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Biphenyl Carboxylic Acid is often employed in the development of liquid crystals and as a reagent in organic reactions, showcasing its importance in material science and chemical synthesis.
Biphenyl Carboxylic Acids ability to enhance the thermal stability of polymers makes it particularly valuable in the production of heat-resistant materials. Additionally, its applications extend to the formulation of various specialty chemicals, where it contributes to improved performance and efficiency.
Biphenyl Carboxylic Acid stands out as a crucial compound for professionals seeking reliable and effective solutions in their projects.
CAS Number: 14498-95-4
Molecular Formula: C13H9ClO2
Molecular Weight: 232.66
Synonyms:o-Phenylbenzoic acid, EINECS 213-432-1, NSC 76051, 213-432-1, 2-Biphenylcarboxylic acid, 947-84-2, 2-Phenylbenzoic acid, [1,1'-Biphenyl]-2-carboxylic acid, Biphenyl-2-carboxylic acid, Biphenylcarboxylic acid, MFCD00002463, 1,1'-Biphenyl-2-carboxylic acid, 51317-27-2, Diphenyl-2-carboxylic acid, CHEMBL3092388, (1,1'-Biphenyl)carboxylic acid, phenylbenzoic acid, 2-phenyl benzoic acid, 2-phenyl-benzoic acid, Conivaptan Impurity 1, biphenyl carboxylic acid, 2-Biphenylcarboxylic acid2, Biphenylcarboxylic acid-(2), 1,1'-biphenylcarboxylic acid, SCHEMBL133057, SCHEMBL180988, SCHEMBL298628, SCHEMBL1510151, SCHEMBL3368727, SCHEMBL3368730, SCHEMBL6157634, SCHEMBL7459760, ILYSAKHOYBPSPC-UHFFFAOYSA-, DTXSID30870814, Biphenyl-2-carboxylic acid, 98%, KUC107406N, NSC76051, STR08660, 1,1'-Biphenyl, 2-carboxylic acid, BDBM50533338, NSC-76051, SBB007790, STK026406, AKOS000120801, AC-3069, CS-W001937, FB03305, HY-W001937, KSC-20-075, NCGC00332644-01, SY003735, TS-02802, DB-029483, NS00042434, P0906, ST50308184, 2-Biphenylcarboxylic acid o-Phenylbenzoic acid, EN300-20886, AB01325741-02, F2173-1248, Z104484440, InChI=1/C13H10O2/c14-13(15)12-9-5-4-8-11(12)10-6-2-1-3-7-10/h1-9H,(H,14,15)., 2-bipheny-2'-Chloro-carboxylic acid, 2-Carboxy-2'-chlorobiphenyl, 2-(2-Chlorophenyl)benzoic acid, 2'-Chloro-2-biphenylcarboxylic acid, [1,1'-Biphenyl]-2-carboxylic acid, 2'-chloro-, 2-BIPHENYL-2'-CHLORO-CARBOXYLIC ACID, 2'-Chloro-[1,1'-biphenyl]-2-carboxylicacid
Biphenyl carboxylic acid is an aromatic organic compound that consists of a biphenyl framework, meaning it has two benzene rings directly connected to each other, and it also contains a carboxylic acid functional group (-COOH) attached to one of the rings. Because of this structural arrangement, the molecule belongs to the family of aryl carboxylic acids, which are known for their chemical stability, relatively high melting points, and their ability to engage in hydrogen bonding, esterification, and other organic reactions.
The presence of both the hydrophobic biphenyl backbone and the polar acidic group makes biphenyl carboxylic acid chemically versatile, since it can interact with both organic solvents and polar environments.
Biphenyl Carboxylic Acid is also often described under different positional isomers, such as 2-biphenylcarboxylic acid (o-phenylbenzoic acid), 3-biphenylcarboxylic acid (m-phenylbenzoic acid), and 4-biphenylcarboxylic acid (p-phenylbenzoic acid), with the number referring to where the carboxylic acid group is located on the biphenyl ring system.
Each isomer has slightly different physical and chemical properties, which influence their solubility, acidity, and reactivity, as well as their potential applications in chemical synthesis and industrial processes.
Biphenyl Carboxylic Acid, also known as 4-phenylbenzoic acid, is a versatile compound widely utilized in various industrial and research applications.
This aromatic carboxylic acid features a biphenyl structure that enhances its stability and solubility, making it an excellent candidate for use in the synthesis of polymers, dyes, and pharmaceuticals.
Its unique properties allow it to act as a coupling agent in the production of high-performance materials, as well as a key intermediate in organic synthesis processes.
In terms of usage, biphenyl carboxylic acid is primarily employed as an intermediate in organic synthesis, because its aromatic carboxylic acid group allows it to form derivatives such as esters, amides, and salts, which are useful for building more complex molecules.
Biphenyl Carboxylic Acid has been investigated in the pharmaceutical industry, where it sometimes appears as an impurity or structural intermediate in the synthesis of drug candidates such as vasopressin receptor antagonists, anti-inflammatory compounds, and other bioactive molecules.
Beyond pharmaceuticals, it can also serve as a building block in material chemistry, where biphenyl-based acids are used in the creation of liquid crystals, specialty polymers, and dyes, since the rigid biphenyl structure contributes to thermal stability and optical properties.
Despite its usefulness, biphenyl carboxylic acid, like many aromatic acids, has potential hazards and safety concerns.
In laboratory and industrial handling, it may act as a skin and eye irritant, and inhalation of dust or fine particles could lead to respiratory discomfort, coughing, or irritation of the mucous membranes.
If ingested in large amounts, it may cause gastrointestinal distress, including nausea, vomiting, and abdominal pain, due to the acidic nature of the compound.
From an environmental perspective, its low biodegradability and aromatic stability mean that if released in significant amounts, it could persist in soil or water and potentially impact aquatic organisms.
Biphenyl Carboxylic Acid is best understood as a structurally rigid and chemically adaptable organic acid that is valuable as a synthetic intermediate, a research chemical, and a potential precursor in pharmaceuticals and advanced materials, but it must be handled with care because of its irritant properties, persistence in the environment, and possible toxic effects upon prolonged exposure.
storage temp.: 2-8°C
Assay: 95%
form: crystals
mp: 220-225 °C (lit.)
SMILES string: OC(=O)c1ccc(cc1)-c2ccccc2
Biphenyl carboxylic acid is an aromatic organic compound that belongs to the family of aryl carboxylic acids, and it is characterized by the presence of a biphenyl core, which consists of two benzene rings connected directly by a carbon–carbon bond, and a carboxylic acid (-COOH) group attached to one of the aromatic rings.
This combination of a rigid, stable biphenyl framework with a reactive acidic group gives the molecule both chemical resilience (from the aromatic structure) and chemical reactivity (from the acidic functional group), which makes it a valuable material in organic synthesis and industrial chemistry.
The compound exists in three main structural isomers, which differ depending on where the carboxyl group is attached: 2-biphenylcarboxylic acid (o-phenylbenzoic acid), 3-biphenylcarboxylic acid (m-phenylbenzoic acid), and 4-biphenylcarboxylic acid (p-phenylbenzoic acid).
Each isomer exhibits slightly different physical and chemical properties, such as melting point, solubility in organic solvents, and acidity levels, which means that they may be chosen for different synthetic, pharmaceutical, or industrial applications.
The ortho isomer (o-phenylbenzoic acid) is often the most studied because the proximity of the carboxyl group to the second benzene ring can create intramolecular interactions, affecting the compound’s reactivity and stability.
Chemically, biphenyl carboxylic acid is important because its carboxyl group makes it possible to form a wide range of derivatives, including esters, amides, salts, and acyl chlorides, all of which are useful intermediates in pharmaceutical research, agrochemical design, and polymer synthesis.
The biphenyl backbone itself is also significant, because biphenyl structures are known to contribute rigidity, thermal stability, and planarity to molecules, which are properties valued in the design of liquid crystals, dyes, and advanced functional materials.
Uses Of Biphenyl Carboxylic Acid:
Biphenyl carboxylic acid is primarily used as an intermediate in organic synthesis, where its rigid biphenyl structure combined with a reactive carboxylic acid group allows chemists to create a variety of derivatives, including esters, amides, salts, and functionalized aromatic compounds, which are in turn employed to build more complex molecules for pharmaceutical, agrochemical, and specialty chemical applications.
In the pharmaceutical industry, it serves as a precursor or impurity marker in the synthesis of drugs, such as Conivaptan and other vasopressin receptor antagonists, where the biphenyl carboxylic acid scaffold provides the necessary planarity, hydrophobicity, and hydrogen-bonding potential that influences biological activity, receptor binding, and pharmacokinetic properties.
Beyond pharmaceuticals, biphenyl carboxylic acid is valuable in materials science and polymer chemistry, because the aromatic biphenyl core contributes to thermal stability, rigidity, and optical properties, while the carboxyl group allows it to be chemically functionalized into polymers, copolymers, or esters that are used in liquid crystal displays, specialty coatings, dyes, and electronic materials.
Its derivatives can also be incorporated into high-performance plastics and composites, enhancing their mechanical strength, dimensional stability, and resistance to heat or chemical attack, which is particularly important in industrial equipment, aerospace components, and advanced consumer products.
In chemical research and fine chemical synthesis, biphenyl carboxylic acid is widely used as a building block for complex aromatic compounds, because its electron-rich biphenyl system can participate in reactions such as cross-coupling, electrophilic substitution, or condensation, enabling the production of specialty dyes, pigments, agrochemicals, and research chemicals.
These capabilities make it a preferred intermediate in laboratories and industry where precision in creating aromatic derivatives is essential for controlling chemical properties and functional performance.
In addition, biphenyl carboxylic acid can be employed in pharmacological and medicinal chemistry research as a structural template for designing new bioactive molecules, given that the combination of a rigid aromatic scaffold with an acidic functional group allows chemists to explore receptor binding interactions, enzyme modulation, or ligand-receptor compatibility.
This has led to applications in the design of anti-inflammatory agents, antimicrobial compounds, and experimental anticancer drugs, where the biphenyl unit contributes to molecular stability, lipophilicity, and electronic distribution, while the carboxyl group mediates hydrogen bonding and ionic interactions with biological targets.
Furthermore, in industrial and laboratory settings, biphenyl carboxylic acid is sometimes used as a reference material, calibration standard, or impurity marker, due to its well-defined chemical structure and stability, which allows scientists and quality-control laboratories to monitor synthesis processes, verify compound purity, and ensure consistency in chemical manufacturing.
Its use in such contexts highlights the versatility of the compound as a functional and analytical tool across multiple scientific and industrial disciplines.
Finally, biphenyl carboxylic acid is explored in advanced materials chemistry, where its planar aromatic structure and acidic functionalization can influence self-assembly, molecular packing, and supramolecular interactions, making it a useful precursor for designing liquid crystal molecules, organic semiconductors, or optoelectronic devices, where both structural rigidity and precise functionalization are critical for achieving desired performance characteristics.
Biphenyl carboxylic acid is extensively employed in organic and medicinal chemistry as a versatile synthetic intermediate, because the combination of its rigid biphenyl backbone and the reactive carboxyl functional group allows chemists to perform targeted modifications such as esterification, amidation, and acylation reactions, enabling the preparation of highly functionalized compounds that serve as key building blocks in the synthesis of pharmaceutical agents, agrochemicals, and fine chemicals, where precise control over molecular geometry, hydrophobicity, and electronic distribution is critical to the biological activity and chemical performance of the final product.
In the pharmaceutical field, biphenyl carboxylic acid is used not only as a precursor for active pharmaceutical ingredients (APIs) but also as a structural reference or impurity standard, particularly in the manufacture of vasopressin receptor antagonists, anti-inflammatory molecules, and other bioactive compounds, where the biphenyl moiety provides planar rigidity and hydrophobic interactions, and the carboxyl group offers hydrogen-bonding capability and potential sites for further chemical derivatization, which are essential characteristics for optimizing drug-receptor interactions, pharmacokinetics, and solubility profiles.
In materials science, biphenyl carboxylic acid plays a significant role in the design of high-performance polymers, liquid crystals, specialty coatings, and optoelectronic devices, because its planar aromatic structure promotes molecular alignment, thermal stability, and rigidity, while the carboxyl group can be chemically modified to introduce cross-linking points or reactive sites, which allows for the production of polymers, resins, and films with enhanced mechanical strength, thermal resistance, and optical properties suitable for applications such as display technology, aerospace materials, industrial protective coatings, and electronics.
Safety Profile Of Biphenyl Carboxylic Acid:
Although biphenyl carboxylic acid is widely used as a synthetic intermediate and building block in pharmaceuticals, polymers, dyes, and advanced materials, it also poses a number of health, environmental, and chemical hazards, which must be carefully considered during handling, storage, and disposal.
One of the primary concerns is its potential for skin and eye irritation, because direct contact with the solid or its solutions can cause redness, itching, burning, or allergic dermatitis, and in the case of eye exposure, it may induce painful irritation, tearing, or even temporary damage to the cornea if not promptly washed with copious amounts of water.
Inhalation of dust, fine particles, or aerosols of biphenyl carboxylic acid may irritate the respiratory tract, causing coughing, sneezing, nasal irritation, sore throat, or shortness of breath, and prolonged or repeated exposure in poorly ventilated environments could exacerbate pre-existing respiratory conditions such as asthma or chronic bronchitis.
Ingestion of significant amounts can lead to gastrointestinal distress, including nausea, vomiting, abdominal pain, or diarrhea, as the acidic functional group may irritate the mucous membranes of the digestive tract.
