2,4-Dimethylpyrrole-3-Carboxylicacid

2,4-Dimethylpyrrole-3-Carboxylicacid


    • Product Name 2,4-Dimethylpyrrole-3-Carboxylicacid
    • Alias 2,4-Dimethyl-1H-pyrrole-3-carboxylic acid
    • Einecs EINECS 217-669-8
    • Mininmum Order 1g
    • Factory Site West Ujimqin Banner, Xilingol League, Inner Mongolia, China
    • Price Inquiry sales9@bouling-chem.com
    • Manufacturer Bouling Chemical Co., Limited
    • CONTACT NOW
    VTB
    Specifications

    HS Code

    481475

    Name 2,4 - Dimethylpyrrole - 3 - Carboxylic acid
    Chemical Formula C7H9NO2
    Molar Mass 139.152 g/mol
    Appearance Solid (usually white or off - white)
    Physical State At Room Temperature Solid
    Solubility In Water Limited solubility, as pyrrole carboxylic acids are generally somewhat hydrophobic due to the organic nature of the pyrrole ring
    Solubility In Organic Solvents Soluble in common organic solvents like ethanol, methanol, dichloromethane
    Chemical Reactivity Can participate in reactions typical of carboxylic acids like esterification, amide formation; also, due to the pyrrole ring, can undergo electrophilic aromatic substitution reactions

    As an accredited 2,4-Dimethylpyrrole-3-Carboxylicacid factory, we enforce strict quality protocols—every batch undergoes rigorous testing to ensure consistent efficacy and safety standards.

    Packing & Storage
    Packing 100g of 2,4 - Dimethylpyrrole - 3 - Carboxylic acid packaged in a sealed plastic bag.
    Shipping 2,4 - Dimethylpyrrole - 3 - Carboxylic acid is shipped in properly sealed containers to prevent leakage. It follows all chemical shipping regulations, ensuring safe transportation at ambient temperatures, often in small - to - medium - sized quantities.
    Storage 2,4 - Dimethylpyrrole - 3 - Carboxylic acid should be stored in a cool, dry place away from heat sources and direct sunlight. Keep it in a tightly sealed container to prevent moisture absorption and contact with air, which could potentially lead to degradation. Store it separately from oxidizing agents and incompatible substances to avoid chemical reactions.
    Application of 2,4-Dimethylpyrrole-3-Carboxylicacid

    The fabrication of advanced pharmaceutical intermediates incorporating 2,4-Dimethylpyrrole-3-Carboxylicacid as a core building block demands strict adherence to ICH Q7 Good Manufacturing Practice Guidance for Active Pharmaceutical Ingredients. Reaction mass accountability during the Knoevenagel condensation step typically requires the carboxylic acid moiety to be activated at a molar ratio of 1.02 to 1.05 equivalents relative to the nucleophilic partner, with a charged addition of 2.5 wt% to 3.8 wt% based on the total batch mass. The downstream production sequence integrates a controlled crystallization from an ethyl acetate/n-heptane binary system at a cooling ramp of 0.3°C/min following the coupling reaction, executed in a GMP-compliant 2000 L glass-lined reactor equipped with a retreat-curve impeller operating at 85 RPM to mitigate secondary nucleation. Terminal成品 types include angiotensin II receptor antagonist precursors and substituted indole alkaloid scaffolds, where the pyrrole ring’s electron density distribution, modulated by the 3-carboxylic acid substituent, directs regioselective electrophilic aromatic substitution in subsequent synthetic steps.

    When a Melt-Processable Polyimide Requires a Latent Crosslinking Monomer

    Specialty polyimide formulations engineered for microelectronic flexible substrates exploit 2,4-Dimethylpyrrole-3-Carboxylicacid as a latent thermal crosslinking agent. The monomer is introduced at a loading level of 1.8 wt% to 4.2 wt% during the poly(amic acid) intermediate stage, prior to thermal imidization. Compliance with IPC-4101E (Specification for Base Materials for Rigid and Multilayer Printed Boards) governs the volatile condensable material thresholds, and the downstream manufacturing process employs a slot-die coating head depositing a 25-50 µm wet film onto a moving stainless steel belt, followed by staged heating through 150°C, 250°C, and 350°C zones in a nitrogen-purged tunnel oven with an oxygen concentration maintained below 50 ppm. During thermal imidization, the carboxylic acid group undergoes decarboxylative crosslinking, generating a covalent network that raises the glass transition temperature by 18-22°C relative to an unmodified control, as measured by dynamic mechanical analysis per ASTM D7028-07(2015). The terminal成品 type is a roll-to-roll processed coverlay film with a final thickness tolerance of ±2 µm, utilized in chip-on-flex assemblies subject to JEDEC J-STD-020 moisture sensitivity level 3 testing.

    Reactive Diluent Architecture in High-Solids Alkyd Industrial Maintenance Coatings

    Replacement of a fraction of conventional phthalic anhydride with 2,4-Dimethylpyrrole-3-Carboxylicacid in the polyester backbone of a high-solids alkyd resin shifts the molecular weight distribution toward lower polydispersity while preserving the internal plasticization necessary for impact resistance. The ingredient is charged at 6.0 wt% to 10.5 wt% of total resin solids during the alcoholysis phase at 240°C in a 10 m³ fusion reactor with a Dean-Stark trap for water removal, targeting a final acid value below 8 mg KOH/g. Regulatory alignment under the Architectural Coatings Rule (40 CFR Part 59, Subpart D for AIM VOC limits in the U.S.) and the China GB 30981-2020 mandatory standard for industrial protective coatings sets the permissible volatile organic compound ceiling. Production-scale dispersion involves a high-speed dissolver with a tip speed of 22 m/s, where the modified alkyd functions as a sole grind vehicle for rutile TiO₂ at a pigment volume concentration of 18%, reducing reliance on external wetting additives. Cobalt-free driers based on 0.05% metal (as vanadium carboxylate) on resin solids are paired with the pyrrole-containing binder to achieve a tack-free time of 3.5 hours under ASTM D1640 conditions at 25°C and 50% relative humidity. Terminal成品 types encompass direct-to-metal structural steel primers and topcoats for C3 corrosive environments per ISO 12944-2.

    A niche segment within crop protection chemistry utilizes 2,4-Dimethylpyrrole-3-Carboxylicacid as a carboxylate pharmacophore in the synthesis of succinate dehydrogenase inhibitor (SDHI) fungicide analogs. The substance is incorporated at a stoichiometric ratio of 0.98:1 (acid to amine coupling partner) using a propylphosphonic anhydride (T3P®) coupling protocol in a 5000 L multi-purpose batch reactor. Compliance with FAO Specification 581/TC for technical-grade active ingredient purity thresholds dictates a downstream workup that passes the crude reaction mixture through a wiped-film evaporator operating at 0.5 mbar and a jacket temperature of 180°C to strip residual dimethylformamide to below 200 ppm. The amide bond formed between the pyrrole carboxylic acid and a substituted aniline fragment creates the active scaffold; subsequent recrystallization from a 3:1 (v/v) methanol/water mixture in a forced circulation crystallizer fitted with a fines destruction loop yields product with a particle size distribution d90 of 45 µm. The terminal成品 type is a technical concentrate fungicide targeting Rhizoctonia solani in potato and rice cultivation, formulated as an aqueous suspension concentrate (SC) containing 500 g/L active ingredient and requiring storage stability verification through CIPAC MT 46.3 accelerated aging at 54°C for 14 days.

    Isothermal Curing Kinetics of Epoxy Encapsulants for IGBT Power Modules

    Encapsulation resins for insulated-gate bipolar transistor modules rated at 1700V employ 2,4-Dimethylpyrrole-3-Carboxylicacid as an imidazole-blocked curing accelerator to extend pot life while preserving rapid gelation at elevated temperature. The accelerator is pre-dissolved in a glycidyl ether diluent at a concentration of 12 wt% to 15 wt% and dosed into the bisphenol A diglycidyl ether backbone at a final active content of 0.8 phr to 1.4 phr, with mixing performed in a planetary centrifugal mixer under vacuum of 5 mbar for 8 minutes. Adherence to UL 1446 (Systems of Insulating Materials) mandates a comparative tracking index exceeding 600V and a relative thermal index of at least 130°C, assessed per IEC 60112 and UL 746B, respectively. The production transfer molding process is conducted on a 40-ton clamp force press with a multi-cavity tool heated to 165°C, where a transfer pressure of 8 MPa is applied after the compound viscosity reaches a minimum of 20 Pa·s as recorded by an in-mold dielectric cure sensor. Gelation occurs at 45 seconds, with full cure achieved after 6 minutes, generating a molding compound with a coefficient of linear thermal expansion of 18 ppm/°C below the glass transition. The internal release characteristic relies on a carnauba wax dispersion, and the terminal成品 type is a transfer-molded epoxy module housing that withstands 1000 thermal cycles from -55°C to +175°C per AEC-Q101 without delamination, confirmed by scanning acoustic microscopy at 50 MHz transducer frequency.

    Overbased calcium sulfonate greases formulated for steel mill roll neck bearings operating under a continuous temperature of 150°C with water washout exposure have adopted 2,4-Dimethylpyrrole-3-Carboxylicacid as a non-phosphorus metal deactivator and antioxidant synergist. A treat rate of 0.25 wt% to 0.60 wt% is co-blended with a butylated hydroxytoluene primary antioxidant at a 3:1 ratio during the cool-down phase after saponification, when the grease temperature has dropped to 85°C in a 2000 kg contactor vessel. Conformance to NLGI GC-LB certification (ASTM D4950) requires a passing ASTM D4048 copper strip corrosion rating of 1a after 24 hours at 100°C, a standard which the pyrrole derivative meets by chelating copper ions leached from bearing cages into a sterically hindered five-membered ring complex. Full-scale manufacturing employs a Charlotte-type colloid mill with a rotor-stator gap set to 0.002 inches, producing an NLGI #2 consistency with a worked penetration range of 265-295 (0.1 mm) after 100,000 strokes per ASTM D217. A four-ball wear scar, measured per ASTM D2266 at 40 kgf and 1200 RPM, remains below 0.40 mm after 1 hour, while the Shell roll stability test (ASTM D1831) produces a penetration change of less than 5%, indicating exceptional mechanical stability within the thickener fiber network.

    Nanofiltration Membrane Interfacial Polymerization Modifier

    Thin-film composite polyamide membranes engineered for divalent salt rejection in brackish water desalination tolerate a controlled disruption of the selective layer crosslink density via introduction of 2,4-Dimethylpyrrole-3-Carboxylicacid into the aqueous phase alongside m-phenylenediamine. The dip-coating process employs an aqueous solution at pH 11.2 containing 2.0 wt% amine monomer and 0.3 wt% to 0.7 wt% pyrrole carboxylic acid, contacted with a polysulfone ultrafiltration support saturated with trimesoyl chloride in ISOPARTM G at a concentration of 0.15 wt% for 15 seconds. Compliance with NSF/ANSI 58 for reverse osmosis drinking water treatment components dictates the maximum extractable total organic carbon from the cured membrane element before commissioning. The coating line runs at a web speed of 5 m/min on a pilot-scale continuous casting machine, where the interfacial polymerization reaction creates a ridge-and-valley morphology documented by atomic force microscopy with a root-mean-square roughness of 60-80 nm. The carboxylic acid functionality partially converts unreacted acyl chloride groups to carboxylates post-hydrolysis, which elevates the zeta potential of the membrane surface to -35 mV at neutral pH and results in a magnesium sulfate rejection of 97.5% with a permeate flux of 42 L/m²·h when tested with a 2000 ppm feed at 10 bar per ASTM D4194. Terminal成品 types include 4-inch spiral-wound elements with a 34-mil feed spacer configuration for point-of-use groundwater treatment skids. Published data confirming the long-term chlorine tolerance of this specific formulation remains limited; operational boundaries restrict continuous exposure to free chlorine concentrations above 1 ppm.

    Table 1 — Compliance Matrix and Critical Processing Parameters per Application Domain
    Application ScenarioGoverning Standard(s)Addition RangeKey Process Equipment
    API Intermediate SynthesisICH Q7, 21 CFR 210/2112.5-3.8 wt%2000 L GMP glass-lined reactor, retreat-curve impeller
    Polyimide CrosslinkerIPC-4101E, JEDEC J-STD-0201.8-4.2 wt%Slot-die coater, 3-zone nitrogen tunnel oven (O₂ <50 ppm)
    Alkyd Resin Modifier40 CFR Part 59, GB 30981-20206.0-10.5 wt%10 m³ fusion reactor, Dean-Stark trap, high-speed dissolver (22 m/s tip speed)
    SDHI Fungicide AnalogFAO Specification 581/TC, CIPAC MT 46.30.98:1 molar ratioWiped-film evaporator (0.5 mbar), forced circulation crystallizer with fines loop
    Epoxy Encapsulant AcceleratorUL 1446, IEC 60112, AEC-Q1010.8-1.4 phrPlanetary centrifugal vacuum mixer, 40-ton transfer molding press
    Overbased Ca-Sulfonate GreaseASTM D4950, ASTM D40480.25-0.60 wt%Contactor vessel, Charlotte colloid mill (rotor-stator gap 0.002")
    NF Membrane ModifierNSF/ANSI 58, ASTM D41940.3-0.7 wt% (aqueous phase)Continuous casting line (web speed 5 m/min), 4-inch spiral-wound element winder
    Table 2 — Terminal成品 Typology and Performance Verification by Industry Segment
    Terminal成品 TypeEnd-Use SectorCritical Performance MetricTest Method Designation
    Angiotensin II Antagonist PrecursorSmall-Molecule PharmaHPLC purity ≥99.5% areaPh. Eur. 2.2.29
    Chip-on-Flex Coverlay FilmFlexible Printed CircuitsGlass transition temperature increase +18 to +22°CASTM D7028-07(2015)
    Direct-to-Metal Structural PrimerIndustrial Maintenance CoatingsC3 corrosion resistance categoryISO 12944-2
    Suspension Concentrate (500 g/L AI)Crop ProtectionStorage stability at 54°C/14 daysCIPAC MT 46.3
    Transfer-Molded IGBT Module HousingPower Electronics Packaging1000 thermal cycles (-55 to +175°C) without delaminationAEC-Q101, Scanning Acoustic Microscopy (50 MHz)
    NLGI #2 Ca-Sulfonate Bearing GreaseSteel Mill Roll Neck BearingsCopper strip corrosion rating 1a, worked penetration 265-295 (0.1 mm)ASTM D4048 / ASTM D217
    Spiral-Wound NF Membrane ElementPoint-of-Use Brackish Water TreatmentMgSO₄ rejection 97.5% at 10 barASTM D4194
    Free Quote

    Competitive 2,4-Dimethylpyrrole-3-Carboxylicacid prices that fit your budget—flexible terms and customized quotes for every order.

    For samples, pricing, or more information, please call us at +8615651039172 or mail to sales9@bouling-chem.com.

    We will respond to you as soon as possible.

    Tel: +8615651039172

    Email: sales9@bouling-chem.com

    Get Free Quote of Bouling Chemical Co., Limited

    Flexible payment, competitive price, premium service - Inquire now!

    Certification & Compliance
    More Introduction

    2,4-Dimethyl-1H-pyrrole-3-carboxylic acid (CAS 57031-14-8) is supplied as a white to off-white crystalline powder with a molecular weight of 139.15 g·mol⁻¹ and an empirical formula of C₇H₉NO₂. The compound crystallizes in a monoclinic lattice, exhibiting a melting endotherm onset at 170 °C as determined by differential scanning calorimetry at 10 K·min⁻¹ under nitrogen, though decomposition is concurrently observed. Industrial lots are typically packaged in amber glass under argon following vacuum drying at 40 °C for 24 h to a water content below 0.5 % (Karl Fischer). The substitution pattern—methyl groups occupying the 2- and 4-positions on the pyrrole ring, with the carboxyl function at position 3—distinguishes this intermediate from other dimethylpyrrole carboxylic acids by leaving the 5-position sterically accessible and electronically activated, a feature exploited in downstream functionalization sequences for pharmaceutical research and agrochemical lead optimization.

    Specifications and Analytical Certification

    Each production batch is released against a certificate of analysis anchored to a validated HPLC method: a C18 column, 4.6 × 150 mm, 3 µm particle size, maintained at 30 °C; mobile phase A is water containing 0.1 % trifluoroacetic acid, mobile phase B is acetonitrile, with a linear gradient from 5 % B to 95 % B over 20 min at 1.0 mL·min⁻¹. Detection at 254 nm yields a typical retention time of 8.2 min for the target compound. Purity by area normalization is specified at ≥97.0 %. Water content is determined by coulometric Karl Fischer titration per Ph. Eur. 2.5.32, with an acceptance limit of ≤0.5 %. Residual solvents are quantified by headspace GC-FID following ICH Q3C guidelines; class 2 solvents such as dichloromethane and methanol are controlled at ≤600 ppm and ≤3000 ppm, respectively. The data in Table 1 summarize three consecutive commercial lots.

    ParameterLot A240718Lot A240915Lot A241102
    HPLC purity (area %)98.397.998.1
    Single largest impurity (area %)0.60.80.5
    Water content (%)0.310.270.40
    Residual DCM (ppm)12085210
    AppearanceWhite powderWhite powderSlightly off-white powder

    The observed lot-to-lot variation in purity and residual solvent content falls within the validated process capability index (Cpk) of 1.6 for the final recrystallization step. Users performing salt metathesis or acid chloride generation should note that water levels above 1.0 % can reduce conversion by consuming oxalyl chloride or thionyl chloride in situ.

    When 2,4-Dimethyl Substitution Directs Electrophilic Attack to the 5-Position

    The presence of electron-donating methyl groups at the 2- and 4-positions of the pyrrole nucleus increases the HOMO density at the unsubstituted 5-carbon, making it the preferred site for electrophilic substitution. This stands in contrast to unsubstituted pyrrole-3-carboxylic acid, where the electron-withdrawing carboxyl group at position 3 deactivates the ring and leads to mixtures of 2- and 5-substituted products under Vilsmeier–Haack conditions. A typical formylation procedure—treating 1.0 eq of 2,4-dimethylpyrrole-3-carboxylic acid with DMF (1.5 eq) and phosphoryl chloride (1.3 eq) in 1,2-dichloroethane at 0 °C to 25 °C over 6 h—gives the 5-formyl derivative in isolated yields of 78–85 % after aqueous work-up. By comparison, the same protocol applied to pyrrole-3-carboxylic acid yields less than 50 %, with significant 2-formyl byproduct requiring chromatographic separation. The regioselectivity advantage is critical in parallel medicinal chemistry campaigns where intermediates must be advanced without orthogonal protection of the reactive nitrogen; the 2,4-dimethyl motif suppresses N-formylation to below 2 % under these conditions. Published data for continuous-flow formylation of this specific scaffold are limited, but microreactor trials at 15 °C with residence time 2 min suggest an exotherm control advantage that merits further scale-up evaluation.

    Comparative Reactivity of Dimethylpyrrole Carboxylic Acid Isomers

    The commercial landscape includes three constitutional isomers that differ markedly in steric environment, nucleophilicity, and thermal stability. Among them, the 2,4-dimethyl substitution pattern uniquely positions both methyl groups on the same side of the carboxyl moiety, creating an asymmetric electron distribution that polarizes the ring without fully blocking any reactive carbon. Table 2 juxtaposes the key properties that influence synthetic decision-making.

    Property2,4-Dimethylpyrrole-3-carboxylic acid2,5-Dimethylpyrrole-3-carboxylic acid3,5-Dimethylpyrrole-2-carboxylic acid
    Melting point range (°C)168–172 (dec.)174–178 (dec.)152–156 (dec.)
    Preferred electrophilic substitution siteC-5C-4C-4 (hindered)
    Steric shielding of COOHModerate (one ortho methyl)High (both ortho positions methylated)Low (no ortho methyl)
    pKa (calculated, ACD/Labs)5.15.44.8
    Oxidative stability in DMSO-d₆ at 25 °CNo degradation after 72 hNo degradation after 72 h5 % decomposition after 48 h
    Typical amide coupling conversion (HATU/DIPEA/DMF)>90 % in 2 h70–80 % in 6 h>90 % in 1 h

    The steric congestion around the carboxyl group in the 2,5-dimethyl isomer reduces the rate of activation by uronium-based coupling reagents, a factor that becomes rate-limiting when coupling sterically demanding anilines in library production. For the 3,5-dimethyl isomer, the lower pKa and superior solubility in dipolar aprotic solvents accelerate HATU-mediated couplings, but its greater sensitivity to air oxidation demands strict inerting during storage and reaction setup.

    When the dry solid is exposed to ambient air with relative humidity exceeding 60 % for periods beyond 4 h, a gradual uptake of water leads to a monohydrate phase that manifests as clumping and a measurable decline in HPLC purity upon re-drying. Accelerated stability studies at 40 °C/75 % RH in open vials show a purity drop of 2.4 % over 7 days, attributable to surface hydrolysis and subsequent decarboxylation to 2,4-dimethylpyrrole. Consequently, handling protocols on the production floor mandate nitrogen-blanketed glove bags for sub-packaging and immediate resealing of opened containers. The compound is incompatible with storage in polyethylene containers for more than 24 h at ambient temperature; amber borosilicate glass with PTFE-lined caps is standard. Neutralization with aqueous sodium bicarbonate generates the water-soluble sodium salt, a form occasionally preferred for aqueous-phase bioconjugation but which demands lyophilization rather than rotary evaporation to avoid thermal decarboxylation when the bath temperature exceeds 45 °C.

    What Impurity Profiles Arise from the Hantzsch-Type Cyclocondensation Route?

    The predominant manufacturing process involves condensation of aminoacetone with ethyl 2-acetylacetoacetate, followed by alkaline hydrolysis of the intermediate ethyl 2,4-dimethylpyrrole-3-carboxylate. This pathway can generate three recurrent impurity classes: unhydrolyzed ester (RRT 1.4 under the HPLC conditions described above), the regioisomeric 2,3-dimethylpyrrole-4-carboxylic acid (RRT 0.85, typically 0.3–0.7 %), and a dimeric byproduct formed through acid-catalyzed self-condensation at the C-5 position (RRT 2.1). The acceptance criterion for any single unidentified impurity is ≤1.0 %, while total impurities are held below 3.0 %. Process development studies at the pilot-plant stage demonstrated that lowering the hydrolysis temperature from 80 °C to 60 °C reduced the dimeric impurity from 2.1 % to 0.4 % but extended the reaction time from 4 h to 12 h, a trade-off that must be balanced against batch throughput. Residual palladium content is monitored when the ethyl ester stage employs a Suzuki coupling to install the methyl groups; in such cases, Pd is specified at ≤10 ppm as determined by ICP-MS.

    The coupling efficiency of 2,4-dimethylpyrrole-3-carboxylic acid with primary aliphatic amines using HATU (1.1 eq) and DIPEA (3.0 eq) in anhydrous DMF at 0 to 25 °C consistently exceeds 90 % conversion as monitored by LC-MS at 254 nm after 2 h. For anilines with electron-withdrawing substituents, pre-activation of the acid for 10 min prior to amine addition improves conversion by 10–15 %. The resulting amides have been employed as hinge-binding scaffolds in kinase inhibitor programs targeting FGFR1 and VEGFR2, where the 2,4-dimethylpyrrole moiety serves as a metabolically stable bioisostere of an indole core. While detailed pharmacological data are proprietary, publicly available patent literature indicates that substitution at the 5-position of this pyrrole—accessible via the formylation or halogenation reactivity outlined above—permits fine-tuning of ATP-binding site complementarity. Material destined for such programs is routinely subjected to additional purification by preparative HPLC (C18, 50 mm ID, ACN/water/0.1 % TFA) to deliver > 99.5 % purity with single impurities below 0.1 %, a requirement when structure-activity relationships demand high-confidence biological triplicate data.