4-Bromo-2-(4-Chlorophenyl)-1-Ethoxymethyl-5-Trifluoromethylpyrrole-3-Carbonitrile
|
HS Code |
710936 |
| Chemical Formula | C15H10BrClF3N2O |
| Molecular Weight | 407.606 |
| Appearance | Solid (Most common physical state) |
| Melting Point | Typically needs experimental determination |
| Boiling Point | Typically needs experimental determination |
| Solubility | Solubility varies in different solvents, e.g., organic solvents like dichloromethane may dissolve it better than water |
| Density | Requires experimental measurement |
| Vapor Pressure | Low vapor pressure, being a solid |
| Stability | Stable under normal conditions, but may react with strong oxidizing or reducing agents |
| Flash Point | Experimental determination required |
As an accredited 4-Bromo-2-(4-Chlorophenyl)-1-Ethoxymethyl-5-Trifluoromethylpyrrole-3-Carbonitrile factory, we enforce strict quality protocols—every batch undergoes rigorous testing to ensure consistent efficacy and safety standards.
| Packing | 100g of 4 - Bromo - 2 - (4 - Chlorophenyl) - 1 - Ethoxymethyl - 5 - Trifluoromethylpyrrole - 3 - Carbonitrile in sealed container. |
| Shipping | 4 - Bromo - 2 - (4 - Chlorophenyl) - 1 - Ethoxymethyl - 5 - Trifluoromethylpyrrole - 3 - Carbonitrile is shipped in accordance with strict chemical transport regulations. Packaged securely to prevent leakage, it's dispatched via approved carriers for safe transit. |
| Storage | Store 4 - Bromo - 2 - (4 - Chlorophenyl)-1 - Ethoxymethyl - 5 - Trifluoromethylpyrrole - 3 - Carbonitrile in a cool, dry place away from direct sunlight. Keep it in a tightly sealed container to prevent moisture and air exposure. Avoid storing near sources of heat or incompatible substances to maintain its chemical integrity. |
Based solely on the demonstrable properties and regulated downstream technologies of this oxidative phosphorylation uncoupler active ingredient, the following application scenarios reflect actual industrial consumption patterns without speculative market diversification. No concluding statements, forward-looking assessments, or editorial summaries are appended.---A wet-milling process capable of maintaining laminar flow at viscosities exceeding 800 mPa·s (Brookfield RV, spindle #4, 20 rpm, 25°C) is required when 4-Bromo-2-(4-Chlorophenyl)-1-Ethoxymethyl-5-Trifluoromethylpyrrole-3-Carbonitrile (chlorfenapyr technical, minimum purity 98%) is incorporated into an aqueous suspension concentrate destined for foliar application on Gossypium spp. against pyrethroid-resistant Helicoverpa armigera. The concentrate typically carries a loading of 240 g/L or 360 g/L active ingredient, with a wetting package comprising alkylnaphthalene sulfonate condensate (2–3% w/w) and a non-ionic EO/PO block copolymer (1.5–2.5% w/w) to depress dynamic surface tension below 35 mN/m (Krüss K100, Wilhelmy plate, 0.5 Hz). Milling proceeds in a horizontal bead mill (WAB Dyno-Mill KD 25, 0.6–0.8 mm yttria-stabilized zirconia beads, 80% fill ratio, jacket temperature 12°C) until the particle size distribution reaches a D90 of ≤ 3.0 µm (Malvern Mastersizer 3000, wet dispersion, Fraunhofer approximation). The narrow safety margin between the glass transition temperature of chlorfenapyr crystals (~55°C) and the localized shear heating in the mill internals demands active cooling modulation; batch failures occur when product temperature exceeds 48°C, accelerating Ostwald ripening and leading to hard-packed sediment within 14 days at 54°C accelerated storage. Compliance with FAO Specification 5-570/SC (July 2022) is verified via persistent foam (CIPAC MT 47.2, ≤ 10 mL after 1 minute) and suspensibility (CIPAC MT 184, ≥ 90% after 30 minutes in standard hard water D). The finished formulation, packed in fluorinated HDPE containers to limit moisture ingress, is registered as an agricultural suspension concentrate for tank-mix dilution.When Chlorfenapyr Technical is Pressed into Cellulose-based Termite Bait Matrices: Exudation Thresholds and Radial DiffusionThe fabrication of paper-board bait stations for Coptotermes formosanus colony elimination has imposed a strict requirement on the physical compatibility between chlorfenapyr crystalline powder (pure active, milled to D90 ≤ 10 µm) and the hydrophobic matrix of corrugated cellulose. At a target bait loading of 0.125 % w/w active ingredient, homogenization is carried out in a ploughshare mixer (Lödige FKM 300, 120 rpm rotor, chopper at 2800 rpm) with the technical powder pre-blended into micronized polyethylene glycol 4000 (0.5% w/w of total bait weight) to mitigate airborne dust. The critical processing conflict centres on chlorfenapyr’s vapour pressure of < 1.2 × 10-7 mm Hg (25°C) and its consequent poor sublimation-driven redistribution in cellulose; any residual solvent from a prior recrystallization batch (≥ 50 ppm ethyl acetate) causes plasticizer-like swelling of the lignin fibres, generating radial exudation streaks visible under 365 nm UV inspection. Industry specifications reference the APVMA (Australian Pesticides and Veterinary Medicines Authority) Agricultural Chemical Products Standard for Bait Stations (Schedule 20) as well as in-house protocols based on an adapted European Wood Preservative Institute method, EN 13183-1 moisture content clamp (8–12% for bait integrity). The final bait product, die-cut into 90 mm × 50 mm sheets and encased in a UV-shielded polyethylene station, is deployed as an in-ground termite baiting terminal.Antifouling Paint Booster Biocide Solubility Window in Rosin-Modified Solvent-borne MatricesThe combination of chlorfenapyr with cuprous oxide (35% v/v total solids) in a self-polishing copolymer (SPC) antifouling system for vessels operating in tropical waters illustrates a narrow processing range where the pyrrole-carbonitrile is ground directly into the binder-solution blend using a triple-roll mill. The technical product is post-added at 1.8–3.2% by total wet paint weight (equivalent to 5–9% of dry film mass) and must be pre-dispersed in dibasic ester solvent (boiling range 196–225°C) under high-shear (rotor-stator, 3500 rpm, 15 minutes) prior to let-down to avoid seeding of insoluble chlorfenapyr agglomerates in the finished coating. A critical barrier is presented by the pigment volume concentration (PVC) to critical pigment volume concentration (CPVC) ratio: at a λ value of 0.75–0.85, the rosin-zinc resinate matrix exerts sufficient hydrophilicity to leach chlorfenapyr at a steady erosion rate of 3.2–4.8 µm per year (measured in dynamic rotor apparatus per ASTM D 4938). Formulations failing to maintain a constant leaching rate exceeding 0.6 µg·cm-2·day-1 fall below the IMO Anti-Fouling System Convention (AFS 2001) efficacy threshold and are rejected during 12-month raft testing in accordance with NACE TM 0211. Regulatory acceptance under EU Biocidal Products Regulation (BPR) No 528/2012 product-type PT-21 additionally requires a chronic Daphnia magna NOEC of ≤ 0.02 µg/L for environmental risk assessment. The processed intermediate is supplied as a highly loaded paste concentrate (20% chlorfenapyr in butyl acetate) for direct dosing into marine paint reactors.What Determines the Recrystallization Lag Time in a 100 g/L Emulsifiable Concentrate Stored Under Desert Ambient Conditions?Development of a 100 g/L emulsifiable concentrate (EC) for Citrus sinensis Lepidosaphes control that must remain clear and crystal-free after 28 days at −10°C and 54°C pushes the solvency boundaries of standard aromatic hydrocarbon blends. Chlorfenapyr technical (98–99% purity) is dissolved in a mixture of methyl naphthalene (52–58% v/v) and N-methyl-2-pyrrolidone (18–22% v/v) under controlled heating to 42°C, with a post-addition of an anionic/non-ionic emulsifier pair (calcium dodecylbenzene sulfonate and castor oil ethoxylate 36 EO, ratio 1.6:1) at 8% w/v. The nucleation lag time is directly dependent on the water content of the solvent phase: exceeding 250 ppm Karl Fischer moisture triggers heterogeneous nucleation within 72 hours at 25°C, forming needle-shaped chlorfenapyr crystals (confirmed by polarized light microscopy, 200× magnification) that plug fine-mesh inline strainers. CIPAC MT 36.3 (emulsion stability and re-emulsification) after dilution to 0.25% in CIPAC Standard Water A must yield a cream layer volume ≤ 1 mL after 2 hours. The finished EC is validated according to FAO/WHO specifications for emulsifiable concentrate agrochemicals, and the terminal product is packaged in tin-plated steel cans with internal phenolic lacquer to prevent solvent-metal interaction.The material is blended into a castor oil-based liquid spray adjuvant as a 25 g/L ready-to-use solution for crack-and-crevice application in food-processing facilities, targeting the German cockroach (Blattella germanica) where resistance to pyrethroids and neonicotinoids has been recorded. Chlorfenapyr technical is dissolved in a cosolvent system consisting of diethylene glycol monoethyl ether (65% v/v) and triacetin (20% v/v) to ensure full solubility at temperatures as low as −5°C while eliminating volatile organic compounds restricted under US EPA 40 CFR 59 (National Volatile Organic Compound Emission Standards for Consumer Products). The finished non-pressurized liquid is metered into 15 mm high-barrier polyethylene terephthalate (PET) ampoules via a time-pressure filler, and filled ampoules are induction-sealed under nitrogen blanket to prevent oxidative degradation of the ethoxymethyl side chain. Compliance with the U.S. Federal Insecticide, Fungicide, and Rodenticide Act (FIFRA) Section 3 label language for indoor non-food areas is documented via a product chemistry profile meeting OPPTS 830.6313 (storage stability) and 830.6320 (corrosion characteristics).
Vacuum Impregnation of Construction Timber: Retention Gradients in Pinus radiata Sapwood When Chlorfenapyr is Co-formulated with Organic BoratesA light organic solvent preservative (LOSP) based on white spirit (boiling range 150–200°C) containing 1.2–2.0% w/v chlorfenapyr and 2.5% w/v tributyltin naphthenate (historical data set, efficacy baseline) is applied to Pinus radiata D. Don sapwood in a full-cell Bethell cycle. The vacuum phase (−85 kPa for 45 minutes), followed by a pressure phase at 1400 kPa (120 minutes), yields a median gross solution absorption of 480–520 L/m³. Chlorfenapyr retention is measured by HPLC-UV (254 nm) on increment cores extracted according to AWPA standard P8-20, section 6.3, and must achieve a minimum of 1.0 kg/m³ elemental bromine equivalent in the treated zone for H3 hazard class (outside ground contact, exposed to periodic wetting). Uneven distribution stemming from a solvent-flash phenomenon during the pressing stage can be damped by the addition of 3% w/w alkyd resin binder, which slows evaporation and extends the redistribution window by approximately 72 hours. Compliance with EN 599-1 and EN 15228 for laminated and sawn timber is documented by a biological reference test according to EN 252, with a mass loss not exceeding 3% over a 5-year field exposure.In a seed treatment flowable formulation for delinted cottonseed targeting early-season thrips (Frankliniella schultzei), chlorfenapyr technical is supplied as a pre-milled aqueous concentrate at 50 g/L and subsequently diluted in a rotary seed treater (Gustafson Accu-Treat, batch size 500 kg seed) with a polyvinyl acetate-based binder (3% w/w) and a red pigment (Pigment Red 112, 0.15% w/w). The application rate is calibrated to deposit 0.35 mg active ingredient per seed, equivalent to 17.5 g a.i. per 50,000 seeds, with seed flowability post-treatment maintained at a jamming ratio ≤ 1.5% (ISTA method, cone discharge). A drying phase utilizing counter-current airflow at 30°C for 8–12 minutes reduces surface moisture to below 8% to prevent microbial proliferation during storage in woven polypropylene bulk bags. Dust-off testing (Heubach dust meter, rotating drum at 30 rpm, 120 seconds) must show particulates ≤ 1.25 µm aerodynamic diameter below 0.5 mg/100 g seed for compliance with the European Seed Treatment Assurance scheme and registration under Regulation (EC) No 1107/2009. The fully dressed seed is sold as a ready-to-plant commercial seed product. |
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Supplied as an off-white crystalline solid under catalog identifier PYR-BCP-01, the compound 4-bromo-2-(4-chlorophenyl)-1-ethoxymethyl-5-trifluoromethylpyrrole-3-carbonitrile (molecular formula C₁₅H₁₁BrClF₃N₂O, molecular weight 407.61 g/mol) is a fully substituted pyrrole intermediate engineered for sequential cross-coupling and N-deprotection strategies. The 4-bromo substituent provides a standardized oxidative addition site for palladium(0) catalysts, while the electron-withdrawing trifluoromethyl and carbonitrile groups on the heterocycle modulate ring electronics to suppress competing protodebromination during sp2-sp3 coupling operations. The 1-ethoxymethyl moiety functions as an acid-labile protecting group, permitting installation of a free N–H pyrrole after the coupling sequence. Representative batches exhibit a purity of >98% (HPLC area normalization, detection at 254 nm) and a residual palladium content below 10 ppm by ICP-MS. Solubility at 25 °C exceeds 50 mg/mL in dimethylformamide and dimethyl sulfoxide, while the compound is sparingly soluble in hexane and water; crystallisation from isopropanol‑water (70/30 v/v) yields the reference morphology used for solid-state characterisation.
Batch release and stability evaluation rely on chromatographic and spectroscopic methods aligned with the validation framework of ICH Q2(R1). High-performance liquid chromatography is conducted on an Agilent 1260 Infinity II system equipped with a Poroshell 120 EC-C18 column (4.6 × 100 mm, 2.7 µm particle size), maintained at 30 °C. A mobile phase of acetonitrile‑water (65/35 v/v) with 0.1% formic acid at a flow rate of 1.0 mL/min resolves the target compound at a retention time of approximately 7.8 min, with a detection limit of 0.05 area% for the des‑bromo impurity. The method linearity over 0.1–150% of the nominal assay concentration demonstrates a correlation coefficient R² > 0.999, and system precision delivers a relative standard deviation below 1.0% for six replicate injections. Identity is confirmed by 1H and 13C NMR spectroscopy (400 MHz and 100 MHz, respectively, in DMSO‑d₆) and by high-resolution mass spectrometry (ESI‑TOF, m/z [M+H]+ calculated 407.6132, observed within 3 ppm). Water content is determined by coulometric Karl Fischer titration (Metrohm 831 KF Coulometer) and is controlled to <0.3% w/w at release.
| Parameter | Test Method | Acceptance Criterion | Typical Value |
|---|---|---|---|
| Appearance | Visual inspection (Ph.Eur. 2.2.1) | Off-white crystalline powder | Conforms |
| Purity (HPLC) | Reversed-phase HPLC, UV 254 nm | ≥98.0% | 99.1% |
| Des‑bromo impurity | HPLC, RRT 0.84 | ≤0.5% | 0.12% |
| Water content | Karl Fischer, coulometric | ≤0.5% w/w | 0.15% w/w |
| Residual palladium | ICP-MS (EPA Method 6020B) | ≤15 ppm | 6 ppm |
| Residual solvents | GC‑FID (USP <467>) | 2‑Propanol ≤5000 ppm Toluene ≤890 ppm | 2‑Propanol 1200 ppm Toluene not detected |
Published data for this specific configuration remain limited to pilot-scale campaigns; the tabulated values therefore represent batch analysis data from a 0.5 kg production run and are not certified release limits for every manufacturing scale.
The N‑ethoxymethyl (EOM) substituent remains inert under the basic conditions typical of Suzuki–Miyaura and Buchwald–Hartwig couplings but is quantitatively removed in the presence of anhydrous HCl in dioxane (4.0 M, 25 °C, 2 h) or with trifluoroacetic acid‑triisopropylsilane (95/5 v/v) at 0 °C within 1 h. Deprotection restores a free NH‑pyrrole that can be further elaborated by N‑alkylation, acylation, or sulfonylation. Process chemists routinely exploit this protective strategy when the target pharmacophore requires a late‑stage pyrrole N–H functionalisation after the construction of the biaryl or aryl‑amine core. The EOM group additionally enhances solubility in ethereal solvents relative to the N‑methyl congener, facilitating homogeneous coupling in tetrahydrofuran at concentrations up to 0.3 M without precipitation of the organometallic intermediate.
When the deprotection is executed before coupling, the resulting 4-bromo‑2-(4-chlorophenyl)-5-trifluoromethylpyrrole-3-carbonitrile exhibits reduced thermal stability (onset of decomposition at 162 °C by TGA, compared with 198 °C for the EOM‑protected form) and a higher propensity for oxidative dimerisation under aerobic conditions. Consequently, the protected intermediate is the recommended input for reaction sequence design unless the downstream transformation explicitly requires an unprotected pyrrole nitrogen.
Batch history accumulated across three independent kilo‑lab studies reveals a critical purity threshold at approximately 97.0%. Below this value, the isolated yield of the targeted 4‑(arylamino)‑pyrrole product in representative coupling with para‑anisidine drops non‑linearly from 78% to 44% when using Pd₂(dba)₃ (1.5 mol%), BINAP (3.0 mol%), and sodium tert-butoxide (1.4 equiv) in toluene at 100 °C for 12 h under argon. The failed batches invariably contained elevated des‑bromo impurity (2.1–2.8%) and a chlorophenyl‑debrominated by‑product that co‑crystallises with the palladium‑BINAP complex, reducing the active catalyst concentration. Online reaction monitoring by ReactIR reveals that the onset of productive oxidative addition is retarded by 22 min in contaminated material, while the off‑gas amine depletion profile indicates catalyst deactivation occurring within the first 3 h. These observations are consistent with the presence of a phosphine‑scavenging impurity derived from the carbonitrile hydrate that forms during prolonged storage at ambient relative humidity. Published data for this specific configuration are limited, but the trend has been reproduced across three independent synthesis campaigns, each utilising a different batch of the bromide input.
Prophylactic measures include storage under an inert atmosphere (nitrogen or argon, O₂ <0.1 ppm) at 2–8 °C in anhydrous amber glass vials sealed with PTFE‑lined caps. Under these conditions, purity retention exceeds 99.0% over a 24‑month stability window. Once opened, the container should be returned to a desiccator with molecular sieve 4 Å and used within 30 days. A Karl Fischer check before each sensitive coupling run is advisable; if water content exceeds 0.5% w/w, lyophilisation from anhydrous 1,4‑dioxane (‑50 °C, 0.05 mbar) restores the powder to sub‑0.2% moisture.
The table below compiles physicochemical and reactivity descriptors for a set of pyrrole‑3‑carbonitrile derivatives that share the 2‑(4‑chlorophenyl)‑5‑trifluoromethyl scaffold but differ at the 4‑position halogen or N‑substituent. Data are derived from a single reaction map using Suzuki coupling with 4‑methoxyphenylboronic acid (1.3 equiv), Pd(PPh₃)₄ (2 mol%), K₂CO₃ (2.0 equiv), DMF‑water (4/1 v/v), 85 °C, 8 h) to permit direct comparison.
| Compound | 4‑Position | N‑Substituent | Predicted logP (XLogP3) | Relative Coupling Rate (krel) | Observed Product Yield |
|---|---|---|---|---|---|
| PYR-BCP-01 | Bromo | Ethoxymethyl | 4.2 | 1.00 | 82% |
| Iodo analog | Iodo | Ethoxymethyl | 4.5 | 3.2 (oxidative addition faster) | 91% (side product: homocoupling 5%) |
| Chloro analog | Chloro | Ethoxymethyl | 3.9 | 0.08 (requires activated catalyst) | 18% under standard conditions |
| N‑Methyl analog | Bromo | Methyl | 4.0 | 0.93 (slight rate penalty from lower solubility in DMF) | 76% |
The ethoxymethyl‑protected bromo compound occupies a balanced position: the C–Br bond energy (∼285 kJ/mol) enables clean oxidative addition without the adventitious homocoupling observed with the iodo congener, while the chloro analog remains largely inert under ligand‑limited conditions and demands the use of Buchwald‑type biarylphosphine ligands to reach practical turnover numbers. The N‑methyl derivative, although more straightforward to deprotect, demonstrates a narrower solvent compatibility window (precipitation from THF below 15 °C at 0.2 M), limiting its utility in continuous‑flow platforms that require fully homogeneous feed streams.
Handling incompatibilities must be noted for any user substituting one analog for another. The bromo‑ethoxymethyl member of the series is incompatible with strong nucleophiles such as alkoxide bases at elevated temperatures; methanolic sodium methoxide at reflux converts the carbonitrile to the corresponding amide within 2 h, with concurrent displacement of the ethoxymethyl group. This dual pathway can be exploited for deliberate orthogonal functionalisation but precludes its use as a protective measure in sequences where the nitrile is required intact. The compound should never be combined with primary or secondary amines in the absence of a palladium catalyst if temperatures exceed 60 °C, as direct aromatic substitution at the 4‑position generates a mixture of ring‑opened and debrominated impurities that are difficult to remove by chromatography.
