179923-32-1

Basic information

• Product Name: 2,3,4,5-TETRAFLUOROBENZENEBORONIC ACID
• Synonyms: 2,3,4,5-TETRAFLUOROBENZENEBORONIC ACID;2,3,4,5-TETRAFLUOROPHENYLBORONIC ACID
• CAS NO: 179923-32-1
• Molecular Formula: C₆H₃BF₄O₂
• Molecular Weight: 193.89
• EINECS: -0
• Product Categories: Aryl;Boronic Acids;Boronic Acids and Derivatives
• Mol File: 179923-32-1.mol

Chemical Properties

• Melting Point: 264-269 °C
• Boiling Point: 257.6 °C at 760 mmHg
• Flash Point: 109.6 °C
• Appearance: /
• Density: 1.53 g/cm³
• Vapor Pressure: 0.00737mmHg at 25°C
• Refractive Index: 1.446
• Storage Temp.: 2-8°C
• PKA: 6.33±0.58(Predicted)
• BRN: 8554485
• CAS DataBase Reference: 2,3,4,5-TETRAFLUOROBENZENEBORONIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: 2,3,4,5-TETRAFLUOROBENZENEBORONIC ACID(179923-32-1)
• EPA Substance Registry System: 2,3,4,5-TETRAFLUOROBENZENEBORONIC ACID(179923-32-1)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• Hazardous Substances Data: 179923-32-1(Hazardous Substances Data)

Usage

Uses

Used in Chemical Synthesis:
2,3,4,5-TETRAFLUOROBENZENEBORONIC ACID is used as a reactant for base-catalyzed hydrodeboration and deuterodeboration reactions. These reactions are essential in the synthesis of various organic compounds, particularly those with deuterated or hydrogenated functional groups. The compound's reactivity and stability make it a valuable intermediate in the production of pharmaceuticals, agrochemicals, and other specialty chemicals.
Used in Catalyst Development:
In the field of catalysis, 2,3,4,5-TETRAFLUOROBENZENEBORONIC ACID is used as a catalyst for amidation reactions. Amidation is a crucial process in the synthesis of peptides, proteins, and other nitrogen-containing compounds. The compound's unique electronic and steric properties enable it to facilitate the formation of amide bonds, which are essential for the structure and function of many biologically active molecules. This application is particularly relevant in the pharmaceutical and biotechnology industries, where the development of new drugs and bioactive compounds is of great importance.
Used in Material Science:
2,3,4,5-TETRAFLUOROBENZENEBORONIC ACID can also be used in the development of new materials with specific properties, such as improved thermal stability, chemical resistance, or electronic properties. The compound's fluorine substitution and boronic acid functionality can be exploited to create novel polymers, coatings, or other materials with tailored characteristics for various applications, including aerospace, electronics, and automotive industries.

InChI:InChI=1/C6H3BF4O2/c8-3-1-2(7(12)13)4(9)6(11)5(3)10/h1,12-13H

Upstream product

• 551-62-2 1,2,3,4-tetrafluorobenzene 
• 121-43-7 Trimethyl borate 
• 7732-18-5 water 

Downstream Products

• 1073339-20-4 4,4,5,5-tetramethyl-2-(2,3,4,5-tetrafluorophenyl)-1,3,2-dioxaborolane 
• 551-62-2 1,2,3,4-tetrafluorobenzene 
• 1447729-96-5 4-methyl-2-(2,3,4,5-tetrafluorophenyl)quinoline 
• 1422263-73-7 [Pd(PPh₃)2(Br)(2-pyridyl-3,4,5,6-tetrafluorophenyl)] 
• 1422200-61-0 2-(2-bromo-3,4,5,6-tetrafluorophenyl)pyridine 
• 263243-16-9 2,3,4,5-tetrafluorophenyldifluoroborane 

Relevant articles and documents

Direct Sulfonamidation of Primary and Secondary Benzylic Alcohols Catalyzed by a Boronic Acid/Oxalic Acid System

The direct sulfonamidation of primary and secondary benzylic alcohols catalyzed by a 2,3,4,5-tetrafluorophenylboronic acid/oxalic acid co-catalytic system was examined. The reaction proceeds under mild conditions with readily available starting materials and has been shown to be gram-scalable without significant decrease of yield. Both primary and secondary benzylic alcohols were evaluated and afforded the desired sulfonamide products with good to excellent yields.

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.

(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).