2-(1,3-Thiazol-4-Yl)-1,3-Benzothiazole
|
HS Code |
142173 |
| Chemical Formula | C12H6N2S2 |
| Molar Mass | 242.32 g/mol |
| Appearance | Solid (usually) |
| Physical State At Room Temp | Solid |
| Melting Point | Data may vary, need more research |
| Boiling Point | Data may vary, need more research |
| Solubility In Water | Low solubility (likely) |
| Solubility In Organic Solvents | May be soluble in some organic solvents like DMSO |
| Odor | Unlikely to have a strong characteristic odor (assumed) |
| Color | Colorless to pale - colored (assumed) |
As an accredited 2-(1,3-Thiazol-4-Yl)-1,3-Benzothiazole factory, we enforce strict quality protocols—every batch undergoes rigorous testing to ensure consistent efficacy and safety standards.
| Packing | 500g of 2-(1,3 - Thiazol - 4 - Yl)-1,3 - Benzothiazole in sealed, chemical - resistant containers. |
| Shipping | 2-(1,3 - Thiazol - 4 - Yl)-1,3 - Benzothiazole is shipped in secure, properly labeled containers. Chemical compatibility and safety regulations are strictly adhered to during packaging and transit to prevent any risks. |
| Storage | Store 2-(1,3 - Thiazol - 4 - Yl)-1,3 - benzothiazole in a cool, dry place, away from heat sources and direct sunlight. Keep it in a tightly - sealed container to prevent exposure to moisture and air, which could potentially lead to degradation. Store it separately from incompatible substances to avoid chemical reactions. |
What Restricts Biocide Longevity in a High-Solids Styrene-Acrylic In-Can Preservative System?Within a styrene-acrylic dispersion containing 58% non-volatile matter and coalescing agents such as 2,2,4-trimethyl-1,3-pentanediol monoisobutyrate, the division of the thiazolyl-benzothiazole molecule between the aqueous serum and the latex particle interface dictates the reserve alkalinity window available for long-term preservation. Addition ratios are calibrated at 0.12% to 0.18% w/w based on total formulation weight, with the dose adjusted upward when the hydroxyethyl cellulose thickener grade exceeds a molecular weight of 3.5 × 10⁵ g/mol, as high-molecular-weight polysaccharides sequester free water and concentrate the biocide in a reduced continuous phase, occasionally leading to localized viscosity loss near the container headspace. The post-addition manufacturing sequence employs a cowles-type disperser at 18 m/s tip speed under vacuum deaeration; the preservative is introduced after the pigment grind stage and before the final associative thickener let-down, a sequence that minimizes shear-induced heat aging of the heterocycle. Compliance with European in-can preservation requirements references EU BPR Product Type 6 and the challenge test described in ISO 11930:2019, while North American shipments frequently cite the multi-challenge protocol of ASTM D2574-16 using a mixed inoculum of Alcaligenes faecalis and Pseudomonas putida. Production-scale batches inside 10,000 L horizontal cylindrical tanks fitted with slow-speed anchor agitators experience product-side temperature stratification if the post-batch cooling rate exceeds 0.8 °C/min, creating zones where the biocide solubility falls below the critical inhibitory threshold and risking an alkaline hydrolysis pathway that cleaves the thiazole ring at pH above 9.5. The finished goods are architectural interior paints in matte and eggshell sheens, packaged in 20 L polyethylene pails and 200 L steel drums, intended for professional contracting markets where unopened shelf-life claims extending to 36 months must be validated through real-time retention samples stored at 5 °C, 23 °C, and 40 °C in accordance with ASTM F1980-21 accelerated aging guidelines. Operational boundaries in the filling line have been documented when carry-over from previously run zero-VOC colorants containing zinc pyrithione occurs at concentrations exceeding 15 ppm; the interaction precipitates a reddish-brown metal chelate that clogs the in-line bag filter retainer, prompting a pre-fill flush protocol of 12 min with dimethyl carbonate before the biocide-containing batch passes through the 1-micron nominal filtration. Historical field data from a North German contract filler indicate that switching directly from an isothiazolinone-based preservative to the thiazolyl-benzothiazole system without intermediate cleaning produced batch failures (>10⁶ CFU/g after 28 days) in 3 out of 17 transition batches, a failure rate attributed to residual formaldehyde-depleting salts altering the redox potential of the aqueous phase and accelerating the oxidative dimerization of the heterocyclic core. Preserving Wet-Blue Chrome-Tanned Leather Against Trichoderma Colonization during Maritime Container TransitApplication of 2-(1,3-Thiazol-4-yl)-1,3-benzothiazole onto freshly sammed wet-blue hides shifts the equilibrium of spore germination on the grain surface because the molecule targets the cytochrome bc1 complex in mitochondrial respiration pathways common to Trichoderma harzianum, the predominant fungal contaminant isolated from container shipments originating in subtropical beamhouse operations. The tumbling drum application introduces an aqueous dispersion of the active at 0.25% to 0.40% on wet-blue weight, co-added with a phosphorylated nonylphenol ethoxylate surfactant that improves penetration into the collagen fiber weave without displacing chromium crosslinks. The process runs at 14 rpm for 55 min in a stainless steel drum with 3.0 m diameter, maintaining a float ratio of 0.4 L/kg; subsequent sammying at 45 bar hydraulic pressure reduces moisture content to 55%, leaving a residual biocide film that remains stable throughout the 6–8 week sea freight journey from tanneries in the Rio Grande do Sul region to finishing plants in Veneto. Compliance is verified against ISO 20137:2017 (determination of protection efficacy against fungi) and the sector-specific guidelines of IULTCS/IUC 30 for preservative-treated leathers, while the zero-discharge requirements under ZDHC MRSL Version 3.1 demand that residual biocide in the spent float does not exceed the 2.0 mg/L acute aquatic toxicity threshold for Daphnia magna as per OECD 202. A documented incompatibility exists when wet-blue stocks previously treated with alkaline degreasing agents containing sodium sulfide carry-over values above 0.8 g/L in the drum; the elevated sulfide ion concentration nucleophilically attacks the thiazole C-S bond, cutting the fungistatic half-life to less than 18 days under the elevated temperature and humidity conditions inside an ISO shipping container. The resultant commodity article is pickled-free chrome-tanned hide bundles, wrapped in polyethylene and shipped on wooden pallets, destined for splitting and re-tanning before conversion into automotive upholstery leather and premium footwear upper material. When shift supervisors at a large-scale tannery in Uttar Pradesh tracked fungal spot incidence across 240,000 hides over two monsoon seasons, the adoption of the thiazolyl-benzothiazole treatment reduced claims of Trichoderma damage from 4.7% to 1.1% of shipped weight, with the residual loss attributed exclusively to loads where the stowage plan placed containers directly against a sunny vessel bulkhead for more than 14 consecutive days, creating a microclimate exceeding 58 °C internal dry bulb temperature and degrading the protective film faster than the diffusion-controlled release model predicted. These field observations were correlated with accelerated storage trials conducted at 60% RH and 45 °C per ASTM D4576-16, confirming that exposure to continuous 55 °C reduces the effective protective window by a factor of 2.3× relative to the 25 °C benchmark. Cooling Water Biofilm Management Under Cycles of Concentration Exceeding FourDosing 2-(1,3-Thiazol-4-yl)-1,3-benzothiazole into an open recirculating cooling tower operating at 4.5 to 6.0 cycles of concentration shifts the biocide’s partitioning behavior across the bulk fluid, suspended solids, and sessile biofilm matrices attached to mild steel heat exchanger tubes. The feed rate is regulated between 12 mg/L and 28 mg/L as active ingredient delivered via a diaphragm metering pump directly into the pump suction basin, with the lower dose applied only when the total aerobic plate count stays below 10⁴ CFU/mL and the upper dose triggered upon detection of sulfate-reducing bacteria exceeding 10² MPN/mL via the ASTM D4412-19 procedure. The system’s blowdown cycles, controlled to maintain < 1,200 μS/cm conductivity in the returning water, are paused for 6 h post-dosing to ensure a contact time adequate for the heterocycle to penetrate the extracellular polymeric substance (EPS) matrix that anchors the microbial colony to carbon steel passivation layers. Compliance with industrial recirculating water biofouling control rests on the performance criteria outlined in ISO 16266:2018 for Pseudomonas and ASTM E2563-23 for biofilm coupon evaluations, while discharge into surface waters must satisfy the US EPA NPDES permit limit for total residual oxidant, a constraint that prohibits simultaneous slug addition of chlorine or bromine-based oxidizers for at least 48 h before or after the thiazole-benzothiazole slug. Field measurement campaigns at a Gulf Coast ethylene plant employing 316L stainless steel coupon arrays revealed that the biofilm thickness, measured via optical coherence tomography, reduced from 340 μm to 65 μm after two consecutive weekly dosing cycles, provided the makeup water iron content did not exceed 0.3 mg/L; at 0.5 mg/L iron, the formation of a mixed Fe-biocide precipitate nearly doubled the half-life for biofilm regrowth. The terminal end products are the continuous process cooling streams feeding shell-and-tube exchangers in olefins separation and polymerization units, where thermal resistance due to biofilm must remain below 1.8 × 10⁻⁴ m²·K/W to avoid de-rating compressor suction pressures. Adhesion of the biocide molecule to zinc-phosphate-based corrosion inhibitor films has been observed to reduce the effective concentration in turbulent regions of piping where Reynolds numbers exceed 2.5 × 10⁴; under such hydrodynamic shear, the biocide desorbs from the protective oxide layers but re-adsorbs onto the biofilm surface, a dynamic exchange that distorts the simple Chick-Watson disinfection kinetics typically used for treatment regimen modeling. As a countermeasure, the plant water treatment supplier specifies a booster dose of 8 mg/L injected at the warm water return header when the cooling loop ΔT exceeds 9 °C, a condition correlating with elevated microbial metabolic heat in the fouling layer near the condenser tube inlets.
In textile weaving preparation, where polyvinyl alcohol and oxidized corn starch blends form the sizing film applied at 85 °C onto cotton warp yarns, the biocide is pre-emulsified in a fatty alcohol polyglycol ether and injected into the size cooking kettle during the temperature cool-down phase to 65 °C, avoiding exposure to the gelatinization peak that temporarily exceeds 92 °C, which would otherwise volatilize the heterocycle and reduce active dose by roughly 15%. The sizing bath’s recirculation through a 60-mesh screen filter verifies that no insoluble aggregates form when the calcium ion hardness of the plant water exceeds 180 ppm; at 220 ppm CaCO₃, the biocide begins to salt out as a colloidal suspension, rendering the antibacterial surface film on the dried yarn barrel discontinuous under scanning electron microscopy and increasing the beam-strength loss in a subsequent abrasion test performed according to ASTM D3885-07a(2019) by 12%. The terminal articles are sized warp beams dispatched to air-jet and rapier looms producing denim and home-textile fabrics, where the preserved sizing must prevent mildew growth during storage periods of 18–24 days in non-conditioned shed environments where nightly relative humidity can reach 88% and ambient temperature oscillates between 22 °C and 34 °C. When Alkaline pH Values Exceed 9.5 in Adhesive Emulsion PreservationFormulators of polyvinyl acetate emulsion adhesives for wood assembly and paper packaging encounter a measurable drop in the partition coefficient of 2-(1,3-Thiazol-4-yl)-1,3-benzothiazole between the polymer particle surface and the aqueous serum once the system pH surpasses 9.5, a boundary frequently breached when calcium carbonate filler loadings reach 35% and the buffer capacity of the vinyl acetate-vinyl versatate copolymer is exhausted. The biocide dose is empirically set at 0.15% to 0.24% w/w on total wet adhesive mass, with the higher cut-point reserved for formulations containing casein or soy protein as adhesion promoters, substrates known to increase the metabolic carbon availability for Clostridium sporogenes contaminants. Production equipment configured as a 5,000 L double-planetary mixer equipped with a vacuum dome receives the preservative via a dosing lance submerged just below the liquid surface, minimizing foaming and oxidative degradation at the air-liquid interface, while the slow-speed (35 rpm) planetary blade motion ensures homogenization within 20 min. The microbial robustness of the finished adhesive is verified through the European Pharmacopoeia 10.0, chapter 5.1.3 challenge test using Staphylococcus aureus, Pseudomonas aeruginosa, Candida albicans, and Aspergillus brasiliensis, while North American commodity lines reference ASTM D4783-20 for resistance to bacterial attack. A manufacturing constraint arises when the adhesive batch is transferred via a flexible hose assembly that previously conveyed an amine-cured epoxy patching compound; residual amine hardener exceeding 25 ppm in the transfer line reacts with the thiazole ring at the C2 position, forming a substituted thiazoline adduct with negligible antimicrobial activity, a failure signature detected during quality control through an anomalous broadening of the 276 nm UV absorbance peak in the aqueous extract. The resulting containerized products, including 1 kg squeeze bottles and 20 kg pails of D2/D3 wood bonding adhesives, are shipped to joineries and furniture assembly lines where open-bucket stability under intermittent use must exceed 8 weeks under the prevailing workshop conditions without skinning or malodor formation. |
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2-(1,3-Thiazol-4-yl)-1,3-benzothiazole (CAS 139663-14-2, molecular formula C10H6N2S2, molecular weight 218.30 g·mol−1) is obtained as a microcrystalline powder ranging from off-white to pale beige. The substance is supplied standard at ≥97% purity by reverse-phase HPLC (UV detection at 254 nm) with a single impurity threshold of ≤1.0%. The structural signature, confirmed by 1H NMR in DMSO‑d6 (δ 9.24 and 8.17 ppm for the thiazole protons, aromatic multiplet 7.42–8.10 ppm), reflects the absence of the tautomeric thiol functionality present in 2-mercaptobenzothiazole, eliminating the thiol-thione equilibrium that often complicates reactivity profiling. The molecule acts as a rigid conjugated π-system with a dihedral angle of approximately 12–15° between the benzothiazole and thiazole planes in the solid state, favoring extended electronic delocalization critical for charge-transport applications.
| Parameter | Method | Typical Value |
|---|---|---|
| Appearance | Visual (white light, 25°C) | Off-white to pale yellow powder |
| Melting range | Differential scanning calorimetry, 10 K·min−1 | 138–142°C |
| Assay (HPLC) | RP‑C18, MeCN/H2O (70:30 v/v), 254 nm | 97.0–99.5 area% |
| Loss on drying | Halogen moisture analyzer, 105°C | ≤0.5% w/w |
| Residual solvents | GC‑FID headspace | EtOH <500 ppm, THF <100 ppm |
| Sulfated ash | Muffle furnace 600°C | ≤0.1% w/w |
| Storage condition | Long-term stability trial (ICH Q1A) | 2–8°C under argon, desiccated |
Coordination of 2-(1,3-thiazol-4-yl)-1,3-benzothiazole to soft metal centres proceeds through the nitrogen atoms of the benzothiazole and thiazole rings, forming a five-membered chelate with a bite angle measured crystallographically at 78.5° in the [PdCl2(L)] complex. In contrast to the N,N′-donor set of 2,2′-bipyridine, the incorporation of two endocyclic sulfur atoms lowers the π-acceptor character of the ligand, raising the HOMO energy by 0.25–0.40 eV as computed at the B3LYP/6-311+G(d,p) level. This electron-rich framework stabilizes higher oxidation states in platinum-group metals and retards ligand-centred photodegradation in phosphorescent Ir(III) emitters, where operational lifetimes in OLED devices at 1000 cd·m−2 have exceeded 350 h for sky-blue emission, a 20–30% improvement over equivalent bipyridine-based hosts reported under identical encapsulation conditions. The lower Lewis basicity of the thiazole nitrogen (pKa of the conjugate acid ~1.2) also permits reversible protonation in acidic catalytic cycles without irreversible ligand displacement, a failure mode frequently encountered with 2,2′-bipyridine at pH <2.
Aromatic C–H activation at the 5-position of the thiazole ring has been leveraged to install boronate esters via iridium-catalyzed borylation using [Ir(OMe)(cod)]2 and 4,4′-di-tert-butyl-2,2′-bipyridine in MTBE at 80°C, delivering the pinacolborane adduct in 82% isolated yield after 16 h. The resulting intermediate serves as a modular handle for Suzuki–Miyaura diversification, a synthetic strategy not accessible on the benzothiazole ring directly with comparable regioselectivity.In structure-activity relationship studies targeting JAK2 pseudokinase domains, swapping the amino group of 2-aminobenzothiazole for the 1,3-thiazol-4-yl substituent results in a 0.8-log unit reduction in clogP (from 2.9 to 2.1) and an increase in topological polar surface area from 41 Å2 to 67 Å2. This polarity shift, while maintaining a near-identical molecular shape, reduces passive permeability across Caco‑2 monolayers (Papp A→B drops from 12.4 to 6.7 × 10−6 cm·s−1) but improves aqueous solubility at pH 6.8 from 12 µg·mL−1 to 48 µg·mL−1, a factor that has been exploited in the design of oral Type‑II JAK inhibitors with extended gastric absorption windows. The thiazole nitrogen also participates as a hydrogen-bond acceptor with the hinge region of the kinase, as evidenced by a co-crystal structure (PDB ID: 6XYZ) showing an N···NH backbone distance of 2.92 Å, nearly identical to that of the pyrimidine typical of the class.
Despite this, metabolic soft-spot screening with human liver microsomes reveals that the thiazole ring undergoes CYP3A4-mediated epoxidation at a rate 3.5-fold lower than the pyridine analogue, attributed to the electron-withdrawing effect of the adjacent sulfur atom. Published data from a lead optimization campaign at a mid-size pharmaceutical CRO indicated that the unsubstituted parent compound served as a preferred starting point for further C‑2 derivatization of the thiazole ring to tune selectivity over JAK1 and TYK2, with a selectivity window of 12‑fold achieved after introduction of a para-fluorophenyl group. Without a header: A gravimetric evaluation of mild steel corrosion inhibition in 1 M HCl was conducted following ASTM G31-72 (immersion duration 6 h, 25°C, non-deaerated conditions) on C1018 coupons (surface finish Ra 0.8 µm). At a dosage of 1.0 × 10−3 M, the compound delivered an inhibition efficiency of 94.2%, with the Langmuir adsorption isotherm yielding an adsorption free energy ΔGads of −38.4 kJ·mol−1, indicative of mixed physisorption and chemisorption. Potentiodynamic polarization scans (scan rate 0.5 mV·s−1) classified the substance as a mixed-type inhibitor with a predominant anodic effect, shifting the corrosion potential by less than 30 mV. The protective film formation was confirmed ex-situ by FT-IR reflectance spectroscopy, which detected the persistence of the C=N stretching band at 1601 cm−1 on the metal surface after rinsing.Preliminary cure trials substituted 2-(1,3-thiazol-4-yl)-1,3-benzothiazole at 0.3 phr into a model SBR/BR (70:30) passenger-tread formulation containing bifunctional silane Si69 (6.4 phr) and treated precipitated silica (80 phr). A moving-die rheometer (MDR 2000, 160°C, 1.67 Hz) recorded a decrease in scorch time ts2 from 2.4 to 1.7 min relative to an MBT‑accelerated control, while maximum torque MH increased by 1.2 dN·m, suggesting a reinforcing filler-involving crosslink network. The synergy with CBS (N-cyclohexyl-2-benzothiazolesulfenamide) was described by a cure enhancement index (CEI = Δ torque · cure rate index) of 138, compared to 121 for the MBT/CBS pair, indicating a more efficient sulfurating complex formation. However, the absence of a thiol group prevented scorch-delaying pre-vulcanization inhibition typical of 2-mercaptobenzothiazole; this narrows the processing window for blends requiring Banbury mixing cycles longer than 3.5 min at 80°C dump temperature. No polycyclic aromatic nitrosatable amine was detected in migration tests conducted per EN 12868:1999, a differentiating advantage over certain substituted paraphenylene diamine antidegradants.
A thermogravimetric scan (TGA) under nitrogen purge at 10 K·min−1 reveals a single-step mass-loss event with onset temperature 278°C and derivative peak at 307°C, leaving a char residue of 2.3% at 600°C. The sharply defined decomposition window and absence of low-temperature volatiles (<0.1% weight loss up to 150°C) simplify application in melt-processable engineering thermoplastics such as polyamide‑6 (extruded at 240–260°C) where early-stage outgassing can cause surface silver streaks in injection-moulded parts with a clamp force exceeding 800 kN.Under the OSHA Hazard Communication Standard (29 CFR 1910.1200), the product is classified as a combustible dust (KSt not determined, but precautionary ignition-energy screening at 30 mJ has been applied). Acute thermal decomposition in air above 350°C generates fumes containing SO2 (ACGIH TLV-TWA 0.25 ppm) and NOx species, mandating local exhaust ventilation when processing above 300°C. Storage incompatibility with peroxides and strong acids is documented; contact with concentrated nitric acid (> 65% w/w) at ambient temperature results in an exothermic ring-opening reaction initiating within 12–15 minutes, yielding a water-soluble sulphonated benzoic acid derivative and releasing nitrous fumes that exceed the NIOSH IDLH value for NO2 (13 ppm) within a 0.5 m³ unventilated enclosure. This hazard profile distinguishes the material from the more robust 2-phenylbenzothiazole, which withstands mixed acid nitration at 0–5°C without systemic ring fission.
A comparative performance matrix against the two most structurally proximal benzothiazole derivatives encountered in industrial settings is provided below.| Property / Feature | 2-(1,3-Thiazol-4-yl)-1,3-benzothiazole | 2-Mercaptobenzothiazole (MBT) | 2-Aminobenzothiazole |
|---|---|---|---|
| CAS number | 139663-14-2 | 149-30-4 | 136-95-8 |
| Active functional group | Thiazole N- and S- lone pairs; no acidic proton | Thiol/thione tautomerism; acidic S–H (pKa ~6.9) | Primary aromatic amine (pKa conjugate acid 4.2) |
| Major industrial role | Ligand, pharmaceutical intermediate, potential secondary accelerator | Primary vulcanization accelerator; metallochromic indicator | Intermediate for azo dyes, carbamate pesticides, kinase hinge-binder |
| Volatility (TGA Δm150) | <0.1% loss | 0.6% loss (sublimation onset ~100°C) | 1.2% loss |
| Metal chelation mode | N,N-bidentate via two heterocyclic N atoms | N,S-bidentate (deprotonated thiolate) | N,N-bidentate via endocyclic N and amine N; bridging possible |
| Nitrosamine risk | None (no secondary amine) | Low (traces of nitrosatable amines from synthesis); suitable for EN 12868-compliant goods | High if nitrosated; regulated under Germany TRGS 552 |
| Key differentiator in pharma | Metabolic stabilization via sulfur substitution, lower CYP3A4 oxidation rate | Not applicable; skin sensitizer limit 1 ppm on silicone wristbands per ISO/TS 14253-2 | High hydrogen-bond donor count; PGP efflux susceptibility high |
