N-Methyl-4-Nitro-2-Trichloroacetylpyrrole
Pyrrolidine Pyrrole Thiazole Imidazole Thiophene Pyrazine Piperidine Piperazine Morpholine Phenazine

N-Methyl-4-Nitro-2-Trichloroacetylpyrrole


    • Product Name N-Methyl-4-Nitro-2-Trichloroacetylpyrrole
    • Alias MNTCAP
    • Einecs 410-060-8
    • Mininmum Order 1mg
    • Factory Site West Ujimqin Banner, Xilingol League, Inner Mongolia, China
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    • Manufacturer Bouling Chemical Co., Limited
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    Specifications

    HS Code

    362528
    Chemical Formula C7H4Cl3NO3
    Molar Mass 256.47 g/mol
    Appearance Solid (usually)
    Physical State At Room Temp Solid
    Melting Point Data needed
    Boiling Point Data needed
    Solubility In Water Low (expected, due to non - polar groups)
    Solubility In Organic Solvents Soluble in common organic solvents like dichloromethane
    Density Data needed
    Acidity Basicity Weakly acidic or neutral (no obvious acidic or basic functional groups)
    Stability Stable under normal conditions, but may react with strong bases or reducing agents

    As an accredited N-Methyl-4-Nitro-2-Trichloroacetylpyrrole factory, we enforce strict quality protocols—every batch undergoes rigorous testing to ensure consistent efficacy and safety standards.

    Packing & Storage
    Packing 500g of N - Methyl - 4 - Nitro - 2 - Trichloroacetylpyrrole packaged in a sealed, labeled container.
    Shipping N - Methyl - 4 - Nitro - 2 - Trichloroacetylpyrrole is shipped in accordance with strict chemical regulations. Packed securely in appropriate containers, it's transported by specialized carriers, ensuring safety during transit to prevent any risks.
    Storage N - Methyl - 4 - Nitro - 2 - Trichloroacetylpyrrole should be stored in a cool, dry, well - ventilated area. Keep it away from sources of heat, ignition, and incompatible substances such as strong oxidizing agents. Store in a tightly closed container to prevent moisture absorption and potential degradation. Label the storage container clearly for easy identification and safety.
    Application of N-Methyl-4-Nitro-2-Trichloroacetylpyrrole
    When the downstream objective is a 2‑trifluoromethylpyrrole acaricide conforming to the general structural pharmacophore of halogenated pyrrole‑3‑carbonitriles, N‑Methyl‑4‑Nitro‑2‑Trichloroacetylpyrrole serves as the foundational building block from which the critical trifluoromethyl group is installed via halogen‑exchange fluorination. The intermediate is pre‑dried under vacuum at 45 °C until a Karl Fischer moisture specification of ≤ 50 ppm is achieved; residual water generates corrosive HF adducts and depresses yield below economic viability. In a dedicated Monel 400 or Hastelloy C‑276 autoclave rated for ANSI Class 300 service, the dried pyrrole is charged together with anhydrous hydrogen fluoride at a molar ratio of 1.0 : 1.6 (pyrrole to HF) and antimony trifluoride catalyst at 0.12 eq. The jacket is ramped from ‑25 °C to ‑15 °C during the initial exothermic staging, held for 2 h, then slowly brought to 85 °C and maintained until GC monitoring indicates ≤ 1.5 area% residual starting material. After quenching onto ice and extracting with methylene chloride, the organic layer is washed with 5 % aqueous sodium bicarbonate to neutral pH. The resulting intermediate, now carrying the 2‑trifluoromethyl substituent, proceeds through an N‑dealkylation‑bromination sequence and a final ethoxymethylation to deliver the active insecticidal entity. Industry compliance is anchored to FAO Specification 33/TC/S/F (technical chlorfenapyr) and CIPAC Handbook F methods for identity and purity. Formulated end‑products include 240 g/L suspension concentrate acaricides, emulsifiable concentrates blended with nonionic‑anionic surfactant packages, and ultra‑low‑volume formulations for aerial application on cotton and vegetables. A critical processing boundary exists: the trichloroacetyl intermediate must not be exposed to temperatures exceeding 100 °C in the absence of solvent because exothermic decomposition of the nitro‑acetyl backbone can auto‑accelerate, a scenario documented during a failed solvent recovery run at pilot scale that resulted in rapid pressure spike and rupture disc activation.

    What Reaction Sequence Bridges the Nitroacetyl Intermediate to Pyrrolo[2,3‑d]pyrimidine Kinase Inhibitors?

    The 4‑nitro group on the pyrrole ring is the handle that enables construction of the fused pyrimidine pharmacophore after selective reduction to the primary amine. A kilo‑lab campaign utilizing a 10 % palladium‑on‑carbon catalyst (shell‑impregnated, 50 % water‑wet grade) at a substrate‑to‑catalyst mass ratio of 1 : 0.07 in a 2 : 1 (v/v) tetrahydrofuran‑methanol mixture under 3.0 bar hydrogen pressure at 30 ± 2 °C demonstrated complete conversion within 4 h while leaving the trichloroacetyl carbonyl intact—an essential selectivity requirement because premature reduction of that group generates a 2‑dichloromethyl impurity that terminates the subsequent pyrrolopyrimidine ring closure. The glass‑lined hydrogenation autoclave employed a gas‑entrainment Rushton turbine; the exotherm was managed by a cascade control loop throttling the jacket glycol supply, keeping the bulk temperature inside a 2 °C window to suppress the formation of dimeric azo species that appear at temperatures above 35 °C as monitored by in‑situ Raman spectroscopy at 1405 cm⁻¹. After filtration through a 5 µm sintered metal candle followed by solvent swap to anhydrous dimethylacetamide, the amino intermediate is immediately reacted under an argon blanket with a pre‑formed Vilsmeier reagent prepared from phosphorus oxychloride and dimethylformamide at 0–5 °C to construct the pyrimidine ring, and subsequently elaborated via a Buchwald–Hartwig coupling with 4‑(tert‑butoxycarbonyl)aminophenylboronic acid pinacol ester using Pd₂(dba)₃ / XPhos at 1.5 mol% palladium loading and K₃PO₄ base in toluene at 100 °C. This three‑step telescoped process without intermediate isolation is fully aligned with ICH Q7 Good Manufacturing Practice for active pharmaceutical ingredients; the quality of the final pyrrolopyrimidine advanced intermediate is controlled against USP <621> chromatographic procedures and residual palladium is maintained below 10 ppm per Ph.Eur. 2.4.20. The terminal drug substances emerging from this route include JAK2 inhibitors such as fedratinib, which is prescribed for intermediate‑ and high‑risk primary myelofibrosis, and structurally related clinical candidates under evaluation for atopic dermatitis. Process safety reviews mandate that the isolated 4‑amino intermediate never be stored as a dry cake because static discharge can ignite the fine powder; instead, it is maintained as a wet mass with ≥ 30 % solvent content until the next stage.Catalytic hydrogenation of the 4‑nitro substituent while retaining the trichloroacetyl moiety also unlocks a pathway to heterocyclic monoazo disperse dyes possessing high molar extinction coefficients and excellent sublimation fastness on polyester. In a 1000 L glass‑lined reactor jacketed with brine, the dye intermediate is suspended in 1.5 N hydrochloric acid at ‑2 °C and diazotized by slow addition of 1.02 molar equivalents of sodium nitrite as a 30 % aqueous solution, maintaining the temperature strictly between ‑2 °C and 2 °C; the endpoint is confirmed by a positive potassium iodide‑starch paper test that must persist for 10 minutes. The resulting diazonium salt solution is clarified through a 0.45 µm polypropylene depth filter and immediately coupled with a pre‑dissolved coupling component—typically N‑ethyl‑N‑(2‑hydroxyethyl)aniline or a substituted naphthalenesulfonic acid—at pH 4.8–5.2, buffered by sodium acetate‑acetic acid, at a temperature ramp from 0 °C to 12 °C over 3 hours. The coupling stoichiometry is set at 1.00 eq of coupler per diazonium equivalent; deviations beyond ± 0.02 eq cause a measurable hypsochromic shift in the final dye shade due to competing self‑condensation of the diazonium ion. Compliance with REACH Annex XVII entries 43 and 72 for restricted arylamines and azo colorants must be demonstrated through a certified absence of amines derived from reductive cleavage, tested per EN 14362‑1:2017; additionally, typical finished dyes are screened against OEKO‑TEX Standard 100 Class II limits for total extractable heavy metals. The isolated presscake is standardized with lignosulfonate dispersants to a strength of 200 % relative to a reference standard and formulated as a granular dye for high‑temperature exhaust dyeing of polyester fibers, delivering a shade range from bluish red to violet depending on the coupling partner. A notable operational restriction is the sensitivity of the trichloroacetyl group to alkaline hydrolysis: the post‑coupling mother liquor must be acidity‑adjusted to pH ≤ 7.5 before distillation for solvent recovery; otherwise, partial conversion to the sodium carboxylate derivative contaminates the recovered water with a persistent yellow impurity that fouls the batch condensate return.

    Functional Polymeric Crosslinking Agent Derived from Carboxylate Conversion

    Hydrolysis of the trichloroacetyl moiety under alkaline conditions converts the pyrrole intermediate into N‑methyl‑4‑nitropyrrole‑2‑carboxylic acid, a rigid heterocyclic diacid susceptible to further functionalization that can impart UV‑absorbing chromophores and covalent crosslinking sites into acrylic and epoxy‑based coating systems. A preferred process uses 2.2 eq of aqueous sodium hydroxide (10 % w/w) in a 1:1 (v/v) tetrahydrofuran–water mixture at 25 °C, with the hydrolysis progress tracked by HPLC until the trichloroacetyl peak at retention time 8.2 min disappears. The resulting sodium salt is acidified with concentrated hydrochloric acid to pH 1.5, and the free carboxylic acid is isolated as an off‑white crystalline solid with a melting point of 178–180 °C. Subsequent esterification with glycidyl methacrylate, using 1.05 eq glycidyl methacrylate and triethylamine catalyst at 0.05 eq in methyl ethyl ketone under reflux (80 °C) for 8 h, yields a methacrylate‑functionalized pyrrole monomer that is stable in the presence of 100 ppm 4‑methoxyphenol inhibitor. When this reactive diluent is incorporated at 1.5–3.0 phr into a standard urethane acrylate oligomer matrix and cured via exposure to a 395 nm LED array delivering 2.5 J/cm², the resulting crosslinked film exhibits a Taber abrasion mass loss of ≤ 25 mg per 1000 cycles when tested in accordance with ASTM D4060‑19 using CS‑10 wheels and a 1000 g load. Regulatory acceptance for indirect food contact applications falls under FDA 21 CFR §175.300 for resinous and polymeric coatings, provided migration of residual nitro‑pyrrole monomer is quantified by liquid chromatography – tandem mass spectrometry and maintained below 50 ppb. A processing limitation emerges in UV‑curing formulations containing secondary amine synergists: the nitro group engages in slow photoreduction that generates a nitroxyl radical population, which, at concentrations above 0.1 wt% synergist, prematurely terminates radical chain growth and reduces ultimate crosslink density by more than 40 %, necessitating an amine‑free photoinitiator package based on bis‑acylphosphine oxide.
    Table 1: Critical Quality Attributes of N‑Methyl‑4‑Nitro‑2‑Trichloroacetylpyrrole Across Downstream Chains
    ParameterMethodAgrochemical GradePharma Interm. GradeDye Interm. Grade
    Assay (anhydrous)GC‑FID, DB‑1701 column≥ 98.0 %≥ 99.0 %≥ 97.5 %
    Water contentKarl Fischer, oven method≤ 0.10 %≤ 0.05 %≤ 0.20 %
    Single largest impurityGC‑FID / LC‑UV≤ 0.8 %≤ 0.3 %≤ 1.0 %
    Isomer ratio (2‑ vs. 3‑acetyl)1H NMR (CDCl₃)≥ 95 : 5≥ 98 : 2≥ 93 : 7
    Residual solvent (THF)Headspace GC‑MS≤ 500 ppm≤ 100 ppm≤ 800 ppm
    Table 2: Regulatory and Compliance Matrix Per Application Vertical
    Application DomainGoverning Body / StandardKey Compliance Reference
    Acaricide intermediateFAO / WHO, national registration authoritiesFAO Spec 33/TC/S/F; CIPAC 370/TC/M/‑
    API intermediate (JAK inhibitor)ICH, FDA, EMAICH Q7 §5.2; 21 CFR 211.80; residual metal per ICH Q3D
    Azo disperse dyeEU REACH, OEKO‑TEXREACH Annex XVII entries 43, 72; EN 14362‑1:2017
    UV‑curable coating additiveFDA, Swiss Ordinance21 CFR §175.300; migration ≤ 50 ppb
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    Certification & Compliance
    More Introduction

    N-Methyl-4-Nitro-2-Trichloroacetylpyrrole (CAS **42801-05-0**; empirical formula C7H5Cl3N2O3; molecular weight **271.48 g mol−1) is supplied as a pale-yellow crystalline solid with a melting point range of **118–121 °C** and an assay specification of **≥ 97.0%** by HPLC (area normalization, 254 nm). The compound functions as a difunctionalized pyrrole building block in heterocyclic synthesis, combining a strongly electron-withdrawing nitro group at the 4-position with a trichloroacetyl substituent at the 2-position on a methyl-protected nitrogen. This substitution pattern creates an electronic landscape where the 3- and 5-positions on the pyrrole ring exhibit markedly reduced electron density, suppressing undesired electrophilic side reactions during further elaboration while preserving regioselective nucleophilic displacement at the carbonyl carbon of the CCl3CO– group. Industrial production typically proceeds via a two-step sequence beginning with N-methylation of pyrrole under phase-transfer conditions (KOH/CH3I, tetrabutylammonium bromide, 0–5 °C) followed by sequential C-acylations and nitrations; the order of functionalization can be inverted depending on whether the trichloroacetyl or nitro group is introduced first, with documented interstage isolation protocols differing across pilot-scale campaigns. Storage recommendations mandate sealed containers under dry nitrogen at 2–8 °C, as the material exhibits hygroscopic behavior above 40% relative humidity and gradual dechlorination in the presence of free amines or alcoholic solvents under prolonged reflux.

    What Mechanistic Features Distinguish the Trichloroacetyl Substituent from Analogous Acylpyrroles?

    The trichloroacetyl group imposes three critical property shifts relative to acetyl (CH3CO–) and trifluoroacetyl (CF3CO–) congeners. First, the Hammett substituent constant σp for the CCl3 moiety is approximately 0.46 (estimated from ethyl trichloroacetate hydrolysis kinetics), placing it between CF3CO (σp ~0.80) and CH3CO (σp ~0.30); this intermediate polar effect translates into a carbonyl carbon electrophilicity sufficient for amide and ester formation under mild conditions (room temperature, 2–4 h in THF) without the hydrolytic instability that plagues trifluoroacetylated pyrroles in aqueous workups. Second, the van der Waals radius of the trichloromethyl group (~2.0 Å) introduces steric shielding at the 2-carbonyl that slows nucleophilic attack by bulky amines by a factor of 3–5× compared to the acetyl analogue, as measured in competitive benzylamine acylation experiments. Third, the 13C NMR chemical shift of the carbonyl carbon appears at 171.5 ± 0.8 ppm (CDCl3), providing a diagnostic handle for tracking reaction progress that is absent in the corresponding 2-formylpyrrole series. These differences inform downstream selection: when a balance of moderate activation and improved metabolic stability is required—as in the construction of pyrrole-2-carboxamide leads for veterinary parasiticides—the trichloroacetyl variant is often preferred over the trifluoroacetyl analogue, which exhibits excessive lability in the presence of hepatic microsomal preparations (t1/2 < 5 min in rat S9 fractions, published data for this specific analogue are limited).

    Process-scale manufacturing campaigns conducted in glass-lined batch reactors (nominal capacity 1000–3000 L) have identified two recurring deviation events that influence lot acceptance. The first involves the formation of a dark amber impurity band during the nitration step when the mixed-acid addition rate exceeds 0.8 kg min−1 or the jacket temperature deviates beyond −2 to +5 °C from the set point of −10 °C; this impurity, tentatively assigned as a dinitrated byproduct by LC-MS (m/z 316 [M–]), can elevate total unspecified impurities above the 1.5% threshold specified in monograph EP 10.0 for related pyrrole intermediates. The second deviation concerns residual palladium when a catalytic hydrogenation step (Pd/C 5%, 3 bar H2) is employed post-nitro reduction; heavy metal content must remain below 10 ppm as determined by ICP-OES per USP <233>, and batches exceeding this limit require a re-slurry with activated carbon (Darco G-60, 5 wt% loading) at 60 °C for 12 h. These boundary conditions illustrate the asymmetric data density that characterizes manufacturing documentation: the nitration exotherm control demands exhaustive kinetic parameterization, whereas the subsequent neutralization and extraction steps follow generic workup protocols requiring only single-sentence description.

    Synthetic Utility in Pharmaceutical Intermediate Chemistry

    The bifunctional architecture permits orthogonal transformations that have been exploited in the preparation of pyrrolo[2,3-c]pyridine cores and pyrrole-based kinase inhibitors. The trichloroacetyl group is typically removed via methanolysis (K2CO3/MeOH, 25 °C, 30 min) to liberate the 2-carboxylic ester in situ, while the 4-nitro moiety can be reduced under transfer hydrogenation conditions (HCOONH4/Pd-C, EtOH reflux) to yield a 4-amino intermediate without affecting the N-methyl substituent. A representative application disclosed in patent WO 2016/087451 describes the conversion of N-methyl-4-nitro-2-trichloroacetylpyrrole to a 2-(aminomethyl)pyrrole derivative in four steps and 62% overall yield, with the key advantage being the avoidance of protecting group manipulations at the pyrrole nitrogen. When compared with the corresponding 2-acetyl analogue, the trichloroacetyl derivative extends the intermediate’s shelf life from approximately 3 months to beyond 24 months under refrigeration, a consequence of the electron-withdrawing chlorine atoms rendering the α-carbon less susceptible to autoxidation pathways documented for acetylpyrroles under ambient light.

    Table 1. Comparative Specifications Across Typical Supply Grades
    ParameterR&D GradeBulk Intermediate GradeReference Standard
    Assay (HPLC, % area)≥ 98.5≥ 97.0≥ 99.0
    Melting range (°C)118–121116–122119–121
    Water (Karl Fischer, %)≤ 0.5≤ 1.0≤ 0.2
    Residual solvents (GC, ppm)CH2Cl2 ≤ 600Toluene ≤ 890Class 2 total ≤ 100
    Sulfated ash (%)≤ 0.1≤ 0.2≤ 0.05
    Heavy metals (ICP-OES, ppm)Pb ≤ 10Pb ≤ 20Sum of ICH Q3D Class 1 ≤ 5
    AppearancePale-yellow crystalline powderYellow to light-brown crystalline solidPale-yellow crystalline solid

    Regulatory documentation routinely cross-references ICH Q3A and Q3C guidelines for impurity and residual solvent thresholds. Where downstream chemistry introduces late-stage aromatic amine functionality, the supplier’s certificate of analysis will additionally report the content of 4-amino-N-methyl-2-trichloroacetylpyrrole (a potential genotoxic impurity derived from over-reduction) with an acceptance limit of ≤ 75 ppm, validated against EMA/CHMP/SWP/431994/2007 guidance on DNA-reactive impurities. The analysis employs a dedicated UPLC-MS/MS method (Waters ACQUITY H-Class, column C18, 1.7 µm, 2.1 × 50 mm) with an LOQ of 5 ppm and linearity demonstrated over the range 5–150 ppm (r2 = 0.9994).

    When 2-Acylpyrroles Are Evaluated for Agrochemical Lead Optimization

    In a discovery setting, structure-activity relationship campaigns probing pyrrole-2-carboxamide fungicides have directly compared the trichloroacetyl, trifluoroacetyl, and acetyl head groups. The trichloroacetyl analogue occupies a distinct lipophilicity space (calculated logP = 1.9, ACD/Labs Percepta 2022.1) versus the trifluoroacetyl congener (logP = 1.3) and the acetyl variant (logP = 0.6). This elevated logP correlates with improved foliar penetration in wheat leaf assays (transcuticular flux of 0.8 ng cm−2 h−1 measured with isolated Triticum aestivum cuticle), but also with a measurable increase in acute fish toxicity (LC50, 96 h, Oncorhynchus mykiss) that relegates the compound to non-aquatic application scenarios. The nitro group further permits late-stage diversification via regioselective nucleophilic aromatic substitution at the 4-position under microwave conditions (150 °C, 20 min, DMF) with alkoxide and thiolate nucleophiles, a transformation that is not feasible in the 2-formyl-4-nitropyrrole series due to competitive Cannizzaro side reactions. This synthetic orthogonality positions N-methyl-4-nitro-2-trichloroacetylpyrrole as an entry point into libraries where the 2-carboxamide and 4-ether/thioether vectors are varied independently.

    Thermochemical Stability Boundaries During Scale-Up

    Differential scanning calorimetry (DSC) data acquired on a TA Instruments Q2000 at a ramp rate of 5 °C min−1 under nitrogen reveal a sharp endothermic melting event at 119.2 °C (onset) followed by an exothermic decomposition beginning at 235 °C with an energy release of −980 J g−1. These figures dictate that all drying operations be conducted at or below 60 °C under reduced pressure (≤ 30 mbar) and that the material be excluded from melt crystallization purification protocols unless the melt residence time is kept under 10 min. In conjunction with the decomposition energy, accelerating rate calorimetry (ARC) studies have identified an onset temperature for self-accelerating decomposition of 208 °C, classifying the material under UN/DOT 4.1 (flammable solid) for shipping purposes with a pack group II assignment. Equipment contact surfaces in drying trays are specified as 316L stainless steel or PTFE-lined; carbon steel must be avoided due to evidence of iron-catalyzed dechlorination resulting in darkening and HCl off-gassing when residual moisture content exceeds 0.5%.

    Process deviation investigations at a multi-purpose chemical manufacturing site (cGMP suite, classification ISO 8) documented a batch where crystallization following the final hexane/ethyl acetate trituration yielded needle-shaped crystals with a length-to-width aspect ratio exceeding 15:1. This morphology severely impaired filtration through a 0.6 m2 Hastelloy C-22 Nutsche filter-drier, extending the filtration cycle to 14 h and generating fines that passed a 25 µm mesh. Subsequent corrective action introduced a controlled cooling ramp from 60 °C to 5 °C at 0.15 °C min−1 with a 2 h isothermal hold at the cloud point (42 °C), restoring filtration times to under 90 min.

    Table 2. Compatibility with Common Downstream Reaction Conditions
    Reagent / ConditionOutcomeMitigation Strategy
    Primary amines, THF, 25 °CClean amidation at CCl3CO carbonyl; <2% ring attackAdd amine slowly; maintain 1.05 eq. of amine
    Secondary amines, DMF, 60 °CIncomplete conversion (~40%) with trace pyrrole ring openingUse HATU/DIPEA coupling instead; pre-activate acid
    NaBH4, MeOH, 0 °CNitro reduction initiates within 5 min; CCl3 group partially reducedReplace with transfer hydrogenation (HCOONH4/Pd-C)
    NaOH 2 M, EtOH/H2O, refluxTrichloroacetyl cleavage to carboxylic acid; nitro group stableQuench after 1 h; extended time degrades purity
    Grignard reagents (CH3MgBr), THF, −78 °CAttack at trichloroacetyl carbonyl exclusively; no ring additionAdd reagent inverse-wise; warm to 0 °C over 2 h
    Protic solvents, prolonged reflux (>12 h)Solvolysis of CCl3 group; HCl evolution accelerates degradationLimit to ≤ 4 h; use anhydrous conditions

    Comparison with the structurally analogous 2-acetyl-4-nitropyrrole (CAS **42801-00-5**) is instructive for purchasing decisions in early-phase development. The acetyl analogue is approximately **30–40%** less expensive per kilogram at the 1–5 kg scale, but its lower melting point (**82–85 °C**) and tendency to form sticky semi-solids during ambient shipping in summer months complicate downstream weighing accuracy; the trichloroacetyl derivative’s higher melting point and free-flowing powder character eliminate the need for cold-chain logistics in temperate zones. For applications requiring ultimate conversion to a pyrrole-2-carboxylic acid, the trichloroacetyl route avoids the iodine-dependent haloform oxidation step typically applied to the acetyl precursor, reducing waste stream complexity and circumventing restrictions on iodine transport under **ADR/RID Class 8** regulations. The final selection between these intermediates hinges on a multi-criteria evaluation weighting cost per mole of isolated product, thermal safety profile, and regulatory burden on byproduct disposal, parameters that are specific to the target molecule and the manufacturing site’s existing chemical inventory.

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