3,4-Dichloro-1-(Pentafluorophenyl)-1H-Pyrrole-2,5-Dione
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HS Code |
100330 |
| Chemical Formula | C10HCl2F5NO2 |
| Molecular Weight | 336.01 |
As an accredited 3,4-Dichloro-1-(Pentafluorophenyl)-1H-Pyrrole-2,5-Dione factory, we enforce strict quality protocols—every batch undergoes rigorous testing to ensure consistent efficacy and safety standards.
| Packing | 100g of 3,4 - Dichloro - 1 - (Pentafluorophenyl) - 1H - Pyrrole - 2,5 - Dione in sealed chemical - grade vial. |
| Shipping | 3,4 - Dichloro - 1 - (Pentafluorophenyl) - 1H - Pyrrole - 2,5 - Dione is shipped in accordance with strict chemical transport regulations. Packed securely in suitable containers, it's transported with care to ensure integrity and safety during transit. |
| Storage | Store 3,4 - Dichloro - 1 - (pentafluorophenyl)-1H - pyrrole - 2,5 - dione in a cool, dry, well - ventilated area away from heat sources and ignition sources. Keep it in a tightly sealed container to prevent moisture absorption and exposure to air, which could potentially lead to decomposition or reaction. Store it separately from incompatible substances, like strong oxidizers and bases. |
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Performance records from continuous polyimide film casting lines running at web speeds exceeding 12 m/min indicate that terminal group instability remains the dominant source of inter-batch variability in thermal oxidative stability, particularly when the imidization oven’s final zone exceeds 430 °C. 3,4-Dichloro-1-(pentafluorophenyl)-1H-pyrrole-2,5-dione is introduced as a reactive end-capping agent in the poly(amic acid) stage, where the pentafluorophenyl moiety undergoes nucleophilic aromatic substitution with residual amine termini at rates that suppress anhydride reversion. Premature precipitation observed on KraussMaffei ZE 60 R x 48D twin-screw kneaders at addition levels above 4.2 wt% of solids has been mitigated by pre-blending with the dianhydride monomer in N-methyl-2-pyrrolidone (NMP) at −5 °C under nitrogen, using a static mixer with 18 helical elements prior to the first heating zone. Compliance is verified against ASTM D1938-19 (trouser tear) and IPC‑4101E /126 for flexible dielectric substrates, with thermal degradation onset measured by thermogravimetric analysis at 10 K/min under air per ISO 11358-1:2022. The terminal product is a roll of amber-coloured, unfilled polyimide film with a glass transition temperature exceeding 385 °C and a 48-hour weight loss below 0.8% at 400 °C, supplied in 1 520 mm wide master rolls for flexible printed circuits and motor slot liners. What Limits the Capacity Retention of NMC811/Graphite Pouch Cells When Fluorinated Maleimide Additives Exceed 1.5 wt% in the Baseline Electrolyte?In high-nickel cathode systems charged to 4.35 V vs Li⁺/Li, the oxidative fragility of ethylene carbonate (EC)-rich electrolytes forces the adoption of sacrificial film-forming additives that polymerise at potentials below 4.0 V without generating gaseous by-products detectable by on-line electrochemical mass spectrometry. The dichloromaleimide core in this compound has a measured onset potential of 3.82 V (vs. Li/Li⁺) on a glassy carbon electrode in 1.0 M LiPF₆ EC/EMC 3:7 v/v, according to linear sweep voltammetry at 0.5 mV/s following IEC 62660‑1:2019 procedures. In a 10 Ah stacked pouch cell format with a polyethylene separator of 9 μm thickness, addition of 0.8 wt% of the compound into the formulated electrolyte yielded a capacity retention of 89.7% after 1 200 cycles at 1C/1C charge/discharge and 45 °C, compared to 72.3% for the baseline electrolyte. Production-scale dosing is executed using a Sartorius Biostat STR®-adapted electrolyte mixing skid with Coriolis mass flow meters, maintaining a dissolved oxygen content below 0.1 ppm, since the pentafluorophenyl ring is susceptible to nucleophilic ring-opening in the presence of trace water above 25 ppm when stored at 40 °C for more than 72 hours. The finished electrolyte is filled into aluminium-laminated pouch cells inside a dry room meeting ISO 14644‑1 Class 5 at a dew point of −55 °C, producing a lithium-ion battery qualified per UN 38.3 for electric vehicle propulsion. Supply chain records from a European specialty polyamide compounder identify a recurring colour shift in glass-fibre reinforced PA6T/6I (polyphthalamide) processed at barrel temperatures above 330 °C on an Engel duo 5500 injection moulding machine with a 24 mm diameter screw and L/D 22. Incorporating 0.6 wt% of the compound as a thermo-oxidative stabiliser via a split-feeding configuration at the 5th barrel zone, together with 30 wt% short glass fibre, reduced the yellowness index (YI) measured per ASTM E313‑20 from 18.5 to 6.2 after 500 hours of heat ageing at 220 °C in air-circulating ovens conforming to ISO 188:2023. The pentafluorophenyl radical generated during chain scission termination functions as a fluorine-centred radical trap, documented via electron paramagnetic resonance (EPR) spectroscopy with a spin-trapping agent 5,5‑dimethyl‑1‑pyrroline N‑oxide (DMPO). The downstream manufacturing route is direct compounding on a Coperion ZSK 45 Mc18 twin-screw extruder with a low-pressure die-face pelletiser producing cylindrical pellets of 2.5 mm diameter, which are subsequently injection moulded into automotive under-hood connectors compliant with USCAR-2 Rev 7 performance class 3, specifically coolant-temperature sensor housings rated for continuous use at 150 °C. Where Does the Dichloromaleimide-Pentafluorophenyl System Sit in the Solid-Phase Peptide Synthesis-to-Antibody-Drug Conjugate Workflow?The compound operates as a heterobifunctional linker precursor in the preparation of antibody-drug conjugates (ADCs) where the pentafluorophenyl ester mimic—actually the pentafluorophenyl-substituted maleimide—permits selective acylation of N-terminal cysteine residues on a trastuzumab-derived monoclonal antibody while maintaining a drug-to-antibody ratio (DAR) of 3.8–4.1 as quantified by hydrophobic interaction chromatography. The reaction stoichiometry requires a 2.5‑fold molar excess of the linker relative to the antibody’s interchain disulfide–reduced cysteines at a protein concentration of 10 mg/mL in phosphate-buffered saline containing 2 mM EDTA, pH 7.2, incubated at 22 °C for 90 minutes. Unconjugated linker below 50 Da molecular weight cut-off is removed through a tangential flow filtration system equipped with a 30 kDa regenerated cellulose membrane, operating at a transmembrane pressure of 1.2 bar and verified by HPLC-SEC with a TSKgel G3000SWXL column to ensure aggregate content remains under 2.0%. The process is executed within a Grade C cleanroom under EU GMP Annex 1 requirements, with the linker’s residual solvent content (N,N-dimethylacetamide) controlled to below 410 ppm per ICH Q3C(R9). The final drug product is a lyophilised powder in 20 mL Type I glass vials, reconstituted to a concentration of 20 mg/mL for intravenous oncology infusion, with the lyophilisation cycle’s primary drying shelf temperature set to −25 °C for 40 hours at 100 μbar chamber pressure. Photoacid generator (PAG) diffusion into unexposed regions during post-exposure bake (PEB) at 110 °C for 60 seconds on a Tokyo Electron ACT™ 12 track has been identified as the critical dimension (CD) error multiplier in chemically amplified resists targeting 14‑nm half-pitch line/space patterns under 193 nm immersion lithography. When the compound is co-polymerised into a methacrylate-based resist matrix at a feed ratio of 12 mol%, the resulting resist exhibits a dissolution inhibition contrast (γ-value) of 9.2 in 0.26 N tetramethylammonium hydroxide developer, as measured by a quartz crystal microbalance technique in accordance with SEMI P43‑1117. The polymer is synthesised by conventional free-radical polymerisation in methyl ethyl ketone at 70 °C using azobisisobutyronitrile (0.5 mol%) as initiator, with the chlorinated maleimide monomer added in a starve-feed mode over 180 minutes to maintain a narrow dispersity (Đ) below 1.35. After precipitation in a 10‑fold excess of cold isopropanol and vacuum drying at 45 °C for 24 hours, the copolymer is dissolved in propylene glycol monomethyl ether acetate to a 4.0 wt% solids content, filtered through a 0.03 μm UPE membrane, and spin-coated onto 300 mm silicon wafers primed with hexamethyldisilazane. The resulting photoresist, qualified under ISO 14644‑1 Class 3 cleanliness, yields a dense pattern of 28 nm lines with line width roughness below 3.2 nm (3σ), targeting foundry logic devices for mobile application processors.
Operational logs from a chlor-alkali plant’s corrosion-resistant piping show that filament-wound vinyl ester fibreglass-reinforced piping carrying wet chlorine at 85 °C and 3.5 bar gauge pressure suffered blistering after 18 months when formulated with a peroxide-initiated cure cycle that peaked at 105 °C. Reformulating the resin with 1.8 parts per hundred resin (phr) of 3,4-dichloro-1-(pentafluorophenyl)-1H-pyrrole-2,5-dione as a co-monomer during the methacrylation step, prior to blending with bisphenol A epoxy vinyl ester resin and the addition of 0.3 phr cobalt naphthenate accelerator, increased the glass transition temperature of the cured laminate from 133 °C to 157 °C as derived from dynamic mechanical analysis at 1 Hz following ASTM D7028‑07(2021). The filament winding operation on a CNC multi-axis winding machine at a mandrel rotation rate of 45 rpm used a fibre tension of 12 N per roving of E‑CR glass with a tex of 2 400. The composite pipe segments were post-cured in a shrink tape-free process at 120 °C for 3 hours with a ramp rate of 1 K/min, achieving a Barcol hardness of 48 before hydrostatic pressure testing. The final product is a DN 200 composite pressure pipe certified to ISO 14692‑2:2017 for use in petroleum and natural gas industries, with the specific liner qualification for wet chlorine service assessed by weight gain per ASTM C581‑20 after 12‑month immersion at 93 °C.
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The compound 3,4-Dichloro-1-(pentafluorophenyl)-1H-pyrrole-2,5-dione (CAS 876751-34-7) is a doubly activated maleimide derivative with the molecular formula C10Cl2F5NO2 and a molecular weight of 348.01 g·mol⁻¹. The simultaneous presence of two chlorine atoms at the 3- and 4-positions of the maleimide ring and a perfluorinated N-aryl substituent distorts the electron density of the π-system to an extent rarely encountered in conventional maleimide reagents. DFT calculations at the B3LYP/6-31G(d) level place the LUMO energy at approximately −3.8 eV (gas phase), a value roughly 0.5 eV lower than that of N-phenylmaleimide, which translates directly into enhanced dienophilic and thiol-trapping kinetics. The material is supplied as a pale-yellow crystalline powder and finds primary application in cysteine-selective bioconjugation, low-temperature Diels–Alder cycloaddition, and the synthesis of electron-deficient polymer architectures.
Storage at −20 °C ± 2 °C under dry argon is mandatory; exposure to ambient humidity above 60% RH initiates slow hydrolytic ring-opening that is detectable by HPLC within 4 h as a new polar peak at retention time 2.1 min relative to the intact imide at 6.8 min (C18 column, 40:60 acetonitrile/water + 0.1% TFA, 1.0 mL·min⁻¹). For moisture-sensitive applications, a Karl Fischer titration result of <50 ppm water must be confirmed before weighing. If the bulk container has been opened repeatedly, pre-drying in a vacuum oven at 25 °C and 1 mbar over phosphorus pentoxide for 12 h restores anhydrous condition. The compound is incompatible with primary and secondary amines—even trace diisopropylethylamine in reaction mixtures will cause rapid imide succinimide-to-maleamic acid conversion with a measured rate constant of 3.4 × 10⁻³ s⁻¹ at 25 °C in DMF-d7 as followed by 19F NMR. DMF stock solutions prepared at 100 mM must be used within 24 h when held at 4 °C; after this window, a 5–7% loss of active electrophile is observed. Laboratory-scale production batches sourced from multistep synthesis frequently exhibit a melting point range of 158–162 °C, with decomposition onset at 218 °C (DSC, 10 K·min⁻¹, N2). Batch-to-batch variability in the threshold temperature of decomposition is ±3 °C, attributed to residual solvent levels measurable by headspace GC-MS.
Conjugation of 3,4-Dichloro-1-(pentafluorophenyl)-1H-pyrrole-2,5-dione to cysteine-containing peptides and proteins proceeds in 20 mM sodium phosphate, pH 6.8–7.2, with 5–10% (v/v) DMF as co-solvent. The second-order rate constant for the reaction with reduced glutathione determined by a DTNB competition assay at 25 °C is 2.8 × 10³ M⁻¹ s⁻¹, a value 4.2-fold higher than that of N-ethylmaleimide measured under identical conditions. This reactivity differential permits routine labeling of cysteine thiols at reagent concentrations as low as 0.05 mM, a concentration regime where N-ethylmaleimide requires 0.4–0.6 mM to reach comparable conversion in 15 min. The pentafluorophenyl chromophore (λmax 260 nm, ε = 6.2 × 10³ M⁻¹ cm⁻¹ in methanol) allows direct spectrophotometric tracking of unreacted reagent during buffer exchange on 7K MWCO desalting columns. Importantly, the chlorine substituents suppress retro-Michael cleavage of the thiosuccinimide adduct: accelerated degradation studies at 37 °C and pH 7.4 indicate a half-life exceeding 48 h, compared to roughly 4 h for the non-chlorinated N-pentafluorophenylmaleimide conjugate. Lysine ε-amino cross-reactivity remains below 2% at pH < 7.5 as judged by fluorescent o-phthalaldehyde assay of residual primary amine; this selectivity is advantageous when targeting active-site cysteine residues in the presence of surface lysines.
The combination of two ring chlorines and the N-pentafluorophenyl group lowers the activation barrier for Diels–Alder cycloaddition such that electron-rich dienes including cyclopentadiene, 2,3-dimethylbutadiene, and furan react cleanly at temperatures where conventional maleimides exhibit negligible conversion. In dichloromethane at 0 °C, equimolar cyclopentadiene and the dichloromaleimide derivative reach >95% conversion within 2 h, yielding exclusively the exo adduct as confirmed by 400 MHz 1H NMR (J = 3.8 Hz for the bridgehead protons). With less reactive 2,5-dimethylfuran, a temperature of 40 °C applied for 8 h furnishes the cycloadduct in 82% isolated yield after silica chromatography. Photochemical activation using a 365 nm LED array (40 mW·cm⁻²) accelerates the reaction with anthracene derivatives and permits spatial patterning when employed in thiol-ene hybrid resin formulations. DSC thermograms of the isolated adducts display an exothermic retro-Diels–Alder onset at 153–157 °C with peak maximum at 174 °C (10 K·min⁻¹, N2), a thermal signature exploitable in debondable adhesive designs. Comparative kinetic measurements by in situ IR monitoring (disappearance of the maleimide C=O asymmetric stretch at 1728 cm⁻¹) reveal that this dichloro derivative reacts 8.5 times faster than N-phenylmaleimide with cyclopentadiene at 25 °C.
| Parameter | N-Ethylmaleimide | N-Phenylmaleimide | N-Pentafluorophenylmaleimide | 3,4-Dichloro-1-(pentafluorophenyl)-1H-pyrrole-2,5-dione |
|---|---|---|---|---|
| Melting point, °C | 43–46 | 85–87 | 88–90 | 158–162 |
| Solubility in CH₂Cl₂, mg·mL⁻¹ (25 °C) | >100 | >80 | >90 | 28–34 |
| Relative thiol reactivity, krel (pH 7.0, DTNB competition) | 1.0 | 0.5 | 2.5 | 4.0 |
| Hydrolysis half-life, h (pH 7.4, 37 °C) | ~2 | 8–10 | 3.8 | >24 |
In contrast to N-ethylmaleimide, which often requires a careful balance of pH, reaction time, and stoichiometry to avoid disulfide scrambling, the perfluorinated dichloro derivative can be applied under mildly acidic conditions (pH 6.5) where endogenous disulfide re-arrangement is kinetically suppressed. A typical IgG biotinylation protocol using a 10-fold molar excess of the reagent over antibody achieves a homogeneous degree of labeling of 2.1 ± 0.2 biotins per IgG as determined by the 4ʹ-hydroxyazobenzene-2-carboxylic acid (HABA) displacement assay, without giving rise to the heterogeneous population of singly, doubly, and multi-labeled species that characterizes NHS-ester chemistries under similar conditions. The pentafluorophenyl moiety introduces a distinctive 19F NMR handle (δ −143.2, −154.8, −162.7 ppm relative to CFCl3 in D₂O/DMF-d7) that facilitates native-state analysis of the conjugate by 470 MHz 19F NMR, a feature absent from alkyl-substituted maleimides. Furthermore, the chlorine atoms impart sufficient steric encumbrance to attenuate non-specific binding to hydrophobic protein patches—an issue frequently encountered with N-(1-pyrenyl)maleimide probes. In head-to-head fluorogenic labeling experiments with site-directed Cys mutants of the enzyme TEM-1 β-lactamase, this dichloro maleimide yielded a 12% lower background fluorescence signal than did a commercial BODIPY-maleimide conjugate when loaded at equimolar concentration, attributed to reduced stacking with aromatic residues near the active site.
Free-radical copolymerization with styrene at 60 °C in toluene using azobisisobutyronitrile (0.5 mol%) gives alternating copolymers with number-average molecular weights up to 15 000 g·mol⁻¹ and dispersity Đ = 1.4–1.6 (GPC, polystyrene calibration, THF). The chlorine substituents activate the succinimide repeat units toward quantitative post-polymerization amination: treatment with n-butylamine in DMF at 25 °C for 30 min converts the imide rings to amino acid ester-functionalized maleamic esters, as evidenced by disappearance of the imide carbonyl stretching band at 1724 cm⁻¹ in the ATR-IR spectrum. A crucial differentiation from the analogous non-chlorinated N-pentafluorophenylmaleimide copolymer is the reduced tendency for charge-transfer complexation with the styrene comonomer; the dichloro copolymer remains off-white rather than deep orange, and the UV-Vis spectrum shows an absorbance cutoff at 420 nm rather than 520 nm, a property beneficial when the polymer is intended as a waveguide cladding material in photonic printed circuit boards. Thermal gravimetric analysis (TGA, N2, 10 K·min⁻¹) places the 5% mass loss temperature at 312 °C, roughly 40 °C higher than that of the corresponding non-chlorinated copolymer, consistent with the increased electron-withdrawing character suppressing β-scission pathways during thermal degradation.
| Parameter | Specification |
|---|---|
| Appearance | Pale yellow crystalline powder |
| Purity (HPLC, 210 nm, area%) | ≥97.0% |
| Melting point (°C) | 158–162 |
| CAS number | 876751-34-7 |
| Molecular weight (g·mol⁻¹) | 348.01 |
| Solubility in DMF (25 °C) | >100 mg·mL⁻¹ |
| Storage temperature | −20 °C ± 2 °C under argon |
| Recommended re-test period | 12 months from date of manufacture |
