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(4-Chloro-2-fluorophenyl)boronic acid (CAS 160591-91-3), also known as 4-chloro-2-fluorobenzeneboronic acid, is a halogenated aromatic organoboron compound containing a boronic acid group, a chlorine atom at the 4-position, and a fluorine atom at the 2-position of a benzene ring. Its structure combines the carbon–carbon bond-forming utility of an arylboronic acid with the electronic and steric characteristics of two different halogen substituents. The compound is a useful building block for preparing substituted aromatic structures in medicinal chemistry, pharmaceutical intermediate development, agrochemical research, and specialty organic synthesis.
Chemical Identifiers
| InChI | 1S/C6H5BClFO2/c8-4-1-2-5(7(10)11)6(9)3-4/h1-3,10-11H |
| InChI Key | YBNDRTRLXPEWKQ-UHFFFAOYSA-N |
| Smiles | C1=C(Cl)C=CC(=C1F)B(O)O |
| EC No. | 640-199-7 |
| MDL No. | MFCD02684293 |
| PubChem CID | 4193595 |
Applications
Applications in Suzuki–Miyaura Cross-Coupling Reactions
(4-Chloro-2-fluorophenyl)boronic acid is used as an organoboron coupling partner in Suzuki–Miyaura reactions. Under suitable palladium-catalyzed conditions, its boronic acid group can react with compatible aryl or heteroaryl halides to form carbon–carbon bonds. This enables the introduction of a 4-chloro-2-fluorophenyl fragment into biaryl and heterobiaryl structures. The ortho-fluorine substituent can influence reaction behavior, while the chlorine atom may be preserved for subsequent transformations when appropriate chemoselective conditions are employed.
Applications in Medicinal Chemistry
Fluorine- and chlorine-substituted aromatic rings are frequently investigated in medicinal chemistry because halogen substitution can influence lipophilicity, electronic distribution, metabolic behavior, and molecular recognition. (4-Chloro-2-fluorophenyl)boronic acid provides a convenient route for incorporating a defined dihalogenated phenyl fragment into research compounds. Medicinal chemists may use it to prepare structural analogs, investigate substituent effects, and develop molecular libraries for structure–activity relationship studies.
Applications in Pharmaceutical Intermediate Synthesis
This compound is relevant to the preparation of pharmaceutical intermediates containing substituted aromatic or heteroaromatic frameworks. Its boronic acid functionality enables the formation of a new carbon–carbon bond, while the chlorine and fluorine substituents provide additional structural features for subsequent synthetic development. In appropriately designed routes, the aryl chloride may undergo further catalytic functionalization. This makes the compound useful for sequential coupling strategies and the preparation of complex pharmaceutical research intermediates.
Applications in Agrochemical Research
Halogenated aromatic compounds are important structural building blocks in agrochemical research. Chlorine and fluorine substituents can affect the physicochemical properties of candidate molecules, including their lipophilicity and electronic characteristics. (4-Chloro-2-fluorophenyl)boronic acid may be used to synthesize aromatic and heteroaromatic derivatives for exploratory herbicide, fungicide, or insecticide research. The performance and biological activity of the resulting compounds must be established through appropriate testing.
