Methyl 2-Pyrrolecarboxylate
|
HS Code |
410582 |
| Chemical Formula | C6H7NO2 |
| Molar Mass | 125.13 g/mol |
| Appearance | Colorless to light yellow liquid |
| Boiling Point | 218 - 220 °C |
| Density | 1.12 g/cm³ |
| Solubility In Water | Insoluble |
| Solubility In Organic Solvents | Soluble in common organic solvents like ethanol, ether |
| Flash Point | 95 °C |
| Odor | Characteristic odor |
| Stability | Stable under normal conditions |
| Purity | Typically available in high purity (e.g., 98%+) |
As an accredited Methyl 2-Pyrrolecarboxylate factory, we enforce strict quality protocols—every batch undergoes rigorous testing to ensure consistent efficacy and safety standards.
| Packing | Methyl 2 - Pyrrolecarboxylate, 500g, packaged in a sealed, corrosion - resistant bottle. |
| Shipping | Methyl 2 - Pyrrolecarboxylate is shipped in well - sealed containers, compliant with chemical transport regulations. Packaging safeguards against leakage. Shipment is via carriers experienced in handling hazardous chemicals, ensuring safe and timely delivery. |
| Storage | Methyl 2 - Pyrrolecarboxylate should be stored in a cool, dry, well - ventilated area, away from heat sources and open flames. Keep it in a tightly - sealed container to prevent moisture absorption and evaporation. Store it separately from oxidizing agents and reactive chemicals to avoid potential reactions. Ensure proper labeling for easy identification. |
The Methyl Ester Intermediate Route to Pyrrole-Containing Protease InhibitorsIn the cGMP synthesis of antiviral protease inhibitors targeting HIV-1 or human cytomegalovirus, methyl 2-pyrrolecarboxylate functions as a masked 2‑carboxypyrrole synthon that undergoes N‑alkylation before further elaboration into the pharmacophore. The ester is received with a purity specification of ≥99.0% (GC, area normalization) and an individual residual solvent profile controlled to ≤500 ppm methanol and ≤100 ppm DMF under ICH Q3C guidelines, with certificates of analysis cross‑referenced to USP 〈467〉 Procedure A. Typical stoichiometry for the N‑alkylation step, conducted in jacketed glass‑lined reactors (Pfaudler AE‑series, 6,300 L working volume equipped with retreat‑curve impellers), uses 1.00–1.05 molar equivalents of the alkylating agent relative to the methyl ester, charged alongside powdered anhydrous potassium carbonate (2.5–3.0 eq) in dimethylformamide held at ≤0.1% water by Karl Fischer titration. The batch is heated to 68–72 °C under a dry nitrogen sweep for 16–22 h until in‑process HPLC (C18, 215 nm) shows residual ester <0.5 area%. Premature moisture ingress above 0.15% H₂O leads to partial saponification of the methyl ester, generating the free acid that forms a poorly filterable gelatinous phase during aqueous work‑up, a failure mode documented on production‑scale campaigns where bulk drying of the recovered toluene extract over molecular sieves 4A restored the acid number below 2 mg KOH/g. After phase separation, the organic layer is concentrated under vacuum (≤50 mbar, jacket ≤45 °C) to avoid thermal decarboxylation of the acid impurity. The resulting N‑substituted pyrrole intermediate proceeds through reductive amination and BOC‑deprotection sequences in subsequent stages, ultimately delivering the free‑base API that is formulated as film‑coated tablets or hard gelatin capsules in dedicated solid‑dosage suites compliant with FDA 21 CFR Part 211 and EU GMP Annex 1 conditions where applicable.During the manufacturing of modern broad‑spectrum acaricide and fungicide active ingredients, the 2‑pyrrolecarboxylate ester serves as a primary C‑building block for successive halogenation, cyanation, and cross‑coupling reactions that install the 3‑, 4‑, and 5‑substituents required for target‑site binding at mitochondrial complex II in phytopathogenic fungi and at the GABA‑gated chloride channel in arthropod pests. The technical material intended for agrochemical synthesis is supplied under a minimum purity of 98.5% (HPLC, external standard), with sulfated ash <0.1% and a heavy metals panel (As, Pb, Cd, Hg) conforming to the thresholds of the Joint FAO/WHO Meeting on Pesticide Residues (JMPR) manual, third edition, Appendix D. Registration dossiers filed under REACH Regulation (EC) 1907/2006 typically include the ester as a strictly controlled non‑isolated intermediate used on‑site, which reduces the obligation for full substance evaluation provided tonnage bands remain below 10 tonnes per annum per legal entity. In the pivotal ring‑halogenation stage, the ester is dissolved in acetonitrile (5–7 volumes w/v) and cooled to –10 to –5 °C in a Hastelloy C‑276 reactor before a controlled introduction of sulfuryl chloride (1.02–1.10 eq) or N‑bromosuccinimide (1.00–1.05 eq) via a Coriolis mass‑flow meter to maintain a temperature rise no faster than 2 °C/min. Over‑halogenation above +2 °C generates di‑halogenated by‑products that co‑crystallise with the desired monohalo intermediate and cannot be removed economically by reslurrying, making the thermal profile the single most critical process parameter. Subsequent cyanation employs copper(I) cyanide (1.5 eq) in N‑methyl‑2‑pyrrolidone at 120–130 °C under rigorous exclusion of oxygen to prevent catalyst poisoning. Final active‑ingredient synthesis converges through a Suzuki‑Miyaura coupling with arylboronic acids, after which the technical product is crystallised from ethanol/water mixtures and milled to a mean particle size 3–5 µm (Malvern Mastersizer) for formulation as suspension concentrates (250–480 g a.i./L) or water‑dispersible granules that undergo CIPAC MT 46.3 wet sieve testing and CIPAC MT 184 suspensibility testing before commercial release.Flavour formulations requiring a roasted, nutty top note with a low odour‑threshold profile frequently utilise the neat methyl ester of pyrrole‑2‑carboxylic acid as a direct single‑substance ingredient; its FEMA GRAS 4128 status and JECFA No. 1895 specification permit deployment across confectionery, bakery, and beverage applications in the European Union under Regulation (EC) No 1334/2008 and in the United States under 21 CFR §172.515. The commercial flavour grade carries an assay of ≥99% by GC, a refractive index at 20 °C of 1.517–1.522, and a methanol residue below 50 ppm as verified through headspace GC‑FID against a certified reference standard. In compounded flavour syrups, the ester is typically pre‑dissolved in ethyl alcohol at 1.0–5.0% w/w to form a stock solution, then dosed into the final product matrix at levels corresponding to 2.0–10.0 ppm in finished baked goods, 1.5–8.0 ppm in hard‑boiled candies, and 0.5–3.0 ppm in non‑alcoholic carbonated beverages, figures derived from FEMA‑sponsored use‑level surveys (2018 release). Spray‑dried encapsulated powders for dry mixes are produced on a Niro P‑6.3 spray dryer with inlet/outlet temperatures of 180/90 °C, using gum arabic and maltodextrin carriers, and the resulting powder is sieved to <250 µm. Because the ester exhibits a vapour pressure of approximately 0.15 hPa at 25 °C, headspace loss during open‑vessel blending constitutes a measurable economic concern; closed transfer and immediate capping of intermediate containers constitutes standard practice.
What Impact Does Comonomer Composition Exert on the Electrochromic Switching Lifetime of Pyrrole‑Based Films?Electropolymerisation baths formulated from methyl 2‑pyrrolecarboxylate and pyrrole in acetonitrile containing 0.1 M tetrabutylammonium hexafluorophosphate as the supporting electrolyte are deposited potentiostatically at +0.90 V vs. Ag/AgCl (saturated KCl) onto indium tin oxide‑coated glass substrates with a sheet resistance of 8–12 Ω sq⁻¹. The monomer supply for device‑grade synthesis is subject to a metals specification derived from SEMI C8‑0316, requiring sodium and potassium each below 50 ppb, with total transition metals under 100 ppb as measured by ICP‑MS after microwave digestion, because adventitious iron and copper catalyse uncontrolled branching during chain propagation and shorten the conjugated length. Incorporation of the methoxycarbonyl‑substituted pyrrole unit at 5–35 mol% relative to the unsubstituted pyrrole modifies the redox behaviour: cyclic voltammetry recorded at a scan rate of 50 mV s⁻¹ reveals a shift of the anodic peak from +0.20 V to +0.38 V (vs. Ag/AgCl) as the co‑monomer fraction increases from 15 mol% to 30 mol%, which correlates with improved optical contrast retention after 10⁴ switching cycles when the film thickness is held at 220±15 nm as determined by stylus profilometry. Copolymer films deposited with a charge density of 120 mC cm⁻² and a comonomer content of 15–20 mol% deliver a coloration efficiency of 380–420 cm² C⁻¹ at 550 nm and a switching time (τ90) below 1.8 s in a 0.1 M LiClO₄/propylene carbonate electrolyte, parameters that satisfy the requirements for organic electrochromic displays intended for point‑of‑sale signage. Where the end‑use entails indirect food‑contact smart packaging, overall migration testing per EU 10/2011 (simulant B, 10 days at 40 °C) is executed on the laminated device stack. The processing line in pilot‑scale fabrication uses an automated three‑electrode flow cell with an electrode gap of 2.0 mm and a flow rate of 0.5 L min⁻¹, ensuring a uniform hydrodynamic boundary layer that limits variation in copolymer composition to <3% RSD across a 300 × 300 mm substrate area.Substituting Conventional Azoles with Pyrrole‑2‑Carboxylate Esters in Hydrocarbon Processing Fluid Corrosion PackagesIn crude overhead condensing systems and closed‑loop cooling circuits containing copper‑nickel alloy heat‑exchanger tubes (C70600, 90/10 Cu‑Ni), methyl 2‑pyrrolecarboxylate is hydrolytically activated in‑situ to the corresponding pyrrole‑2‑carboxylic acid anion, which provides anodic inhibition by forming a chemisorbed monolayer on cuprous oxide‑rich surfaces. Immersion corrosion testing conducted in accordance with ASTM G31‑72(2021) on copper coupons (UNS C11000) in synthetic cooling water (pH 7.8±0.2, chloride 300 mg L⁻¹, sulfate 150 mg L⁻¹, temperature 50 °C) shows that a continuous dose of 50–200 mg L⁻¹ of the pre‑hydrolysed acid maintains a corrosion rate below 0.005 mm year⁻¹ over a 168‑h exposure, a threshold that qualifies the fluid as a low‑corrosivity medium under NACE TM0169‑2010 classification. The ester itself is stored as a 30% active concentrate in isopropanol and metered into the cooling‑tower sump via a diaphragm metering pump interlocked with the make‑up water conductivity controller to compensate for blowdown losses. Below pH 6.8 the hydrolysis rate slows markedly, and un‑reacted ester contributes to total organic carbon excursions that risk exceeding discharge permit values under the urban wastewater treatment directive; therefore, a minimum holding time of 45 min in the hot return leg at ≥55 °C is engineered into the dosing layout. Compatibility with oxidising halogen‑based biocides is deliberately constrained: residual free chlorine must not exceed 0.3 mg L⁻¹ as Cl₂, otherwise oxidative cleavage of the pyrrole ring generates short‑chain carboxylic acids that reverse the protective surface film and elevate soluble copper release above 0.1 mg L⁻¹. In petroleum refining overhead injection, the ester‑based package replaces mercaptobenzothiazole and tolyltriazole at a weight‑for‑weight substitution ratio of 1.0:1.0 after a solvent‑deasphalting unit turnaround, achieving comparable iron and copper oxide fouling indices while preventing the formation of organochlorine‑containing deposits that historically challenged catalyst bed longevity in downstream hydrotreaters. Treated fluids are deployed as recirculating cooling‑water mixtures and as process‑side anti‑foulant streams in atmospheric crude distillation columns, and the inhibitor package itself holds NSF/ANSI 60 certification for incidental contact with potable water when used at concentrations not exceeding 20 mg L⁻¹ of neat ester equivalent. |
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| Parameter | Specification | Method |
|---|---|---|
| Appearance | Pale yellow to off-white crystalline solid | Visual (USP ⟨630⟩) |
| Purity (GC) | ≥ 98.0% | ASTM E202 / EP 2.2.28 |
| Water content | ≤ 0.5% | KF, USP ⟨921⟩ |
| Melting point | 50–52 °C | USP ⟨741⟩ capillary |
| Residue on ignition | ≤ 0.1% | USP ⟨281⟩ |
| Heavy metals (total) | ≤ 10 ppm | USP ⟨231⟩ Method II |
| Residual solvents | Meets ICH Q3C Option 1 | EP 2.4.24 |
| Feature | Methyl 2‑pyrrolecarboxylate | Pyrrole‑2‑carboxylic acid |
|---|---|---|
| Solubility in THF | > 100 g L⁻¹ | 8–12 g L⁻¹ |
| Melt stability | Stable up to 200 °C (no decarboxylation) | Decarboxylation onset 160 °C |
| Direct amidation | DMAP-catalyzed, short cycle | Requires coupling reagent |
| Protection requirement | None; ester can be a latent acid | Often needs esterification for protection |
| Moisture sensitivity during storage | Gradual hydrolysis above RH 60% | Hygroscopic; forms hydrates |
