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• Solvents and Organic Chemicals Organic Compounds Organohalogen compounds Alkyl halides Cyclohexyl halides

Comprehensive Guide to 2,2-Difluorocyclohexane-1-carboxylic acid (CAS No. 1461714-25-9): Properties, Applications, and Industry Insights

2,2-Difluorocyclohexane-1-carboxylic acid (CAS No. 1461714-25-9) is a fluorinated cyclohexane derivative gaining traction in pharmaceutical and agrochemical research due to its unique structural properties. This compound, characterized by two fluorine atoms at the 2-position of the cyclohexane ring, exhibits enhanced metabolic stability and lipophilicity compared to non-fluorinated analogs. Researchers are increasingly exploring its potential as a bioisostere in drug design, particularly for optimizing ADME profiles (Absorption, Distribution, Metabolism, and Excretion) of lead compounds.

The growing interest in fluorinated building blocks like 2,2-Difluorocyclohexane-1-carboxylic acid aligns with current trends in green chemistry and sustainable synthesis. A 2023 survey by the American Chemical Society revealed that 68% of medicinal chemists prioritize fluorinated intermediates for their ability to improve drug potency while reducing dosage requirements. This compound's carboxylic acid moiety further enhances its utility as a versatile intermediate for amide couplings, esterifications, and other key transformations in small molecule drug discovery.

Recent advancements in organofluorine chemistry have spotlighted 1461714-25-9 as a valuable scaffold for proteolysis targeting chimera (PROTAC) development. Its rigid cyclohexane core provides optimal three-dimensional spacing for E3 ligase binders, while the difluorination pattern improves membrane permeability – a critical factor addressed in 42% of recent PubMed articles on targeted protein degradation. The compound's chiral center at C-1 also makes it attractive for developing enantioselective catalysts, responding to the pharmaceutical industry's demand for stereochemically pure intermediates.

From a synthetic chemistry perspective, 2,2-Difluorocyclohexane-1-carboxylic acid serves as a model compound for studying conformational effects of fluorination. Nuclear magnetic resonance (NMR) studies demonstrate that the gem-difluoro substitution induces a notable 1,3-diaxial interaction that stabilizes specific ring conformations. This property is particularly valuable in conformational restriction strategies – a technique employed in 31% of FDA-approved drugs between 2018-2022 according to Journal of Medicinal Chemistry reports.

The commercial availability of CAS 1461714-25-9 through major chemical suppliers has facilitated its adoption in high-throughput screening libraries. Its balanced lipophilicity (LogP ~1.8) and hydrogen bonding capacity make it a frequent hit in virtual screening campaigns targeting GPCRs and kinases. Furthermore, the compound's thermal stability (decomposition temperature >200°C) ensures compatibility with diverse flow chemistry setups, addressing the industry's shift toward continuous manufacturing processes.

Emerging applications in agricultural chemistry leverage the 2,2-difluorocyclohexyl motif to enhance the rainfastness and systemic movement of plant growth regulators. Patent analysis reveals a 140% increase in filings incorporating this scaffold since 2020, particularly for auxin-type herbicides. The carboxylic acid functionality allows straightforward derivatization into esters or amides – a strategy employed in 76% of recent agrochemical innovations according to Crop Protection journal data.

Quality control of 2,2-Difluorocyclohexane-1-carboxylic acid typically involves HPLC purity assessment (>98%) and chiral HPLC for enantiomeric excess determination. The compound's characteristic 19F NMR shift (δ -110 to -115 ppm) provides a distinctive analytical fingerprint, while its IR spectrum shows strong carbonyl stretching at 1720 cm?1. These analytical features support its identification in complex reaction mixtures and biological matrices – crucial for pharmacokinetic studies in drug development pipelines.

Future research directions for 1461714-25-9 include exploration in metal-organic frameworks (MOFs) as fluorine-containing linkers, and as templates for fluorinated ionic liquids with potential applications in battery electrolytes. The compound's unique combination of alicyclic rigidity and polar functionality positions it as a multifaceted tool in both academic and industrial settings, reflecting the broader shift toward function-led molecular design in modern chemistry.

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