168267-99-0

Basic information

• Product Name: 3-Fluoro-4-methylphenylboronic acid
• Synonyms: CHEMBRDG-BB 4003301;AKOS BRN-0218;3-FLUORO-4-METHYLBENZENEBORONIC ACID;3-FLUORO-4-METHYLPHENYLBORONIC ACID;3-FLUORO-P-TOLYLBORONIC ACID;3-Fluoro-4-methbenzene boronic acid;Boronic acid, (3-fluoro-4-methylphenyl)- (9CI);3-Fluoro-4-Methylphenylboronic
• CAS NO: 168267-99-0
• Molecular Formula: C₇H₈BFO₂
• Molecular Weight: 153.95
• Product Categories: HALIDE;blocks;BoronicAcids;FluoroCompounds;Aryl;Boronic acid;Organoborons;Boronic Acids;Boronic Acids and Derivatives;Boronic Acids;Aryl Boronic Acids;Boronic Acids and Derivatives;Chemical Synthesis;Disubstituted Aryl Boronic Acids;Organometallic Reagents
• Mol File: 168267-99-0.mol

Chemical Properties

• Melting Point: 232-237 °C(lit.)
• Boiling Point: 278.7 °C at 760 mmHg
• Flash Point: 122.3 °C
• Appearance: White/Crystalline Powder
• Density: 1.2 g/cm³
• Vapor Pressure: 0.00201mmHg at 25°C
• Refractive Index: 1.505
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• PKA: 7.76±0.10(Predicted)
• BRN: 8544594
• CAS DataBase Reference: 3-Fluoro-4-methylphenylboronic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Fluoro-4-methylphenylboronic acid(168267-99-0)
• EPA Substance Registry System: 3-Fluoro-4-methylphenylboronic acid(168267-99-0)

Safety Data

• Hazard Codes: Xi,T
• Statements: 36/37/38-25
• Safety Statements: 26-36/37/39-45-37
• WGK Germany: 3
• HazardClass: IRRITANT
• Hazardous Substances Data: 168267-99-0(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
3-Fluoro-4-methylphenylboronic acid is used as a reactant for the synthesis of various pharmaceutical compounds. Its unique structure allows for the creation of novel molecules with potential therapeutic applications.
Used in Chemical Synthesis:
3-Fluoro-4-methylphenylboronic acid is used as a reactant in regioselective Suzuki coupling reactions. This type of reaction is a powerful tool in organic chemistry, enabling the formation of carbon-carbon bonds with high selectivity and efficiency. The use of this boronic acid in Suzuki coupling reactions contributes to the development of complex molecular structures with potential applications in various industries.
Used in Material Science:
3-Fluoro-4-methylphenylboronic acid is used as a building block for the development of new materials with specific properties. Its incorporation into the molecular structure of these materials can lead to enhanced performance characteristics, such as improved stability, reactivity, or selectivity.
Used in Bacterial Quorum Sensing Inhibition:
3-Fluoro-4-methylphenylboronic acid is used as an inhibitor of bacterial quorum sensing in Vibrio harveyi. Quorum sensing is a communication mechanism used by bacteria to coordinate their behavior based on population density. By inhibiting this process, 3-Fluoro-4-methylphenylboronic acid can potentially be used to control bacterial growth and prevent the spread of infections.

InChI:InChI=1/C7H8BFO2/c1-5-2-3-6(8(10)11)4-7(5)9/h2-4,10-11H,1H3

Upstream product

• 121-43-7 Trimethyl borate 
• 51436-99-8 2-fluoro-4-bromotoluene 
• 39998-81-7 2-fluoro-4-iodotoluene 

Downstream Products

• 292050-23-8 2-[1-Acetylamino-2-(4-borono-2-fluorophenyl)ethyl]malonic acid diethyl ester 
• 923982-00-7 C₁₃H₁₂FNO₂ 
• 923981-97-9 C₁₃H₁₂FNO₂ 
• 923982-15-4 C₁₄H₁₄FNO₂ 
• 923982-39-2 C₂₀H₁₈FNO₄ 
• 1048338-36-8 C₁₁H₈ClFN₂ 
• 903895-56-7 2-(3-fluoro-4-methylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 1312996-59-0 3-(3-fluoro-4-methylphenyl)-4-(3,4,5-trimethoxyphenyl)thiophene 
• 1574275-62-9 C₁₉H₂₃FN₂O₂S₂ 

Relevant articles and documents

Lithium aminoborohydrides 17. Palladium catalyzed borylation of aryl iodides, bromides, and triflates with diisopropylaminoborane prepared from lithium diisopropylaminoborohydride

The Alcaraz-Vaultier borylation of aryl halides and triflates is reported utilizing diisopropylaminoborane (BH2N(iPr)2) prepared from the corresponding lithium aminoborohydride (LAB reagent). BH 2N(iPr)2, prepared by reacting lithium diisopropylaminoborohydride with trimethylsilyl chloride, provided the most consistent isolated yields from this reaction. Catalytic amounts of palladium dichloride produced the highest yields from aryl iodides, while catalytic tris(dibenzylideneacetone)dipalladium(chloroform) provided the best yields for aryl bromides and triflates. This route to boronic acids is mild enough to tolerate various functionalities and for the first time employs aryl triflates as substrates for the Alcaraz-Vaultier borylation. In addition, it was found that both boronic acid and ester compounds could be isolated from the reaction mixture utilizing simple work-up procedures. Treatment of the reaction intermediate with an acid/base work-up provided the corresponding boronic acid, while treating the same intermediate with a diol, such as neopentyl glycol, afforded the corresponding boronic ester.

A modular approach to catalytic synthesis using a dual-functional linker for Click and Suzuki coupling reactions

The stable benzylazido-boronate ester 1 is presented as an example of a dual-functional linker that allows the synthetically valuable boronate motif to be clicked onto other molecules under mild conditions. The utility of the azido-boronate motif as a modular building block is demonstrated in the rapid synthesis of drug-like structures employing sequential catalytic azide-alkyne cycloaddition and Suzuki coupling reactions.