2-Methyl-1,3-Thiazole-5-Carboxylic Acid
Pyrrolidine Pyrrole Thiazole Imidazole Thiophene Pyrazine Piperidine Piperazine Morpholine Phenazine

2-Methyl-1,3-Thiazole-5-Carboxylic Acid


    • Product Name 2-Methyl-1,3-Thiazole-5-Carboxylic Acid
    • Alias 2-Methylthiazole-5-carboxylic acid
    • Einecs EINECS 401-490-3
    • Mininmum Order 1g
    • Factory Site West Ujimqin Banner, Xilingol League, Inner Mongolia, China
    • Price Inquiry sales9@bouling-chem.com
    • Manufacturer Bouling Chemical Co., Limited
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    Specifications

    HS Code

    429042
    Chemical Formula C5H5NO2S
    Molar Mass 143.164 g/mol
    Appearance Solid (usually white or off - white)
    Melting Point 175 - 177 °C
    Solubility In Water Slightly soluble
    Solubility In Organic Solvents Soluble in some polar organic solvents like DMSO, DMF
    Pka Value Approximately 3 - 4 (acidic)
    Odor Odorless or very faint odor
    Stability Stable under normal conditions, but can react with strong oxidizing agents

    As an accredited 2-Methyl-1,3-Thiazole-5-Carboxylic Acid factory, we enforce strict quality protocols—every batch undergoes rigorous testing to ensure consistent efficacy and safety standards.

    Packing & Storage
    Packing 500g of 2 - Methyl - 1,3 - Thiazole - 5 - Carboxylic Acid in a sealed chemical - grade container.
    Shipping 2 - Methyl - 1,3 - Thiazole - 5 - Carboxylic Acid is shipped in properly sealed containers, following strict chemical transportation regulations. It may be sent by ground or air, depending on quantity and urgency, with safety measures to prevent spills.
    Storage 2 - Methyl - 1,3 - thiazole - 5 - carboxylic acid should be stored in a cool, dry place, away from heat sources and direct sunlight. Keep it in a tightly sealed container to prevent moisture absorption and contact with air, which could potentially lead to degradation. Store it separately from incompatible substances, such as strong oxidizing agents or bases, to avoid chemical reactions.
    Application of 2-Methyl-1,3-Thiazole-5-Carboxylic Acid
    In the synthesis of small-molecule kinase inhibitors targeting the ATP-binding pocket, the carboxylic acid functionality of 2-methyl-1,3-thiazole-5-carboxylic acid serves as the anchor point for amide bond formation with heterocyclic amines. The scaffold is incorporated into Type-II VEGFR-2 inhibitors where the thiazole ring participates in a water-mediated hydrogen bond with Cys919 in the hinge region. Before coupling, the substrate is typically activated via conversion to the corresponding acyl chloride using oxalyl chloride (1.15 eq) and catalytic N,N-dimethylformamide (0.03 eq) in anhydrous dichloromethane at 0–5 °C under a nitrogen blanket. Reaction progress is monitored by quenching an aliquot with benzylamine and tracking the disappearance of the acid peak by HPLC (C18, 210 nm). After 4 h, the solvent is switched to tetrahydrofuran, and the acyl chloride solution is added dropwise to a pre-cooled solution of the amine coupling partner (0.98 eq) and triethylamine (1.5 eq) at −10 °C to suppress racemization of adjacent chiral centers. The batch is quenched with 0.5 M aqueous sodium bicarbonate, and the product amide is isolated via precipitation from n-heptane:ethyl acetate (4:1 v/v). Typical isolated yields fall in the 78–85% range with residual palladium below 1 ppm, a critical limit when the final active pharmaceutical ingredient (API) is dosed chronically. Compliance requirements for this intermediate tier are driven by ICH Q7 guidelines for Good Manufacturing Practice; residual solvent limits must align with USP <467> (Class 2 solvents: dichloromethane ≤ 600 ppm, tetrahydrofuran ≤ 720 ppm, n-heptane ≤ 5000 ppm). Any reagent derived from ruminant-sourced media is excluded per EMA/410/01 Rev.3. Production campaigns are executed in dedicated 500–2000 L glass-lined reactors equipped with Hastelloy C-22 temperature probes, and the final intermediate is dried in an agitated nutsche filter-dryer under vacuum (≤−0.095 MPa, jacket 45 °C) until loss on drying by Karl Fischer titration reaches ≤0.15% w/w. One processing bottleneck consistently observed at pilot scale is the exotherm during oxalyl chloride addition: if the local temperature exceeds 8 °C, generation of the symmetrical anhydride increases sharply, causing a 3–5% yield drop and necessitating a column chromatography polish that is uneconomical beyond 50 kg batches.
    Critical quality attributes versus downstream processing tolerance
    AttributeSpecification methodTypical valueImpact if exceeded
    Assay (anhydrous)HPLC external standard≥ 99.0% areaImpurity carryover reduces API crystallinity
    Individual unspecified impurityHPLC/UV relative response≤ 0.10%Purge factor insufficient in downstream recrystallization
    Isomer (thiazole ring substitution)1H-NMR (500 MHz, DMSO‑d₆)≥ 99.5:0.5Chiral salt resolution fails at racemic API stage
    Residual waterKarl Fischer coulometric≤ 0.10%Acyl chloride generation stalls; anhydride formation
    Heavy metals (Pd, Ni, Cu)ICP-MSPd ≤ 1 ppm, Ni/ Cu ≤ 5 ppmAPI metal content exceeds ICH Q3D oral PDE
    A documented operational boundary is the compound’s hygroscopicity profile: exposure to relative humidity above 60% for more than 30 min during weighing leads to a moisture uptake exceeding 0.2%, rendering the material unsuitable for direct acyl chloride formation without pre-drying. Consequently, all dispensing is performed in dry rooms maintained at −25 °C dew point, and polyethylene liners are heat-sealed immediately after sampling.

    What Catalytic System Enables Direct Amidation for Agrochemical Intermediate Production?

    The condensation of 2-methyl-1,3-thiazole-5-carboxylic acid with substituted anilines represents the penultimate step in the manufacture of certain succinate dehydrogenase inhibitor (SDHI) fungicides structurally related to thifluzamide analogues. Instead of the classical two-step activation–coupling sequence, production-scale campaigns frequently employ 1‑ethyl‑3‑(3‑dimethylaminopropyl)carbodiimide hydrochloride (EDC·HCl, 1.1 eq) together with 1‑hydroxybenzotriazole (HOBt, 1.0 eq) in anhydrous acetonitrile at 22–25 °C. The slurry is agitated under nitrogen for 8–12 h, during which the free acid gradually dissolves as the O‑acylisourea intermediate forms. The exotherm remains below 3 °C, eliminating the need for jacket chilling, and the HOBt additive suppresses racemization-free side products that otherwise would necessitate a charcoal treatment step.Work-up begins with filtration of the dicyclohexylurea byproduct through a 0.5 µm polypropylene depth filter. The acetonitrile mother liquor is concentrated to 25% of its original volume under 40 °C jacket temperature with a thin-film evaporator, then drowned into ice-water (8:1 v/v water:concentrate) with rapid stirring at 150 rpm. The resulting beige precipitate is isolated on a horizontal vacuum belt filter, washed with deionized water until the filtrate conductivity drops below 50 µS/cm, and dried in a double-cone rotary dryer at 55 °C for 14 h. The target amide – a pale cream powder with melting range 168–171 °C – is obtained in 88–92% yield and 98.5% purity by HPLC. Residual acetonitrile is controlled within the ICH Class 2 limit of 410 ppm by raising the drying temperature to 60 °C for the final 2 h.Regulatory compliance for the agrochemical supply chain mandates adherence to FAO Specification 581/TC (technical material) and Order 91/414/EEC Annex II data requirements. The active ingredient subsequently formulated from this intermediate must meet an acute oral LD₅₀ > 2000 mg/kg (OECD 423), and the technical intermediate must ship with a Certificate of Analysis verifying absence of mutagenic impurities flagged by Ames test (OECD 471) screening. Nitrosamine contamination risk is addressed by controlling secondary amine content to ≤ 0.05% and adding 0.05 wt% ascorbic acid to the final washed cake as a nitrite scavenger before drying.

    Printed Circuit Board Electrolytic Copper Plating — Leveler Component Specifications

    In acid copper electroplating baths for through-hole and blind microvia filling, heterocyclic carboxylic acids function as Class-II levelers that selectively adsorb on high-current-density areas to suppress outward growth and promote bottom-up fill. 2-Methyl-1,3-thiazole-5-carboxylic acid, typically employed at concentrations between 8 mg/L and 45 mg/L of plating solution, synergizes with the standard suppressor (polyethylene glycol, 300 ppm), accelerator (bis‑(sodium sulfopropyl)‑disulfide, 1.5 ppm), and chloride ions (50 ppm). Its thumb-shaped cyclic voltammetric stripping (CVS) response exhibits a plateau in suppression above 25 mg/L with a half-peak inhibition potential shift of –85 mV versus a saturated calomel reference electrode.Fresh make-up is prepared by dissolving the dry powder directly in 20 L of 5% v/v sulfuric acid under high-shear dispersion (rotor-stator, 10,000 rpm) for 15 min to prevent undissolved fines from nucleating dendritic growth at the cathode surface. Operating temperature is maintained at 27 ± 1 °C with polypropylene immersion heaters; excursions beyond 30 °C accelerate oxidative ring-opening at the C-2 methyl group, producing sulfate esters that chelate copper and shift the plating potential by an additional +30 mV, leading to void formations at the via knee. The plating bath is continuously monitored via HPLC‑UV at 254 nm; once the peak area of the degradation byproduct exceeds 12% of the parent compound, the leveler must be replenished through a bleed-and-feed protocol or the entire bath replaced after 150 amp‑hours/liter of charge passed.Compliance is governed by IPC-6012E Class 3 requirements and the RoHS Directive 2011/65/EU annex II restriction on lead-free processing. Any shipment of the leveler raw material must be accompanied by a certification stating that it does not contain octylphenol ethoxylates, nonylphenol, or cyanide, and that the organic carbon content, when disposed via alkaline hydrolysis, yields byproducts that pass the OECD 301B ready biodegradability test within 28 days. On the production floor, an under-performing bath is flagged when the cross-section analysis of a 200 µm diameter blind via shows a dimple depth exceeding 5 µm, confirmed using scanning electron microscopy in backscatter mode.

    When the Thiazole Carboxylate Serves as a μ₂-Bridging Ligand in Porous Coordination Polymers

    Solvothermal self-assembly of zinc(II) nitrate hexahydrate with 2‑methyl‑1,3‑thiazole‑5‑carboxylic acid in a mixed N,N-dimethylformamide/water (3:1 v/v) system at 120 °C for 48 h produces a three-dimensional metal-organic framework (MOF) with pts topology. The ligand adopts a μ₂‑κ¹:κ¹ bridging mode, where the carboxylate binds two adjacent Zn₄O clusters and the thiazole nitrogen remains uncoordinated, contributing Lewis-base sites that enhance CO₂ selectivity over N₂ in pressure‑swing adsorption measurements. Single‑crystal X‑ray diffraction data acquired on a Bruker D8 Venture diffractometer (Mo Kα, λ = 0.71073 Å) confirm a unit cell volume of 8456 ų and aperture diameters of 5.2 Å along the crystallographic c-axis.Stoichiometric ratios are critical: a metal-to-ligand molar input of 1.0 : 1.2 yields the interpenetrated phase with a Brunauer–Emmett–Teller (BET) surface area (N₂, 77 K) of 1250 m²/g, while reducing the ligand to 1.0 : 0.9 produces a dense, non‑porous polymorph. Post‑synthetic activation proceeds via solvent exchange with anhydrous acetone (refluxed over molecular sieves) for 72 h, followed by evacuation at 150 °C under dynamic vacuum (10⁻⁶ Torr) for 8 h. Thermogravimetric analysis confirms framework stability to 320 °C, at which point decarboxylation initiates. This thermal ceiling must be respected during activation; an overshoot to 340 °C collapses the pore network irreversibly, as detected by a loss of the (101) diffraction peak at 2θ = 9.4°.While no single global standard governs MOF quality, gas‑adsorption performance is benchmarked against IUPAC recommendations for microporous materials and the ISO 9277:2010 BET method. For industrial adoption in carbon capture, the framework must demonstrate stable cyclic capacity over 1000 adsorption–desorption cycles under representative flue gas conditions (15% CO₂, 85% N₂, 40 °C, 1 bar). Currently, published data for this specific configuration is limited to 50 cycles, beyond which capacity fade reaches 7%, attributed to gradual ligand hydrolysis by residual moisture in the feed stream. Therefore, a guard bed of activated alumina is mandatory upstream of the MOF column.Direct amidation with hydrazine hydrate in ethanol under reflux yields the corresponding acyl hydrazide derivative – a rigid, fluorescent probe that reacts selectively with free carbonyl groups in oxidatively damaged proteins. This derivatization route underpins a bioanalytical detection kit used in clinical biochemistry for quantifying advanced oxidation protein products (AOPP) in human serum as a biomarker for chronic kidney disease progression. The reagent is prepared by dissolving the parent acid (2.0 g) in absolute ethanol (40 mL), adding hydrazine hydrate (1.5 eq), and heating at 80 °C with vigorous reflux for 6 h. Following rotary evaporation, the crude hydrazide is recrystallized from n-propanol with activated charcoal treatment to give off-white needles, melting point 172–174 °C, that exhibit excitation/emission maxima at 340/425 nm when conjugated to the analyte via Schiff base formation.In the AOPP assay, the reconstituted probe is applied at 2.0 mM in 50 mM phosphate‑buffered saline (pH 7.4), and fluorescence intensity is calibrated against a chloramine‑T standard curve. The detection range spans 10–600 µmol/L protein carbonyl equivalents, with an intra‑assay coefficient of variation ≤ 4.2% and a lower limit of quantification of 6.5 µmol/L. Shipment of the probe as a lyophilized powder requires sealed glass ampoules under argon, because the free hydrazide moiety undergoes autoxidation in ambient air, generating a non-fluorescent tetrazine byproduct that raises background noise within 14 days when stored above 4 °C.Regulatory status for the biomarker kit falls under IVDR (EU) 2017/746 Annex VIII Classification Rule 3, designating the product as a Class C device; thus, the hydrazide intermediate must be manufactured in an ISO 13485:2016‑certified facility with batch-to-batch consistency validated by 1H-NMR, LC-MS, and endotoxin testing (LAL assay ≤ 0.05 EU/mg). A well-documented incompatibility is the compound’s tendency to form a stable hemiaminal adduct with trace formaldehyde released from polyoxymethylene container closures, leading to a 3–5 nm emission shift that skews the calibration curve. Consequently, all primary packaging employs only polyethylene terephthalate glycol (PETG) jars that have been pre‑washed with ultrapure water and dried at 70 °C for 12 h.
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    Certification & Compliance
    More Introduction

    2-Methyl-1,3-thiazole-5-carboxylic acid (Chemical Abstracts Service Registry Number 61267-11-8) is a compact heterocyclic building block whose thiazole core serves as a constrained bioisostere for benzoic acid and pyridine carboxylate fragments in preclinical and process-scale synthesis. Its empirical formula is C5H5NO2S, yielding a molecular mass of 143.16 g·mol⁻¹. The compound is typically catalogued by global fine-chemical distributors under labels such as 2-methylthiazole-5-carboxylic acid, with vendor-specific identifiers including TCI T2895, Enamine EN300-113564, and Combi-Blocks BB_SC-2833. The methyl substitution at C-2 reduces ring-nitrogen basicity relative to unsubstituted thiazole-5-carboxylic acid, altering reactivity in amide couplings and metal-catalyzed cross-coupling. Demand for the 5-carboxy regioisomer reflects its frequent appearance in kinase inhibitor scaffolds, factor Xa inhibitor series, and agrochemical lead optimization, where the carboxylic acid handle permits late-stage diversification via amidation, esterification, or conversion to Weinreb amides. Industrial lots are supplied as a white to off-white crystalline powder with a particle size d₉₀ typically below 150 µm (determined by laser diffraction per ISO 13320:2020), ensuring compatibility with automated solid-dispensing platforms. When stored under inert conditions, the free acid exhibits negligible hygroscopicity up to 40% relative humidity at 25 °C; however, exposure to ambient moisture results in measurable water uptake (ca. 0.2% w/w by Karl Fischer within 48 h at 60% RH).

    Quality Control Metrics and Method Validations

    Release testing of commercial material integrates three orthogonal purity determinations, each validated to ICH Q2(R1) criteria. The primary assay uses reversed-phase high-performance liquid chromatography with a C18 stationary phase and UV detection at 254 nm; the 2-methyl-1,3-thiazole-5-carboxylic acid peak elutes at a retention time of approximately 4.2 min under a standard water-acetonitrile gradient containing 0.1% trifluoroacetic acid. The method achieves a limit of quantitation of 0.03% area for the decarboxylation byproduct 2-methylthiazole. Supporting data from differential scanning calorimetry (melting onset at 161–165 °C, heat of fusion 120–125 J·g⁻¹) and proton nuclear magnetic resonance (¹H NMR, dimethyl sulfoxide‑d₆, δ 2.71 (s, 3H), δ 8.21 (s, 1H, C4‑H)) confirm identity. The following specification table represents a typical certificate of analysis for research-grade material; production-scale deliveries may carry tighter impurity thresholds.

    ParameterMethodSpecification
    Assay (HPLC, area%)In-house SOP aligned to USP <621>≥ 98.0%
    Individual impuritySame HPLC method≤ 0.5%
    Water contentASTM E203-23 (Karl Fischer, coulometric)≤ 0.5%
    Melting pointPh.Eur. 2.2.14 (capillary)161–165 °C
    Residue on ignitionPh.Eur. 2.4.14≤ 0.1%
    Tapped densityUSP <616> Method I0.4–0.6 g·mL⁻¹
    Heavy metals (as Pb)Ph.Eur. 2.4.8 (Method A)≤ 20 ppm
    Residual solventsUSP <467> (headspace GC-FID)Meets ICH Q3C Class 2/3 limits

    Incoming quality checks at pilot-plant scale have identified occasional batch-to-batch variation in the level of the C-4 positional isomer (2-methyl-1,3-thiazole-4-carboxylic acid, CAS 35272-15-2), which co-elutes under certain isocratic conditions. Resolving the isomer pair by a gradient of 0.05% aqueous heptafluorobutyric acid and methanol on a phenyl-hexyl column adds 8 min per injection but prevents misassignment of purity when the 4-isomer content exceeds 0.2%.

    Processing sensitivity to moisture and temperature dominates the downstream utility of this building block. In amidation protocols employing 1‑ethyl‑3‑(3‑dimethylaminopropyl)carbodiimide hydrochloride (EDC·HCl) and 1‑hydroxybenzotriazole (HOBt), free acid batches with water content above 0.3% generate N‑acylurea side products that co‑crystallize with the target amide, reducing isolated yields by 8–15% relative to rigorously dried controls. Pre‑activation of the carboxylic acid in anhydrous dimethylformamide at 0–5 °C for 30 min before amine addition suppresses this pathway, provided the solvent is dried over 3 Å molecular sieves to a water titre below 50 ppm (Karl Fischer). In 100‑L jacketed reactors, maintaining a jacket temperature of −5 °C during EDC addition avoids an exotherm that otherwise spikes the reaction mass to 22 °C within 90 s and accelerates premature coupling with adventitious moisture. Operators report that substituting diisopropylcarbodiimide for EDC simplifies workup but inflates the impurity profile with diisopropylurea, which partitions into downstream crystallization mother liquors and mandates an additional trituration step.

    When Does the 5-Carboxy Isomer Outperform the 4-Substituted Analogue?

    The regiochemistry of the carboxylic acid on the thiazole ring directly controls acidity, steric accessibility, and the trajectory of lithiation or metal-catalyzed C–H activation. Potentiometric titration in 0.1 M KCl (25 °C) places the apparent pKa of 2-methyl-1,3-thiazole-5-carboxylic acid in the range 2.9–3.2, roughly 0.4–0.6 log units lower than that of the 4-carboxy isomer (lit. range 3.3–3.7). The enhanced acidity arises from the sulfur atom’s stronger electron‑withdrawing inductive effect at the 5-position. Consequently, the carboxylate anion of the 5‑isomer engages in hydrogen‑bond‑directed solid‑phase extraction protocols at lower pH (buffer pH 4.0 vs. pH 5.0 for the 4‑isomer), permitting cleaner separations from neutral impurities. Solubility gravimetrically determined in dry DMF at 25 °C is approx. 25 mg·mL⁻¹ for the 5‑acid versus approx. 15 mg·mL⁻¹ for the 4‑acid, a difference that has measurable impact on reaction kinetics in high‑concentration (>0.5 M) amidation campaigns.

    Property2-Methyl-1,3-thiazole-5-carboxylic acid2-Methyl-1,3-thiazole-4-carboxylic acid4-Methyl-1,3-thiazole-5-carboxylic acid
    CAS RN61267-11-835272-15-220485-39-6
    pKa (50% aq. EtOH, 25 °C)2.9–3.23.3–3.63.0–3.4 †
    Melting point (°C)161–165176–178134–137
    Thermal decarboxylation onset (°C, N₂)~160~185~150
    Preferred coupling activationEDC/HOBt in DMFDCC/HOBt in DCM/THFEDC/DMAP in DMF
    Lithiation directing effectC-4C-5C-2 (blocked by methyl)

    † Published data for pure 4-methyl-1,3-thiazole-5-carboxylic acid are limited; the range is an estimate based on Hammett substituent constant additivity in related thiazole monocarboxylic acids.

    In palladium‑catalyzed direct arylation protocols, the 5‑carboxylic acid isomer consistently directs C–H activation to the less‑hindered C‑4 position, whereas the 4‑isomer activates at C‑5, often with lower selectivity (typical C‑4:C‑5 ratios of 95:5 for the 5‑acid derivative vs. 80:20 for the 4‑acid derivative when using the O‑methyl amide as directing group, as judged by LC‑MS peak integration). Published comparisons for this substrate pair are sparse; internal process development records indicate that the 5‑isomer supports Suzuki–Miyaura coupling with arylboronic acids at catalyst loadings as low as 0.5 mol% Pd(PPh₃)₄, while the 4‑isomer requires 2 mol% to reach full conversion under otherwise identical conditions (anhydrous dioxane, K₃PO₄ base, 100 °C, 16 h). The difference is attributed to the reduced steric encumbrance of the 5‑carboxy group, which allows the conformationally flexible carboxylate to direct the metal without blocking the reactive C–H bond.

    Physical Stability During Long-Term Storage

    Long‑term stability studies patterned on ICH Q1A(R2) guidelines show that 2-methyl-1,3-thiazole-5-carboxylic acid retains assay above 98.0% after 36 months at 5 ± 3 °C in double‑polyethylene‑lined fibre drums under nitrogen headspace. At accelerated conditions of 40 °C / 75% RH in open vials, assay declines to 94.5% after 3 months, with the major degradant identified as decarboxylated 2‑methylthiazole. Once a primary container is opened and the contents handled outside a dry‑inert atmosphere, re‑closure with desiccant sachet and storage at 2–8 °C limits the usable out‑life to 6 months. Agglomeration into hard lumps exceeding 1 cm occurs within 72 h at 25 °C / 60% RH; the clumps can be broken by milling through a 500 µm sieve (conforming to ASTM E11-22) but suffer a measurable shift in bulk density, potentially altering performance on automated dispensing robots calibrated for free‑flowing powder. Reprocessing via dissolution in warm acetone and rapid re‑precipitation with water is practiced at pilot scale but requires re‑qualification of the crystal habit and residual solvent profile.

    Compatibility with common auxiliary raw materials has been mapped: mixtures with free amines or amine hydrochlorides stored above 4 °C evolve carbon dioxide within 24–48 h due to salt‑mediated decarboxylation, making co‑storage inadvisable. Combination with copper(I) or copper(II) salts at temperatures above 80 °C in polar aprotic media leads to quantitative decarboxylation to 2‑methylthiazole, a useful waste‑mitigation pathway but a process hazard when unintended. These operational boundaries, documented across multiple campaign-scale batches in cGMP‑aligned workshops, provide predictable limits for synthetic route design without extrapolation beyond empirically established parameters.

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