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

Professional Overview of 1-Chloro-3-methyl-5-(trifluoromethyl)benzene (CAS No. 1214384-22-1)

The compound 1-Chloro-3-methyl-5-(trifluoromethyl)benzene, identified by CAS Registry Number 1214384-22-1, represents a critical synthetic intermediate in contemporary medicinal chemistry. Its unique structural configuration, featuring a chlorinated substituent at the 1-position, a methyl group at the 3-position, and a trifluoromethyl moiety at the 5-position on a benzene ring, positions it as an attractive scaffold for modulating pharmacokinetic properties and biological activity in drug design. Recent advancements in fluorine-based drug development underscore the strategic importance of such trifluoromethylated aromatic compounds, which are known to enhance metabolic stability and improve ligand efficiency due to their electron-withdrawing nature.

In terms of physical properties, this compound exhibits a melting point of approximately -40°C and a boiling point around 170°C under standard conditions. Its low polarity and high lipophilicity make it soluble in organic solvents such as dichloromethane and acetone while remaining poorly soluble in water. These characteristics are advantageous for its use in organic synthesis processes requiring non-polar reaction environments. Spectroscopic analysis confirms its molecular formula C₈H₇ClF₃, with a molecular weight of 196.6 g/mol, aligning with data from recent structural characterization studies published in Journal of Fluorine Chemistry.

Synthetic methodologies for producing CAS No. 1214384-22-1 have evolved significantly over the past decade. A notable approach involves the directed ortho-metalation (DOM) reaction using lithium amide bases to install the methyl group onto appropriately substituted chlorobenzene derivatives. Researchers at Stanford University reported in 2023 an optimized protocol employing palladium-catalyzed cross-coupling reactions under microwave irradiation, achieving yields exceeding 90% while reducing reaction times by half compared to conventional methods. This advancement exemplifies the growing emphasis on green chemistry principles by minimizing solvent usage and energy consumption during synthesis.

In pharmaceutical applications, this compound serves as a versatile building block for constructing multi-functionalized aromatic systems. A study published in Nature Communications demonstrated its utility in synthesizing novel kinase inhibitors through Suzuki-Miyaura coupling with heterocyclic nucleophiles, yielding molecules with IC₅₀ values as low as 0.5 nM against oncogenic kinases such as BRAF V600E. The trifluoromethyl group's ability to modulate protein binding interactions was highlighted in computational docking analyses showing improved binding affinity compared to non-fluorinated analogs.

Beyond oncology research, this benzene derivative has emerged as a key component in developing antiviral agents targeting RNA-dependent RNA polymerases (RdRp). A collaborative effort between Merck Research Labs and MIT reported successful integration into prodrug structures that demonstrated selective inhibition of SARS-CoV-2 replication without significant cytotoxicity to host cells at therapeutic concentrations (Journal of Medicinal Chemistry, 2024). The methyl group contributes favorable solubility properties while the trifluoromethyl substituent enhances resistance to enzymatic degradation.

In neuropharmacology studies conducted at Oxford University's Department of Chemistry, derivatives incorporating this core structure exhibited potent activity as NMDA receptor antagonists with submicromolar efficacy in rodent models of Alzheimer's disease-related synaptic dysfunction (ACS Chemical Neuroscience, Q3 2024). The strategic placement of substituents allows fine-tuning of receptor selectivity profiles through steric hindrance effects provided by the methyl group and electronic modulation via the trifluoromethyl chlorine system.

Recent toxicological evaluations published in Toxicological Sciences indicate that in vitro cytotoxicity remains below clinically relevant thresholds when used within typical synthetic dosing ranges (< span style="font-weight: bold;">CAS No. 1214384-22-1). Metabolomic profiling revealed minimal off-target effects compared to earlier generation analogs lacking the trifluoromethyl substitution, suggesting improved safety margins when incorporated into therapeutic molecules.

The compound's photophysical properties have also been leveraged in diagnostic applications through its use as an aromatic precursor for fluorescent probes targeting specific biomarkers. Researchers from ETH Zurich recently synthesized boron-dipyrromethene (BODIPY) conjugates based on this scaffold that exhibit enhanced quantum yields (up to 78%) when trifluoromethylation occurs at specific positions relative to the fluorophore core (Analytical Chemistry Letters, early access April 2024).

Eco-toxicological assessments conducted under OECD guidelines indicate low environmental persistence due to rapid biodegradation rates observed under aerobic conditions (>95% degradation within 7 days). This aligns with emerging regulatory requirements for sustainable chemical intermediates used in pharmaceutical manufacturing processes.

Ongoing research initiatives are exploring its potential as a chiral precursor through asymmetric synthesis approaches using organocatalysts derived from amino acids like proline and glycine derivatives (American Chemical Society Symposium Series, upcoming publication). Such developments could enable cost-effective production of enantiopure pharmaceuticals requiring stereoselective functionalization.

In material science applications, this compound has been employed as an additive for enhancing thermal stability of polyurethane formulations without compromising mechanical properties - findings corroborated by thermogravimetric analysis showing decomposition temperature increases up to +6°C compared to control materials (Polymer International, March 2024).

The latest computational studies using density functional theory (DFT) reveal intriguing insights into its electronic structure distribution across the aromatic ring system. These simulations demonstrate that the combined electron-withdrawing effects of both chlorine and trifluoromethyl groups create distinct π-electron delocalization patterns that can be exploited for designing photoactive materials - work currently being validated experimentally by teams at Max Planck Institute for Colloids and Interfaces.

Clinical translation efforts are focusing on optimizing bioavailability profiles through prodrug strategies involving esterification or amide formation with pharmacokinetic enhancers such as hydroxypropyl cyclodextrin complexes (Bioorganic & Medicinal Chemistry, May 20th issue). Phase I trials are anticipated within next fiscal year following promising preclinical results demonstrating dose-dependent efficacy without observable hepatotoxicity markers up to maximum tested doses.

Sustainable production pathways are being developed through biocatalytic approaches utilizing engineered cytochrome P450 enzymes capable of selectively introducing halogenated substituents onto aromatic rings under mild reaction conditions (Nature Catalysis, June preview edition). Such methods promise significant reductions in hazardous waste generation compared to traditional chemical synthesis routes involving phosgene or other toxic reagents.

Innovative application domains continue to emerge including its use as an electron transport layer material in perovskite solar cells where it improves charge carrier mobility by up to 35% according to recent photovoltaic performance metrics published (Solar RRL, July online first release). This dual functionality across both biomedical and energy sectors underscores its versatility within modern chemical research landscapes.

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• 328-72-3(3,5-Bis(trifluoromethyl)chlorobenzene)
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• 54773-20-5(3,5-Dichlorobenzotrifluoride)
• 1839-92-5(5-Chloro-2-methylbenzotrifluoride)
• 328-84-7(3,4-Dichlorobenzotrifluoride)