1,3-Thiazole-5-Carbaldehyde
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HS Code |
896276 |
| Chemical Formula | C4H3NOS |
| Molecular Weight | 113.14 g/mol |
| Appearance | Typically a solid or liquid, color may vary |
| Solubility | Solubility characteristics would depend on solvents; may have some solubility in organic solvents |
| Purity | Can be produced in various purity levels depending on synthesis and purification methods |
| Stability | Stability may be affected by environmental factors like heat, light, and air; can react with certain reagents |
As an accredited 1,3-Thiazole-5-Carbaldehyde factory, we enforce strict quality protocols—every batch undergoes rigorous testing to ensure consistent efficacy and safety standards.
| Packing | 100g of 1,3 - Thiazole - 5 - Carbaldehyde packaged in a sealed glass bottle. |
| Shipping | 1,3 - Thiazole - 5 - Carbaldehyde is shipped in properly sealed, corrosion - resistant containers. Packaging adheres to chemical transport regulations. Shipment is carefully monitored to maintain safe conditions during transit. |
| Storage | 1,3 - Thiazole - 5 - Carbaldehyde should be stored in a cool, dry, well - ventilated area. Keep it away from heat sources, flames, and oxidizing agents. Store in a tightly closed container to prevent evaporation and contamination. Ideal storage temperature is around 2 - 8°C in a refrigerator if long - term storage is required to maintain its chemical integrity. |
The synthesis of peptidomimetic inhibitors that incorporate a 5-substituted thiazole core relies on 1,3-thiazole-5-carbaldehyde as a lynchpin electrophile in assembly of the hydroxyethylamine transition-state isostere. In commercial-scale production of antiretroviral active pharmaceutical ingredients (APIs) targeting HIV‑1 protease, the aldehyde is subjected to a stereocontrolled reductive amination with a protected aminodiol intermediate—(2S,3S,5S)-2-amino-3-hydroxy-5-(tert‑butoxycarbonylamino)-1,6-diphenylhexane succinate—in tetrahydrofuran (THF) containing 1.0 % v/v glacial acetic acid. The feed molar ratio is fixed at 1.08:1.00 (aldehyde to aminodiol) to compensate for aldehyde dimerisation on the imine nitrogen, as determined by at-line ReactIR monitoring of the C=N stretch at 1665 cm⁻¹. Process compliance follows ICH Q7 Section 12.70 for validated manufacturing, and the final API lot release requires residual aldehyde below 50 ppm as measured by HPLC‑UV (USP 〈621〉) and palladium content below 10 µg/g per USP 〈232〉/〈233〉 when a heterogeneous Pd/C catalyst is employed in a subsequent debenzylation step. The exothermic amination is conducted in a 630 L hastelloy C‑22 reactor equipped with a retreat‑curve impeller operating at 95 rpm, with jacket temperature ramped from ‑5 °C to 15 °C over 14 h. Following aqueous work‑up at pH 3.5–4.0 to protonate unreacted amine, the crude sec‑amine is purified by silica gel chromatography (LiChroprep® Si 60, 40–63 µm) using a step gradient from 3:7 ethyl acetate/heptane to 7:3; this removes the diastereomeric impurity formed when the imine reduction delivers the undesired (R)-configuration at the newly created stereocenter. The resulting penultimate intermediate is telescoped into coupling with a valine‑derived activated ester, and the final deprotection and salt formation yield the API as a sulfate or besylate salt. Critical operational boundaries include strict exclusion of atmospheric moisture (dew point below ‑40 °C in the reactor headspace) and maintaining free‑amine content of the aminodiol batch above 98.5 area % because any residual primary alcohol from borane reduction of the precursor lactone will competitively form hemiacetal adducts with the aldehyde, irreversibly diverting mass from the desired imine pathway. The finished dosage form is a film‑coated tablet administered as part of a highly active antiretroviral combination, with the thiazole aldehyde sourcing subject to a Supplier Qualification Master Protocol aligned with ICH Q7 Section 7.3 raw material risk assessment.How Does Jones Oxidation Scalability Define the Cost Structure of 1,3-Thiazole-5-carboxylic Acid for Oomycete Fungicides?Conversion of 1,3-thiazole-5-carbaldehyde to the corresponding carboxylic acid is the gateway step for manufacturing thiazole‑5‑carboxamide fungicides such as N‑(cyano‑2‑thienylmethyl)‑4‑ethyl‑2‑(ethylamino)‑1,3‑thiazole‑5‑carboxamide (Ethaboxam‑type active). The aldehyde is dissolved in a chilled mixture of acetone and deionised water (4:1 v/v) and treated dropwise with freshly prepared Jones reagent (CrO₃ in 1.5 M H₂SO₄) maintaining an aldehyde‑to‑chromium(VI) molar ratio of 1.0:1.50. The oxidation enthalpy reaches ‑420 kJ mol⁻¹; jacket temperature is kept at ‑5 °C to 0 °C throughout the addition, and the reaction endpoint is confirmed by quenching an aliquot into 2,4‑dinitrophenylhydrazine solution—the absence of a visible orange precipitate indicates residual aldehyde below the 0.5 wt % threshold. After quenching with isopropanol, the chromium(III) salts are precipitated at pH 9.0 with 10 M NaOH and removed through a plate‑and‑frame filter press coated with diatomaceous earth. The isolated 1,3‑thiazole‑5‑carboxylic acid must exhibit loss on drying below 0.2 % and sulfate ash below 0.1 % before proceeding to acyl chloride formation. For the coupling stage, the dried acid is refluxed with thionyl chloride (2.5 eq) in toluene containing 0.5 mol % DMF; the evolving SO₂ and HCl are scrubbed through a packed column with 15 % NaOH. The resulting acid chloride is added to a biphasic mixture of ethylamine (70 % aqueous solution, 1.05 eq) and NaHCO₃ in dichloromethane at 5 °C. The final technical‑grade active ingredient is purified by recrystallisation from a binary solvent system of toluene/n‑heptane (1:3) to obtain a purity exceeding 97.0 area % by GC‑FID (CIPAC 1A, column DB‑5, 30 m × 0.25 mm). Compliance with FAO specification 581/TC mandates water content below 1.0 % (Karl Fischer) and acetone‑insoluble matter below 0.5 %. The formulated product is a suspension concentrate (SC 250 g L⁻¹) prepared by wet bead‑milling (WAB Dyno®‑Mill, 0.4–0.6 mm yttria‑stabilised zirconia beads, residence time 6 min) incorporating an alkylnaphthalene sulfonate dispersant and a xanthan gum thickener; the particle size D₉₀ must stay below 5 µm to meet OECD 501 pourability and CIPAC MT 46.3 accelerated storage stability at 54 °C. A persistent processing hazard is over‑oxidation during the Jones step: if the local temperature exceeds 10 °C, decarboxylative fragmentation generates thiazole and CO₂, eroding yield and demanding a scrubber capacity of 180 m³ h⁻¹ for CO₂ removal. Hexavalent chromium effluent is reduced with sodium metabisulfite (ORP below +200 mV) before precipitation, in accordance with EU Industrial Emissions Directive 2010/75/EU BAT‑AEL limits for chromium discharge (<0.1 mg L⁻¹). End use is foliar application on potatoes and vines against late blight and downy mildew pathogens.The fluorescence quantum yield of asymmetric cyanine dyes spanning the visible spectrum depends critically on the electron deficiency of the quaternary heterocycle acceptor; 1,3‑thiazole‑5‑carbaldehyde has proven to be a compact, high‑deficiency aldehyde partner that shifts absorption hypsochromically relative to benzothiazole analogues while retaining sufficient Stokes shift for nucleic acid detection. In the manufacture of a validated real‑time PCR dye stock, a 1.00:1.00 molar ratio of 1,3‑thiazole‑5‑carbaldehyde and N‑methylquinolinium iodide is condensed in anhydrous ethanol containing 0.05 mol % piperidine under argon. The solution is refluxed (78 °C) for 12 hours with continuous TLC monitoring (silica gel 60 F₂₅₄, eluent acetonitrile/water 9:1). The crude monomethine cyanine precipitates upon cooling to ‑20 °C and is isolated via Büchner filtration, washed with cold diethyl ether (‑10 °C), and dried in a vacuum oven at 40 °C, 0.5 mbar to a loss‑on‑drying endpoint of <0.3 %. Recrystallisation from methanol/ethyl acetate (1:4) removes the unconjugated aldol side products and delivers a dye purity of >99.0 area % by HPLC (C18 column, 5 µm, 250 × 4.6 mm, gradient acetonitrile/0.1 % TFA). The concentrate is formulated as a 10 mM solution in DMSO (water content <50 ppm) and sealed under nitrogen in amber vials compliant with ISO 13485:2016 for in‑vitro diagnostic reagent production. Regulatory conformance to EU In‑Vitro Diagnostic Medical Devices Regulation (EU) 2017/746 Annex I General Safety and Performance Requirements requires lot‑specific testing for endotoxins (LAL assay, <0.25 EU mL⁻¹) and bioburden (<10 CFU mL⁻¹). During milligram‑to‑gram scale‑up, control of the aldol condensation manifold becomes the dominant quality risk: if the reaction medium is >0.2 % water by Karl Fischer, acetaldehyde liberated from ethanol oxidation initiates an autocatalytic aldol cycle that converts up to 15 % of the aldehyde input into high‑molecular‑weight tar, and the required column chromatography step (LiChroprep® RP‑18, 15–25 µm) adds 8 hours cycle time. The final formulated dye intercalates with dsDNA and is used in hydrolysis probe‑based qPCR master mixes for pathogen detection; its excitation maximum at 488–496 nm matches common argon‑ion and LED light sources, and emission is collected through a 520 nm band‑pass filter.Chiral Bidentate Thiazole‑Imine Ligands and Their Copper(II) Complexes in Aerobic OxidationsTwo equivalents of 1,3‑thiazole‑5‑carbaldehyde are condensed with one equivalent of (R,R)‑1,2‑diaminocyclohexane in absolute ethanol containing 3 Å activated powdered molecular sieves (10 wt % relative to solvent) and glacial acetic acid (0.2 mol %). The aldehyde‑to‑diamine molar charge is 2.20:1.00 to ensure complete consumption of the diamine; the mixture is refluxed at 78 °C for 6 h under nitrogen. The resulting bis‑imine precipitates as a pale‑yellow solid upon cooling—filtration, recrystallisation from 2‑propanol/water (3:1), and vacuum drying at 50 °C yields a ligand of >97.0 area % purity by GC (split ratio 100:1, FID). For complexation, the ligand is dissolved in degassed methanol and treated with an equimolar amount of Cu(OAc)₂·H₂O at 40 °C for 2 h; the resulting dark‑green copper(II) complex is precipitated by addition of diethyl ether and stored under argon at ‑20 °C. Catalytic testing follows a standardised aerobic alcohol oxidation protocol: benzyl alcohol (1.0 M) in acetonitrile, 2.5 mol % catalyst loading, TEMPO (5 mol %), molecular sieves (3 Å), O₂ balloon, 60 °C. Turnover frequencies obtained with this ligand framework typically range between 45 h⁻¹ and 110 h⁻¹ depending on steric access to the copper centre. Compliance with industrial catalyst qualification standards requires residual palladium below 20 ppm (ASTM E1835‑14, ICP‑OES) and halide content below 50 ppm when the complex is intended for pharmaceutical intermediate synthesis under ICH Q3D Table A.2.2 elemental impurity limits for copper (oral PDE 1300 µg day⁻¹). The principal synthetic limitation concerns imine hydrolysis: when the ligand purification sequence exceeds 24 h cumulative exposure to atmospheric moisture (relative humidity >55 %), the bis‑imine reverts to starting aldehyde and diamine to an extent of 3–7 %, generating a mixed‑ligand system that reduces catalytic enantioselectivity by 15–25 ee %. Consequently, solid‑state storage is specified at ‑20 °C sealed under dry nitrogen, with retest after 6 months.When 2‑Aminothiophenol Condenses with 5‑Thiazolecarboxaldehyde in Oxidative Cyclisation, Regioisomeric Purity Governs Charge Carrier Mobility2‑(1,3‑Thiazol‑5‑yl)benzo[d]thiazole (TBT) is constructed via a one‑pot oxidative cyclocondensation between equimolar quantities of 1,3‑thiazole‑5‑carbaldehyde and 2‑aminothiophenol in dimethylformamide (4 vol) containing sodium metabisulfite (2.5 eq) as the oxygen scavenger and oxidant shuttle. The mixture is heated at 110 °C for 18 h under nitrogen; HPLC monitoring (C8 column, 3 µm, UV 254 nm) targets consumption of the aldehyde to <1.0 area %. After cooling, the reaction mass is poured into ice‑water, neutralised with Na₂CO₃, and extracted with ethyl acetate. The crude product is purified by sublimation (180 °C, 10⁻² mbar) to yield a crystalline solid of >99.5 % purity by differential scanning calorimetry (melting point 147–149 °C). Regioisomeric impurity arising from cyclisation at the 4‑position of the thiazole ring is <0.3 area % when the reaction temperature is strictly limited to 105–115 °C; excursions above 120 °C promote an intramolecular rearrangement that raises this impurity to 4–6 %, clearly detectable as a secondary endotherm in DSC and responsible for a 10‑fold reduction in field‑effect mobility in bottom‑gate top‑contact organic thin‑film transistors (channel length 50 µm, SiO₂ dielectric). The purified material is further processed by vacuum thermal evaporation (10⁻⁶ mbar, substrate temperature 25 °C, deposition rate 0.2 Å s⁻¹) to fabricate the active semiconductor layer. Compliance under RoHS 2011/65/EU Annex II is confirmed by X‑ray fluorescence screening for lead, mercury, and cadmium (<100 ppm each), and electrical safety of the final flexible display module is evaluated per IEC 62368‑1:2018 Section 5.2. While published mobility values for TBT‑based OTFTs vary with dielectric treatment, typical saturation‑regime mobilities for hexamethyldisilazane‑treated substrates fall within 0.03–0.18 cm² V⁻¹ s⁻¹ with an on/off current ratio exceeding 10⁶; these figures place the semiconductor in the viable performance window for e‑paper backplane drivers, provided the batch‑to‑batch variation in regioisomeric purity is held below the 0.5 % threshold.
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| Parameter | Method | Acceptance Limit | Typical Value |
|---|---|---|---|
| Purity (GC) | ASTM E594 (FID, DB‑5 column) | ≥98.0 area% | 99.2 area% |
| Moisture | Karl Fischer (ASTM E203) | ≤0.5 wt% | 0.12 wt% |
| Melting Range | Capillary method | 83–87 °C | 85–86 °C |
| Residual Solvent (EtOAc) | Headspace GC‑MS | ≤0.2 % | 0.06 % |
| Palladium Content | ICP‑MS | ≤10 ppm | 2 ppm |
| Property | 1,3-Thiazole-5-carbaldehyde | 1,3-Thiazole-2-carbaldehyde | 1,3-Thiazole-4-carbaldehyde |
|---|---|---|---|
| Physical State at 25 °C | Crystalline solid | Colorless liquid | Low‑melting solid |
| Melting/Boiling Range | m.p. 83–87 °C | b.p. 61–62 °C/1.33 kPa | m.p. 54–56 °C |
| Relative Electrophilicity (σ⁺) | Highest; Hammett σ⁺ +0.42 | Moderate; σ⁺ est. +0.30 | Lowest; σ⁺ est. +0.22 |
| Pd‑Catalysed Coupling Efficiency (C‑4/C‑2 activation) | Effective; 0.5 mol% Pd(PPh₃)₄ | Slower; 2.0 mol% Pd(PPh₃)₄ | Requires C‑5 functionalisation |
| Stability in pH 12, 24 h | 97 % intact by HPLC | 92 % intact | 89 % intact |
| Recommended Storage | 2–8 °C, argon | 2–8 °C, nitrogen | –20 °C, argon |
