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(5-Chloro-2-fluorophenyl)boronic acid (CAS 352535-83-2), also known as 5-chloro-2-fluorophenylboronic acid, is a halogenated aromatic organoboron compound featuring a chlorine atom at the 5-position, a fluorine atom at the 2-position, and a boronic acid group attached to the benzene ring. This compound combines the synthetic versatility of an arylboronic acid with the electronic and structural characteristics of a chlorofluorinated aromatic framework. The fluorine substituent influences the electronic distribution and physicochemical properties of the aromatic ring, while the chlorine substituent provides an additional potential site for chemical modification. The boronic acid group enables suitable carbon–carbon bond-forming reactions, making this compound a useful building block for medicinal chemistry, pharmaceutical intermediate development, agrochemical research, Suzuki–Miyaura cross-coupling chemistry, and specialty organic synthesis.
Chemical Identifiers
| InChI | 1S/C6H5BClFO2/c8-4-1-2-6(9)5(3-4)7(10)11/h1-3,10-11H |
| InChI Key |
GGTUVWGMCFXUAS-UHFFFAOYSA-N |
| Smiles | OB(C1=CC(Cl)=CC=C1F)O |
| EC No. | 675-613-5 |
| MDL No. | MFCD05664225 |
| PubChem CID | 3718925 |
Applications
Applications in Suzuki–Miyaura Cross-Coupling Reactions
(5-Chloro-2-fluorophenyl)boronic acid is useful in Suzuki–Miyaura cross-coupling reactions for preparing halogenated biaryl and aryl–heteroaryl compounds. Under appropriately optimized palladium-catalyzed conditions, the boronic acid group can react with compatible aryl or heteroaryl halides and pseudohalides to form new carbon–carbon bonds. This transformation enables the introduction of a 5-chloro-2-fluorophenyl fragment into more complex molecular frameworks. The chlorine and fluorine substituents may remain intact under suitably selective reaction conditions, providing opportunities for subsequent chemical modification. Reaction conditions should be selected carefully because catalyst systems, substrate structure, and competing functional groups can influence coupling efficiency and chemoselectivity.
Applications in Medicinal Chemistry
In medicinal chemistry, (5-Chloro-2-fluorophenyl)boronic acid serves as a building block for preparing halogenated aromatic compounds and investigating structure–activity relationships. Fluorine and chlorine substituents are frequently introduced into pharmaceutical research molecules because they can influence electronic distribution, lipophilicity, molecular conformation, and interactions with biological targets. The boronic acid functionality provides a convenient route for incorporating the chlorofluorinated phenyl fragment into structurally diverse candidate molecules. Researchers may use this compound during lead optimization, analog synthesis, and molecular library development to evaluate how specific halogen substitution patterns affect the properties of target compounds.
Applications in Pharmaceutical Intermediate Synthesis
(5-Chloro-2-fluorophenyl)boronic acid may support pharmaceutical research programs requiring intermediates containing a chlorofluorinated aromatic structural unit. Through suitable cross-coupling reactions, the compound can be connected to aromatic or heteroaromatic coupling partners to produce more complex molecular frameworks. The resulting compounds may undergo additional transformations depending on the desired target structure. The chlorine substituent can potentially participate in selected transition-metal-catalyzed reactions, while the fluorine substituent may influence the reactivity of the aromatic system. This combination of functional groups provides flexibility for developing multistep synthetic routes and preparing advanced pharmaceutical research intermediates.
Applications in Agrochemical Research
Halogenated aromatic compounds are widely investigated in agrochemical chemistry because chlorine and fluorine substituents can influence molecular properties and interactions with biological targets. (5-Chloro-2-fluorophenyl)boronic acid may serve as an intermediate for preparing research compounds containing a chlorofluorinated phenyl fragment. Through suitable coupling and functionalization reactions, researchers can incorporate this structural unit into larger aromatic or heteroaromatic frameworks. The resulting compounds may be evaluated for physicochemical characteristics and potential biological activity in exploratory crop protection research. Their practical suitability depends on the properties and performance of the final molecules.
