Chlorfenapyr - Moligand™, 10 mM in DMSO , CAS No.122453-73-0

CAS: 122453-73-0 Cat. No.: C1499424 Formula: C₁₅H₁₁BrClF₃N₂O Molecular Weight: 407.62 Beilstein Registry Number: 6940152 EC Number: 602-782-4

GRADE & PURITY Moligand™, 10 mM in DMSO

Storage

Store at -80°C

Shipped In

Dry ice packs + Cold packs

Overview

Chlorfenapyr is a pyrrole insecticide. Chlorfenapyr has a mode of action: the mixed function oxidase oxidizes and removes the Nethoxymethyl group to form the active metabolite, CL 303268. Chlorfenapyr is used for termite control and crop protection against a variety of insect and mite pests .

Specifications

Specifications & Purity

Moligand™, 10 mM in DMSO

Storage

Store at -80°C

Shipped In

Dry ice packs + Cold packs

This product requires cold chain shipping. Ground and other economy services are not available.

Grade

Moligand™

Names and Identifiers

• Isomeric SMILES: CCOCN1C(=C(C(=C1C(F)(F)F)Br)C#N)C2=CC=C(C=C2)Cl
• WGK Germany: 3
• UN Number: 2811
• Molecular Weight: 407.62
• Beilstein: 6940152

References

1. Zhi-Xiang Liu, Xiao-Rong Xing, Xin-Hao Liang, Jian-hao Ding, Yi-Jiangcheng Li, Ying Shao, Fu-An Wu, Jun Wang, Sheng Sheng.  (2021)  The role of Glutathione-S-transferases in phoxim and chlorfenapyr tolerance in a major mulberry pest, Glyphodes pyloalis walker (Lepidoptera: Pyralidae).  PESTICIDE BIOCHEMISTRY AND PHYSIOLOGY,      [PMID:35082028] [10.1016/j.pestbp.2021.105004]

2. Yifan Li, Hong Sun, Hassan Yasoob, Zhen Tian, Yue Li, Ruichi Li, Shengli Zheng, Jiyuan Liu, Yalin Zhang.  (2021)  Biogenetic cantharidin is a promising leading compound to manage insecticide resistance of Mythimna separata (Lepidoptera: Noctuidae).  PESTICIDE BIOCHEMISTRY AND PHYSIOLOGY,      [PMID:33518040] [10.1016/j.pestbp.2020.104769]

Application Protocols

No manufacturer-validated protocols are provided for this item. The following generalized, literature-style procedures are offered as starting points for research method development.

1. Preparation of DMSO stock and plate dosing (cell-based assays):

• Dissolve Chlorfenapyr in anhydrous DMSO to 10 mM.
• Aliquot into amber microtubes; store at −80 °C. Thaw once and keep on ice during use.
• For a 96-well plate, prepare serial dilutions (e.g., 10-point, 1:3). Maintain final DMSO ≤0.5% v/v in wells. Include vehicle and positive-control uncoupler controls.

2. LC–MS/MS residue analysis (example workflow):

• Sample extraction: Homogenize 10 g matrix with 10 mL acetonitrile; add MgSO4/NaCl (QuEChERS). Vortex and centrifuge. Collect ACN layer.
• Cleanup: Dispersive SPE with PSA/C18 as needed.
• Chromatography: C18 column, ACN/H2O + 0.1% formic acid gradient. Monitor parent and characteristic fragments in MRM mode. Validate recovery (70–120%), matrix effects, LOD/LOQ.

3. Microsomal activation assay (mechanism study):

• Incubate Chlorfenapyr (0.5–10 μM) with insect or liver microsomes (0.5–1 mg/mL protein), NADPH-regenerating system, 30–60 min at 37 °C.
• Quench with cold ACN, centrifuge, and analyze supernatant by LC–MS for the de-alkylated metabolite.

Always perform appropriate controls and safety assessments; adapt conditions to your instrumentation.

Biological Roles

Context: Provided for background on mechanism and pathways; not a statement of suitability for clinical/therapeutic use.

Literature-based overview:

• Pro-insecticide: Chlorfenapyr is bioactivated by oxidative N-dealkylation (e.g., by cytochrome P450 monooxygenases) to a pyrrole metabolite that acts as a protonophore/uncoupler of oxidative phosphorylation in mitochondria.
• Site of action: Disrupts mitochondrial proton gradient, leading to increased oxygen consumption and reduced ATP synthesis. Effects are energy deprivation and eventual organismal lethality in susceptible arthropods.
• Selectivity rationale: Activation-dependent toxicity; metabolic capacity and detoxification pathways influence species sensitivity. The parent compound is comparatively less active until converted to the uncoupling metabolite.
• Biotransformation: Major processes include N-dealkylation (activation), hydroxylation, and conjugation; environmental photolysis and hydrolysis can also occur, yielding less active products over time.

Research implications:

• Tool compound for studying bioenergetics, mitochondrial coupling efficiency, and xenobiotic metabolism in insect systems.
• Useful in resistance mechanism studies (e.g., P450-mediated activation variance, metabolic detoxification), without implying any pest control recommendations here.

Note: Use strictly for research; observe institutional biosafety and chemical safety protocols.

Buffer Applications

This product is not a buffer reagent. Chlorfenapyr is a hydrophobic small molecule with negligible water solubility and is not used to formulate laboratory buffers.

Practical guidance:

• If dosing into aqueous buffers for bioassays, prepare concentrated DMSO stocks and dilute into the target buffer, keeping cosolvent typically ≤0.1–1% v/v to maintain biological compatibility.
• For stability, protect assay plates or tubes from light and excessive heat during incubations.

Green Alternatives

Chlorfenapyr is an active pesticidal research compound; there are no direct “green” drop-in substitutes for its bioactivity. However, greener practices apply to its handling and analytical workflows.

Greener practice suggestions (general):

• Solvent choice: Prefer acetonitrile over dichloromethane for sample preparation and HPLC where performance allows; use ethanol or ethyl acetate for extractions when compatible with target recovery.
• Miniaturization: Adopt microscale extraction (e.g., μQuEChERS) to reduce solvent volumes.
• Energy: Cold-chain storage is required for stability; mitigate impact by aliquoting to minimize freezer door openings and by consolidating shipments.
• Waste: Segregate halogenated organic waste; use adsorbents to capture residuals before aqueous disposal streams. Treat as persistent/toxic waste per local regulations.

Comparison (illustrative; not bioequivalent):

• Alternative analytes for method development: benign surrogates (e.g., halogenated aromatics without pesticidal activity) can be used to validate retention windows before introducing Chlorfenapyr standards.
• Alternative extraction systems: Switch from chlorinated solvents to acetonitrile or ethyl acetate when recovery and matrix effects remain acceptable.

Pharmaceutical Uses

Not applicable. Chlorfenapyr is an agricultural/entomological research compound and is not used as a pharmaceutical excipient or in drug product formulation.

Laboratory-related notes (general):

• It may serve as a reference material in analytical method development for xenobiotic detection in biological matrices but has no recognized pharmacopeial monograph as an excipient.
• Any handling in a pharmaceutical lab context should be confined to nonclinical research and method development with appropriate containment.

Physical Properties

Item-specific specifications (this catalog listing):

• Appearance: Not specified for this item; refer to CoA/Spec Sheet.

Literature and reference values (for Chlorfenapyr as a pure substance; not product specifications):

• Physical state: crystalline solid (literature)
• Melting point: reported ~82–84 °C (literature)
• Boiling point: not typically distilled; thermal decomposition before boiling at 1 atm (literature)
• Density: reported around 1.5–1.6 g/cm³ at 20–25 °C (literature)
• Log Kow (octanol/water partition): ~4.5–5.0 (literature), indicating strong hydrophobicity
• Aqueous solubility (25 °C): very low (on the order of 0.1–1 mg/L, literature)
• Vapor pressure: very low (literature; sub-Pa at 25 °C)
• pKa: not applicable (neutral molecule without ionizable centers in physiologic range; literature rationale)
• UV–vis: strong absorbance in the UV region typical for halogenated aromatics/heteroaromatics (literature, qualitative)

Practical notes (general):

• Due to hydrophobicity, Chlorfenapyr dissolves readily in nonpolar/medium-polar organic solvents (e.g., DMSO, DMF, acetone, acetonitrile) and poorly in water.
• For analytical work, LC–MS/MS or HPLC–UV methods commonly use acetonitrile/water (with 0.1% formic acid) gradients to track elution of this moderately nonpolar analyte.

Quality & Grades

• Grade/Purity: Moligand™ (as listed for this item)

What Moligand™ implies (general explanation):

• Moligand™ designates compounds curated for small-molecule screening, ligand discovery, and chemical biology libraries. Emphasis is on identity confirmation and suitability for high-throughput screening workflows rather than chromatographic-grade solvent purity.
• Typical controls for such library-grade materials include structure confirmation (e.g., NMR/HRMS), purity assessment suitable for screening, and barcoded/traceable packaging. Exact acceptance criteria are batch-specific.

Item-specific notes:

• Exact purity assay method and limits: Not specified for this item; refer to CoA/Spec Sheet.
• Stabilizers/inhibitors: Not specified for this item; refer to CoA/Spec Sheet.
• UV cutoff, water content, residual solvents, and elemental impurities: Not specified for this item; refer to CoA/Spec Sheet.

When to choose this grade:

• Appropriate for discovery screening, target validation assays, environmental fate method development, and as a reference standard in chromatographic or spectrometric methods where Moligand™ quality suffices.
• For regulated applications (GxP) or quantitative reference standards with metrological traceability, request a dedicated analytical standard grade and full certificate of analysis.

Reaction & Applications

This compound is primarily a bioactive small molecule rather than a synthetic reagent. Accordingly, laboratory use centers on analytical, environmental, and biological testing rather than as a reaction solvent or substrate.

Research application themes (literature/general):

• Mode-of-action studies: Chlorfenapyr is a pro-insecticide that undergoes oxidative N-dealkylation to an active metabolite that uncouples mitochondrial oxidative phosphorylation. It is used to probe bioenergetics disruption in invertebrates and model systems.
• Analytical reference: Employed as a calibration/reference standard for LC–MS/MS and GC–MS methods in residue analysis (soil, water, food matrices) and in degradation/photolysis studies.
• Environmental fate: Used in hydrolysis, photolysis, and biodegradation studies to establish DT50 values and identify transformation products.

Practical tips:

• Handle solutions under subdued light to minimize photolysis during long analytical runs.
• For metabolism studies, microsomal or S9 fraction incubations (insect or mammalian) can generate the de-alkylated active metabolite; control for protein binding given hydrophobicity.
• For adsorption/fate assays, pre-equilibrate with organic-rich matrices and account for strong sorption to plastics—use glass when feasible.

Reaction Conditions

As Chlorfenapyr is generally used as an analyte or bioactive probe rather than a reagent, there are no standard “reaction conditions” in the synthetic sense. The following notes pertain to analytical and bioassay handling (literature/general):

• Stock solutions: 10–50 mM in anhydrous DMSO are commonly prepared for screening; filter through PTFE (0.2 μm) if particulate is present. Avoid adsorption losses by using glass vials.
• Working concentrations: In cellular or enzymatic bioenergetics assays, exploratory ranges of 0.01–30 μM are typical for concentration–response curves; optimize per system and include vehicle controls.
• Chromatography: HPLC or UPLC on C18 using ACN/H2O (±0.1% formic acid) gradients; detection by UV (200–300 nm) or MS (ESI/APCI). Flow and gradient depend on column and matrix complexity.
• Stability: Protect from strong light and elevated temperature during extended runs. Monitor for de-alkylated metabolite formation in oxidative systems.

These are general literature-style guidelines; adjust conditions to your platform and consult primary sources and your method validation plan.

Safety & Handling

Safety information specific to this item:

• Signal word: Not specified for this item; refer to SDS.
• Hazard statements (H-codes): Not specified for this item; refer to SDS.
• GHS classification and pictograms: Not specified for this item; refer to SDS.

General safety considerations for Chlorfenapyr (literature/typical for this class):

• Toxicity: Chlorfenapyr is a bioactivated insecticidal compound; handle as acutely toxic and environmentally hazardous. Avoid inhalation, ingestion, and skin contact.
• Aquatic hazard: Expected to be very toxic to aquatic life with long-lasting effects; prevent release to the environment. Collect spillage using inert absorbents.
• PPE: Use lab coat, nitrile gloves (double-gloving recommended for extended handling), and splash-resistant safety goggles. Work in a certified chemical fume hood.
• Incompatibilities: Strong oxidizers and strong acids/bases may cause degradation; avoid excessive heat and UV exposure.
• First aid overview: If inhaled, move to fresh air and seek medical advice; if on skin, wash with soap and water; if in eyes, rinse cautiously with water for several minutes; if swallowed, rinse mouth—do NOT induce vomiting—seek medical attention.
• Fire response: Use CO2, dry chemical, or foam. Combustion/thermal decomposition may release hydrogen halides and other toxic fumes; firefighters should wear self-contained breathing apparatus.

Always consult the product SDS for authoritative hazard, exposure limits, spill response, and disposal guidance.

Solvent Selection

Applicability: Chlorfenapyr is a hydrophobic, neutral solid; solvent choice impacts solubility, stability, and assay compatibility.

General solvent behavior (literature/general):

• Polarity class: low-to-moderate polarity solute with high hydrophobicity (log Kow ~4.5–5.0).
• Recommended stock solvents: DMSO (primary choice for bioassays), DMF, acetone, acetonitrile, ethyl acetate, dichloromethane, toluene. Poorly soluble in water and aqueous buffers.
• Miscibility profile: DMSO and DMF stocks can be diluted into aqueous media; keep final cosolvent typically ≤0.1–1% v/v in biological assays to minimize vehicle effects.

Selection tips:

• For LC–MS/HPLC method development: start with acetonitrile/water gradients (0.1% formic acid optional) using C18 columns; Chlorfenapyr elutes in the mid-to-late organic phase.
• For stability during storage: prepare anhydrous DMSO stocks, aliquot, and store at −80 °C; avoid repeated freeze–thaw.
• For extraction from matrices: nonpolar/medium-polar solvents (hexane:acetone, acetonitrile:water with salts—QuEChERS-type approaches) are commonly effective.

Comparison (general):

• DMSO: maximal solubility and cryostability; may affect some enzyme assays at >0.5% v/v.
• Acetonitrile: excellent for chromatography; limited solubility versus DMSO but volatile and MS-friendly.
• Ethyl acetate: good for extractions; less suitable for long-term stocks due to volatility.

Storage & Reconstitution

Item-specific storage conditions (from Product Data):

• Storage: Store at −80 °C.
• Shipped in: Dry ice packs + Cold packs.

General guidance for this compound type (supporting, not replacing item-specific instructions):

• Container: Store as tightly sealed, light-protected aliquots (amber glass vials) under dry, inert atmosphere if feasible to limit oxidative degradation.
• Reconstitution: For most applications, reconstitute in anhydrous DMSO to prepare concentrated stocks (e.g., 10–50 mM). Vortex thoroughly; gentle warming (to ~25–30 °C) may aid dissolution. Avoid water ingress.
• Aliquoting: Prepare single-use aliquots to minimize freeze–thaw cycles. Record preparation date and lot traceability on each aliquot.
• Handling: Allow frozen aliquots to equilibrate briefly on ice before opening to prevent moisture condensation. After use, promptly refreeze unused aliquots.
• Stability monitoring: Periodically verify integrity by LC–MS or HPLC (single major peak) if stocks are stored for >6 months.

Note: When formulating into aqueous systems, add DMSO stock to the buffer under vigorous mixing to avoid precipitation. Final vehicle content should be minimized consistent with assay tolerance.

Structure & Identity

Chlorfenapyr is a halogenated pyrrole insecticide widely used as a research reference standard and library compound.

• SKU: C1499424
• Product Name: Chlorfenapyr
• CAS: 122453-73-0 (literature)
• PubChem CID: 91778 (literature)
• Molecular formula: C15H11BrClF3N2O (literature)
• Molecular weight: ~407.6 g/mol (literature)
• InChIKey: Not specified for this item; refer to CoA/Spec Sheet.
• SMILES: Not specified for this item; refer to CoA/Spec Sheet.

Structural features (literature description):

• Core heteroaromatic ring: substituted pyrrole.
• Substituents: para-chlorophenyl, bromine on the pyrrole ring, a trifluoromethyl group, and an N-ethoxymethyl moiety (pro-insecticide masking group).
• Functional groups: halogens (Br, Cl), trifluoromethyl (–CF3), ether (–O–), and a bioactivation-labile N-alkoxymethyl group.
• 2D structure in words: a polysubstituted pyrrole bearing an aryl substituent and multiple electron-withdrawing/halogen substituents; the pyrrolic nitrogen is protected as an ethoxymethyl ether-like group that is cleaved metabolically to the active uncoupler.

Note: Exact structural identifiers (SMILES/InChI) may vary across tautomeric/neutral representations; consult the CoA/SDS for definitive identifiers for this specific lot.

Synthetic Utility

Chlorfenapyr is typically a target/analyte rather than a synthetic reagent. Its synthetic relevance to practicing chemists is mainly as follows:

• Reference standard: Used to validate extraction, cleanup, and detection workflows (e.g., QuEChERS LC–MS/MS) for halogenated heteroaromatics.
• Metabolite synthesis: Serves as a starting point for preparing and characterizing its active de-alkylated metabolite and other transformation products for toxicology and environmental fate studies.
• Structural motif insight: The molecule exemplifies design elements common in modern agrochemicals—polysubstituted pyrroles, heavy halogenation for metabolic stability, and bio-reversible masking groups (N-alkoxymethyl) for pro-activation.

Retrosynthetic considerations (general):

• Disconnections often target formation of the substituted pyrrole core (e.g., Paal–Knorr-type strategies or cyclizations from 1,4-dicarbonyl surrogates), followed by late-stage halogenation, aryl substitution, CF3 introduction, and N-alkoxymethyl protection.
• Regiochemical control in halogenation and arylation of the pyrrole nucleus is a key challenge addressed via directed metalation or cross-coupling approaches in literature syntheses.

Target Specificity

This section is primarily applicable to biological macromolecules (e.g., antibodies, enzymes). For this small-molecule library compound, no antigen/clone/isotype information applies.

• Target binding specificity data: Not specified for this item; refer to literature on mitochondrial uncouplers for mechanistic context.

Summary (general literature): Chlorfenapyr’s bioactivity arises from metabolic conversion to an uncoupling agent that broadly disrupts mitochondrial proton gradients rather than binding a single protein target with high specificity.