4-Fluorophenylboronic Acid丨CAS 1765-93-1

4-Fluorophenylboronic Acid丨CAS 1765-93-1
Product Introduction:
CAS No.: 1765-93-1
Product Name: 4-Fluorophenylboronic acid
Molecular Formula: C6H6BFO2
Molecular Weight: 139.92
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Technical Parameters
Description

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4-Fluorophenylboronic acid (CAS 1765-93-1) is an aromatic organoboron compound containing a boronic acid group and a fluorine atom positioned para to each other on a benzene ring. Its molecular structure combines the versatility of boronic acid chemistry with the distinctive properties of an aryl fluoride substituent. It is an important building block in organic synthesis, particularly in palladium-catalyzed Suzuki–Miyaura cross-coupling reactions for constructing carbon–carbon bonds and preparing substituted biaryl compounds. The fluorine atom can influence the electronic properties, lipophilicity, and metabolic stability of resulting molecules, making this compound valuable in pharmaceutical research and functional materials development.

 

 

Chemical Identifiers

 

InChI 1S/C6H6BFO2/c8-6-3-1-5(2-4-6)7(9)10/h1-4,9-10H
InChI Key LBUNNMJLXWQQBY-UHFFFAOYSA-N
Smiles C1=C(C=CC(=C1)F)B(O)O
EC No. 605-778-0
MDL No. MFCD00039136
PubChem CID 285645

 

 

 

Applications

 

Applications in Pharmaceutical Intermediate Synthesis

4-Fluorophenylboronic acid is widely useful in medicinal chemistry for introducing a 4-fluorophenyl group into complex molecular structures. Through Suzuki–Miyaura coupling with suitable aryl or heteroaryl halides, it enables the preparation of fluorinated biaryl compounds and related pharmaceutical intermediates. Fluorine substitution is frequently explored in drug discovery because it can affect molecular conformation, lipophilicity, metabolic stability, and biological activity. Consequently, this compound supports the synthesis of research compounds, lead structures, and intermediates for pharmaceutical development.

Applications in Organic Synthesis and Cross-Coupling Reactions

One of the principal applications of 4-Fluorophenylboronic acid is palladium-catalyzed Suzuki–Miyaura cross-coupling. Its boronic acid group reacts with suitable aryl, heteroaryl, and other compatible electrophilic partners to form carbon–carbon bonds. This provides an efficient route to fluorinated biaryl structures and more complex aromatic frameworks. The para-fluorine substituent generally remains available in the coupled product for further transformations or as a permanent structural feature. The compound is therefore useful in synthetic route development and the preparation of functionalized aromatic molecules.

 

Applications in Agrochemical and Fine Chemical Research

Fluorinated aromatic structures are important in the design and synthesis of various specialty chemicals and agrochemical research compounds. 4-Fluorophenylboronic acid provides a convenient route to incorporating a para-fluorophenyl fragment into target molecules through cross-coupling chemistry. Researchers can use it to prepare fluorinated intermediates and explore how fluorine substitution affects molecular properties, stability, and performance. Its value depends on the structure and intended application of the target compound.

 

Applications in Functional Materials Research

The fluorinated phenyl group can be introduced into extended aromatic structures used in the development of functional organic materials. Through coupling reactions, 4-Fluorophenylboronic acid can contribute to the synthesis of substituted biphenyls and other aromatic compounds investigated for their electronic, optical, and thermal properties. Fluorine substitution can influence molecular polarity, intermolecular interactions, and material behavior, making the compound a useful building block in materials chemistry research.

 

 

 

 

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