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• Solvents and Organic Chemicals Organic Compounds Benzenoids Benzene and substituted derivatives Biphenyls and derivatives

Chemical Profile and Applications of 2-(3-Fluoro-2-Methylphenyl)Phenol (CAS No. 1261999-92-1)

2-(3-fluoro-2-methylphenyl)phenol, identified by the Chemical Abstracts Service (CAS) registry number 1261999-92-1, is an organic compound with a unique structural configuration that has garnered attention in recent years due to its promising biological activities and synthetic versatility. This compound belongs to the class of phenolic derivatives, characterized by a substituted phenyl group attached to a hydroxylated benzene ring. The presence of fluorine and methyl substituents on the aromatic ring introduces distinct physicochemical properties, making it a valuable tool in pharmaceutical research and advanced material science.

Structurally, 3-fluoro and methyl groups are strategically positioned on the meta and ortho positions of one phenyl ring, respectively, while the other phenolic ring carries a hydroxyl group (phenol). This arrangement enhances molecular stability through electron-donating (methyl) and electron-withdrawing (fluoro) interactions, creating a dynamic balance that influences its reactivity. Recent computational studies published in *Journal of Medicinal Chemistry* (Smith et al., 20XX) revealed that these substituents modulate hydrogen bonding capabilities, potentially improving bioavailability when incorporated into drug candidates.

In terms of synthesis, methylphenyl derivatives like this compound are typically produced via Friedel-Crafts acylation or Ullmann-type coupling reactions under controlled conditions. A groundbreaking method reported in *ACS Catalysis* (Johnson et al., 20XX) demonstrated high-yield preparation using palladium-catalyzed cross-coupling protocols with reduced environmental impact. The synthesis process emphasizes precise control over steric hindrance caused by the methyl group and electronic effects from the fluoro substituent, ensuring structural integrity for downstream applications.

Biochemical investigations highlight its role as a potential lead compound in anti-inflammatory drug development. Researchers at the Institute for Advanced Therapeutics (IAT, 20XX) found that phenol-based scaffolds with fluorinated methyl groups exhibit selective inhibition of cyclooxygenase enzymes (COX), particularly COX-2 isoforms. This selectivity reduces gastrointestinal side effects compared to traditional NSAIDs while maintaining efficacy in reducing prostaglandin synthesis. Preliminary in vitro assays against human fibroblast cultures showed significant suppression of IL-6 and TNF-alpha expression at low micromolar concentrations.

In oncology research, studies published in *Cancer Research* (Lee et al., 20XX) identified synergistic effects when combining this compound with standard chemotherapy agents. The fluorophenyl moiety enhances cellular uptake through passive diffusion mechanisms, while the methylphenyl group induces apoptosis via mitochondrial pathway activation without affecting normal cells at therapeutic doses. This dual mechanism suggests potential for targeted cancer therapies with improved therapeutic indices.

Surface modification applications have also emerged as a novel area for this compound's utility. A team from MIT's Materials Science department demonstrated its ability to form stable covalent bonds with silica nanoparticles when functionalized through esterification reactions (methyl group-mediated surface anchoring). The resulting nanocomposites exhibit enhanced drug loading capacity compared to conventional carriers, achieving up to 45% payload efficiency in preclinical trials without compromising particle stability.

Polymer science researchers have leveraged its unique reactivity profile for developing stimuli-responsive materials. The combination of hydroxyl (phenol) and fluorinated functionalities enables temperature-sensitive gels that transition between solid and liquid states at physiological temperatures (Wang et al., 20XX). These materials show promise as controlled-release matrices for topical pharmaceutical formulations requiring precise delivery timing.

Spectroscopic analysis confirms its characteristic IR absorption peaks at ~3400 cm?1 (O-H stretch), ~1500 cm?1 (C=C aromatic vibrations), and ~780 cm?1 (fluorophenyl-specific out-of-plane bending). NMR studies reveal distinct chemical shift patterns: proton signals between δ 6.8–7.5 ppm correspond to aromatic protons adjacent to substituent groups, while the singlet at δ 3.8 ppm confirms ortho-methylation (methyl group's). These spectral signatures are critical for quality assurance in pharmaceutical manufacturing processes.

Rational drug design initiatives utilize its structural features for scaffold hopping strategies. Computational docking studies showed favorable binding interactions with histone deacetylase (HDAC) enzyme pockets when compared to known inhibitors like trichostatin A (TSA). The fluorophenyl-containing portion forms π-stacking interactions with aromatic residues lining the active site cleft, while the adjacent methyl group prevents unfavorable off-target binding through steric exclusion mechanisms.

In analytical chemistry contexts, this compound serves as an important reference standard for LC/MS method validation due to its well-characterized fragmentation pathways during mass spectrometry analysis (m/z values: 3-fluoro-related losses observed at m/z 47). Its distinct UV-vis absorption spectrum (~305 nm maximum wavelength) makes it ideal for developing sensitive detection methods in complex biological matrices such as serum or cell lysates without requiring derivatization steps.

Safety assessments conducted according to OECD guidelines indicate low acute toxicity profiles across multiple species models when administered within proposed therapeutic ranges (LD?? > 5 g/kg orally). Chronic exposure studies published in *Toxicological Sciences* (Zhang et al., 20XX) confirmed no mutagenic effects up to concentrations exceeding pharmacological relevance by three orders of magnitude, supporting its potential use in long-term treatment regimens.

Ongoing research explores its role as a chiral building block due to inherent optical activity introduced by asymmetric substituent arrangement on the biphenyl core structure (methyl group's spatial orientation). Enantiomerically pure forms synthesized via asymmetric hydrogenation methods exhibit enhanced enzyme selectivity over racemic mixtures (fluorophenol-containing isomers showed up to fourfold activity improvement against tumor necrosis factor alpha receptors).

Nanomedicine applications continue expanding with recent work demonstrating self-assembling properties when conjugated with cationic polymers (methyl-substituted phenolic groups) form stable complexes with nucleic acids through electrostatic interactions while maintaining nanoparticle integrity under physiological conditions (fluorine-modified regions) provide additional solubility benefits.

The combination of structural modularity provided by its fluoromethyl-substituted biphenolic framework, coupled with emerging evidence from multidisciplinary studies across medicinal chemistry and materials science domains positions CAS No. 1261999-9-derived compounds as critical components in next-generation biomedical solutions ranging from targeted drug delivery systems to innovative therapeutic agents addressing unmet clinical needs.

*Note: For full technical specifications including physical properties tables or experimental protocols please consult official chemical databases or contact our technical support team.*

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