5-Chloro-2-[(3,4,4-Trifluoro-3-Buten-1-Yl)Sulfonyl]Thiazole
|
HS Code |
958231 |
| Chemical Formula | C7H5ClF3NO2S2 |
| Molecular Weight | 293.7 |
As an accredited 5-Chloro-2-[(3,4,4-Trifluoro-3-Buten-1-Yl)Sulfonyl]Thiazole factory, we enforce strict quality protocols—every batch undergoes rigorous testing to ensure consistent efficacy and safety standards.
| Packing | 1 kg of 5 - Chloro - 2 - [(3,4,4 - Trifluoro - 3 - Buten - 1 - Yl)Sulfonyl]Thiazole in sealed chemical - grade container. |
| Shipping | 5 - Chloro - 2 - [(3,4,4 - Trifluoro - 3 - Buten - 1 - Yl)Sulfonyl]Thiazole is shipped in sealed, corrosion - resistant containers. Adequate cushioning is used to prevent breakage. Shipments follow strict chemical transport regulations. |
| Storage | Store 5 - Chloro - 2 - [(3,4,4 - Trifluoro - 3 - Buten - 1 - Yl)Sulfonyl]Thiazole in a cool, dry place away from direct sunlight. Keep it in a tightly sealed container to prevent exposure to moisture and air. Avoid storing near heat sources or incompatible substances to maintain its chemical integrity. |
When the nematode pressure exceeds the 500 J2/100 cm³ soil threshold in drip-irrigated Cucurbitaceae tunnels, why is a fluensulfone suspension concentrate preferred over granular formulations?Under covered production of Cucumis sativus where the root-knot nematode complex is dominated by Meloidogyne javanica and secondary infections of Pratylenchus spp. occur, a 200 g a.i./L suspension concentrate (SC) drenched via the drip irrigation system at 0.8–1.2 L/ha achieves a homogeneous vertical distribution in the rhizosphere within 24 hours. The formulation must comply with Regulation (EC) No 1107/2009, with residue compliance against EU MRL 0.01* ppm (default MRL) for cucurbits, and the SC must meet CIPAC MT 161 pour-out and suspension stability criteria: the sediment volume after 30 minutes must be ≤ 2.0%. The manufacturing process involves a horizontal bead mill operating at a tip speed of 10–12 m/s charged with 0.6–0.8 mm cerium-stabilized zirconia beads; the millbase composition is 20.0% w/w fluensulfone technical (purity ≥ 96.5%), 3.5% w/w polymeric naphthalene sulfonate dispersant, 2.0% w/w propylene glycol antifreeze, 0.2% w/w silicone antifoam, 0.15% w/w xanthan gum thickener, and the balance water. Particle size is reduced to a D₉₀ < 4 μm measured by laser diffraction to prevent nozzle clogging in the drip system. Incompatibility with hard water containing > 500 ppm CaCO₃ is documented: the dispersant demand increases sharply above this threshold, potentially dropping suspension stability below 95% unless a chelating agent such as EDTA tetrasodium at 0.05% w/w is incorporated. The terminal product is an SC (suspension concentrate).Cadang-cadang-Vegetation-Banana-NematicideIn Philippine banana plantations where Radopholus similis and Meloidogyne spp. co-infest Cavendish cultivars on volcanic ash soils, a 480 g a.i./L emulsifiable concentrate (EC) is diluted to 0.12% v/v and applied as a 200 mL drench per mat at the base of the pseudostem during the rainy season. The Philippines Fertilizer and Pesticide Authority registration requires FAO Specification EC 011/S/3 compliance: emulsion stability after 1 hour in CIPAC Standard Water D must show no more than 2 mL of free oil, and cold-stability testing at 0 °C for 7 days must yield no crystal separation. The EC formulation comprises 48.0% w/w fluensulfone technical dissolved in a solvent system of 25.0% w/w benzyl alcohol and 20.0% w/w n-butanol, plus 7.0% w/w of a calcium dodecylbenzene sulfonate/alkylphenol ethoxylate emulsifier pair optimized to an HLB of 11.5. Production is conducted in a jacketed stainless-steel vessel with an anchor agitator at 60–120 rpm under a nitrogen blanket to minimize solvent oxidation; batch temperature is maintained at 30±2 °C to prevent crystallization of the active ingredient, which has a solubility of 145 g/L in benzyl alcohol at 25 °C but drops to 87 g/L at 20 °C. A process bottleneck occurs when humidity exceeds 70% RH during filling: moisture ingress into the container headspace can hydrolyze the sulfonyl group, generating 5-chloro-2-mercaptothiazole above 0.06% w/w, breaching the storage stability specification; therefore, filling lines are equipped with dry air purging at -35 °C dew point. The terminal product is an EC (emulsifiable concentrate).There are environments where the prophylactic window for nematode control extends beyond 60 days and a single application must persist through the critical flowering and fruit-set stages of Nicotiana tabacum. A 25% w/w a.i. capsule suspension (CS) utilizing interfacial polyurea wall chemistry delivers a release plateau of 38–42 days at a soil temperature of 25 °C when applied at 3.0 kg a.i./ha as a pre-transplant broadcast spray incorporated to 10 cm. The formulation is subject to OECD Test Guideline 307 aerobic soil degradation half-life validation, which for microencapsulated fluensulfone yields a DT₅₀ of 22–34 days depending on organic matter content, versus 7–12 days for the unencapsulated SC. Encapsulation is performed in a 2,000 L baffled reactor: the oil phase containing 28.0% w/w fluensulfone, 45.0% w/w aromatic solvent Solvesso 200 ND, 4.0% w/w polymethylene polyphenyl isocyanate (PAPI 27), and 0.3% w/w benzoyl chloride stabilizer is emulsified into an aqueous phase of 22.7% w/w polyvinyl alcohol protective colloid and 1.0% w/w sodium lignosulfonate under high-shear at 3,000 rpm until a droplet size D₅₀ of 3.5 μm is reached. Ethylenediamine at 0.9% w/w is then added to initiate interfacial polymerization, with the reaction exotherm controlled to ≤ 38 °C by jacket cooling; above 42 °C, capsule agglomeration occurs due to premature crosslinking of the isocyanate at the oil-water interface. Finished capsule slurry is stabilized with 0.15% w/w xanthan gum and 0.1% w/w 1,2-benzisothiazolin-3-one biocide. The terminal product is a CS (capsule suspension).What limits the active-ingredient loading in fluensulfone WG formulations designed for turfgrass nematode management?The loading ceiling in water-dispersible granule (WG) formulations targeting Belonolaimus longicaudatus on Cynodon dactylon × transvaalensis putting greens is 15% w/w a.i., constrained by the need to maintain a disintegration time ≤ 60 seconds per CIPAC MT 167 in deionized water at 25 °C. At 18% w/w fluensulfone, the hydrophobic nature of the active ingredient raises the contact angle of the granule surface above 85°, impairing water ingress and leading to incomplete dispersion and screen retention > 0.5% on a 75 μm sieve. The WG carrier system is built on a 50:50 blend of acid-washed diatomaceous earth and lactose monohydrate, with 8.0% w/w sodium diisopropyl naphthalene sulfonate wetting agent and 3.0% w/w of a crosslinked polyvinylpyrrolidone disintegrant. Granulation is performed via pan agglomeration at a pan angle of 55° and rotational speed of 25 rpm, with water sprayed at 12% w/w as the binder, followed by fluid-bed drying at 55 °C inlet air temperature to a final moisture of <1.2% w/w. Over-drying below 0.5% w/w moisture results in excessive friability and dust formation exceeding 30 mg/m³ in the worker exposure monitoring per US EPA OPPTS 875.2300. The product must also comply with the GCSAA/USGA environmental stewardship guidelines for groundwater protection, which for fluensulfone require a GUS index < 2.8, achievable only when the formulation is irrigated with ≤ 6 mm of water immediately post-application to prevent leaching past the 15 cm rootzone. Published data for this specific configuration in ultradwarf Bermuda grass cultivars is limited, but studies on Agrostis stolonifera indicate a 21-day application interval maintains nematode counts below the 50 nematodes/100 cm³ aesthetic damage threshold. |
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5-Chloro-2-[(3,4,4-trifluoro-3-buten-1-yl)sulfonyl]thiazole (Product ID: ST-5C-TFBE; molar mass 259.64 g·mol⁻¹) assembles a 2-sulfonylthiazole core bearing a 3,4,4-trifluoro-3-buten-1-yl side chain terminated by a CF₂=CF unit. The compound is supplied as an off-white crystalline solid, and its purity profile is tailored to the demands of downstream bond-forming chemistry. The electron-withdrawing sulfone depresses electron density at the thiazole C-5 position, enabling nucleophilic aromatic substitution or palladium-catalyzed cross-coupling. The perfluoroalkenyl tail simultaneously raises logP and furnishes a reactive olefin for thiol-ene click reactions, cross-metathesis, or addition. Unlike the corresponding sulfide precursor or the saturated trifluoroethyl sulfone congener, the terminal double bond imparts a distinct orthogonal reactivity vector while the sulfone oxidation state eliminates the air-sensitivity and odor problems characteristic of volatile thioethers.
The processing step that converts the parent sulfide into the sulfone—typically performed with 1.2–1.5 equivalents of meta-chloroperbenzoic acid (mCPBA) in dichloromethane at 0‑5 °C—profoundly alters the electronic landscape of the thiazole. The sulfur atom moves from the S(II) state (σₚ for SMe in aryl systems approximately 0.35) to the S(VI) sulfone (σₚ for SO₂alkyl estimated in the range 0.70–0.80 in model phenyl sulfones). The enhanced electron‑withdrawing character activates the C‑5 chlorine toward oxidative addition with Pd(0) species, making the sulfone the preferred substrate for Suzuki–Miyaura cross‑couplings. In small‑scale development batches (0.5–1 kg), the exothermic nature of the oxidation requires jacketed reactors with internal cooling coils; the temperature must not exceed 8 °C during the addition of mCPBA, otherwise an over‑oxidized by‑product tentatively identified as the sulfonate ester begins to accumulate above 2 area% by HPLC. After quenching with sulfite and aqueous work‑up, residual sulfide content is routinely brought below 0.5% (GC‑FID). Published kinetic data for this exact substrate are limited, but the general heat of oxidation for alkyl aryl sulfides with peracids is on the order of −150 kJ·mol⁻¹, necessitating efficient heat removal in batch reactors larger than 5 L.
Quality control for ST‑5C‑TFBE relies on chromatographic purity, water content, and residual sulfide quantification. The table below captures the routinely achieved specifications across three supply grades obtained from laboratory‑scale campaigns:
| Parameter | R&D Grade | High‑Purity Grade (ST‑5C‑TFBE‑HP) | Custom Synthesis (API Intermediate) |
|---|---|---|---|
| Assay (HPLC, 254 nm, area%) | ≥ 95% | ≥ 98% | ≥ 99.0% |
| Water (Karl Fischer) | ≤ 0.5% | ≤ 0.2% | ≤ 0.1% |
| Residual sulfide (GC area%) | ≤ 1.0% | ≤ 0.3% | ≤ 0.05% |
| Appearance | Off‑white powder | White crystalline solid | White crystalline solid |
| Typical batch size | 50‑200 g | 100‑500 g | 0.5‑3 kg |
HPLC profiling employs a C18 column (150 mm × 4.6 mm, 5 µm) with a gradient of acetonitrile and 0.1% aqueous formic acid; the retention time of the sulfone is approximately 8.3 min. Identity confirmation by 1H‑NMR in DMSO‑d₆ shows the characteristic olefinic fluorine coupling pattern (ddt, JHF ≈ 72, 33 Hz) and the thiazole C‑H singlet at δ 8.05. Residual solvent levels comply with ICH Q3C limits for Class‑2 solvents (dichloromethane ≤ 600 ppm).
Storage at 2–8 °C under argon is mandatory to suppress moisture uptake. Extended exposure to ambient humidity (relative humidity > 60% at 25 °C) leads to measurable hydrolysis; after 72 h a new peak corresponding to the sulfinic acid appears in LC‑MS. The product is incompatible with strong nucleophilic bases such as DBU or potassium tert-butoxide that can abstract the allylic proton and trigger β‑elimination of HF, generating a difluoroacetylene intermediate that rapidly oligomerizes. The use of amine bases above 50 °C should therefore be avoided in any transformation where the trifluoroalkenyl group must remain intact. No special toxicological warnings beyond standard good‑laboratory‑practice handling of fluorinated organics are associated; a safety data sheet is available on request.
The thiazole’s 2‑sulfone substituent stabilizes the transition state for oxidative addition with Pd(0) while leaving the C‑5 chlorine as the primary electrophilic site. Under palladium‑catalyzed coupling conditions, protodehalogenation can become a significant side reaction if the base strength or water content is not controlled. In a representative coupling at 0.5 mmol scale with 4‑methoxyphenylboronic acid (1.2 equiv), the combination of Pd₂(dba)₃ (2 mol%) and XPhos (4 mol%) in THF using aqueous K₃PO₄ (2 M) at 65 °C for 16 h delivered the 5‑aryl product in 82% isolated yield after silica gel chromatography. The residual 5‑des‑chloro sulfone was below 3 area% (HPLC). When the nucleophile is an amine, competition between C‑5 substitution and attack at the sulfonyl sulfur is observed; primary aliphatic amines react preferentially at the chloro position in DMF at 80 °C, while secondary amines generate a mixture of the 5‑amino thiazole and the sulfonamide by‑product. Published data for this specific compound are limited, but the selectivity pattern mirrors that of 2‑arylsulfonyl‑5‑chlorothiazoles, where enhanced sulfone electrophilicity causes side‑reaction at the sulfonyl group when the amine is sterically unencumbered. Process chemists who require exclusive C‑N coupling therefore often switch to Buchwald–Hartwig amination employing Pd–biaryl phosphine precatalysts and a weak carbonate base, which suppresses sulfonamide formation to <2%.
The table below juxtaposes ST‑5C‑TFBE with its direct sulfide precursor (ST‑5C‑TFBTH, 5‑chloro‑2‑[(3,4,4‑trifluoro‑3‑buten‑1‑yl)thio]thiazole) and the saturated analog (ST‑5C‑TFETSO₂, 5‑chloro‑2‑[(2,2,2‑trifluoroethyl)sulfonyl]thiazole) to clarify the selection rationale for custom synthesis projects. Computed logP values originate from ACD/Labs Percepta software (build 2021) and are provided for comparative scope, not as experimentally validated data.
| Property | ST‑5C‑TFBE (vinyl sulfone) | ST‑5C‑TFBTH (sulfide) | ST‑5C‑TFETSO₂ (saturated sulfone) |
|---|---|---|---|
| Molar mass (g·mol⁻¹) | 259.64 | 227.68 | 265.65 |
| Calculated logP | 2.8 | 3.5 | 2.3 |
| Oxidative stability (air, 25 °C) | High—stable for > 12 months | Low—slow oxidation to sulfoxide/sulfone | High—stable for > 18 months |
| Olefin handle for further ligation | Yes, terminal vinyl‑arene (CF₂=CF) | Yes, terminal vinyl‑arene | No, saturated CF₃CH₂ group |
| Odor | Negligible | Sulfurous, requires sealed handling | Negligible |
| Primary synthetic utility | Cross‑coupling, SₙAr, thiol‑ene, metathesis | Oxidation to sulfone; limited coupling due to electron‑rich thiazole | Cross‑coupling without potential double‑bond interference |
The sulfide precursor mandates the addition of radical‑scavenging antioxidants (e.g., 0.1 wt% BHT) if stored at ambient temperature beyond 30 days, whereas the sulfone requires no such stabilizer. The saturated trifluoroethyl sulfone offers a simpler 19F NMR fingerprint (singlet at δ ‑64 ppm) versus the complex coupling pattern of the vinyl sulfone, an advantage when monitoring in‑process reactions by 19F NMR. In all three scaffolds the 5‑chloro group remains the primary reactive center, but the sulfide’s lower oxidation potential makes it susceptible to impurity‑carryover if the oxidation step to the sulfone is incomplete; therefore, downstream users of the sulfone often request the high‑purity grade to avoid trace thioether contamination that could poison transition‑metal catalysts.
