DifluoroPhenylboronic acid is used as a reactant in the synthesis of N-thiazol-2-yl-benzamides, which are glucokinase (GK) activators. These compounds have potential applications in the treatment of type 2 diabetes mellitus (T2DM) by regulating glucose metabolism and improving insulin sensitivity.
6. Used in the Production of Liquid Crystals:
3,5-DifluoroPhenylboronic acid is used as an intermediate in the production of liquid crystals, which are essential components in the manufacturing of display devices, such as televisions, computer monitors, and smartphones.

InChI:InChI=1/C13H11BF2O3/c15-12-10(14(17)18)6-7-11(13(12)16)19-8-9-4-2-1-3-5-9/h1-7,17-18H,8H2

Upstream product

• 461-96-1 3,5-difluorobromobenzene 
• 121-43-7 Trimethyl borate 
• 5419-55-6 Triisopropyl borate 
• 1435-43-4 1-chloro-3,5-difluorobenzene 
• 11113-50-1 boric acid 

Downstream Products

• 137528-87-1 3,5-difluoro-4'-propylbiphenyl 
• 62351-48-8 3,5-difluorobiphenyl 
• 221018-03-7 3',5'‐difluoro‐[1,1'‐biphenyl]‐4‐carbaldehyde 
• 212126-32-4 2-(3,5-difluorophenyl)-3-(4-(methylsulfonyl)phenyl)-2-cyclopenten-1-one 
• 328081-58-9 N-(3,5-difluorophenyl)-phenoxyphtalimide 
• 672958-47-3 (2,6-difluoro-phenyl)-[2-(3,5-difluoro-phenyl)-9-methyl-9H-purin-6-yl]-amine 
• 588731-38-8 3',5'-difluoro-6-methyl-biphenyl-3-carbonitrile 
• 330935-77-8 6-(3,5-difluoro-phenyl)-8-isopropyl-4-methyl-chromen-2-one 
• 1027204-95-0 5-(3,5-difluoro-phenyl)-6-(4-methylsulfanyl-phenyl)-benzo[1,3]dioxole 
• 705250-75-5 trans-3,5-difluorocinnamic acid methyl ester 
• 599202-21-8 2-(3-nitro-4-methoxyphenyl)-5-(3,5-difluorophenyl)benzoxazole 
• 599204-14-5 2-(3-nitro-6-methoxyphenyl)-5-(3,5-difluorophenyl)benzoxazole 
• 599204-47-4 2-(3-nitro-6-propylaminophenyl)-5-(3,5-difluorophenyl)benzoxazole 

Relevant articles and documents

Meso-substituted boron-dipyrromethene compounds: synthesis, tunable solid-state emission, and application in blue-driven LEDs

In this work, we depict the synthesis and characterization of a series of meso-substituted boron-dipyrromethene (BODIPY) compounds. Their optical and electrochemical properties were investigated systematically. All these compounds exhibited intense absorption bands in the ultraviolet (UV) and visible regions, which arise from the π–π* transitions based on their BODIPY core segments. By comparing electron-withdrawing substituents and electron-donating substituents, we found that these compounds exhibited some similar photophysical properties but exhibited different fluorescence in the solid state. All compounds were highly emissive in dichloromethane at room temperature (λem = 512–523 nm, ΦPL > 0.9). When these compounds were applied in blue-driven light-emitting diodes (LEDs) as light-emitting materials, the devices showed luminescence efficiency ranging from 1.09 to 34.13 lm/W. Their luminescence and electrochemical properties could be used for understanding the structure–property relationship of BODIPY compounds and developing functional fluorescent materials.

Preparation method of 3, 5-difluorophenol

The invention provides a 3, 5-difluorophenol preparation method, which comprises the steps of S1, dissolving 3, 5-difluorobromobenzene in an organic solvent under inert gas protection, adding a bromine pulling agent to carry out a bromine pulling reaction, adding boric acid, filtering, and drying under reduced pressure to obtain 3, 5-difluorophenylboronic acid, and S2, dissolving the 3, 5-difluorophenylboronic acid, and adding an oxidizing agent and a catalyst to obtain the 3, 5-difluorophenol. The 3, 5-difluorophenol preparation method provided by the invention has the advantages of short steps and high yield, and is suitable for industrial production.

COMPOUND HAVING 2-FLUOROPHENYLOXYMETHANE STRUCTURE

The present invention relates to a compound having a 2-fluorophenyloxymethane structure and useful for organic electronic materials and medical and agricultural chemicals, particularly materials for liquid crystal display elements. A problem to be solved

Scope of the palladium-catalyzed aryl borylation utilizing bis-boronic acid

The Suzuki-Miyaura reaction has become one of the more useful tools for synthetic organic chemists. Until recently, there did not exist a direct way to make the most important component in the coupling reaction, namely the boronic acid. Current methods to make boronic acids often employ harsh or wasteful reagents to prepare boronic acid derivatives and require additional steps to afford the desired boronic acid. The scope of the previously reported palladium-catalyzed, direct boronic acid synthesis is unveiled, which includes a wide array of synthetically useful aryl electrophiles. It makes use of the newly available second generation Buchwald XPhos preformed palladium catalyst and bis-boronic acid. For ease of isolation and to preserve the often sensitive C-B bond, all boronic acids were readily converted to their more stable trifluoroborate counterparts.

LIQUID CRYSTALLINE COMPOUND, LIQUID CRYSTAL COMPOSITION, LIQUID CRYSTAL DISPLAY ELEMENT

The invention provides a liquid crystal compound which has stability to heat, light and so forth, shows liquid crystal phases in a wide temperature range, and has a small viscosity, an appropriate optical anisotropy, a large dielectric anisotropy, and an

Antipsychotic cyclic N-aralkylamines

The invention relates to benzene derivatives, to pharmaceutical compositions containing them, to processes for preparing them, and to the method of use thereof in the treatment of psychotic disorders.

(Fluoroorgano)fluoroboranes and -fluoroborates I: Synthesis and spectroscopic characterization of potassium fluoroaryltrifluoroborates and fluoroaryldifluoroboranes

A convenient preparation of K[ArBF3] (Ar=2-C6H4F, 3-C6H4F, 4-C6H4F, 2,6-C6H3F2, 3,5-C6H3F2, 2,4,6-C6H2F3, 3,4,5-C6H2F3, 2,3,4,5-C6HF4 and C6F5) is offered and the IR and multinuclear NMR spectra of these salts are reported. Treatment of the trifluoroborate salts with BF3 in chlorocarbon solvents provides an easy synthetic route to the corresponding aryldifluoroboranes ArBF2. The multinuclear NMR spectra of ArBF2 are presented. The electron substituent effect of the [-BF3]--group shows this substituent as one of the strongest σ-electron donors, while its π-electron influence is negligible (σI=-0.32, σR=-0.07).

Efficient syntheses of 2-(3',5'-difluorophenyl)-3-(4'- methylsulfonylphenyl)-cyclopent-2-enone, a potent COX-2 inhibitor

2-(3',5'-Difluorophenyl)-3-(4'-methylsulfonylphenyl)cyclopent-2-enone (1) displays high selectivity and potency against COX-2. Three efficient syntheses of this diarylcyclopentenone are described. The first approach employs a Suzuki coupling reaction as the key step while the second synthesis features an intramolecular Friedel-Crafts acylation. The third, and preferred route to this compound involves a sequential malonate alkylation and acylation and ring-closure sequence.

2-(3,5-difluorophenyl)-3-(4-(methyl-sulfonyl)phenyl)-2-cyclopenten-1-one useful as an inhibitor of cyclooxygenase-2

The invention encompasses the novel compound A, 2-(3,5-difluorophenyl)-3-(4-(methylsulfonyl)phenyl)-2-cyclopenten-1-one, pharmaceutical compositions and use of the compound in the preparation of medicaments for the treatment of cyclooxygenase-2 mediated diseases.

Insecticidal 5-substituted-2,4-diaminopyrimidine derivatives

An insecticidal composition comprising, in admixture with an agriculturally acceptable carrier, an insecticidally effective amount of a compound of the formula: STR1 wherein R, R1, R2, R3, R7, R8, m, n, and p are as defined herein, and agriculturally acceptable salts thereof, and methods of using the same.