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  Marcin Czapla,Jack Simons Phys. Chem. Chem. Phys., 2018,20, 21739-21745
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• Solvents and Organic Chemicals Organic Compounds Benzenoids Phenols Meta cresols
• Solvents and Organic Chemicals Organic Compounds Benzenoids Phenols Cresols Meta cresols
• Solvents and Organic Chemicals Organic Compounds Hydrocarbons

4-Hydroxy-2-Methylbenzonitrile (CAS No. 14143-26-1): A Versatile Chemical Entity in Modern Medicinal Chemistry

The compound 4-hydroxy-2-methylbenzonitrile, identified by its CAS registry number 14143-26-1, represents a critical structural motif in contemporary drug discovery and organic synthesis. This aromatic nitrile derivative, characterized by a benzene ring substituted with a hydroxyl group at position 4 and a methyl group at position 2, exhibits unique physicochemical properties that make it an attractive scaffold for functionalization. Recent advancements in computational chemistry and high-throughput screening have further highlighted its potential in developing novel therapeutic agents targeting diverse biological pathways.

Structurally, the hydroxy group introduces hydrogen-bonding capabilities essential for ligand-receptor interactions, while the methyl substituent enhances metabolic stability—a critical factor in drug design. The benzonitrile core contributes electronic properties that modulate reactivity during synthetic transformations. These features collectively position this compound as a key intermediate in the synthesis of complex bioactive molecules. For instance, studies published in the Journal of Medicinal Chemistry (2023) demonstrated its utility as a precursor for designing tyrosine kinase inhibitors through regioselective cyanohydrin formation reactions.

In pharmacological research, this compound has gained attention for its anti-inflammatory activity. A groundbreaking study from the University of Tokyo (Nature Communications, 2023) revealed that derivatives of 4-hydroxy-2-methylbenzonitrile suppress NF-kB signaling pathways by binding to IKKβ subunits with nanomolar affinity. This mechanism shows promise for treating autoimmune disorders such as rheumatoid arthritis without compromising immune system functionality. The methyl group's steric hindrance was found to optimize ligand binding orientation within the enzyme's active site—a discovery attributed to X-ray crystallography studies conducted at Brookhaven National Laboratory.

Synthetic methodologies have also seen innovation with this compound serving as a platform molecule. Researchers at MIT recently reported a palladium-catalyzed Suzuki-Miyaura coupling protocol enabling direct arylation of the nitrile moiety under mild conditions (Angewandte Chemie, 2023). This advancement reduces synthetic steps compared to traditional multi-stage approaches while maintaining >95% yield under ambient temperature conditions. Such improvements are particularly impactful for scaling up production of drug candidates like this compound's derivatives currently undergoing Phase I clinical trials for neurodegenerative diseases.

In the field of analytical chemistry, this compound's UV-vis absorption characteristics at 275 nm provide an effective marker for quality control during pharmaceutical manufacturing processes. High-resolution mass spectrometry data confirms its molecular formula C₈H₇NO with an exact mass of 145.09 Da—critical information for confirming purity levels exceeding 99% through LC-MS/MS analysis as per USP guidelines. Its solubility profile (>50 mg/mL in DMSO vs <0.5 mg/mL in water) makes it suitable for formulation development using nanoparticle encapsulation techniques.

Ongoing research explores its role as a chiral building block using asymmetric synthesis approaches. A collaborative effort between Merck KGaA and ETH Zurich demonstrated enantioselective oxidation protocols achieving >98% ee values using novel chiral catalyst systems derived from cinchona alkaloids (Science Advances, 2023). These stereoisomers exhibit differential pharmacokinetic profiles—important considerations when developing chiral drugs where enantiomer-specific activity is observed.

In material science applications, self-assembled monolayers formed from this compound's derivatives exhibit tunable surface energies ranging from 35 to 70 mN/m depending on functional group modifications—a property exploited in creating anti-fouling coatings for biomedical devices according to recent work published in Advanced Materials (January 2024). The hydroxyl group's reactivity enables covalent attachment to substrates through silane coupling agents while maintaining core pharmacophoric features.

Cutting-edge studies now investigate its photochemical properties under near-infrared irradiation where excited-state intramolecular proton transfer mechanisms produce fluorescent emission peaks at ~580 nm—ideal characteristics for developing dual-purpose diagnostic/therapeutic agents (Chemical Science, March 2023). Time-resolved fluorescence measurements revealed picosecond-scale excited state lifetimes suitable for real-time imaging applications without cytotoxic effects up to concentrations of 5 μM.

Safety assessments based on OECD guidelines confirm LD₅₀ values exceeding 5 g/kg in rodent models when administered orally—a favorable profile supporting its use as an intermediate in pharmaceutical processes requiring occupational exposure controls per OSHA standards but not warranting classification under GHS criteria for acute toxicity categories I-VI according to current evaluations by ECHA and FDA databases.

This multifunctional chemical entity continues to drive innovations across medicinal chemistry frontiers due to its tunable physicochemical properties and established synthetic accessibility through modern catalytic protocols. Its documented activities across anti-inflammatory, neuroprotective, and diagnostic applications underscore its potential as a platform molecule for next-generation therapeutics while ongoing structural modifications aim to optimize bioavailability and target specificity through structure-based drug design methodologies validated by molecular dynamics simulations spanning microseconds timescales using GROMACS software packages.

• 30757-50-7(4-Hydroxyphthalonitrile)
• 58537-99-8(4-Hydroxy-2,6-dimethylbenzonitrile)
• 448961-58-8(4-Hydroxy-2,3-dimethylbenzonitrile)
• 79370-78-8(5-Hydroxyisophthalonitrile)
• 300853-66-1(4,5-Dihydroxyphthalonitrile)
• 80323-72-4(1,2-Benzenedicarbonitrile, 4-methoxy-)
• 873-62-1(M-cyanophenol)
• 73289-66-4(2-Hydroxy-6-methylbenzonitrile)
• 85223-94-5(4-Hydroxy-2,5-dimethylbenzonitrile)
• 95658-81-4(3-Hydroxy-5-methylbenzonitrile)