Chemical Structure and Physicochemical Properties

4-Chloro-[1,1'-biphenyl]-3-carboxylic acid consists of a biphenyl core — two phenyl rings joined by a single carbon–carbon bond — bearing a chlorine atom at the 4-position and a carboxylic acid group (–COOH) at the 3-position of the substituted ring. This ortho-like relationship between the chloro and carboxyl substituents influences both the electronic character and the steric environment of the molecule.

The molecular formula is C₁₃H₉ClO₂, giving a molecular weight of approximately 232.66 g/mol. As a solid aromatic carboxylic acid, it is expected to exhibit moderate solubility in polar aprotic solvents such as dimethyl sulfoxide (DMSO) and dimethylformamide (DMF), and in alcohols such as ethanol, while showing limited solubility in water due to the hydrophobic biphenyl scaffold. The carboxylic acid group can participate in hydrogen bonding, influencing crystal packing and melting point. Specific melting point and solubility data should be confirmed against the certificate of analysis supplied with SKU C728860.

Synthesis and Role as a Building Block

Halogenated biphenyl carboxylic acids such as 4-Chloro-[1,1'-biphenyl]-3-carboxylic acid are valued in synthetic chemistry because they contain two orthogonal reactive handles: the aryl chloride, which is amenable to transition-metal-catalysed cross-coupling reactions (e.g., Suzuki–Miyaura, Buchwald–Hartwig), and the carboxylic acid, which can be converted to esters, amides, acyl chlorides, or used directly in condensation chemistry.

The biphenyl scaffold itself is a privileged structure in medicinal chemistry, frequently found in drug candidates owing to its planarity, lipophilicity, and ability to engage in π–π stacking interactions with biological targets. Incorporating a chloro substituent modulates electronic density on the ring, potentially tuning binding affinity and metabolic stability of derived compounds. Researchers commonly employ this type of building block in fragment-based drug discovery and in the preparation of liquid-crystal materials or functional polymers.

Standard synthetic manipulations — such as Fischer esterification, amide coupling using reagents like HATU or EDC, and palladium-catalysed cross-coupling — are directly applicable to this compound, facilitating library synthesis and lead optimisation workflows.

Applications in Research

Medicinal Chemistry: 4-Chloro-[1,1'-biphenyl]-3-carboxylic acid serves as a versatile intermediate for the preparation of biaryl-containing drug candidates. The carboxylic acid moiety enables coupling with amine-containing pharmacophores to yield amide bonds, a prevalent linkage in approved pharmaceuticals. The aryl chloride allows further diversification via cross-coupling, enabling rapid exploration of structure–activity relationships (SAR).

Materials Science: Biphenyl carboxylic acids are used as linker molecules in metal–organic frameworks (MOFs) and as monomers or chain-extenders in high-performance polyimide and polyamide syntheses. The chloro group can serve as a reactive handle for further functionalisation of the polymer backbone.

Chemical Biology: Halogenated biphenyls are employed as probes to study cytochrome P450 enzyme activity and as reference standards in environmental analytical chemistry, given the structural relationship to polychlorinated biphenyls (PCBs). Researchers should be aware of relevant safety regulations when handling chlorinated aromatic compounds.

Handling, Storage, and Safety Considerations

As with all aromatic carboxylic acids bearing halogen substituents, appropriate laboratory safety practices should be followed when handling 4-Chloro-[1,1'-biphenyl]-3-carboxylic acid. Personnel should wear appropriate personal protective equipment (PPE) including gloves, safety glasses, and a laboratory coat. Work in a well-ventilated area or fume hood to minimise inhalation of dust or aerosols.

The compound should be stored in a tightly sealed container in a cool, dry location away from strong bases, strong oxidising agents, and incompatible materials. Specific hazard classifications, GHS pictograms, and first-aid measures are detailed in the Safety Data Sheet (SDS) available from Aladdin Scientific for SKU C728860. Always consult the SDS before use.

For long-term storage stability, it is advisable to store the compound under an inert atmosphere if the material has been opened, and to confirm purity by appropriate analytical methods (e.g., HPLC, NMR) before use in sensitive synthetic applications.

Why Choose Aladdin Scientific for C728860

Aladdin Scientific supplies 4-Chloro-[1,1'-biphenyl]-3-carboxylic acid (SKU C728860) as a research-grade reagent supported by rigorous quality control. Each lot is accompanied by a certificate of analysis (CoA) confirming identity and purity by standard analytical techniques, ensuring reproducibility in your synthetic workflows.

Our catalogue encompasses a broad range of halogenated aromatic building blocks, carboxylic acid derivatives, and biphenyl scaffolds, enabling researchers to source structurally diverse intermediates from a single, reliable supplier. Bulk quantities and custom packaging options may be available; contact our technical sales team for details on pricing, lead times, and regulatory documentation requirements for your jurisdiction.