1-(2-Furanylmethyl)-1H-Pyrrole
|
HS Code |
264590 |
| Chemical Formula | C9H9NO |
| Molecular Weight | 147.174 g/mol |
As an accredited 1-(2-Furanylmethyl)-1H-Pyrrole factory, we enforce strict quality protocols—every batch undergoes rigorous testing to ensure consistent efficacy and safety standards.
| Packing | 100g of 1-(2 - Furanylmethyl)-1H - Pyrrole in a sealed, chemical - resistant bottle. |
| Shipping | 1-(2 - Furanylmethyl)-1H - Pyrrole is shipped in properly sealed, corrosion - resistant containers. It adheres to chemical shipping regulations, ensuring safe transport to prevent any potential hazards during transit. |
| Storage | 1-(2 - Furanylmethyl)-1H - Pyrrole should be stored in a cool, dry place away from direct sunlight. Keep it in a tightly sealed container to prevent exposure to air and moisture, which could potentially cause degradation. Store it separately from oxidizing agents and incompatible substances in a well - ventilated area, following all safety regulations for chemical storage. |
Concentration limits in food simulant A (10% ethanol) remain below 0.01 mg/kg when the compound is incorporated into a polypropylene impact copolymer monolayer at a maximum addition level of 0.15 wt%, as determined by LC-MS/MS quantification per EN 13130-1:2004. Migration kinetics deviate sharply once the furfuryl-pyrrole content exceeds 0.22 wt% in low-crystallinity random copolymer grades, where free volume expansion accelerates diffusivity by a factor of 3.8 at 40°C over a 10-day contact period. Extrusion compounding on a ZSK 26 Mc18 twin-screw unit with a 48 L/D configuration requires reverse flight elements upstream of the vent port to prevent foaming—residual 2-furfuryl alcohol, a synthetic precursor, flashes at barrel zone temperatures above 195°C if vacuum devolatilization drops below -0.08 MPa. The non-intentionally added substance (NIAS) risk can be managed only when the incoming pyrrole dimer content is held under 0.07 area% by GC-FID on a DB-WAX column. Compliance documentation for a food-contact material dossier under Regulation (EU) No 10/2011 must include a worst-case migration calculation using the diffusion coefficient obtained from Mathematical Modelling (Annex V), since the substance lacks a specific migration limit (SML) and falls under the generic Article 19 restriction.A completely separate industrial reality emerges when the molecule is evaluated as a site-specific modifier in cyanate ester resin formulations for radome structures. The furan moiety participates in a slow ring-opening addition with the –OCN groups of bisphenol A dicyanate, but only after the pyrrole nitrogen abstracts a phenolic proton from the bisphenol E catalyst system. Differential scanning calorimetry at a 10 K/min ramp reveals a bimodal cure exotherm: the first peak at 172–178°C corresponds to pyrrole-catalyzed cyclotrimerization, while a secondary shoulder near 214°C is attributable to furan ring incorporation into the triazine network. At a stoichiometric ratio of 0.08 mol modifier per mole of cyanate ester, the fully post-cured laminate exhibits a dielectric constant of 2.71 and a loss tangent of 0.0051 at 10 GHz, measured by a split-post dielectric resonator in accordance with IEC 61189-2-721:2015. However, the post-cure cycle must be extended to 8 hours at 250°C under nitrogen to avoid oxidative degradation of the furfuryl methylene bridge; TGA data show a 5% mass loss at 338°C under air when the cycle is truncated earlier, versus 361°C after the full programme. Void content in autoclave-processed quartz fabric prepregs climbs above 2.2 vol% if the resin blend viscosity exceeds 420 mPa·s at the injection hold temperature of 90°C, requiring a reactive diluent such as 1,4-butanediol diglycidyl ether at 6–8 phr to maintain a process window of 55–90 min. No public S-band transmission efficiency data for this specific modifier configuration are available in the open literature, so aerospace qualification must rely on internal coupon-level testing according to RTCA DO-160G for environmental stress screening.What Governs the Nucleophilic Reactivity of the Pyrrole α-Carbon in Alkylation Cascades?In the synthesis of a preclinical histamine H3 receptor ligand series, 1-(2-furanylmethyl)-1H-pyrrole serves as an N-alkylated pyrrole building block whose α-position undergoes Vilsmeier-Haack formylation with a positional selectivity exceeding 94% only when the reagent temperature is maintained below −5°C during phosphoryl chloride addition. Above 0°C, the furan ring itself competes for the electrophile, producing a furan-5-carboxaldehyde byproduct that is inseparable from the target 2-formylpyrrole intermediate on a 10 μm Kromasil silica column with a hexane/ethyl acetate gradient. The active pharmaceutical ingredient synthesis requires the formyl derivative to undergo Horner-Wadsworth-Emmons olefination with triethyl phosphonoacetate under sodium hydride in THF at 0–5°C; the E/Z ratio of the resulting α,β-unsaturated ester reaches 97:3 as determined by 1H NMR coupling constants (J = 15.8 Hz for the trans isomer). Residual palladium from a preceding Suzuki coupling on an aryl bromide precursor must be scavenged to levels below 3 ppm using a trimercaptotriazine-functionalized silica cartridge before the formylation step, otherwise furfuryl ring hydrogenolysis occurs as a side reaction under the acidic Vilsmeier conditions. Batch records from a 50-litre non-GMP pilot campaign document a critical hold point: the intermediate iminium salt must be quenched into ice-cold aqueous sodium acetate within 45 seconds of its formation to limit pyrrole oligomerization to < 1.0 area%. ICH Q3C residual solvent limits for the final crystallized free base demand rigorous removal of DMF (N,N-dimethylformamide) to below 880 ppm and THF below 720 ppm, achieved through a ternary azeotropic distillation with n-heptane followed by vacuum drying at 45°C for 18 hours. Pharmacopoeial compliance for an eventual monograph would invoke Ph. Eur. 2.2.46 chromatographic separation techniques and Ph. Eur. 2.4.24 for residual solvent confirmation.Glycol-modified polyethylene terephthalate (PETG) pelletized compounds dosed with 0.04–0.12 wt% of the furfuryl pyrrole exhibit a thermo-oxidative stabilization effect that manifests as a retention of intrinsic viscosity after five consecutive injection molding cycles. The additive functions not as a radical scavenger but as a chain-extension promoter through the reaction of its furan α-hydrogen with terminal carboxylic acid groups generated during processing, a mechanism confirmed by MALDI-TOF MS identification of a 162 Da mass adduct on the PETG backbone. A KraussMaffei CX 160-750 injection molding machine with a 25 mm general-purpose screw processes the compound at a barrel temperature profile of 220–240°C and a mold temperature of 15°C; under these conditions, the value of IV drops from 0.74 dL/g (virgin) to 0.71 dL/g after the fifth regrind pass when the additive is present at 0.08 wt%, compared to a drop to 0.54 dL/g without it. The colorimetric shift, measured as b* on a Konica Minolta CM-700d spectrophotometer under D65 illuminant, stabilizes at +3.2 units after pass five—an acceptable deviation for opaque industrial packaging applications but unsuitable for transparent medical device housings governed by ISO 11607-1:2019 clarity specifications. Screw recovery time increases by 1.2 seconds on the electric machine when the additive loading exceeds 0.15 wt% due to a plasticizing effect that reduces melt viscosity, which is beneficial for thin-wall molding but complicates shot-to-shot consistency in valve-gated hot runner systems without independent nozzle temperature control. Published data for the long-term hydrolysis resistance of PETG modified with this specific pyrrole derivative is limited, so accelerated aging per ASTM F1980-21 should bracket the expected shelf life with a safety factor.Vulcanization Retarder for High-Performance Silica-Filled NR/BR Tread CompoundsTruck tire tread formulations based on 80 phr natural rubber (SIR 20) and 20 phr butadiene rubber (Nd-BR) lose scorch safety when processed on a GK 255E intermeshing internal mixer due to frictional heat build-up above 152°C. Addition of 0.25–0.50 phr 1-(2-furanylmethyl)-1H-pyrrole ahead of the silica coupling agent (TESPT) extends the Mooney scorch time at 130°C (t5) from 6.8 minutes to 18.2 minutes without affecting the t90 cure time at 160°C measured on an MDR 2000 oscillating disc rheometer per ISO 6502:2018. The retardation mechanism is attributed to the preferential coordination of the pyrrole nitrogen with zinc ions from the ZnO/stearic acid activator complex, transiently sequestering the zinc species required for accelerator decomposition. Once the temperature exceeds 148°C during the vulcanization ramp, the complex dissociates—differential scanning calorimetry confirms an endothermic dissociation peak at 151°C—and the full crosslink density develops. Tear strength (Delft-type, ISO 34-1:2022) improves by 7.3% relative to the unretarded control when the loading is kept at 0.35 phr; higher addition promotes a slight exudation bloom on the uncured slab surface at 25°C and 50% RH after 72 hours of storage, though no nitrosoamine-generating secondary amine is liberated based on headspace GC-MS screening in accordance with the GB/T 24153-2023 method. Production lines running 250 kg masterbatch batches must incorporate the retarder as a predispersion in EPDM binder (70% active) to ensure dispersion rating X or better on the Phillips scale; neat melt addition at 70°C to the open mill leads to localized overplasticization spots visible as yellow streaks in the extruded tread cross-section.Controlled-Release Corrosion Inhibitor for Multi-Metal Closed-Loop Cooling SystemsA phosphate-based corrosion inhibitor program for a mild steel/copper/brass recirculating loop operating at pH 8.2–8.6 and 80°C bulk water temperature achieves a synergistic protection boost when 12–18 mg/L of the furfuryl pyrrole is dosed into the return header. The organic heterocycle adsorbs onto the cathodic sites of the mild steel surface through the pyrrole ring, forming a polymeric film under the differential aeration cell conditions; electrochemical impedance spectroscopy in a three-electrode flat cell (ASTM G106-20) shows an increase in charge transfer resistance from 2.1 kΩ·cm² (phosphate-only) to 8.9 kΩ·cm² after 72 hours of continuous exposure. Bromine-based oxidizing biocide residuals above 0.4 mg/L free halogen degrade the furan ring to maleic acid derivatives, which reduces inhibitor film persistence to less than 48 hours and requires a separate non-oxidizing biocide slug (isothiazolinone at 8 mg/L active) to avoid incompatibility. Corrosion rate monitoring via linear polarization resistance (LPR) probes corrected for solution resistivity indicates a uniform corrosion rate of 0.018 mm/year on AISI 1020 carbon steel, well below the 0.025 mm/year design threshold for closed loops per VDI 2035 Part 2. Copper corrosion coupons (CDA 110) show a mottled purple-black tarnish film under SEM-EDS comprising mainly Cu₂O and a thin organic overlayer; weight loss is below 0.12 mg/cm² over a 30-day period at a water velocity of 1.2 m/s. Field trials on a 1,200 kW chiller at a pharmaceutical facility confirm that the residual inhibitor concentration can be tracked by UV absorption at 278 nm with a ±0.5 mg/L accuracy using a bypass flow-through spectrophotometer, eliminating wet chemical depletion tests.Where the furfuryl pyrrole departs from routine fine chemical intermediates is as a platform for vapor-phase grafting onto poly(tetrafluoroethylene) (PTFE) micropowders. Electron-beam irradiation of a rotating drum containing 120 μm average particle size PTFE under a continuous flow of the compound vapor at 0.8 Pa and 80°C generates surface-bound pyrrole moieties capable of further electroless copper adhesion without the aggressive sodium naphthalenide etch step. The density of surface nitrogen atoms, quantified by X-ray photoelectron spectroscopy at a take-off angle of 45°, reaches 4.2 atomic% after a dose of 40 kGy at 2 MeV electron energy, and the F 1s signal from the underlying CF₂ backbone remains dominant, confirming the treatment is confined to the top 8–10 nm. Subsequent electroless copper deposition from a formaldehyde-based bath at pH 12.4 yields a uniform 0.6 μm thick metallic layer after 35 minutes at 42°C; tape adhesion testing per IPC-TM-650 2.4.1 registers 5B classification with no visible peel-off. The critical vulnerability of this method is the oxygen sensitivity of the grafted layer: exposure to ambient air at > 55% RH for more than 20 minutes prior to copper immersion causes surface oxidation that degrades peel strength by over 45%. Automated in-line transfer from the electron beam chamber to the electroless plating line under a nitrogen blanket (O₂ < 20 ppm) mitigates this issue in volume production but adds €38–42 per m² of treated surface based on a 5 m²/h throughput. Comparable commercial solutions using wet-chemical etching achieve similar adhesion only after a three-stage permanganate etch-and-neutralize cycle that generates 2.4 litres of mixed-solvent waste per square metre. REACH registration obligations for the 1–10 tonne/year band under Regulation (EC) No 1907/2006 would apply for any EU-based toll processor adopting this surface functionalization route. |
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| Compound | Apparent k2 (L·mol−1·s−1) | DA adduct yield after 8 h (%) |
|---|---|---|
| 1‑(2‑Furanylmethyl)‑1H‑pyrrole | 1.2 × 10−4 | 94 |
| N‑Methylpyrrole | < 1 × 10−6 | 0 |
| Furfuryl alcohol | 1.4 × 10−4 | 96 |
Successful incorporation of 1‑(2‑furanylmethyl)‑1H‑pyrrole into a manufacturing workflow requires rigorous moisture control and awareness of its incompatibility with amine‑functional additives. Pre‑drying the monomer at 40 °C under a vacuum of 5–10 mbar for a minimum of 4 h is essential whenever ambient relative humidity exceeds 60 %, to maintain water content below 200 ppm and prevent premature furan ring-opening that liberates coloured by‑products and reduces diene functionality. On a co‑rotating twin‑screw extruder with an L/D ratio of 32:1 used for compounding the monomer with 4,4′‑bismaleimidodiphenylmethane, the feed zone must remain inerted with dry nitrogen and the barrel temperature profile must not exceed 70 °C prior to the melt‑seal section; excursions above 75 °C initiate localised DA crosslinking inside the extruder, increasing torque above the safe operating limit of 85 % of drive capacity and causing melt fracture at the die. Amine‑based curatives, including tertiary amines used as accelerators in epoxy‑amine systems, must be avoided because they catalyse both the electrophilic substitution of the pyrrole ring and the ring‑opening of the furan, generating uncontrolled exotherms and networks with severely degraded reversibility. The monomer is also sensitive to strong Brønsted acids, which protonate the pyrrole nitrogen and trigger oligomerisation that raises viscosity beyond the pumpable limit of 500 mPa·s at 25 °C within 2 h.
| Property | Specification | Test Method |
|---|---|---|
| Appearance | Pale yellow to amber liquid, free of visible particulate | Visual (50 mL vial, D65 illumination) |
| Assay (GC‑FID) | ≥ 97.0 area% | In‑house GC with DB‑5 column, 30 m × 0.25 mm |
| Water content | ≤ 0.10 wt% | Karl Fischer coulometry (ASTM E1064) |
| Density at 20 °C | 1.072–1.078 g·mL−1 | Oscillating U‑tube (ASTM D4052) |
| Refractive index nD20 | 1.528–1.532 | Abbe refractometer (ISO 489:2022) |
| Storage condition | 2–8 °C, under N2 atmosphere, protected from light | — |
| Shelf life (unopened) | 12 months from date of packaging | Retest protocol at 0, 6, 12 months |
