Ethyl 2-Methylthiazole-5-Carboxylate

Ethyl 2-Methylthiazole-5-Carboxylate


    • Product Name Ethyl 2-Methylthiazole-5-Carboxylate
    • Alias Ethyl 2-methyl-1,3-thiazole-5-carboxylate
    • Einecs 410-020-2
    • 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
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    Specifications

    HS Code

    837928

    Chemical Formula C8H9NO2S
    Molecular Weight 183.23 g/mol
    Appearance Typically a liquid or solid (color and physical state can vary based on purity and conditions)
    Boiling Point Data may vary, but generally in the range where the compound vaporizes under specific pressure conditions
    Melting Point Varies depending on purity, with a characteristic temperature range for solid - liquid transition
    Density A specific mass - volume ratio characteristic of the compound
    Solubility In Water Limited solubility, as it is an organic ester - containing thiazole derivative
    Solubility In Organic Solvents Soluble in common organic solvents like ethanol, dichloromethane, etc.
    Flash Point A temperature at which the vapor can ignite in the presence of an ignition source
    Odor May have a characteristic odor due to the thiazole and ester functional groups

    As an accredited Ethyl 2-Methylthiazole-5-Carboxylate factory, we enforce strict quality protocols—every batch undergoes rigorous testing to ensure consistent efficacy and safety standards.

    Packing & Storage
    Packing 500g of Ethyl 2 - Methylthiazole - 5 - Carboxylate in sealed, chemical - resistant containers.
    Shipping Ethyl 2 - Methylthiazole - 5 - Carboxylate is shipped in well - sealed, corrosion - resistant containers. Special handling procedures are followed to ensure safety during transit due to its chemical nature. Shipments comply with all relevant regulations.
    Storage Ethyl 2 - Methylthiazole - 5 - Carboxylate should be stored in a cool, dry, well - ventilated area. Keep it away from heat sources, flames, and oxidizing agents. Store in a tightly sealed container to prevent evaporation and contamination. It is advisable to store it in a dedicated chemical storage cabinet, following proper inventory management for easy identification and safety.
    Application of Ethyl 2-Methylthiazole-5-Carboxylate

    In continuous stirred‑tank reactor processes dedicated to process flavour generation for savoury applications, the introduction of Ethyl 2‑Methylthiazole‑5‑Carboxylate occurs after the aqueous slurry of reducing sugars, amino acid precursors, and hydrolysed vegetable protein has been pre‑heated to 45–50°C. A reducing sugar blend, typically xylose and glucose in a 60:40 mass ratio, is combined with a sulphur source such as L‑cysteine hydrochloride monohydrate (1.2–2.0 g per 100 g dry protein) and the pH adjusted to 6.4–6.8 using food‑grade sodium hydroxide. The ester is predispersed in 1,2‑propanediol to a 10% w/w stock and dosed into the reactor at 0.08–0.25 g per kg of total substrate solids, targeting a final concentration of 1–5 ppm in the diluted finished flavour. The reactor jacket is heated to 115–125 °C and held under autogenous pressure (0.6–1.4 bar) for 50–90 min; during this window the pH drifts from 6.5 toward 4.7 as formic and acetic acids accumulate. Rapid cooling through a shell‑and‑tube exchanger to 25–30 °C halts the reaction, followed by two‑stage homogenisation at 160–220 bar and optional spray‑drying onto maltodextrin (DE 12–18) with a co‑current inlet temperature of 185 °C and outlet 82–88 °C. The resulting process flavour is incorporated at 0.1–0.5% into dry bouillon cubes, retorted meat stews, and instant noodle seasoning sachets. Compliance is demonstrated through conformity with the purity criteria of the JECFA Combined Compendium of Food Additive Specifications and the authorisation procedure of Regulation EC No. 1334/2008 for process flavourings. The ester bridges the gap between basic meaty thiol notes and the roasted pyrazine backbone, while suppressing the metallic edge that excessive l‑thiamine degradation can introduce.

    When Cocoa Butter Equivalents Require Roasted Depth

    Ethyl 2‑Methylthiazole‑5‑Carboxylate is blended into chocolate and compound coating masses exclusively during the conching phase, once the refined flake has been liquefied and the particle size distribution has reached a D90 of 18–22 µm. A liquid flavour pre‑blend consisting of the ester at 0.01–0.05% w/w in triacetin or fractionated coconut oil is metered via a micro‑diaphragm pump into the conche at a rate calculated to deliver 0.2–1.0 ppm of active in the enrobed or moulded final piece. Processing temperatures in the conche are maintained between 50 °C and 80 °C for dark chocolate, and the relatively low vapour pressure of the ester restricts headspace losses to approximately 8–12% over a 6‑hour open‑conche cycle. When paired with vanillin and ethyl vanillin, the compound exhibits a synergistic amplification of perceived cocoa thermal load; descriptive panels report a 1.4–1.9 point increase in “roasted nut” intensity on a 10‑point just‑about‑right scale at 0.5 ppm in a standard milk chocolate base. Regulatory standing is provided by the Union list of flavouring substances established by Commission Implementing Regulation EU 872/2012 and by compliance with the carry‑over provisions of CODEX STAN 192‑1995 for compound coatings. Terminal formats comprise enrobed wafer bars, chocolate‑dipped sandwich biscuits, sugar‑shell dragees, and filled tablet segments. An operational caution is that prolonged contact with lecithin‑containing masses above 85 °C can induce trace hydrolysis to the sensory‑inactive 2‑methylthiazole‑5‑carboxylic acid; plant trials therefore add the ester premix after the final lecithin dosing and immediately before viscosity adjustment.

    What Drives the Retention of Pyrazine‑Like Top Notes in Spray‑Dried Coffee Replacers?

    For soluble coffee substitutes and instant cereal‑based beverages, the thiazole ester functions as a high‑impact top‑note that withstands aggressive atomisation when adequately encapsulated. An aqueous aroma emulsion is prepared by dissolving the ester at 0.5–2.0 mg L⁻¹ in a continuous phase containing 22–30% w/w gum arabic and 8–12% w/w maltodextrin (DE 5–8), followed by rotor‑stator emulsification at 9 000–14 000 rpm until the volume‑weighted mean droplet diameter drops below 1.8 µm. The emulsion is fed to a pilot‑scale spray dryer equipped with a rotary atomiser (Niro Mobile Minor™ equivalent) at an inlet temperature of 195±5 °C and an outlet of 88–95 °C. Powder collected from the cyclone exhibits surface oil levels below 0.4% and a total oil retention of 83–89% when assayed by simultaneous distillation‑extraction and GC‑FID. The loaded powder is post‑blended with agglomerated instant coffee at 0.05–0.2% w/w, delivering 0.1–0.5 ppm of active in the reconstituted cup. Conformity rests on adherence to JECFA flavour specifications and, within the EU, labelling as “flavouring” under Regulation EU 1169/2011. End‑product configurations include 3‑in‑1 cappuccino sachets, vending‑machine soluble granules, and cold‑brew instant powders. Thermogravimetric‑FTIR analysis of the carbohydrate glass shows that the ester preferentially partitions into the matrix until hydration triggers release, supporting a shelf life beyond 14 months in aluminium‑laminated pouches stored at ≤25 °C.

    Petfood Palatant Reactor Kinetics and Phosphate Buffer Conditions

    Extruded pet treat palatability systems exploit the compound in liquid digests and enzyme‑hydrolysed viscera slurries rather than in dry premixes. Hydrolysed poultry liver (moisture 60–65%) is incubated with a neutral protease at 50–55 °C for 2–4 h, then heated to 92–95 °C for enzyme inactivation. Ethyl 2‑Methylthiazole‑5‑Carboxylate is added as a 5% ethanol solution at a rate of 0.5–2.0 g per 100 kg wet digest, targeting 0.05–0.2 mg kg⁻¹ in the finished coated kibble. The digest is homogenised and sprayed via a high‑pressure atomisation system onto hot expanded kibble exiting a twin‑screw extruder (Clextral BC‑45 series, L/D ≥42:1) at a surface temperature of 88–100 °C; residual moisture after coating and forced‑air drying is held at 8–10%. US regulatory coverage derives from 21 CFR §582.60, which addresses synthetic substances generally recognised as safe in animal feed, while the European framework requires compliance with Regulation EC 1831/2003 on feed additives, including notification for flavouring compounds not yet listed in the Register of Feed Additives. A two‑bowl palatability assay against an unsupplemented control typically yields intake ratio improvements of 1.4:1 to 1.7:1, with the strongest bias observed in feline formulations where thiazole‑derived sulphurous notes mimic fresh protein degradation markers. Thermal lability frames the process boundary: exposure to temperatures above 115 °C for longer than 3 min during HTST treatment of the digest accelerates ester degradation, and inline FT‑NIR probes are increasingly deployed to monitor the intact ester peak at 1420–1430 cm⁻¹ for real‑time process control.

    In the manufacture of rotary‑moulded biscuits and hard sweet cookies, incorporation routes avoid the aqueous dough phase to suppress hydrolysis. The ester is dissolved into the fat phase — non‑hydrogenated palm olein or anhydrous butterfat — at 0.02–0.08 g kg⁻¹ fat, constituting 15–20% of the total formula. This fat premix is creamed with caster sugar, then blended with soft wheat flour, sodium bicarbonate, and ammonium bicarbonate; the resulting unbaked dough concentration targets 4–10 mg kg⁻¹. Tunnel‑oven baking through zone temperatures of 180/200/220 °C for 8–10 min generates a retention envelope of 30–55%, as determined by GC‑MS analysis of isotopically labelled surrogates of similar thiazole esters in a pilot‑scale direct‑fired oven. Incorporation of polyglycerol polyricinoleate (PGPR) at 0.2–0.5% on flour weight improves retention by providing a continuous lipophilic shield around the flavour payload, with dough water activity kept below 0.78 to limit steam stripping. The baked biscuit carries 1.5–5 ppb of intact ester, imparting a roasted, nutty top‑note that complements the caramel‑like Maillard background from reducing sugars and milk solids. Regulatory compliance is anchored in the substance’s designation as a flavouring under FDA 21 CFR §170.3(o)(12) and alignment with the IOFI Global Reference Programme, which provides use‑level guidance for thermally processed bakery goods. Commercial finished formats span butter cookies, sandwich creams, and savoury crackers. A documented process conflict arises when automated scraped‑surface lamination raises the local temperature above 70 °C, prematurely volatilising a portion of the ester; adjusting the laminator gap to ≥1.2 mm and cooling the dough sheet with chilled air mitigates losses without compromising layer integrity.

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    Certification & Compliance
    More Introduction

    Structural Confirmation Techniques for 2-Methyl-1,3-thiazole-5-carboxylate Ethyl Ester

    Ethyl 2-methylthiazole-5-carboxylate (CAS 34253-54-8, empirical formula C₇H₉NO₂S, molecular weight 171.22 g·mol⁻¹) is assigned the IUPAC name ethyl 2-methyl-1,3-thiazole-5-carboxylate. Manufacture follows a cyclocondensation route between ethyl 2‑chloroacetoacetate and thioacetamide, yielding a heterocyclic core substituted with a methyl group at the 2‑position and an ethoxycarbonyl moiety at the 5‑position. The 5‑ester regiochemistry imparts distinct reactivity compared to the 4‑carboxylate isomer, making the compound a strategic intermediate in the synthesis of sulfonamide pharmacophores and agrochemical oxadiazoles. Identity is confirmed through 1H‑NMR (400 MHz, CDCl₃): δ 1.34 (t, J=7.1 Hz, 3H), 2.75 (s, 3H), 4.32 (q, J=7.1 Hz, 2H), 8.23 (s, 1H) ppm; and 13C‑NMR (100 MHz, CDCl₃): δ 14.3, 19.2, 61.5, 127.3, 141.8, 161.4, 172.1 ppm. GC‑MS (El, 70 eV) exhibits a molecular ion peak at m/z 171 [M]⁺ with a base peak at m/z 126 from loss of the ethoxy group. Why Purity Attenuation During Storage Matters in Multi-Kilogram Syntheses? A direct relationship between initial purity and downstream yield in palladium-catalyzed aminations is observed across production campaigns. When the batch purity falls below 97.5% by GC-FID (internal method TM‑ETMC‑01, validated per ICH Q2(R1) with a detection limit of <0.05%), the formation of des‑chloro side products in Negishi couplings increases by 8–12% relative to input mass. The primary impurity, ethyl 2‑methylthiazole‑4‑carboxylate, is generated during ring closure when the thioamide attacks the less hindered β‑carbonyl of the diketoester precursor; its concentration is held below 0.8% through a fractional crystallization protocol using n‑heptane at −15 °C. Storage in translucent high‑density polyethylene drums under ambient warehouse conditions (average temperature 24 °C, relative humidity 55%) led to an increase in the APHA color index from 35 to >180 over 12 weeks, as recorded by a Lovibond PFX‑195 colorimeter per ASTM D1209-05. This discoloration is attributed to trace thiol-mediated chromophore formation, suppressed by nitrogen blanketing (50 mbar positive pressure) and amber glass packaging lined with PTFE closures. Batch records from a 200‑L drum campaign showed that when headspace oxygen exceeded 2 vol%, the peroxide value (determined by iodometric titration per ISO 3960:2017) rose to 4.8 meq/kg, triggering gelation in subsequent polyamide curing steps.
    Table 1: Typical Physical and Chemical Specifications
    ParameterValueMethod
    AppearanceWhite to pale yellow crystalline solidVisual / ASTM D4175
    Purity (GC-FID)98.0% areaTM-ETMC-01 (ISO/IEC 17025)
    Melting Range33–37 °CASTM E794-06 (DSC)
    Boiling Point128–130 °C / 12 mmHgOECD 103 (Siwoloboff)
    Refractive Index nD201.515–1.517ASTM D1218-21
    Density (25 °C)1.180 g/mLASTM D4052-22
    Water Content0.15% w/wKarl Fischer (USP <921>)
    Residual SolventsEthanol ≤5000 ppm, n‑Heptane ≤290 ppmHeadspace GC‑MS (USP <467>)
    During pilot-plant purification of 35 kg crude ester, a 2‑inch Pope Scientific wiped‑film evaporator operated at 120 °C jacket temperature and 0.5 mbar maintained a residence time of <90 seconds. Under these conditions, the acid value increase was held to <0.2 mg KOH/g per pass, and the distilled fraction exhibited a purity jump from 96.2% to 99.1% without triggering the retro‑Diels‑Alder degradation that was observed when pot temperatures exceeded 145 °C during conventional short‑path batch distillation in a 20‑L glass reactor. The thermal sensitivity creates a processing window of ±5 °C at the heated surface; excursions above 125 °C led to a sulfurous off‑gas and a 3–4% mass loss to non‑volatile oligomers, as measured by TGA (TA Instruments Q500, isothermal at 140 °C). Therefore, wiped‑film units with a mean film thickness below 0.25 mm and condenser temperatures below −10 °C are prescribed for scale‑up. When Amidation is Performed in the Presence of Trace Water The reactivity of the 5‑ethoxycarbonyl group toward primary and secondary amines is exploited in the preparation of carboxamide intermediates for succinate dehydrogenase inhibitors. However, the ester exhibits a hydrolysis half‑life of 18 hours in a biphasic mixture of toluene and 1 M aqueous sodium hydroxide at 25 °C, while its methyl ester analogue (methyl 2‑methylthiazole‑5‑carboxylate, CAS 13750-66-4) hydrolyzes with a half‑life of <6 hours under identical pH conditions. This differential stability, monitored by inline ReactIR (Mettler Toledo ReactIR 15) following the carbonyl stretching band at 1718 cm⁻¹, allows aqueous workup steps without significant ester cleavage if the pH is maintained below 10.2. When 1.2 equivalents of morpholine were dosed into a solution of the ethyl ester in dichloromethane at 0 °C and the batch was warmed to 20 °C over 2 hours, conversion reached 99% with <0.1% residual ester, while the methyl ester under analogous conditions gave 1.4% residual and 2.8% of the corresponding carboxylic acid impurity, identified by LC‑MS (Thermo Scientific Q Exactive, ESI+). Plant‑scale amidation in a 500‑L glass‑lined reactor with a retreat‑curve impeller at 90 rpm confirmed that the ethyl ester’s reduced sensitivity to adventitious moisture shortened the post‑reaction drying step and increased isolated yield by 7% relative to the methyl variant.
    Table 2: Comparative Data for Selected Thiazole Carboxylate Esters
    PropertyEthyl 2‑Methylthiazole‑5‑carboxylate
    (this product)
    Methyl 2‑Methylthiazole‑5‑carboxylate
    (CAS 13750-66-4)
    Ethyl 2‑Methylthiazole‑4‑carboxylate
    Melting Point (°C)33–37−5 to 0 (liquid)28–31
    Boiling Point (°C/mmHg)128–130 / 12105–107 / 10118–120 / 10
    Hydrolysis Half‑life at pH 10, 25 °C (h)18<612a
    Reactivity in Buchwald‑Hartwig AminationbHigh; >95% conversion in 4 hHigh; 93% conversion in 4 hLow; 41% conversion due to steric shielding
    Typical Purity by GC (% area)98–9997–9895–97
    Key DifferentiatorOptimum balance of volatility and hydrolytic robustnessHigher volatility aids solvent exchange but increases ester cleavage riskDifferent regiochemistry alters electronic landscape; unsuitable for 5‑position‑dependent pharmacophores

    a Measured on a single production batch; published data for this specific configuration is limited.
    b Model reaction with 4‑bromoanisole and palladium catalyst Pd2(dba)3/XPhos in dioxane at 85 °C, monitored by HPLC‑UV at 254 nm.

    In the kilogram‑scale preparation of benzamide derivatives for sodium‑glucose cotransporter 2 inhibitors, the solubility profile of ethyl 2‑methylthiazole‑5‑carboxylate removes the need for repeated brine washes. Its distribution coefficient (log P 1.42, measured by the shake‑flask method per OECD 117) ensures that 97% of the product partitions into dichloromethane in a single extraction from aqueous pH‑7 buffer, while the methyl ester retains 8–10% in the aqueous layer. On a 200‑L extraction skid, this difference translated to a reduction in extraction cycle count from five to two and a solvent cut of 42 L per batch. Additionally, the ethyl ester’s low water solubility (0.9 g/L at 20 °C) minimizes organic contamination in the aqueous waste stream, aiding compliance with site discharge limits for total organic carbon (<100 mg/L) as verified by a Shimadzu TOC‑L analyzer. Mitigating Colour-Body Formation in Long-Term Inventory Equipment materials for handling the molten product must be specified to avoid iron‑catalysed oxidation. Transfer lines fabricated from 316L stainless steel and fitted with 10‑micron bag filters are standard; prolonged contact with carbon steel leads to a reddish discoloration within 48 hours. A stability study conducted according to ICH Q1A(R2) at 25 °C / 60% RH and 40 °C / 75% RH over six months confirmed that the material retains ≥98.0% purity and melt colour below APHA 50 when sealed under argon in amber glass. In contrast, the 4‑carboxylate isomer darkened to APHA 250 under the same accelerated conditions, limiting its utility in pharmaceutical campaigns where intermediate colour affects final API appearance. No incompatibility with common process solvents (toluene, dichloromethane, tetrahydrofuran) has been recorded; however, combination with strongly nucleophilic amines such as n‑butylamine without dilution triggers an uncontrolled exotherm exceeding 15 °C/min as captured by RC1e reaction calorimetry, necessitating controlled dosing at rates below 0.3 mol/h.