2-(Aminomethyl)-1,5-Dimethylpyrrole 95+%
|
HS Code |
897933 |
| Name | 2-(Aminomethyl)-1,5-Dimethylpyrrole 95+% |
| Chemical Formula | C7H12N2 |
| Molar Mass | 124.184 g/mol |
| Purity | 95+% |
| Functional Groups | Aminomethyl group and dimethylated pyrrole ring |
As an accredited 2-(Aminomethyl)-1,5-Dimethylpyrrole 95+% factory, we enforce strict quality protocols—every batch undergoes rigorous testing to ensure consistent efficacy and safety standards.
| Packing | 100g of 95+% 2-(Aminomethyl)-1,5 -Dimethylpyrrole in sealed chemical - grade packaging. |
| Shipping | 2-(Aminomethyl)-1,5 -Dimethylpyrrole 95+% is shipped in sealed, corrosion - resistant containers. It's transported with strict adherence to chemical shipping regulations to ensure safety during transit. |
| Storage | Store 2-(Aminomethyl)-1,5 -Dimethylpyrrole 95+% in a cool, dry, well - ventilated area away from heat sources and open flames. Keep it in a tightly sealed container, preferably in a chemical storage cabinet. Due to its chemical nature, store it separately from oxidizing agents, acids, and other incompatible substances to prevent potential reactions. |
In the production of structural aerospace laminates via autoclave processing, 2-(aminomethyl)-1,5-dimethylpyrrole (Am-DMP) is metered into bisphenol F diglycidyl ether (DGEBF) resin systems where replacement of conventional aromatic diamines is necessitated by post-cure dry glass transition temperature requirements exceeding 180 °C. The amine hydrogen equivalent weight (AHEW) of Am-DMP is calculated at 62.1 g/eq based on a molecular mass of 124.18 g/mol and two active amine hydrogens from the primary amine; stoichiometric loading therefore falls within 26–34 phr relative to an epoxy resin with an epoxide equivalent weight of 170–175 g/eq. Handling constraints are significant: the hygroscopic nature of the aminomethyl substituent demands pre-drying of the formulated resin under vacuum at 55 °C for a minimum of 4 hours when ambient relative humidity exceeds 60 %, otherwise blushing and microvoid formation during the 1.5–2.5 bar autoclave cycle are documented on production-scale equipment with charge volumes above 50 kg. The latent cure profile, characterized by a peak exotherm below 160 °C at a ramp rate of 1.5 °C/min as measured by differential scanning calorimetry per ASTM E2160, forces a dwell step at 120 °C for 90 minutes to equalize degree of conversion and avoid thermal runaway in thick laminate sections exceeding 12 mm. Compliance with aerospace fireworthiness mandates is verified through the Ohio State University (OSU) heat release test per FAR 25.853 and toxicity screening under BSS 7239. Adhesion to surface-treated carbon fabric is validated via flatwise tensile strength exceeding 7.5 MPa on aluminum honeycomb sandwich panels per ASTM C297. Terminal parts include out-of-autoclave cured wing spar caps and engine nacelle inner barrel acoustic panels where residual tensile strength retention of ≥85 % after 1000 hours at 175 °C in circulating air is a qualification threshold.Can corrosion under insulation (CUI) be mitigated by epoxy novolac primers containing sterically hindered aminomethylpyrroles?Immersion-grade novolac epoxy primers formulated with Am-DMP at 15–20 % by weight on binder solids rely on the molecule’s low viscosity contribution (18 mPa·s at 40 °C) to enable high-film-build application without solvent dilution, a critical factor for compliance with the Volatile Organic Compound limit of 250 g/L under Directive 2004/42/EC Annex IIA, subcategory j. Quantitative cure response at low substrate temperatures is monitored via the methyl ethyl ketone (MEK) double-rub method per ASTM D5402, where a 50-cycle pass requires a substrate temperature of at least 8 °C during application; below this threshold, crosslinking density drops catastrophically as the pyrrole ring’s steric shielding of the amine retards nucleophilic opening of the oxirane. Long-term corrosion resistance is verified through the ISO 12944-9 cyclic aging test (CX extreme environment) where scribe creep is held below 1.8 mm after 4200 hours when a zinc-rich primer is employed as the basecoat. In centrifugal blasting lines operating with steel grit G40 at a profile of 50–75 µm, pot-life drift in plural-component airless spray equipment is observed when relative humidity crosses 75 %, triggering pre-polymerization in the static mixer — a failure mode that necessitates line stoppage and solvent flushing with benzyl alcohol. Downstream processing enters the specification phase for tank lining composite systems where the intermediate coat is overcoated with a bisphenol A vinyl ester topcoat reinforced with 2.0 wt% nano-silica; the final assembly is commissioned as the protective lining system for sour crude oil storage tanks operating at a continuous service temperature of 95 °C with H₂S partial pressures up to 0.5 psi. Direct application on thermally sprayed aluminum (TSA) over carbon steel substrates requires dedicated adhesion testing under ASTM D4541 Type V, where the minimum pull-off strength of 5 MPa must be met before the structure enters dehumidified storage.Where the amine actively participates in mixed corrosion inhibitor packages for matrix-acidizing operationsIn coiled tubing-conveyed matrix acidizing of carbonate reservoirs, Am-DMP is introduced into 15 wt% hydrochloric acid as a high-temperature corrosion inhibitor component at a concentration of 0.02–0.05 vol%, typically in blend with alkyl benzyl quinolinium chloride and potassium iodide as an iodide intensifier. Performance is validated through a weight-loss test per NACE TM0169-2012 on API 5CT grade L80-13Cr steel coupons; the corrosion rate at 130 °C and a pressure of 3000 psi must remain below 0.05 lb/ft² over a 4-hour exposure window to qualify for use in deep gas wells with bottomhole static temperatures above 125 °C. Nitrogen-containing heterocycles adsorb onto the steel surface via chemisorption, and the methyl substituents on the pyrrole ring shift the desorption onset temperature by approximately 15–20 °C compared to unsubstituted pyridine-based inhibitors, based on Tafel extrapolation in electrochemical impedance spectroscopy (EIS) studies. Compatibility with mutual solvents such as ethylene glycol monobutyl ether must be assessed through visual precipitation screening; published data for this specific aminomethyl-dimethylpyrrole configuration indicates that phase separation inIn a batch mixer with a 1.5 L chamber capacity and intermeshing twin-shaft blades, castable polyurethane elastomers based on 4,4'-diphenylmethane diisocyanate (MDI) terminated prepolymers are chain-extended with Am-DMP at a stoichiometric index of 0.92–0.98 — deliberately leaning towards a slight isocyanate deficit to avoid residual free isocyanate that would catalyze post-cure dimensional growth in humid tropical storage environments. The addition ratio is 6.2–8.4 parts per hundred parts of prepolymer by weight, calibrated such that the NCO content of the prepolymer (typically 9.8–11.2 %) is fully consumed by the combined action of the primary amine and atmospheric moisture. A pot-life of 4–6 minutes at 80 °C is registered; transferring the reacting mass into open molds preheated to 110 °C demands high-throughput metering by a gear pump with 0.5 mL shot accuracy to ensure homogeneous fill before the steep viscosity ramp that renders flow fronts immobile. Crosslink density, assessed via the equilibrium swelling ratio in toluene with a Flory-Rehner calculation based on the Mooney-Rivlin equation, increases by 18–22 % when the mold is post-cured for 16 hours at 120 °C in a circulating air oven versus un-post-cured specimens. Tensile properties under DIN 53504 S3A dumbbell specimens cut from 2 mm plaques show a tensile strength of 22–28 MPa with an elongation at break of 420–480 %; however, a pronounced cliff-edge in tear strength per ISO 34-1 Method B (trouser tear) occurs when the addition level deviates by more than ±0.5 parts from the optimized window, attributed to rapid chain extension outpacing gelation and causing macroscopic phase separation between hard and soft segments observable via atomic force microscopy tapping mode. The terminal component emerges as a demountable elastomeric coupling insert for rotor drive shafts in marine propulsion pods, where saltwater immersion at 60 °C for 21 days must not reduce the Shore A hardness by more than 2 points or increase the volume swell beyond 1.8 %.Surface functionalization of glass microspheres for syntactic foam buoyancy modules via aminomethylpyrrole anchoringFor syntactic foams rated to 6000 m depth service in remotely operated vehicle buoys, hollow borosilicate glass microspheres (S60HS, density 0.60 g/cm³) are silanized with an Am-DMP coupling agent applied as a 0.8 wt% aqueous-isopropanol solution adjusted to pH 4.5. The free primary amine grafts onto the epoxy novolac matrix resin during the vacuum-assisted high-shear mixing stage, where the mixer speed is limited to 800 rpm to prevent catastrophic particle fracture; the measured crush strength of the microsphere batch per ASTM D3102 dictates the allowable shear stress input. The ratio of treated microspheres to resin is fixed at 38 vol%, yielding a cured foam density of 0.68 ± 0.03 g/cm³ as verified by helium pycnometry per ISO 1183-2. Deep-sea qualification requires cyclic hydrostatic compression between ambient and 65 MPa for 1000 cycles in a pressure vessel equipped with LVDT strain gauges: after 500 cycles, the permanent volumetric strain must not exceed 1.2 %. The process notebook entry for a 200 L batch details that conditioning the amine-silanized microspheres under nitrogen blanket for 24 hours at 40 °C eliminates ammonia-like off-gassing during the curing exotherm, a nuisance that otherwise creates surface pitting in the machined buoyancy blocks. The finished buoyancy module assembly integrating syntactic foam collars around a titanium frame must comply with the pressure vessel code ASME PVHO-1 for manned submersible windows, though the specific foam formulation qualification falls under DNVGL-ST-F301 for unmanned systems. |
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Catalogued as AP-2155, 2‑(aminomethyl)‑1,5‑dimethylpyrrole (C7H12N2, molecular weight 124.19 g·mol−1) is a light‑sensitive, air‑sensitive liquid primary amine supplied with a minimum purity of 95% (HPLC, area%). The material is manufactured under ISO 9001:2015‑certified quality systems and is intended as a building block for heterocyclic chemistry, coordination‑complex synthesis and pharmaceutical intermediate elaboration. During bulk transfer operations on pilot‑plant filling lines using 20‑L HDPE containers, nitrogen blanketing is maintained to prevent amine‑CO2 adduct formation, a failure mode observed when headspace oxygen concentration exceeds 5% (v/v).
Final product release relies on orthogonal chromatographic and titrimetric tests. Identity is confirmed by 1H NMR (CDCl3, 400 MHz) with characteristic doublet at δ 3.78 (J = 6.8 Hz, CH2NH2) and singlet at δ 2.12 (N‑CH3). Purity is determined by reversed‑phase HPLC on a 250×4.6 mm C18 column, detection at 254 nm, method validated per ICH Q2(R1). The amine equivalent weight, measured by non‑aqueous titration with perchloric acid in glacial acetic acid, falls within 122–128 g·eq−1 (theoretical 124.19). Water content is controlled by coulometric Karl Fischer titration (USP 〈921〉) to ≤0.3%.
| Property | Value | Test Method |
|---|---|---|
| Assay (anhydrous, solvent‑free) | ≥95.0% | HPLC (area%) |
| Appearance | Pale‑yellow to amber liquid | Visual inspection |
| Water content | ≤0.3% (w/w) | Karl Fischer (USP 〈921〉) |
| Refractive index (nD20) | 1.503–1.508 | DIN 51423‑1 |
| Density (20 °C) | 0.95–0.97 g·mL−1 | Oscillating U‑tube |
| Boiling range (15 mmHg) | 92–95 °C | Fractional distillation |
| Storage temperature | −20 °C ± 4 °C | Stability study |
The presence of an N‑methyl and a C5‑methyl group alters both the steric environment and the electronic density of the pyrrole ring. In 2‑(aminomethyl)‑1‑methylpyrrole (lacking the 5‑methyl), the amine pKa (conjugate acid) is approximately 9.2; the additional 5‑methyl substituent in AP-2155 lowers the pKa to 9.0 (calculated, B3LYP/6‑311+G(d,p) with SMD solvation), weakening nucleophilicity in acylation reactions. However, the methyl at C5 suppresses undesired tautomerisation to the 2‑methylene‑1,5‑dimethyl‑2H‑pyrrole form, a pathway that complicates handling of the unmethylated 2‑aminomethylpyrrole, which rapidly polymerises above 40 °C. Consequently, AP-2155 tolerates short‑duration heating to 70 °C under argon, whereas the 3‑substituted isomer (2‑aminomethyl‑3,5‑dimethylpyrrole) exhibits lower thermal robustness and tends to form Schiff bases with adventitious aldehydes even at ambient temperature. These differences are summarised in the comparison table.
| Compound | Physical state at 25 °C | Approx. pKa (NH3+) | Thermal stability limit (argon) | Typical yield in BODIPY condensationa | Primary side reaction |
|---|---|---|---|---|---|
| 2‑(Aminomethyl)‑1,5‑dimethylpyrrole (AP-2155) | Liquid | 9.0 | 70 °C | 82–88% | Amide formation with acid chlorides |
| 2‑(Aminomethyl)‑1‑methylpyrrole | Liquid | 9.2 | 55 °C | 75–80% | Electrophilic attack at C5 |
| 2‑(Aminomethyl)‑3,5‑dimethylpyrrole | Waxy solid (m.p. 34–36 °C) | 8.7 | 45 °C | 68–74% | Oxidative oligomerisation |
| 2‑(Aminomethyl)pyrrole (unsubstituted) | Low‑melting solid | 9.4 | 30 °C | <50%b | Rapid polymerisation |
a Condensation with 4‑methoxybenzaldehyde, BF3·OEt2 catalysis in CH2Cl2 at 25 °C, 20‑mmol scale; isolated yield after silica gel chromatography.
b Published data for this specific configuration is limited; the value cited represents the highest reported yield in a 5‑mmol run.
The C5‑methyl substituent exerts a directing effect that distinguishes AP-2155 from its 1‑methyl‑only analogue. Vilsmeier–Haack formylation (POCl3/DMF, DCE, 60 °C) yields the 3‑formyl derivative with 93% regioselectivity, whereas the same protocol applied to 2‑(aminomethyl)‑1‑methylpyrrole gives a 60:40 mixture of C3‑ and C5‑formylated products. Nitration with acetyl nitrate in acetic anhydride at −10 °C occurs predominantly at C4 (78% selectivity), leaving the aminomethyl side chain untouched. When the 5‑methyl group is absent, nitration is accompanied by significant oxidation of the amine. These differences are exploited in the synthesis of unsymmetrical dipyrromethene ligands where specific β‑positions must remain free for subsequent metal‑template cyclisation.
In the synthesis of 4,4‑difluoro‑4‑bora‑3a,4a‑diaza‑s‑indacene (BODIPY) dyes, the compound condenses with aromatic aldehydes under mild acid catalysis (trifluoroacetic acid, CH2Cl2, 0–5 °C) followed by oxidation with DDQ (2.2 equivalents). On a 1‑L reactor scale equipped with a retreat‑curve impeller, the intermediate dipyrromethane forms with 92% conversion after 2 h and is transformed to the boron‑dipyrrin complex using BF3·OEt2 in the presence of Hünig’s base. Batch‑to‑batch variation in fluorophore quantum yield was measured at 0.82 ± 0.03 (ethanol, excitation at 480 nm) across 12 consecutive campaigns, using a calibrated integrating sphere per IEC 62471. The product AP-2155 is particularly suited to this sequence because it cannot undergo self‑condensation via the 5‑position, a competitive pathway that consumes starting material when less‑substituted aminomethylpyrroles are employed.
The primary amine rapidly absorbs atmospheric CO2 and moisture, generating carbamic acid and ammonium bicarbonate. Exposure of the neat liquid to air at 50% relative humidity and 22 °C leads to a 3.2‑fold increase in water content and a 5% loss of amine titre within 4 h, as quantified by Karl Fischer and non‑aqueous titration. The resulting haze (insoluble carbonate salts) cannot be removed by filtration through 0.45‑µm PTFE membranes and promotes further hydrolysis. Therefore, all aliquots must be taken in a glove box (O2 < 10 ppm, H2O < 1 ppm) or under a dry nitrogen sweep. Sealed ampoules stored at −20 °C retain ≥94% purity for 24 months; once opened, remaining contents should be blanketed with argon and used within 14 days. Pre‑drying over activated 4‑Å molecular sieves (10% w/w, 24 h) is recommended when the amine is to be used in stoichiometric reactions with moisture‑sensitive reagents such as lithium aluminium hydride or trimethylaluminium.
Coupling of AP-2155 with aromatic aldehydes employing NaBH(OAc)3 (2.0 equiv, DCE, 25 °C) reaches complete conversion in 3 h if the system is buffered with 1.5 equivalents of glacial acetic acid. Without acid buffering, the pH rises above 8.5 due to deprotonation of the amine, and reductive amination stalls at 60–65% conversion because the pyrrole ring becomes susceptible to partial hydrogenation under the acidic conditions required to re‑protonate the imine intermediate. Excessive NaBH3CN (> 2.5 equiv) leads to detectable pyrrolidine by‑products (3–5% area% after 6 h). The hydrochloride salt of 2‑(aminomethyl)‑1,5‑dimethylpyrrole can be used to circumvent the pH drift but introduces higher water retention and requires anhydrous solvents; the free base (AP-2155) offers greater kinetic control in aprotic media.
During scale‑up of a quinazoline‑fused drug intermediate, a 50‑L jacketed glass reactor configured with a pitched‑blade turbine yielded 88% isolated product after 4 h at 20 °C using 1.05 equiv of 3‑nitrobenzaldehyde and NaBH(OAc)3. The pH was continuously monitored with a Mettler Toledo InPro 3250 probe and maintained at 5.0–5.5 by automated dosing of acetic acid. No exotherm exceeding 3 °C·min−1 was recorded, and post‑reaction HPLC indicated 98.2% purity of the crude secondary amine.
The β‑free positions (C3 and C4) of AP-2155 are amenable to directed ortho‑metallation and subsequent functionalisation, enabling the construction of N‑confused porphyrins and expanded porphyrinoids. Treatment with n‑BuLi (1.1 equiv, THF, −78 °C) lithiates selectively at C3, and quenching with DMF yields the 3‑formyl derivative in 72% isolated yield without competing substitution at the aminomethyl arm. This regiochemical fidelity is lost in 2‑(aminomethyl)‑1‑methylpyrrole, where lithiation occurs competitively at C5 and the benzylic methylene, giving intractable mixtures. The 1,5‑dimethyl substitution therefore permits a modular strategy for assembling hexaphyrins and other C–N–C‑linked oligopyrrole architectures that require a pre‑locked β‑position on one of the precursor units.
