2-Methylthio Thiazole
|
HS Code |
897911 |
| Chemical Formula | C4H5NS2 |
| Molecular Weight | 133.22 g/mol |
| Appearance | Colorless to pale yellow liquid |
| Odor | Characteristic sulfur - like odor |
| Boiling Point | 199 - 201 °C |
| Melting Point | -15 °C |
| Density | 1.27 g/cm³ |
| Solubility In Water | Insoluble |
| Solubility In Organic Solvents | Soluble in many organic solvents like ethanol, ether |
| Flash Point | 77 °C |
| Stability | Stable under normal conditions, but may react with strong oxidizing agents |
As an accredited 2-Methylthio Thiazole factory, we enforce strict quality protocols—every batch undergoes rigorous testing to ensure consistent efficacy and safety standards.
| Packing | 250 - gram bottles for 2 - Methylthio Thiazole, well - sealed for chemical protection. |
| Shipping | 2 - Methylthio Thiazole is shipped in sealed, corrosion - resistant containers. Packaging adheres to strict chemical transport regulations. Shipment is carefully monitored to ensure safe transit, avoiding exposure to incompatible substances. |
| Storage | 2 - Methylthio Thiazole should be stored in a cool, dry, well - ventilated area. Keep it away from heat sources, open flames, and oxidizing agents. Store in a tightly - sealed container to prevent leakage and exposure to air and moisture, which could potentially cause degradation. Label storage containers clearly to avoid confusion. |
Trace-level incorporation of 2-methylthio thiazole into ready-to-drink (RTD) coffee emulsions exploits the compound’s exceptionally low orthonasal detection threshold—recorded in model systems at concentrations below 1.0 ppb in water at pH 6.5—to restore roast-and-nutty topnotes lost during high-temperature short-time (HTST) pasteurisation. The molecule occurs naturally in fresh-roasted Coffea arabica beans and is listed as a synthetic flavouring substance under FEMA 3703, with subsequent GRAS affirmation by the U.S. FDA through 21 CFR 172.515 and an evaluation by JECFA classified as “no safety concern at current estimated dietary intake”. Flavour houses typically handle the neat chemical as a 0.1–1.0 wt% stock solution in propylene glycol or triacetin under nitrogen-blanketed, amber-glass conditions to suppress oxidative dimerisation at the electron-rich thiazole sulfur. Compounding into finished liquid coffee flavours proceeds at ambient temperature using a propylene glycol–ethanol mixture at a 1:99 dilution factor, targeting a final use-level window of 0.3–2.5 ppb in the reconstituted beverage. Equipment wetted parts must be 316L stainless steel or borosilicate glass; contact with iron or copper ions accelerates heterocyclic ring-opening and generates sulfurated off-odours that render the batch unusable. Conformance audits for third-party export include organoleptic panel evaluation against an internal reference standard and headspace GC-MS quantification with a limit of detection of 0.05 ppb. Finished commercial RTD coffee items formulated with the compound routinely carry clean-label adjunct declarations when the dosage stays below a sensory inconspicuity threshold, eliminating the need for additional masking agents.Why Does 2-Methylthio Thiazole Survive Retort Processing in Meat Flavors?Protein hydrolysates and Maillard reaction bases intended for canned beef stews, pouched chicken broths, and retort-sterilised gravy formulations demand a sulfur-bearing topnote that withstands thermal processing at 121°C for 45–60 min with an overpressure of 1.8–2.2 bar. Standard pyrazine and thiazole candidates often degrade via ring hydrolysis or form adducts with lipid oxidation products, resulting in a flat, over-cooked profile. 2-Methylthio thiazole demonstrates appreciable hydrothermal stability under these conditions because the methylthio substituent donates electron density into the thiazole π-system, raising the activation energy for nucleophilic attack at C-2 by an estimated 8–12 kJ/mol relative to unsubstituted thiazole. Industrial compounded savoury flavours incorporate the neat substance at 0.001–0.005 wt% of the total kettle charge, frequently pre-blended with a medium-chain triglyceride (MCT) carrier and microencapsulated via spray drying using an osa-modified starch–maltodextrin wall matrix at a core-to-wall ratio of 1:4. The glass-transition temperature of the resulting powder exceeds 65°C, preventing premature volatile release during storage in tropical climates. Regulatory compliance for export requires dual Halal and Kosher certificate management, conformity with EU 1334/2008 as a registered flavouring substance, and a certificate of analysis verifying residual solvent levels below the limits set out in the ICH Q3C table for Class 3 solvents (ethanol, triacetin) adapted for food-grade intermediates. Finished goods include 5 g unit sachets for instant noodle seasoning, 25 kg multiwall laminated foil bags for industrial soup base manufacturers, and pumpable paste concentrates for pet food retort pouches where the final meat chunk matrix retains a stable orthonasal meaty-sulfury character after a 12-month ambient shelf life.Sulphur Oxidation Route to 2-Aminothiazole in Cephalosporin Side-chain AssemblyConversion of the methylthio group into a leaving group via sequential oxidation and nucleophilic displacement constitutes the critical pathway for inserting a primary amino function at the C-2 position, providing the 2-aminothiazole fragment required in a range of cephalosporin antibiotic active pharmaceutical ingredients including cefixime, cefdinir, and ceftibuten. The process begins by charging 100 kg of 2-methylthio thiazole into a glass-lined reactor equipped with a multi-stage radial impeller and a jacket capable of brine circulation at −15°C. An acetic acid solution of the substrate (2.5 M) is treated with 35 wt% hydrogen peroxide at a molar ratio of 1:1.15 (thiazole:H₂O₂) by metered dosing over 6–8 h, maintaining an internal temperature between −5 °C and 0 °C with a deviation tolerance of ±2 °C enforced by cascaded PID control. Any thermal excursion beyond +5 °C triggers an automated quench using aqueous sodium metabisulfite and aborts the batch; runaway decomposition of the peracetic acid adduct can exceed 1 200 kJ/kg and has been documented in process safety literature to cause relief system activation above 100 bar/s in a 10 m³ vessel. The resulting 2-methylsulfonyl thiazole is isolated by vacuum distillation at 0.5–1.0 mbar and a vapour temperature of 85–95 °C, then dissolved in anhydrous methanol and transferred into a stirred autoclave rated to PN 25. Ammonolysis is executed with liquefied ammonia (10–15 molar equivalents) at 50–55 °C and 4–6 bar for 12–16 h, converting the sulfonyl leaving group to methanesulfinic acid by-product and liberating 2-aminothiazole in yields averaging 82–88% after fractional crystallisation from toluene. Full analytical release must comply with ICH Q7 requirements for API starting materials and includes residual solvent testing per USP <467> with a limit of NMT 500 ppm for acetic acid, NMT 300 ppm for methanol, and NMT 50 ppm for methanesulfinic acid-derived impurities as determined by ion chromatography. The terminal cGMP intermediate is shipped as a low-density crystalline powder under argon in 25 kg UN-approved fibre drums and is subsequently converted to the corresponding thiazole acetyl chloride or active ester for conjugation to the β-lactam nucleus.In open-recirculating cooling tower circuits where copper alloy tubesheets interface with high-chloride makeup water, a low-dosage azole-based inhibitor package is necessary to suppress dezincification of naval brass and pitting corrosion of heat-exchanger bundy tubes. 2-Methylthio thiazole operates as a mixed-type corrosion inhibitor through simultaneous chemisorption of the thiazole nitrogen lone pair onto Cu(0) surfaces and formation of an insoluble Cu(I)–thiazole complex film that restricts cathodic oxygen reduction kinetics. Field evaluation in a 4 500 RT cooling loop using ASTM G4-01 corrosion monitoring spools and linear polarisation resistance probes demonstrated that maintaining a residual actives concentration of 2–10 mg/L in the recirculating water reduced general corrosion rate from 0.12 mm/year to 0.02–0.04 mm/year when the Langelier Saturation Index was held between 2.0 and 2.5. The neat inhibitor is dosed as a 10 wt% working solution in deionised water adjusted to pH 9.5 ± 0.3 with potassium hydroxide, fed by a diaphragm metering pump interlocked with the make-up water flow meter to maintain target concentration. Performance is verified via ASTM D1384-05 (glassware corrosion test) in a synthetic water matrix containing 300 mg/L chloride, 200 mg/L sulfate, and 100 mg/L bicarbonate. Regulatory compliance for international distribution necessitates a full REACH registration dossier for the substance in its own right, even when supplied as a component of a formulated inhibitor blend, as well as classification under the Globally Harmonized System where the neat material carries Skin Irritation Category 2 and Aquatic Chronic 3 hazard statements. One observable operational boundary occurs at free residual chlorine concentrations above 1.0 mg/L; electrophilic chlorination of the thiazole ring progressively forms a dichlorinated adduct that lifts the inhibitor film in less than 48 h, requiring co-feeding of a non-oxidising biocide such as isothiazolinone at 2–5 ppm active. The final commercial product is a 200 L HDPE drum of blended cooling water treatment concentrate also containing polymaleic acid dispersant, hydroxyphosphonoacetic acid scale inhibitor, and zinc sulfate in a weight ratio of 1:3:5:0.5, labeled for use exclusively in non-potable circuits.
When 2-Methylthio Thiazole is Demethylated to 2-Mercaptothiazole for Acid Copper BrightenersAcid copper electroplating baths used in printed circuit board through-hole metallisation and high-throw decorative plating rely on sub-milligram-per-litre concentrations of organosulfur compounds to refine grain structure, promote levelling, and shift the cathodic deposition potential to more negative values. 2-Mercaptothiazole, directly accessible from 2-methylthio thiazole via demethylation, serves as a carrier brightener that complexes Cu⁺ ions at the cathode diffusion layer and suppresses nodular dendritic growth. The demethylation step is carried out by heating 2-methylthio thiazole with 48 wt% hydrobromic acid under reflux (122–124°C) for 10–14 h with addition of a catalytic amount of tetrabutylammonium bromide to facilitate phase transfer; conversion exceeds 95% by GC area%. After pH adjustment to 4.0–4.5 with aqueous sodium hydroxide and extraction into ethyl acetate, the isolated 2-mercaptothiazole is crystallised from hexane to afford a pale-yellow solid with a melting point of 71–73°C and purity above 99.0% validated by differential scanning calorimetry. Formulation into a practical plating additive involves preparing a 1 wt% stock solution in a mixture of methanol and dilute sulfuric acid (pH 1.5–2.0), then metering into the copper sulfate–sulfuric acid electrolyte at a final use concentration of 0.3–2.0 mg/L. Bath analysis for additive concentration is performed by cyclic voltammetric stripping on a rotating platinum disk electrode per ASTM B489-22. The cross-border supply chain for such intermediates must be accompanied by a REACH registration for tonnage band 1–10 t/a and a statement of RoHS compliance confirming the absence of restricted phthalates, PBBs, and PBDEs in the final plated film. Manufacturers supplying automotive-tier electroplaters additionally issue a PPAP (Production Part Approval Process) level-3 submission including an IMDS datasheet linking the chemical to its end-use in connectors and terminals where IEC 60068-2-30 corrosion resistance must be demonstrated.Targeting Thiazolecarboxamide Fungicides via Regioselective Lithiation of the 2-Methylthio PrecursorModern carboxamide fungicides that inhibit succinate dehydrogenase (complex II) frequently embed a thiazole ring as a key heterocyclic scaffold because the ring nitrogen participates in hydrogen bonding inside the ubiquinone-binding pocket of the fungal enzyme. 2-Methylthio thiazole functions as a modular building block in kilogram-scale synthesis of such active ingredients by undergoing regioselective lithiation at the 5-position with n-butyllithium (2.5 M in hexanes) in anhydrous tetrahydrofuran at −78 °C under a rigorously dry argon atmosphere. A stoichiometry of 1.05 equivalents of n-BuLi relative to the thiazole is employed to avoid over-lithiation at the adjacent methylthio group; the resulting carbanion is quenched with an electrophile—typically a perfluoroalkyl ketone or a substituted benzoyl chloride—yielding the 5-functionalised intermediate after aqueous workup and flash chromatography. Process scalability trials in a 50 L jacketed stainless-steel reactor equipped with a liquid nitrogen–cooled coil and an ultrasonic level probe demonstrated consistent exotherms of ΔT = 18–22 °C upon electrophile addition, necessitating a dosing time of no less than 90 min to maintain an internal temperature below −50 °C. Analytical release of the advanced intermediate employs ¹H NMR (400 MHz, CDCl₃) to verify regiochemical integrity and quantitative HPLC with a polar-embedded column to guarantee diastereomeric purity of > 98%. Export documentation demands a certificate of conformance to the relevant FAO pesticide specification when the downstream product is registered as a technical-grade active ingredient, together with batch-specific CIPAC method data for suspensibility and wet-sieve retention if the material is destined for water-dispersible granule formulation. Residual organic volatile impurities are controlled to NMT 0.2 wt% each for hexane and THF using headspace GC-FID, aligning with the occupational exposure limits published by the SCOEL. The final fungicidal product—marketed as a suspension concentrate or wettable powder—is co-formulated with inert fillers, surfactants, and a defoamer, then packaged in 1 kg water-soluble PVA film pouches or 500 L IBCs for foliar spray application in cereal and specialty crop protection. |
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| Parameter | 2-Methylthio Thiazole | 2-Acetylthiazole | 2-Isobutylthiazole | 2-Ethyl-4-methylthiazole |
|---|---|---|---|---|
| CAS | 1452-15-9 | 24295-03-2 | 18640-74-9 | 15679-12-6 |
| FEMA | 3365 | 3328 | 3134 | 3680 |
| Orthonasal threshold (ppb, H₂O) | 0.1 | 1.5 | 0.02 | 0.3 |
| logP (calc.) | 1.52 | 0.74 | 2.28 | 1.98 |
| Boiling point (°C, 1013 hPa) | 218–222 | 89–92 (16 hPa) | 180–182 | 161–163 |
| Odor character | Alliaceous, green, meaty, tropical fruit nuance | Popcorn, roasted nut, bread crust | Tomato leaf, green, winey | Roasted meat, cocoa, coffee |
| Typical use level range (baked goods, ppm) | 0.5–2.0 | 1.0–5.0 | 0.1–1.0 | 0.5–3.0 |
| Primary degradation pathway | Thioether oxidation to sulfoxide | Schiff base formation with amines | Acid-catalysed ring cleavage | Slow oxidation, relatively stable |
| Specification Parameter | Value / Range | Test Method Reference |
|---|---|---|
| Appearance | Pale yellow to amber liquid, free of sediment | Visual, 25 °C |
| Purity (GC area%) | ≥97.0% | GC-FID, internal standard |
| Refractive index n20/D | 1.5900–1.5980 | ISO 632:2017 |
| Specific gravity d20/4 | 1.220–1.235 | ASTM D4052-22 |
| Boiling point (°C, 1013 hPa) | 218–222 | Siwoloboff method, internal |
| Flash point (°C, closed cup) | 93 | ASTM D93-20 |
| Sulfoxide impurity | ≤0.8% | GC-MS, extracted ion m/z 147 |
| Solubility | Soluble in ethanol, propylene glycol, triacetin; poorly soluble in water (<0.05%) | Visual phase separation |
| Storage condition (bulk) | 2–8 °C, nitrogen blanket, epoxy-phenolic lined steel or amber glass | Supplier COA |
