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Purchasing 2,5-Dichlorobenzeneboronic acid丨CAS 135145-90-3
2,5-Dichlorobenzeneboronic acid (CAS 135145-90-3), also known as 2,5-dichlorophenylboronic acid, is a halogenated aromatic organoboron compound containing a boronic acid group and two chlorine substituents at the 2- and 5-positions of a benzene ring. Its combination of reactive boronic acid functionality and a dichlorinated aromatic framework makes it a useful building block for pharmaceutical intermediate synthesis, medicinal chemistry, agrochemical research, and specialty organic chemistry.
Chemical Identifiers
| InChI | 1S/C6H5BCl2O2/c8-4-1-2-6(9)5(3-4)7(10)11/h1-3,10-11H |
| InChI Key | NNTFPBXQPOQRBT-UHFFFAOYSA-N |
| Smiles | OB(O)C1=C(Cl)C=CC(Cl)=C1 |
| EC No. | 680-174-8 |
| MDL No. | MFCD01863182 |
| PubChem CID | 2773371 |
Applications
Applications in Suzuki–Miyaura Cross-Coupling Reactions
2,5-Dichlorobenzeneboronic acid can serve as a coupling partner in Suzuki–Miyaura reactions to prepare substituted biaryl and aryl–heteroaryl compounds. Under appropriately optimized palladium-catalyzed conditions, the boronic acid group reacts with compatible aryl or heteroaryl halides to form carbon–carbon bonds. The chlorine substituents can remain intact under suitable conditions, allowing the introduction of a 2,5-dichlorophenyl fragment into complex aromatic structures.
Applications in Medicinal Chemistry
In medicinal chemistry, 2,5-Dichlorobenzeneboronic acid provides a convenient route for incorporating a dichlorinated phenyl group into research molecules. The chlorine substituents can affect molecular conformation, hydrophobic interactions, and metabolic behavior, depending on the overall molecular structure. Researchers may use this compound in analog synthesis, lead optimization, and structure–activity relationship studies.
Applications in Pharmaceutical Intermediate Synthesis
This compound is useful for preparing dichlorinated aromatic intermediates in pharmaceutical research. Its boronic acid group enables the construction of substituted aromatic frameworks, while the chlorine atoms influence molecular electronic properties and lipophilicity. These characteristics make it relevant to the development of specialized pharmaceutical building blocks and multistep synthetic pathways.
Applications in Agrochemical Research
2,5-Dichlorobenzeneboronic acid may be used to synthesize halogenated aromatic compounds for agrochemical research. Chlorinated phenyl groups are investigated in crop protection chemistry because their substitution patterns can influence physicochemical properties and biological interactions. The compound provides a useful intermediate for preparing specialized aromatic and heteroaromatic research compounds.
