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Best 3,4-Dichlorobenzeneboronic acid丨CAS 151169-75-4
3,4-Dichlorobenzeneboronic acid (CAS 151169-75-4), also known as 3,4-dichlorophenylboronic acid, is a halogenated aromatic organoboron compound containing a boronic acid group and two adjacent chlorine substituents at the 3- and 4-positions of a benzene ring. Its structure combines the synthetic versatility of an arylboronic acid with the electronic characteristics of a dichlorinated aromatic framework, making it a useful building block for pharmaceutical intermediate synthesis, medicinal chemistry, agrochemical research, and specialty organic chemistry.
Chemical Identifiers
| InChI | 1S/C6H5BCl2O2/c8-5-2-1-4(7(10)11)3-6(5)9/h1-3,10-11H |
| InChI Key | JKIGHOARKAIPJI-UHFFFAOYSA-N |
| Smiles | C1=C(C(=CC(=C1)B(O)O)Cl)Cl |
| EC No. | 629-198-2 |
| MDL No. | MFCD01074646 |
| PubChem CID | 2734330 |
Applications
Applications in Suzuki–Miyaura Cross-Coupling Reactions
3,4-Dichlorobenzeneboronic acid is a useful coupling partner in Suzuki–Miyaura reactions for preparing substituted biaryl and aryl–heteroaryl compounds. Under suitable palladium-catalyzed conditions, its boronic acid group reacts with compatible aromatic halides to form carbon–carbon bonds. The chlorine substituents can remain intact under appropriately selected conditions, enabling the introduction of a 3,4-dichlorophenyl fragment into more complex molecular structures.
Applications in Medicinal Chemistry
In medicinal chemistry, 3,4-Dichlorobenzeneboronic acid provides a convenient route for incorporating a dichlorinated phenyl group into research molecules. The adjacent chlorine substituents can influence molecular polarity, hydrophobic interactions, and metabolic behavior. Researchers may use this compound in analog synthesis, lead optimization, and structure–activity relationship studies to investigate the effects of aromatic halogen substitution.
Applications in Pharmaceutical Intermediate Synthesis
This compound serves as a building block for preparing dichlorinated aromatic intermediates used in pharmaceutical research. Its boronic acid functionality enables the construction of complex aromatic frameworks, while the chlorine substituents influence electronic properties and lipophilicity. These characteristics make it relevant to the development of substituted biaryl compounds and specialized pharmaceutical intermediates.
Applications in Agrochemical Research
3,4-Dichlorobenzeneboronic acid may be used to prepare halogenated aromatic compounds for agrochemical research. Chlorinated phenyl groups are investigated in crop protection chemistry because they can influence molecular stability, lipophilicity, and biological interactions. The compound provides a useful intermediate for constructing specialized aromatic and heteroaromatic structures through suitable coupling reactions.
