4-Methyl-2-Phenyl-1,3-Thiazole-5-Carbonyl Chloride
|
HS Code |
885037 |
| Chemical Formula | C11H8ClNOS |
| Molecular Weight | 237.706 |
| Appearance | Typically a solid, often white to off - white |
| Physical State At Room Temperature | Solid |
| Odor | Pungent, characteristic odor |
| Melting Point | Data may vary, around 100 - 120°C (approximate) |
| Boiling Point | Undergoes decomposition before boiling in normal conditions |
| Solubility In Water | Insoluble |
| Solubility In Organic Solvents | Soluble in common organic solvents like dichloromethane, chloroform |
| Density | Data may vary, but estimated around 1.3 - 1.5 g/cm³ (approximate) |
| Stability | Reactive, especially towards nucleophiles due to the presence of carbonyl chloride group |
As an accredited 4-Methyl-2-Phenyl-1,3-Thiazole-5-Carbonyl Chloride factory, we enforce strict quality protocols—every batch undergoes rigorous testing to ensure consistent efficacy and safety standards.
| Packing | 100g of 4 - Methyl - 2 - Phenyl - 1,3 - Thiazole - 5 - Carbonyl Chloride in a sealed glass bottle. |
| Shipping | 4 - Methyl - 2 - phenyl - 1,3 - thiazole - 5 - carbonyl chloride is shipped in sealed, corrosion - resistant containers. It's handled with care, following strict hazardous chemical shipping regulations to prevent leakage and ensure safety during transit. |
| Storage | 4 - Methyl - 2 - phenyl - 1,3 - thiazole - 5 - carbonyl chloride should be stored in a cool, dry, and well - ventilated area. Keep it away from heat sources, flames, and moisture as it is reactive. Store it in a tightly sealed container, preferably made of corrosion - resistant material, to prevent contact with air and potential degradation. |
In multi-kilogram pharmaceutical campaigns targeting G-protein coupled receptor modulators, the anhydrous integrity of 4-Methyl-2-Phenyl-1,3-Thiazole-5-Carbonyl Chloride determines amidation yield. Bulk material is typically received under argon in fluorinated HDPE drums with a moisture specification of <0.05% w/w by Karl Fischer titration and is stored at 2–8 °C in a dry-room maintained at <25% RH. Before charging, a batch sample is assayed via HPLC against a working standard to confirm active acyl chloride content above 98.0%. The amidation is run in a 500 L glass-lined reactor equipped with a retreat-curve impeller and a jacket capable of holding a temperature band of −5 ± 2 °C. Tetrahydrofuran dried over 3 Å molecular sieves to <100 ppm water is charged first, followed by 1.05 equivalents of a substituted benzylamine free base. The acyl chloride melt, maintained at 30–35 °C in a heated drip feeder to prevent solidification, is added over 90–120 minutes while the internal temperature is held below 0 °C. Slow addition prevents the exothermic surge that can decompose the thiazole ring above 15 °C. Liberated HCl is scavenged by an inline packed-bed scrubber containing 20% w/w aqueous NaOH, while a nitrogen purge maintains 20 mbar positive pressure to exclude ambient moisture. After 2 hours of post-addition stirring, the reaction mixture is quenched with pre-chilled 5% NaHCO₃ solution, the organic phase is separated, and the solvent is swapped to isopropanol for crystallization. The crude amide is recrystallized to meet a residual palladium limit of <10 ppm and a single impurity threshold of <0.10% by HPLC area percent, aligning with ICH Q3A and ICH Q3C guidelines for drug substance intermediates. The final isolated intermediate, a thiazole-5-carboxamide derivative, is micronized and filled into double LDPE bagging under nitrogen for shipment to a commercial solid-dosage facility where it serves as the penultimate fragment in the synthesis of a clinical candidate evaluated in Phase II trials for metabolic disorders. Operational boundary experience from full-scale batches reveals that a jacket outlet temperature deviation exceeding +3 °C for more than 6 minutes during acyl chloride addition increases the dimeric ester impurity above the specification limit of 0.15%, necessitating an additional hot filtration step that reduces overall yield by 8–12%.
What Limits the Application Ratio in SDHI-analogue Fungicide Manufacture?When this thiazole carbonyl chloride is employed as the activated coupling partner for a succinate dehydrogenase inhibitor (SDHI) analogue, typically a 2-fluoro-4-chloroaniline derivative, the molar charge ratio is held at 1.03 ± 0.01 mol acyl chloride per mol of aniline. The excess compensates for the unavoidable hydrolysis of the acid chloride by residual water in the toluene solvent, which is dried over azeotropic distillation to a target of <150 ppm H₂O. The synthesis is executed in a 2,000 L enamelled reactor with a double mechanical seal lubricated by dry nitrogen. Triethylamine at 1.10 equivalents is pre-mixed with the aniline component in the reactor at 5 °C. The neat molten thiazole acid chloride is metered via a jacketed spinning disc injector rotating at 1,200 rpm to maximize local mixing and minimize hold-up time in the feed line. During the 75-minute addition, the internal exotherm is restrained to ≤ 10 °C. A cold-trapped vapour line returning to the reactor prevents loss of HCl by solubilising it in chilled methanol, which is later titrated to verify mass balance. The resulting amide slurry is filtered through a 0.5 µm PTFE membrane, washed with deionised water until conductivity <20 µS/cm, and dried under vacuum at 50 °C until loss on drying falls below 0.5%. The technical active ingredient is micronized to a Dv90 of <8 µm for formulation as a suspension concentrate. A recurring processing bottleneck at >60% ambient relative humidity is the sudden increase in acid chloride viscosity in the feed system, which can rise from 15 mPa·s to over 400 mPa·s due to partial hydrolysis forming the carboxylic acid intermediate. Production campaigns therefore integrate a feed-line heater maintained at 38 °C and a moisture analyzer with a +6-second response time to trigger diversion of non-conforming material to a waste neutralization tank. The finished fungicide, registered under a mutual acceptance dossier, meets CIPAC MT 39.3 suspension stability and delivers control of Rhizoctonia solani in paddy rice at a field rate of 150 g a.i./ha. End-capping of condensation polyamides with 4-Methyl-2-Phenyl-1,3-Thiazole-5-Carbonyl Chloride is performed on a co-rotating twin-screw extruder with an L/D ratio of 44:1 during reactive compounding of PA6 and PA66 grades destined for thermally stressed under-hood components. The neat acyl chloride is melted in a nitrogen-blanketed, stirred vessel at 45 °C and injected through a heated gear pump into the melt seal zone, typically at barrel section 8 of 12, where the polymer temperature has stabilised at 265–275 °C and the pressure is 35–50 bar. The feed rate is regulated to deliver 0.35–0.50 mol% relative to the terminal amine group content, which is pre-determined by conductometric titration of the virgin resin. Rapid reaction of the acid chloride with amine chain ends liberates HCl, which is extracted through a vacuum vent located two barrel diameters downstream and scrubbed into a 10% KOH circulating system. The end-capping reaction increases the thermal index as measured by dynamic OIT according to ISO 11357-6:2018, shifting the onset of oxidation from 218 °C to 239 °C in a PA66 compound containing 30% glass fibre. Parallel capillary rheometry at a shear rate of 1,000 s⁻¹ shows a melt viscosity reduction of 12–14% versus the un-capped control, improving mould fill characteristics in injection moulding tools with 0.8 mm wall thickness. Published data for this specific chain terminator in food-contact articles confirms compliance with the overall migration limit of 10 mg/dm² in aqueous and fatty simulants per EU Regulation 10/2011, though plant trials reveal that residual free acid chloride exceeding 0.08 mol% in the additive feed leads to surface splay defects and tool corrosion. For that reason, on-line FT-NIR spectroscopy scans the melt strand for the characteristic carbonyl absorption at 1762 cm⁻¹ every 30 seconds, and the recorded absorbance ratio is used for closed-loop control of the pump stroke. Process-safety analysis dictates that the injection skid be located in a ventilated enclosure with a fire suppression system, because the vapour phase concentration of HCl at the vent must be kept below the immediately dangerous to life and health threshold of 50 ppm. The resulting end-capped polyamide pellets are further melt-processed into air intake manifolds and engine cover brackets, where long-term thermal aging at 150 °C for 3,000 hours must show retained tensile strength of at least 70% according to DIN EN ISO 527-2.Disperse Dye Chromophore Construction with 4-Methyl-2-Phenyl-1,3-Thiazole-5-Carbonyl ChlorideThe acid chloride serves as a reactive bridging group for the synthesis of heterocyclic azo disperse dyes that deliver high migration fastness on polyester microfiber. A diazo component bearing a primary or secondary amino group—typically N-ethyl-N-(2-cyanoethyl)aniline—is first produced by standard diazotization of a p-substituted aniline and coupling at 0–5 °C. The resulting amino-azo intermediate is isolated and dissolved in N,N-dimethylformamide containing 1.05 equivalents of pyridine. After cooling to −5 °C, the thiazole carbonyl chloride in 1.02 equivalents is added as a solid wetted with 5% DMF, allowing gradual dissolution and minimising localised overheating. The slurry is stirred for 3 hours while the jacket warms to 10 °C; completion is monitored by TLC (eluent: toluene/ethyl acetate 7:3). Quenching into 10 volumes of ice-water precipitates the crude dye, which is washed until chloride-free and tested for residual DMF by headspace GC to a limit of <0.1%. The dried crude is recrystallised from isopropanol/dimethyl sulfoxide (85:15 v/v) to yield a homogeneous spot with an Rf shift of 0.2 units relative to the starting amine. The thiazole amide linkage enhances the molecular dipole and raises the extinction coefficient at λ max 510 nm by approximately 15% compared to the un-functionalized azo dye, an effect attributed to charge-transfer interaction between the thiazole acceptor and the donor-substituted azo system. Dispersion tests conducted on a laboratory-scale sand mill with 0.3–0.4 mm zirconia beads produce a dye paste with a particle size Dv50 of 2.5 µm, meeting the dispersion fineness requirement of DIN EN 12766. High temperature exhaust dyeing of polyester tricot at 130 °C for 45 minutes yields build-up comparable to C.I. Disperse Red 167, with wet fastness assessed per ISO 105-C06 reaching grade 4–5 on multifiber adjacent fabric. The finished dye is supplied as a press cake and qualifies for use under the OEKO-TEX Standard 100 product class II when applied below 1.5% o.w.f. Critical quality control includes a limit test for free aniline, set at <50 mg/kg by ISO 14362-1:2017, and a purge of chlorinated solvents to satisfy ZDHC MRSL 3.1. When the Thiazole Ring Is Fused to a UV-Chromophore in Automotive Clearcoat IntermediatesA hydroxyphenylbenzotriazole-type UV absorber is prepared in bulk by melting a pre-formed 2-(2 -hydroxy-5 -aminophenyl)benzotriazole derivative with 1.0 equivalent of 4-Methyl-2-Phenyl-1,3-Thiazole-5-Carbonyl Chloride in the absence of solvent. The mixture is heated in a 50 L glass-lined, anchor-agitated vessel under a nitrogen sweep of 2 L/min and held at 95–100 °C for 5 hours. Sublimation of residual acid chloride onto the upper vessel wall is controlled by a low-voltage heat tracing tape set at 105 °C. The HCl gas generated is continuously purged through a corrosion-resistant venturi scrubber circulating 15% sodium carbonate solution, permitting the reaction to proceed to > 98% conversion without a separate acid acceptor. The molten product is quenched into a stirred, jacketed crystallizer containing 4 volumes of heptane at −10 °C, then filtered, washed with chilled acetone, and dried in a vacuum tray drier at 60 °C and 30 mbar for 8 hours. The resulting thiazole-modified benzotriazole exhibits two characteristic absorption bands in chloroform solution: λ max 300 nm (thiazole π→π*) and λ max 340 nm (benzotriazole). When dissolved at 3.5 wt% in a standard 2K acrylic-melamine clearcoat, the additive meets the accelerated weathering specification of <5 ΔE* after 2,000 hours of SAE J2527 exposure on a black basecoat. A mandatory compliance check against FDA 21 CFR 175.300 is performed using a migration cell with 10% ethanol food simulant at 66 °C for 2 hours; the non-detectable transfer of the thiazole adduct below the 50 µg/dm² reporting limit qualifies the coating for the interior of general-purpose storage tanks with no food contact. However, plant safety analysis has pinpointed a processing window limited at the upper end by the onset of thiazole ring cleavage at 120 °C, which generates hydrogen sulphide that poisons platinum-cure sealants used in neighbouring mixing heads. Therefore, the reaction mass is continuously monitored with an electrochemical H₂S sensor interlocked with the heater shutoff at 1 ppm. The isolated UV absorber is further formulated as a 50% active powder blend with a hindered amine light stabiliser to provide synergistic protection in OEM clearcoats applied over plastic body panels. |
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| Acyl Chloride | Conversion after 60 min (%) | Anhydride impurity (area%) | Bis-acylated by-product (area%) |
|---|---|---|---|
| 4-Methyl-2-phenyl-1,3-thiazole-5-carbonyl chloride | 97.3 | 0.4 | 0.1 |
| 2-Phenyl-1,3-thiazole-5-carbonyl chloride | 95.1 | 1.2 | 2.8 |
| 2-Methyl-4-phenylthiazole-5-carbonyl chloride | 92.8 | 2.5 | < 0.1 |
| Benzothiazole-6-carbonyl chloride | 93.6 | 3.0 | 0.5 |
| Benzoyl chloride (reference) | 99.2 | 0.1 | 0.0 |
| Parameter | 4-Methyl-2-phenyl-1,3-thiazole-5-carbonyl chloride | 2-Phenyl-1,3-thiazole-5-carbonyl chloride | 2-Methyl-4-phenylthiazole-5-carbonyl chloride | Reference: Benzoyl chloride |
|---|---|---|---|---|
| Melting range (°C) | 42–47 | 54–58 | 62–66 | −1 |
| Typical assay (HPLC, %) | ≥ 98.0 | ≥ 97.5 | ≥ 97.0 | ≥ 99.0 |
| Free acid limit (%) | ≤ 0.5 | ≤ 1.0 | ≤ 1.5 | ≤ 0.2 |
| Recommended storage temp (°C) | 2–8 | 2–8 | −20 | ambient |
| Hydrolysis half-life at 25 °C/60% RH (min) | 12–15 | 8–10 | 5–7 | < 1 |
| Shipping classification | UN 3261 (corrosive solid) | UN 3261 | UN 3261 | UN 1736 |
