652-18-6 | 2,3,5,6-Tetrafluorobenzoic acid

CAS:652-18-6 | 2,3,5,6-Tetrafluorobenzoic acid,Description

Synthesis Analysis

The synthesis of 2,3,5,6-tetrafluorobenzoic acid involves multiple steps starting from different precursors, demonstrating the versatility of approaches to obtain this compound. Wang Wei-jie (2008) outlines a method that begins with 2,3,5,6-tetrafluorobenzoic acid as raw material, proceeding through acyl chlorination, amidation, and Hofmann degradation, yielding a product with high purity (98%) and considerable yield (75.6%) (Wang Wei-jie, 2008). Another method described by Orthaber et al. (2010) involves reacting 1,2,4,5-tetrafluorobenzene with n-butyllithium and carbonation with CO2, achieving high yields (95%) of pure product without extensive purification (Orthaber et al., 2010).

Molecular Structure Analysis

Investigations into the molecular structure of 2,3,5,6-tetrafluorobenzoic acid reveal its potential for forming dimers and the presence of extensive hydrogen bonding networks. The crystal structure analysis by Zhu (2009) demonstrates intermolecular O—H⋯N hydrogen bonds linking molecules into a trimeric structure, further assembled into a three-dimensional network through weak C—H⋯F interactions (Xiao-Hong Zhu, 2009) .

Chemical Reactions and Properties

2,3,5,6-Tetrafluorobenzoic acid participates in various chemical reactions, leading to the formation of diverse functional compounds. The study by Fielding and Shirley (1992) on the synthesis and reactions of 4-sulpho-2,3,5,6,-tetrafluorobenzoic acid shows its reactivity towards different chemical agents, resulting in a variety of derivatives with potential applications in materials science and chemistry (Fielding & Shirley, 1992).

Physical Properties Analysis

The physical properties of 2,3,5,6-tetrafluorobenzoic acid, such as phase transitions and molecular interactions, have been explored. Subhapriya et al. (2017) conducted a conformational study using density functional theory (DFT), revealing the existence of hydrogen bonding through vibrational frequencies, NBO analysis, and molecular electrostatic potential (MEP) studies. This analysis helps understand the compound's stability and interactions with other molecules (Subhapriya et al., 2017).

Chemical Properties Analysis

The chemical properties of 2,3,5,6-tetrafluorobenzoic acid, including its reactivity and the formation of complexes with metals, offer insights into its application in designing new materials. Ma et al. (2006) synthesized a series of new organotin(IV) derivatives with 2,3,5,6-tetrafluorobenzoic acid, demonstrating the compound's versatility in forming complexes with interesting topological properties (Ma et al., 2006).

Scientific Research Applications

• Scientific Field: Biochemistry

  • Application : 2,3,5,6-Tetrafluorobenzoic acid is used as a pharmaceutical intermediate. An intermediate is a substance produced during the middle steps of a reaction between two chemicals. A pharmaceutical intermediate is used in the production of pharmaceuticals.

• Scientific Field: Analytical Chemistry

  • Application : This compound has been used in the development of a new method for measuring thiol concentration using 19F NMR spectroscopy. Thiols are organic compounds that contain a sulfur-hydrogen bond. They are important in biochemistry because they are found in many enzymes and proteins.
  • Results or Outcomes : This method can be applied to measuring glutathione and albumin concentrations in rat blood. Glutathione is an important antioxidant in plants, animals, fungi, and some bacteria and archaea, preventing damage to important cellular components. Albumin is a protein made by your liver. It helps keep fluid in your bloodstream so it doesn’t leak into other tissues.

• Scientific Field: Proteomics

  • Application : This compound has been used in the development of a new method for measuring protease activity. Proteases are enzymes that break down proteins and peptides, and they play a crucial role in many biological processes.
  • Method of Application : The method involves using a probe that is intrinsically non-fluorescent but only becomes fluorescent after reacting with a target protease. 2,3,5,6-Tetrafluoro-4-hydroxybenzoic acid is employed in the preparation of this probe.

• Scientific Field: Medicinal Chemistry

  • Application : 2,3,5,6-Tetrafluorobenzoic acid is used as a pharmaceutical intermediate. It is used in the synthesis of various pharmaceuticals.

• Scientific Field: Chemical Research

  • Application : This compound is used as a pharmaceutical intermediate. It is used in chemical research.

• Scientific Field: Protein Biochemistry

  • Application : This compound has been used in the development of novel inhibitors for protein farnesyltransferase (FTase) and geranylgeranyltransferase (GGTase), through Mitsunobu reaction.
  • Method of Application : The method involves using a probe that is intrinsically non-fluorescent but only becomes fluorescent after reacting with a target protease. 2,3,5,6-Tetrafluoro-4-hydroxybenzoic acid is employed in the preparation of this probe.

Safety And Hazards

The safety information for 2,3,5,6-Tetrafluorobenzoic acid includes several hazard statements: H302-H315-H319-H332-H335. Precautionary measures include P280-P305+P351+P338-P310.

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