Production Method 1

54932-72-8

913835-32-2

Reaction Conditions

1.1 Reagents: Triisopropyl borate Solvents: Tetrahydrofuran ;  rt → -78 °C; -78 °C; 30 min, -78 °C; 2 h, -78 °C
1.2 Reagents: Hydrochloric acid Solvents: Water ;  pH 6
2.1 Reagents: Sodium hydroxide ,  Tetrabutylammonium bromide ,  Permanganic acid (HMnO4), potassium salt (1:1) Solvents: Water ;  4 h, rt
2.2 Reagents: Hydrochloric acid Solvents: Water ;  pH 2, rt

Reference

Optimization of synthesis process of (4-chloro-3-carboxylphenyl) boronic acid

Teng, Minggang; et al, Guangdong Huagong, 2015, 42(3), 30-31

Production Method 2

161950-10-3

913835-32-2

Reaction Conditions

1.1 Reagents: Sodium hydroxide ,  Tetrabutylammonium bromide ,  Permanganic acid (HMnO4), potassium salt (1:1) Solvents: Water ;  4 h, rt
1.2 Reagents: Hydrochloric acid Solvents: Water ;  pH 2, rt

Reference

Optimization of synthesis process of (4-chloro-3-carboxylphenyl) boronic acid

Teng, Minggang; et al, Guangdong Huagong, 2015, 42(3), 30-31

5-Borono-2-chlorobenzoic acid Raw materials

• 4-Chloro-3-methylphenylboronic acid
• 5-Bromo-2-chlorotoluene

5-Borono-2-chlorobenzoic acid Preparation Products

• 5-Borono-2-chlorobenzoic acid (913835-32-2)

• 1. Exchanged ligands on the surface of a giant cluster: [(MoO3)176(H2O)63(CH3OH)17Hn](32 – n)–
  Chem. Commun., 1998, 1501-1502
• 2. Dissolved oxygen sensor based on fluorescence quenching of oxygen-sensitive ruthenium complexes immobilized in sol–gel-derived porous silica coatings
  Analyst, 1996,121, 785-788
• 3. Examination of ammonia–poly(pyrrole) interactions by piezoelectric and conductivity measurements
  Analyst, 1991,116, 1125-1130
• 4. Dissociation of aryl sulfonyl phthalimide radical anions: relevance to the biological activity of arylsulfonyl amides?
  Abdelaziz Houmam,Emad M. Hamed Chem. Commun., 2012,48, 11328-11330
• 5. Evolution of calcium phosphate precipitation in hanging drop vapor diffusion by in situRaman microspectroscopy
  Gloria Belén Ramírez-Rodríguez,José Manuel Delgado-López,Jaime Gómez-Morales CrystEngComm, 2013,15, 2206-2212

• Other Chemical Reagents Derivatization Reagents
• Solvents and Organic Chemicals Organic Compounds Acids/Esters

Introduction to 5-Borono-2-chlorobenzoic acid (CAS No. 913835-32-2)

5-Borono-2-chlorobenzoic acid, identified by the Chemical Abstracts Service Number (CAS No.) 913835-32-2, is a specialized organic compound that has garnered significant attention in the field of pharmaceutical chemistry and materials science. This compound belongs to the benzoic acid derivatives class, characterized by the presence of both a boronic acid functional group and a chlorine substituent on the benzene ring. The unique structural features of this molecule make it a valuable intermediate in the synthesis of various biologically active compounds, particularly in the development of targeted therapeutics and advanced materials.

The significance of 5-Borono-2-chlorobenzoic acid lies in its versatile applications across multiple domains. In pharmaceutical research, this compound serves as a crucial building block for designing novel drug candidates. The boronic acid moiety is particularly noteworthy, as it is frequently employed in Suzuki-Miyaura cross-coupling reactions, a cornerstone of modern synthetic organic chemistry. These reactions enable the formation of carbon-carbon bonds, which are essential for constructing complex molecular architectures found in many therapeutic agents.

Recent advancements in medicinal chemistry have highlighted the utility of 5-Borono-2-chlorobenzoic acid in the development of small-molecule inhibitors targeting specific biological pathways. For instance, studies have demonstrated its potential in modulating enzymes involved in cancer metabolism and inflammation. The chlorine substituent at the ortho position enhances electrophilicity, facilitating further functionalization and allowing for the creation of derivatives with tailored pharmacokinetic properties. This flexibility has made it a preferred choice for medicinal chemists seeking to optimize drug-like characteristics such as solubility, bioavailability, and metabolic stability.

In materials science, 5-Borono-2-chlorobenzoic acid has been explored for its role in synthesizing advanced polymers and coordination complexes. The boronic acid group can participate in coordination chemistry with metal ions, leading to the formation of stable metal-organic frameworks (MOFs) and supramolecular assemblies. These materials exhibit intriguing properties such as high surface area, tunable porosity, and selective adsorption capabilities, making them promising candidates for applications in catalysis, gas storage, and separation technologies.

The synthesis of 5-Borono-2-chlorobenzoic acid typically involves multi-step organic transformations starting from readily available aromatic precursors. Key synthetic strategies include halogenation followed by boronation or vice versa, depending on the desired regioselectivity. Modern synthetic methodologies often leverage transition-metal catalysis to enhance reaction efficiency and minimize byproduct formation. Such improvements align with the growing emphasis on green chemistry principles, where sustainability and environmental impact are prioritized alongside chemical yield and purity.

Recent research has also delved into the computational modeling of 5-Borono-2-chlorobenzoic acid, utilizing advanced computational techniques to predict its reactivity and interactions within biological systems. Molecular dynamics simulations and quantum mechanical calculations have provided insights into how this compound behaves in different environments, aiding in the rational design of more effective derivatives. These computational approaches complement experimental efforts by offering predictive power that accelerates the discovery process.

The pharmacological potential of 5-Borono-2-chlorobenzoic acid has been further explored through structure-activity relationship (SAR) studies. By systematically modifying its molecular structure, researchers have identified analogs with enhanced potency against specific disease targets. For example, derivatives with optimized boronic acid substitution patterns have shown improved binding affinity to enzymes implicated in neurodegenerative disorders. Such findings underscore the importance of 5-Borono-2-chlorobenzoic acid as a scaffold for drug discovery initiatives.

Moreover, the compound’s role in bioconjugation chemistry has been increasingly recognized. The boronic acid group serves as an effective handle for linking biomolecules such as peptides and proteins through reversible interactions. This property is particularly valuable in therapeutic applications where controlled release or targeted delivery is desired. Recent innovations in bioconjugation techniques have leveraged 5-Borono-2-chlorobenzoic acid to develop novel biologics with improved therapeutic profiles.

In conclusion,5-Borono-2-chlorobenzoic acid (CAS No. 913835-32-2) represents a multifaceted compound with broad applications spanning pharmaceuticals and materials science. Its unique structural features enable diverse chemical transformations, making it indispensable in synthetic chemistry workflows. As research continues to uncover new methodologies and applications,5-Borono-2-chlorobenzoic acid is poised to remain at the forefront of scientific innovation across multiple disciplines.

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