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• Solvents and Organic Chemicals Organic Compounds Amines/Sulfonamides

Professional Overview of 2,5-Difluorophenylhydrazine Hydrochloride (CAS No. 175135-73-6)

The 2,5-difluorophenylhydrazine hydrochloride, identified by the Chemical Abstracts Service (CAS) registry number 175135-73-6, is an organofluorine compound with significant utility in advanced chemical synthesis and biomedical research. This hydrazone derivative exhibits unique structural characteristics due to the fluorine substituents at the 2 and 5 positions of the phenyl ring, which modulate its electronic properties and reactivity. Recent studies highlight its emerging roles in drug discovery processes and as a versatile reagent in organic chemistry.

In terms of physical properties, this compound adopts a crystalline solid form with a molecular weight of 198.60 g/mol. Its fluorinated aromatic system contributes to enhanced thermal stability compared to non-fluorinated analogs, as demonstrated by thermogravimetric analysis (TGA) studies published in the Journal of Fluorine Chemistry in 2023. The hydrochloride salt form ensures optimal solubility in polar solvents such as water and methanol, while maintaining inertness under ambient conditions. Spectroscopic data confirms the presence of characteristic N-NH? and C-F vibrational modes in infrared spectroscopy (IR), along with distinct proton resonance peaks in nuclear magnetic resonance (1H NMR) spectra at δ 7.8–8.0 ppm corresponding to the fluorinated aromatic protons.

From a synthetic perspective, this compound serves as an important building block for constructing bioactive molecules through carbonyl condensation reactions. A groundbreaking 2024 study in Organic Letters described its use as a key intermediate in synthesizing novel isoquinoline derivatives with potential anti-inflammatory activity. The regioselective substitution pattern of fluorine atoms provides precise control over reaction pathways when employed in multistep synthesis protocols involving Friedel-Crafts acylation or Gabriel synthesis methodologies.

In pharmacological research, recent investigations have explored its role in developing enzyme inhibitors targeting metabolic pathways. A notable 2024 publication in Medicinal Chemistry Communications reported that derivatives synthesized using 2,5-difluorophenylhydrazine hydrochloride showed selective inhibition of histone deacetylase (HDAC) enzymes with IC?? values below 10 nM in vitro assays. The fluorine substituents enhance lipophilicity without compromising aqueous solubility—a critical balance for drug candidates—while also improving metabolic stability according to ADME studies conducted by pharmaceutical researchers at Stanford University.

Biochemical applications benefit from its ability to form Schiff bases with carbonyl compounds under controlled conditions. This property was leveraged in a 2024 Angewandte Chemie paper describing its use as a probe molecule for studying protein glycation processes associated with diabetes mellitus pathogenesis. The compound's unique reactivity profile allows selective conjugation with advanced glycation end products (AGEs), enabling precise detection mechanisms without interfering with native protein structures.

Safety evaluations published in the European Journal of Medicinal Chemistry (2024) emphasize its low acute toxicity profile when handled under standard laboratory protocols. These findings align with recent regulatory guidelines promoting fluorinated hydrazines as safer alternatives to traditional hydrazine derivatives through optimized substitution patterns that reduce undesirable side reactions. Proper storage conditions include maintaining it under nitrogen atmosphere at temperatures below 4°C to preserve its chemical integrity over extended periods.

Synthetic strategies for preparing this compound have evolved significantly since its initial characterization in the late 1990s. Modern protocols utilize palladium-catalyzed cross-coupling reactions combined with selective fluorination techniques described in a 2023 Synlett article achieving >98% purity levels through recrystallization from ethanol/water mixtures followed by high-resolution mass spectrometry verification (HRMS). This method represents an improvement over earlier procedures by minimizing reaction steps and eliminating environmentally hazardous reagents traditionally used.

In material science applications, recent work published in ACS Applied Materials & Interfaces (Q3 2024) demonstrates its utility as a dopant additive for enhancing polymer electrolyte conductivity in lithium-ion batteries. The spatial arrangement of fluorine atoms creates favorable interactions within polymer matrices that increase ion mobility without compromising structural integrity—a discovery validated through impedance spectroscopy and electrochemical testing under varying temperature conditions.

Cross-disciplinary studies highlight its role as an intermediate for producing fluorescent probes used in live-cell imaging applications. A Nature Communications paper from January 2024 detailed how conjugation with coumarin moieties via Knoevenagel condensation generates bright red-emitting dyes suitable for tracking intracellular processes without photobleaching issues common among conventional markers.

The compound's regioisomeric specificity is particularly advantageous when synthesizing asymmetric molecules for chiral drug development programs reported by Merck Research Laboratories' December 2024 preprint submission on enantioselective synthesis techniques using chiral auxiliaries derived from this base structure.

In vivo pharmacokinetic studies conducted on murine models revealed prolonged half-life characteristics compared to non-fluorinated counterparts when administered via subcutaneous injection at therapeutic dosages up to 50 mg/kg body weight according to data presented at the 2024 American Chemical Society National Meeting.

Current research directions focus on optimizing its use within continuous flow chemistry systems where microreactors enable precise control over reaction parameters such as temperature and residence time—critical factors when handling reactive intermediates like hydrazines—as evidenced by work published last quarter in Green Chemistry demonstrating improved yield efficiency using such systems compared to traditional batch methods.

Surface-enhanced Raman scattering (SERS) studies involving this compound have provided new insights into intermolecular interactions when immobilized on gold nanoparticle surfaces according to an October 2024 Analytical Chemistry article that characterized its vibrational fingerprinting capabilities useful for trace analysis applications requiring sub-picomolar detection limits.

In peptide chemistry applications, recent advances reported by Bioorganic & Medicinal Chemistry Letters authors describe how this reagent enables efficient solid-phase synthesis of bioactive peptides containing fluorinated aromatic residues—a breakthrough method reducing coupling times by up to 60% while maintaining purity standards required for preclinical testing phases.

Cryogenic NMR experiments conducted at -60°C revealed novel hydrogen bonding patterns between hydrochloride counterions and solvent molecules during solution-state studies published Q4 2024 issue of Magnetic Resonance Chemisty providing fundamental insights into solvation dynamics influencing reaction selectivity profiles observed under different experimental conditions.

Sustainable synthesis approaches highlighted at the Royal Society of Chemistry's annual symposium proposed using microwave-assisted methods coupled with reusable heterogeneous catalysts achieving near-stoichiometric yields while reducing energy consumption by approximately 40% compared conventional reflux techniques—a development aligning perfectly with current green chemistry initiatives within academic laboratories worldwide.

Biomaterial compatibility tests performed according to ISO standard protocols confirmed negligible cytotoxicity effects on human fibroblast cultures even after prolonged exposure periods exceeding seven days when tested at concentrations up to millimolar levels—findings validated through MTT assays and live/dead cell imaging analyses presented during March's Biomedical Engineering Conference proceedings.

Liquid chromatography-mass spectrometry (LC-MS) based metabolomics research has recently identified this compound's metabolites following hepatic biotransformation processes studied across multiple species models including rodents and non-human primates according to data shared openly via PubChem CID database updates released November last year which cataloged three primary phase I metabolites detected consistently across all test subjects studied thus far.

• 2368-80-1(2-Fluorophenylhydrazine)
• 51523-79-6(2,4-Difluorophenylhydrazine hydrochloride)
• 8002-53-7(2,4,6-Trifluorophenylhydrazine)
• 828-73-9(Pentafluorophenylhydrazine)
• 97108-50-4(2,5-Difluorophenylhydrazine)
• 80025-72-5(2,4,6-Trifluorophenylhydrazine)
• 119452-66-3(2,6-Difluorophenylhydrazine)
• 40594-30-7((2,4-difluorophenyl)hydrazine Hydrochloride)
• 2924-15-4((2-fluorophenyl)hydrazine hydrochloride)
• 653-11-2(2,3,5,6-tetrafluorophenylhydrazine)