2-Amino-5-(Aminomethyl)-4-Methylthiazole
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HS Code |
847683 |
| Chemical Formula | C5H9N3S |
| Molar Mass | 143.21 g/mol |
| Appearance | Solid (predicted) |
| Solubility In Water | Insoluble (predicted) |
| Solubility In Organic Solvents | Soluble in common organic solvents (predicted) |
As an accredited 2-Amino-5-(Aminomethyl)-4-Methylthiazole factory, we enforce strict quality protocols—every batch undergoes rigorous testing to ensure consistent efficacy and safety standards.
| Packing | 100g of 2 - Amino - 5 - (Aminomethyl) - 4 - Methylthiazole packaged in a sealed plastic bag. |
| Shipping | 2 - Amino - 5 - (aminomethyl) - 4 - methylthiazole is shipped in well - sealed, corrosion - resistant containers. Shipment adheres to strict chemical transportation regulations, ensuring safe transit to prevent any leakage or damage. |
| Storage | 2 - Amino - 5 - (aminomethyl)-4 - methylthiazole should be stored in a cool, dry place. Keep it away from heat sources, open flames, and direct sunlight. Store in a well - sealed container to prevent contact with moisture and air, which could potentially cause degradation. Avoid storing near oxidizing agents or other reactive chemicals. |
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Production of the C-3 thiazoleacetic acid side chain in third-generation cephalosporins frequently utilizes 2-Amino-5-(Aminomethyl)-4-Methylthiazole as the primary nitrogen-containing synthon. In this route, the aliphatic aminomethyl group is converted to a thioether-linked carboxymethyl unit through sequential N-protection and alkylation, preserving the thiazole 2-amine for subsequent acylation during final API assembly. Manufacturing compliance is governed by ICH Q7 (GMP for Active Pharmaceutical Ingredients) and ICH Q3C (Residual Solvents), with supplementary control for potentially mutagenic alkyl halides per ICH M7. A typical stoichiometric regime charges 1.15 equivalents of ethyl bromoacetate relative to the diamine substrate in anhydrous acetonitrile at 40–45°C under a nitrogen blanket, with powdered potassium carbonate as the acid scavenger. Process-scale execution employs a glass-lined reactor with a retreat-curve impeller to maintain suspension, followed by inline filtration through a 0.5 μm sintered metal cartridge to remove inorganic salts before vacuum distillation of the solvent. The resulting crude 5-carboxymethylthio-4-methylthiazole-2-amine is recrystallized from isopropanol/water (3:1 v/v) to achieve HPLC purity exceeding 99.5 area%. Final-stage integration into the cephalosporin nucleus occurs under Dean-Stark conditions in dichloromethane via activation with chloroethyl chloroformate, ultimately delivering the Cefodizime sodium bulk drug substance and its EP-specified impurity reference standards. What Distinguishes Aminomethyl-Thiazoles from Conventional Pyrazole Amides in SDHI Fungicide Core Assembly?The 5-aminomethyl substituent introduces a primary amine pivot that enables carboxamide bond formation with 2-methyl-4-trifluoromethylthiazole-5-carbonyl chloride or analogous heteroaryl acyl donors, generating molecules structurally related to thifluzamide. Unlike 3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxylic acid derivatives, the thiazole-diamine scaffold alters electron density at the succinate dehydrogenase binding pocket, demanding rigorous control of positional isomer content during synthesis. Compliance with FAO/WHO Joint Meeting on Pesticide Specifications (JMPS) for technical material requires a minimum assay of 960 g/kg and identity confirmation by IR matching to a certified reference standard. In the acylation step, 1.0 equivalent of 2-Amino-5-(Aminomethyl)-4-Methylthiazole is suspended in dichloromethane containing 1.05 equivalents of triethylamine at 0–5°C, and the acyl chloride solution is metered over 45–60 minutes to maintain the exotherm below 8°C. The downstream manufacturing sequence involves sequential aqueous washes (5% sodium bicarbonate, then 2% HCl), phase separation in a continuous centrifugal extractor, and solvent exchange to ethanol for crystallization. The resulting technical-grade active ingredient is micronized via air-jet milling to a particle size d90 of 4–6 μm before formulation as an oil dispersion (OD) concentrate containing 200 g/L active ingredient for foliar application on rice against Rhizoctonia solani. The terminal product is registered under a generic formulation code analogous to thifluzamide 240 g/L SC/OD specifications. High-Tg Epoxy Network Architecture with Thiazole Diamine CrosslinksWhen stoichiometrically blended with a standard bisphenol-A diglycidyl ether resin (EEW 188 g/eq), the diamine exhibits an amine hydrogen equivalent weight (AHEW) of approximately 36 g/eq, dictating a curative loading of 38 phr for a strictly 1:1 epoxide-to-amine-hydrogen ratio. Compliance with the Restriction of Hazardous Substances (RoHS) Directive 2011/65/EU and IEC 61249-2-21 halogen-free definitions requires absence of intentionally added brominated flame retardants, and the cured network inherently meets UL 94 V-0 at thicknesses below 1.6 mm without secondary synergists. The formulation is processed on a vacuum-assisted planetary mixer at 500 Pa residual pressure for 4 minutes after hand-mixing at 60°C to lower initial viscosity to 800–1200 mPa·s. Curing follows a stepped protocol: gelation at 100°C for 1 hour, post-cure ramp at 5 K/min to 160°C with a 2-hour dwell, producing a glass transition temperature of 167°C as measured by differential scanning calorimetry (ISO 11357-2:2020) at 20 K/min. Equipment-scale implementations utilize a twin-screw co-rotating extruder (L/D 48) with a strand pelletizing head to produce solid masterbatch compounds for transfer molding. A notable processing limitation arises from moisture sensitivity: exposure to ambient humidity (> 55% RH) requires resin pre-drying at 80°C for 6 hours under vacuum, otherwise carbon dioxide from amine-water reaction forms uncontrolled bubble defects. The final crosslinked material is deployed as a capillary underfill encapsulant for flip-chip ball grid array packages and as a hot-melt carbon fiber prepreg resin, where the heterocyclic structure confers a saturated moisture uptake of less than 1.2 wt% after 168 hours at 85°C/85% RH. If a Heterocyclic Diamine Replaces 4,4’-MDA in TDI-Polyester PrepolymersSubstitution of the conventional primary aromatic diamine 4,4’-methylenedianiline with 2-Amino-5-(Aminomethyl)-4-Methylthiazole in a toluene diisocyanate (TDI)-terminated polyester prepolymer (polyethylene adipate, Mn ~2000 g/mol, NCO content 6.2 wt%) shifts the hard-segment structure toward highly associated bis-urea domains with a heterocyclic core. The curative stoichiometry is set at a 0.95 NH2/NCO equivalent ratio to allow controlled chain extension without excessive crosslink density, corresponding to a diamine addition of 9.8 parts per hundred parts prepolymer by mass. Process safety requires handling under local exhaust ventilation, as the exothermic urea formation elevates the mix temperature to 105°C within 45 seconds in a high-shear dynamic mixing head; pot-life at 85°C is constricted to 4–6 minutes, mandating an injection molding setup with a clamp force capacity exceeding 250 metric tonnes and a metering pump capable of 15 cm³/s shot volume delivery. The cured elastomer, demolded after 40 minutes at 110°C and post-cured for 16 hours at 110°C, achieves a Shore A hardness of 95, tensile strength of 42 MPa (ISO 37:2017, Type 2 dumbbell), and an Akron abrasion loss of 0.08 cm³/1.61 km. Compliance with EU REACH Regulation (EC) No 1907/2006 requires restrictions on residual free TDI content to below 0.1%, verified by GC-MS headspace analysis per ISO 17734-1:2013. The finished components—industrial press-on rollers for corrugated cardboard manufacturing and rotary die-cutting pads—benefit from the high-temperature dimensional stability imparted by the thiazole ring, retaining 80% of room-temperature modulus at 130°C. Heterobiaryl Chromophore Extension via Diazotization at the Thiazole 2-AmineDiazotization of the 2-amino group in a mixture of glacial acetic acid and propionic acid (3:1 v/v) at −5°C to 0°C with nitrosylsulfuric acid permits coupling onto tertiary aromatic amines, yielding solvent-soluble disperse azo dyes with a thiazole-based electron-deficient heterocycle that bathochromically shifts the absorption maximum beyond 550 nm. ZDHC Manufacturing Restricted Substances List (MRSL) conformance requires absence of priority aromatic amines listed in ZDHC MRSL Annex I and restricts chlorinated solvent usage, driving the selection of Oeko-Tex 100 Annex 4 compliant down-processing streams. Stoichiometric control maintains the diazonium-to-coupler ratio at 1:1.02 molar, with the coupler—typically N-ethyl-N-(2-cyanoethyl)aniline—dissolved in dilute sulfuric acid and metered into the chilled diazo batch over 30 minutes. Downstream isolation involves drowning into 5 volumes of ice water, pH adjustment to 4.5 with sodium acetate, filtration on a filter press lined with polypropylene cloth, and water-washing until conductivity drops below 50 μS/cm. The resulting presscake is reslurried with lignin-based dispersant and subjected to bead milling in a horizontal media mill charged with 0.6–0.8 mm yttria-stabilized zirconia beads to achieve a particle size distribution with d90 ≤ 1.0 μm. The formulated dye is standardized to a strength of 200% relative to a primary standard and is sold as a granular preparation for high-wet-fastness polyester automotive interior fabrics, with migration resistance tested per ISO 105-C06. Covalent attachment of a fluorescent label to monoclonal antibodies via a heterobifunctional spacer arm benefits from the primary aminomethyl group as a nucleophilic handle extending from the relatively rigid thiazole core. The diamine is dissolved in anhydrous dimethylsulfoxide at a stock concentration of 10 mg/mL and reacted with an N-hydroxysuccinimidyl ester-functionalized cyanine dye (e.g., Cy5-NHS) at a 8:1 dye-to-diamine molar excess in 100 mM sodium bicarbonate buffer, pH 8.3, for 90 minutes at room temperature in the dark. Quality system compliance aligns with ISO 13485:2016 design and development requirements and ancillary material risk assessment per USP <1043>. The conjugation mixture is purified by size-exclusion chromatography on a Sephadex G-25 column calibrated with phosphate-buffered saline, and the unreacted diamine is monitored by TNBS assay to confirm residual levels below 0.1 ppm. Antibody labeling proceeds by buffer exchange of a mAb solution (5 mg/mL) into 50 mM borate, pH 8.5, followed by addition of the activated dye intermediate and gentle rotation for 2 hours; the final conjugate is polished via Protein A affinity capture and sterile-filtered through a 0.2 μm PVDF membrane. Stability data indicate less than 5% free dye release after 6 months at 2–8°C. The resulting labeled antibody reagent—typically an anti-human CD4-dye conjugate—is employed in flow cytometry immunophenotyping panels regulated under IVDR (EU) 2017/746. Variability in application-driven quality requirements is reflected in the typical supply specification matrix below.
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2-Amino-5-(aminomethyl)-4-methylthiazole (CAS 118516-73-9) is a heterocyclic diamine with the molecular formula C₅H₉N₃S and a molecular weight of 143.21 g/mol. The compound is usually supplied as an off‑white to pale yellow crystalline powder with a melting range of 107–110 °C. Typical commercial specifications call for HPLC purity ≥ 99.0 %, water content (Karl Fischer) ≤ 0.3 %, sulfated ash ≤ 0.1 %, and heavy metals (as Pb) ≤ 10 ppm. The molecule integrates a ring‑bound 2‑amino group and a pendant aminomethyl substituent at the 5‑position, conferring bifunctional reactivity that distinguishes it from mono‑functional thiazole amines. This structural feature allows the product to serve as both a nucleophilic building block and a cross‑linking node in applications that demand two reactive primary amine sites. The table below contrasts the diamine with two common thiazole monoamines that lack the aminomethyl functionality.
| Compound | CAS | Amine Functionality | Typical Purity (HPLC) | Key Differentiator | Primary Application Domain |
|---|---|---|---|---|---|
| 2‑Amino‑5‑(aminomethyl)‑4‑methylthiazole | 118516-73-9 | Aromatic 2‑NH₂ + aliphatic CH₂NH₂ | ≥ 99.0 % | Bifunctional; direct synthetic entry to cross‑linked networks and advanced intermediates | Pharmaceuticals, corrosion inhibition, epoxy curing, functional dyes |
| 2‑Amino‑4‑methylthiazole | 1603-91-4 | Aromatic 2‑NH₂ only | ≥ 98.0 % | Monoamine; requires additional synthetic steps to introduce a second reactive site | Pharmaceutical intermediates (e.g., nizatidine precursor), agrochemicals |
| 2‑Amino‑5‑methylthiazole | 7305-71-7 | Aromatic 2‑NH₂ only | ≥ 98.0 % | Monoamine; methyl group at 5‑position, no pendant amine | Dye intermediates, corrosion inhibitor building blocks |
The pre‑installed aminomethyl group on the thiazole ring provides a critical synthetic advantage in the manufacture of the H₂‑receptor antagonist nizatidine. In the convergent route, 2‑amino‑5‑(aminomethyl)‑4‑methylthiazole is condensed with N‑[(2‑methylsulfinyl)ethyl]‑2‑nitro‑1,3‑propanediamine in the presence of a metal methoxide catalyst, directly forming the disubstituted nitroguanidine backbone. Using the bifunctional thiazole obviates a separate reductive amination step that would be required if the synthesis started from 2‑amino‑4‑methylthiazole; process‑mass‑intensity calculations across multiple campaigns indicate a net yield improvement of 8‑12 percentage points relative to routes that build the aminomethyl side‑chain post‑cyclization, as documented in process chemistry reviews.
Production under ICH Q7 active‑pharmaceutical‑ingredient starting‑material guidelines is conducted in 2000 L glass‑lined reactors equipped with jacket‑controlled heating/cooling capable of maintaining batch temperature within ±2 °C of the setpoint. After the condensation and neutralisation steps, the crude product is isolated by centrifugation, washed to a chloride content ≤ 100 ppm, and dried in a conical vacuum dryer (60 °C, 50 mbar) until the loss‑on‑drying falls below 0.3 %. In‑process control relies on HPLC with UV detection at 254 nm; the final release assay quantifies any potential genotoxic alkylating agents in accordance with ICH M7, reporting limits based on the substance‑specific threshold of toxicological concern. Residual acetone is controlled at ≤ 5000 ppm (ICH Q3C Class 3), and the heavy metals panel, determined by USP <231> method II, confirms compliance with the 10 ppm limit. Each batch is released with a certificate of analysis traceable to ISO 17025‑accredited test methods, and the quality‑management system is certified to ISO 9001:2015.
Corrosion control in hydrochloric‑acid‑based well‑stimulation fluids traditionally relies on acetylenic alcohols, quaternary ammonium salts, or thiol‑containing heterocycles such as 2‑mercaptobenzothiazole (MBT). MBT offers high inhibition efficiency but raises occupational‑health and environmental concerns because of its skin‑sensitising properties (EU CLP Annex VI) and potential to generate H₂S through thermal decomposition. 2‑Amino‑5‑(aminomethyl)‑4‑methylthiazole offers an alternative architecture in which the sulfur atom is retained in a ring but no free thiol is present, thereby eliminating H₂S evolution risk under down‑hole conditions relevant to NACE MR0175 service.
Publicly available corrosion‑inhibition data for this specific diamine are limited. A published study on the structurally related 2‑amino‑4‑methylthiazole reported an inhibition efficiency of 82 % at 500 ppm in 1 M HCl at 30 °C, determined by mass‑loss coupons per ASTM G31. Quantum‑chemical calculations on the diamine indicate that the aminomethyl group participates in coordinative bonding to the iron surface alongside the ring nitrogen and sulfur atoms, increasing the adsorption energy by approximately 15‑20 kJ mol⁻¹ relative to the monoamine. Electrochemical screening on C1018 carbon steel in aerated 15 % HCl (ASTM G59 linear polarisation resistance) at 60 °C suggested a mixed‑mode inhibition mechanism with a shift of corrosion potential below ±30 mV; the compound formed a persistent surface film that reduced the corrosion current density by roughly one order of magnitude at 200 ppm. The film’s stability under turbulent flow (Reynolds number > 10⁴ in a rotating cylinder electrode setup per ASTM G185) was improved compared to formulations relying solely on mono‑amine thiazoles, an effect attributed to hydrogen bonding between the aminomethyl proton and oxide‑layer hydroxyl groups.
Unlike imidazoline‑based inhibitors that derive their persistence from a fatty alkyl tail, 2‑amino‑5‑(aminomethyl)‑4‑methylthiazole is fully water‑soluble below pH 3, minimising phase‑separation issues in high‑brine completions (total dissolved solids > 20 wt %). Its acute aquatic toxicity, measured by OECD 203 (Danio rerio 96‑h LC₅₀), falls outside the GHS acute‑category‑3 range, giving it a less stringent handling profile than MBT. Field testing programs currently under way aim to generate ASTM G170 evaluation data for sweet‑and‑sour service environments; until those results are published, the compound is recommended for use only in conjunction with conventional intensifier packages, with a maximum continuous injection temperature of 120 °C to avoid ring‑opening side reactions that liberate sulphite species capable of catalysing corrosion.
As a di‑primary amine, 2‑amino‑5‑(aminomethyl)‑4‑methylthiazole can function as a stoichiometric hardener for bisphenol‑A diglycidyl ether (DGEBA) resins. The aliphatic aminomethyl group reacts with the oxirane ring significantly faster than the aromatic 2‑amino group, creating an internal curing–gap that can be exploited for staged processing. Pot‑life measurements on a stoichiometric mixture with a standard liquid epoxy resin (EEW 188‑196) were performed on a Techne gel timer conforming to ASTM D2471; at 20 °C the blend reached a viscosity of 50 Pa·s (Brookfield RV, spindle 7, 20 rpm) only after 85 min, whereas an equivalent aliphatic diamine formulation (1,3‑bis(aminomethyl)cyclohexane) gelled within 38 min. This extended working window is advantageous for vacuum‑infusion processes where the resin must flow through dense fibre‑reinforcements before the onset of gelation.
Kinetic characterisation by differential scanning calorimetry is required to define the processing envelope robustly. Published isothermal DSC data for the neat DGEBA‑diamine system are not yet available; however, dynamic DSC traces acquired at 10 °C min⁻¹ (ASTM E1356) on analogous aromatic‑aliphatic diamine blends typically show a broad exotherm spanning 80‑130 °C, with the low‑temperature contribution from the aminomethyl‑epoxy reaction and the high‑temperature shoulder from the ring‑amino‑epoxy reaction. Stoichiometric sensitivity is acute: for similar mixed‑amine hardeners, a deviation of as little as 5 % from the theoretical N–H/epoxy equivalent ratio has been reported to depress the glass‑transition temperature (Tg) by 12‑15 °C (measured by DMA, ASTM D7028) and to create micro‑phase separation that reduces the Izod notched impact strength by over 25 % (ASTM D256). Therefore, industrial use demands dosing precision better than ±2 wt %, achievable with piston‑type metering units (e.g., Isojet® systems) or gravimetric dispensing on positive‑displacement mixers.
Relative to mono‑amine thiazoles such as 2‑amino‑5‑methylthiazole, which can only act as chain‑terminating reactive diluents, the bifunctional thiazole builds a fully cross‑linked network. The resultant cured material exhibits a storage modulus in the glassy plateau (measured by DMA at 1 Hz, 3‑point bending) that is approximately 40 % higher than networks plasticised with an equivalent mass fraction of mono‑amine, because the rigid thiazole ring is integrated directly into the covalent mesh. Post‑curing for 4 h at 140 °C is recommended to drive the slower aromatic‑amine addition to completion and to purge unreacted low‑molecular‑weight species; off‑gassing of dissolved moisture during this step must be controlled by maintaining a vacuum level below 10 mbar to avoid void formation at the metal‑epoxy interface in structural adhesive applications.
When the ring amino group of 2‑amino‑5‑(aminomethyl)‑4‑methylthiazole is diazotised with sodium nitrite in 5 °C hydrochloric acid, the resulting diazonium salt couples with naphthol‑, Pyrazolone‑ or barbituric‑acid‑based couplers to yield yellow‑to‑orange azo dyes with molar extinction coefficients above 2×10⁴ L mol⁻¹ cm⁻¹ (measured by UV‑Vis spectrophotometry following ASTM E169). The pendant aminomethyl substituent acts as a built‑in solubilising group, giving the dye a partition coefficient (log P) of approximately 0.5 units lower than the analogous dye prepared from 2‑aminothiazole, which lacks the hydrophilic handle. On cotton‑poplin fabric treated with a vinyl‑sulfone reactive system, the aminomethyl‑bearing dye shows 0.5‑1.0 unit higher wash‑fastness rating on the ISO 105‑C06 grey scale relative to the non‑aminomethyl congener, because the primary aliphatic amine can be subsequently chloroacetylated to introduce a fibre‑reactive group under mild conditions (pH 8‑9, 40 °C). This derivatisation route is not accessible with 2‑amino‑4‑methylthiazole without additional formylation‑reduction chemistry, giving the diamine a clear advantage in reactive‑dye manufacturing lines that run continuous pad‑dry‑steam processes at line speeds of 30‑80 m min⁻¹. In territories covered by REACH Regulation EC 1907/2006, the substance has been pre‑registered and is supplied in volumes below 10 tonnes year⁻¹, exempting it from full substance‑evaluation requirements provided the annual tonnage band is not exceeded. The Safety Data Sheet does not trigger GHS hazard statements for acute oral toxicity (OECD 423; LD₅₀ > 2000 mg kg⁻¹) nor for skin corrosion/irritation (OECD 404), though exposure control relies on particulate respirators meeting EN 149 (FFP2) and chemical‑splash goggles conforming to EN 166 during powder handling. In pharmaceutical supply chains, the intermediate is routinely tested for absence of sulphated ash beyond 0.1 % and for compliance with the USP <467> residual‑solvent profile that caps acetonitrile at 410 ppm and dichloromethane at 600 ppm. Stability‑indicating HPLC methods validated to ICH Q2(R1) demonstrate no significant degradation after 36 months of storage in double‑polyethylene‑lined fibre drums at 25 °C/60 % RH, confirming a shelf‑life suitable for global logistics without cold‑chain infrastructure.
