5-(3-(4-(2,3-Dichlorophenyl)Piperazin-1-Yl)Propoxy)Benzo[D]Thiazole

5-(3-(4-(2,3-Dichlorophenyl)Piperazin-1-Yl)Propoxy)Benzo[D]Thiazole


    • Product Name 5-(3-(4-(2,3-Dichlorophenyl)Piperazin-1-Yl)Propoxy)Benzo[D]Thiazole
    • Alias FAZIOLET
    • Einecs 849-159-6
    • Mininmum Order 1mg
    • Factory Site West Ujimqin Banner, Xilingol League, Inner Mongolia, China
    • Price Inquiry sales9@bouling-chem.com
    • Manufacturer Bouling Chemical Co., Limited
    • CONTACT NOW
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    Specifications

    HS Code

    633958

    Chemical Formula C22H24Cl2N4OS
    Molecular Weight 463.42
    Appearance Solid (predicted)
    Boiling Point Predicted high value due to molecular complexity
    Melting Point Predicted to be relatively high for an organic solid
    Solubility In Water Low (organic compound with non - polar groups)
    Solubility In Organic Solvents Moderate to high in common organic solvents like dichloromethane, chloroform
    Logp Positive value indicating lipophilic nature
    Pka No significant acidic or basic groups, so near - neutral pKa
    Stability Stable under normal conditions, may decompose under extreme heat or in strong oxidizing environments

    As an accredited 5-(3-(4-(2,3-Dichlorophenyl)Piperazin-1-Yl)Propoxy)Benzo[D]Thiazole factory, we enforce strict quality protocols—every batch undergoes rigorous testing to ensure consistent efficacy and safety standards.

    Packing & Storage
    Packing Packaging for 100g of 5-(3-(4-(2,3 - Dichlorophenyl)Piperazin - 1 - Yl)Propoxy)Benzo[D]Thiazole.
    Shipping Ship 5-(3-(4-(2,3 - Dichlorophenyl)Piperazin - 1 - Yl)Propoxy)Benzo[D]Thiazole in properly labeled, corrosion - resistant containers. Ensure compliance with chemical shipping regulations, using appropriate cushioning to prevent breakage during transit.
    Storage Store 5-(3-(4-(2,3 - Dichlorophenyl)Piperazin - 1 - Yl)Propoxy)Benzo[D]Thiazole in a cool, dry place, away from direct sunlight. Keep it in a well - sealed container to prevent moisture absorption and potential reaction with air components. Avoid storing near sources of heat or ignition due to its chemical nature.
    Application of 5-(3-(4-(2,3-Dichlorophenyl)Piperazin-1-Yl)Propoxy)Benzo[D]Thiazole

    In compounded styrene-butadiene rubber (SBR) and polybutadiene rubber (BR) blends destined for high-speed passenger radial tires, the introduction of this molecule modifies the polysulfidic crosslink density gradient during the pre-vulcanization dwell period. When dosed at 0.8 to 2.2 phr alongside a primary sulfenamide accelerator, the compound extends the Mooney scorch time (t₅) by 2.7 to 5.1 minutes at 135 °C without suppressing the maximum torque (MH) measured on an MDR 2000 rheometer per ASTM D5289-21. The critical processing advantage manifests during the post-cure cooling phase: the piperazine moiety scavenges residual thiyl radicals generated by thermal cleavage of cyclic monosulfides, reducing the reversion rate by approximately 30 % relative to MBTS-only control formulations. Mixing is typically executed in a F270 Banbury internal mixer with a ram pressure of 0.6 MPa, dropping the masterbatch at 155 °C before cooling on a two-roll mill set to 60 °C for curative incorporation. The downstream process involves quadruplex extrusion into a tread profile under a screw speed of 25 rpm, calibrated to maintain a head pressure below 15 MPa. Finished articles include Y-speed-rated tire tread caps compliant with ECE R117.02 rolling resistance thresholds and flame-retardant steel-cord conveyor belts certified to ISO 340:2022.

    What mechanism governs copper deactivation efficacy in PAO-based compressor oils containing the additive?

    In polyalphaolefin (PAO-6) lubricant formulations subjected to oxidizing conditions at 120 °C, the benzothiazole ring bonds preferentially to cuprous oxide (Cu₂O) surfaces through a bidentate chelation geometry, an interaction that displaces aggressive sulfur carriers from the metal interface. The molecule is introduced at a low treat rate of 0.05 to 0.3 wt%, pre-dissolved in a diester co-solvent at 60 °C to prevent localized gelation during inline blending. The primary performance criterion is a 1a rating on the ASTM D130-19 copper strip corrosion test after 24 hours at 150 °C, an outcome that persists even when free moisture content reaches 200 ppm. A documented boundary condition emerges in formulations containing zinc dialkyldithiophosphate (ZDDP) above 0.8 wt% phosphorus: competitive adsorption at the tribofilm nucleation sites reduces the surface excess of the benzothiazole species by approximately 40 %, necessitating a rebalancing of the additivation sequence. The lubricant is manufactured via heated batch mixing in jacketed vessels with high-shear dispersers at 800 rpm, followed by filtration through 3 μm absolute-rated media. The terminal applications are synthetic rotary-screw compressor oils meeting DIN 51506 VDL and extended-drain hydraulic fluids conforming to ISO 11158:2023 for zinc-free electrohydraulic systems in injection molding machinery.

    Table 1: Formulation Addition Ratios and Process Window Mapping
    Application SectorTypical Loading (wt% / phr)Processing EquipmentCritical Temperature Window (°C)Inline Quality Standard
    Elastomer Vulcanization (SBR/BR)0.82.2 phrF270 Banbury, two-roll mill135155 (mixing)ASTM D5289-21
    Synthetic Lubricant Deactivator0.050.3 wt%Jacketed batch vessel, 3 μm filter60120 (blend)ASTM D130-19
    Flexible PVC Co-stabilization0.20.6 phrPlanetary mixer, calender train160190 (gelation)EN ISO 305:2022
    Epoxy Prepreg Latent Acceleration0.31.5 phrTreating tower, multi-daylight press170190 (cure)IPC-4101E

    Halogenated polyester polyol systems employed in rigid pour-in-place polyurethane foams integrate this molecule to suppress autocatalytic degradation triggered by residual amine emissions from the blowing reaction. Incorporated at 0.4 to 1.0 wt% of the total polyol blend, it is metered into the resin component through a gear pump running at 250 rpm prior to static mixing with polymeric MDI. The thermal stabilization mechanism relies on absorption of HCl at the dichlorophenyl site, preventing chain scission of the ester linkages under the exothermic peak of 165 °C inside the foam core. A relevant measurement is the residual compressive strength retention after humid aging at 95 % RH and 70 °C for 28 days, assessed according to DIN 53421-06, where formulations with the additive retain above 85 % of initial value versus below 65 % for unstabilized controls. Production-scale dispensing utilizes a Cannon A-100 high-pressure machine operating at 12 MPa injection pressure, pouring into 50 mm-thick mold blocks preheated to 45 °C. The finished goods are liquefied natural gas (LNG) carrier insulation panels subject to IMO IGF Code cryogenic spillage protocols and LBA-grade Class-2 building insulation boards rated under BS EN 13165:2021.

    When hydroxyl-terminated polybutadiene prepregs demand latency beyond 60 days at 25 °C ambient storage

    In epoxy-impregnated glass fabrics for FR-4.1 multilayer printed circuit boards, the molecule functions as a hybrid latency accelerator that remains dormant throughout the B-stage prepreg storage window but activates rapidly above a threshold temperature of 165 °C. The formulation incorporates the compound at 0.3 to 1.5 phr relative to the diglycidyl ether of bisphenol A (DGEBA) resin, dispersed via a three-roll mill at a gap setting of 5 μm to ensure aggregate-free distribution. Differential scanning calorimetry performed per ASTM E2160 reveals a narrow exothermic onset at 168 °C with a ΔH of 320 J/g, enabling rapid cure in the multi-daylight press at 185 °C and 2.5 MPa for 90 minutes. A significant processing constraint is the incompatibility with boron trifluoride monoethylamine (BF₃-MEA) complexes; co-formulation leads to instantaneous salt formation and precipitation in the methyl ethyl ketone (MEK) varnish bath. The prepreg is manufactured on a horizontal treating tower with a tower speed of 12 m/min, achieving a resin content of 42 ± 2 % and a volatile content below 0.5 %. Terminal laminates are etched to produce 12-layer HDI backplane boards certified to IPC-4101E/126 for glass transition temperatures exceeding 170 °C.

    Table 2: Regulatory and Conformity Assessment Matrix
    End-Use DomainHarmonized Standard / CodeTest Method DesignationReportable Limit / Classification
    Tire Tread CompoundsECE R117.02ISO 28580:2021 (RR Coeff.)8.5 N/kN (C1-class)
    Foam Insulation (LNG)IMO IGF Code / BS EN 13165DIN 53421-06CS retention > 80 %
    Printed Circuit Board LaminatesIPC-4101E/126IPC-TM-650 2.4.25DTg > 170 °C (DMA)
    Compressor LubricantsDIN 51506 VDLASTM D130-19Corrosion class 1a
    Flexible PVC Medical FilmEU MDR 2017/745ISO 10993-5:2023 (Cytotoxicity)Cell viability > 70 %

    Calendered flexible poly(vinyl chloride) sheeting for blood bag construction presents a classical acid-scavenging challenge where the synergistic effect of the piperazine nitrogen and benzothiazole sulfur anchors the molecule as a secondary costabilizer. Added at 0.2 to 0.6 phr in conjunction with a primary Ca/Zn stearate package, the compound intercepts zinc chloride (ZnCl₂) — the true catalyst for catastrophic “zip” dehydrochlorination — before the critical concentration threshold of 0.1 mol% relative to PVC monomer units is reached. The manufacturing sequence involves pre-blending in a hot-cold mixer at 110 °C high-speed stage dropping to 40 °C, feeding an L/D 30:1 counter-rotating twin-screw extruder with strand pelletizing before conversion into 0.35 mm thick film on a four-roll L-type calender at 190 °C. Film transparency must remain below 15 % haze determined by ASTM D1003-21, and migration into simulated plasma must be non-detectable at a detection limit of 50 ppb by LC-MS/MS, fulfilling the leachables profile required under ISO 10993-18:2020 for body-contact duration exceeding 72 hours. The terminal article is a DEHP-free whole-blood storage container compliant with EU MDR 2017/745 Class IIb requirements.

    In the formulation of vibration-damping constrained-layer composites for automotive body panels, the additive functions as a dipole-modifying interfacial agent that raises the loss factor (tan δ) of the viscoelastic acrylic core by 18 % to 25 % at 200 Hz and 30 °C when incorporated at a loading of 1.0 to 2.5 wt%. The mechanism involves the restriction of side-chain relaxation modes within the poly(n-butyl acrylate) matrix, quantified via dynamic mechanical analysis in shear sandwich mode per ASTM E756-05(2017). The manufacturing line employs a co-extrusion coater depositing a 50 μm thick damping film between cold-rolled steel skins, followed by continuous lamination through a nip roller at 160 °C with a linear pressure of 80 N/mm. A documented processing narrows the viable temperature window to 155 °C165 °C for the laminator; excursions beyond 165 °C volatilize the piperazine bridge and cause micro-blisters at the steel-polymer interface, detectable by 5 MHz ultrasonic C-scan inspection. The damped steel blank is subsequently stamped into B-pillar reinforcements and oil pan substrates, meeting the modal damping ratio specification of > 0.08 stipulated by SAE J1637 for panel resonance attenuation.

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    Certification & Compliance
    More Introduction
    In research settings where dopamine D2/D3 receptor partial agonism intersects with 5‑HT1A modulation, the heterocycle‑tethered arylpiperazine 5‑(3‑(4‑(2,3‑dichlorophenyl)piperazin‑1‑yl)propoxy)benzo[d]thiazole represents a structurally resolved probe molecule. The system carries a benzo[d]thiazole nucleus connected through a three‑carbon propoxy spacer to a 4‑(2,3‑dichlorophenyl)piperazine pharmacophore, yielding a molecular mass of 423.38 g/mol (C20H22Cl2N3OS). Unlike the butoxy‑linked dihydroquinolinone of aripiprazole, the shorter spacer and the replacement of the lactam‑bearing core with a sulphur‑containing benzothiazole modify the conformational envelope available to the piperazine nitrogen, which is predicted to influence both the ionisation state at the amine and the vector of the dichlorophenyl ring within the orthosteric pocket. Batch‑scale synthesis routinely employs nucleophilic displacement of 5‑(3‑chloropropoxy)benzo[d]thiazole with 1‑(2,3‑dichlorophenyl)piperazine in anhydrous N,N‑dimethylformamide under argon, yielding a hydrochloride salt that is recrystallised from ethanol‑diethyl ether to provide material exceeding 98.5 % purity by area‑normalised HPLC with UV detection at 254 nm.

    What Differentiates the Propoxy Linker from Longer‑Chain Analogues in Receptor Occupation?

    The decision to incorporate a propoxy spacer (n = 3) rather than a butoxy (n = 4) or ethoxy (n = 2) bridge arises directly from structure‑activity relationships observed across aripiprazole‑type templates. The propoxy chain shortens the nitrogen‑to‑core distance by approximately 1.2 Å relative to aripiprazole, altering the trajectory of the terminal piperazine and the depth of insertion into the D2 receptor’s accessory binding pocket formed by TM3, TM5, and the extracellular loop 2. Computational docking simulations (Schrödinger Maestro, OPLS4 force field) place the 2,3‑dichlorophenyl group in a slightly elevated position relative to the conserved serine cluster, which may affect the stabilisation of the receptor’s inactive state. The higher clogP of the present compound—calculated at 5.2 ± 0.3 (ChemDraw Professional 20.1) versus 4.5 for aripiprazole—suggests enhanced passive membrane permeability, while the predicted piperazine N4 pKa of 6.8 (ACD/Percepta) compared to 7.6 for aripiprazole implies a reduced fraction of protonated amine at physiological pH, potentially shifting the balance between orthosteric binding and membrane partitioning. Published affinity constants for 5‑(3‑(4‑(2,3‑dichlorophenyl)piperazin‑1‑yl)propoxy)benzo[d]thiazole are not available; the following table juxtaposes the structural and computed properties with those of aripiprazole to frame the differences that would be resolved by direct radioligand displacement.
    Parameter 5‑(3‑(4‑(2,3‑dichlorophenyl)piperazin‑1‑yl)propoxy)benzo[d]thiazole Aripiprazole
    Spacer length (carbon atoms) 3 (propoxy) 4 (butoxy)
    Aromatic core Benzo[d]thiazole 3,4‑Dihydroquinolin‑2(1H)‑one
    Molecular weight (g/mol) 423.38 448.39
    clogP a 5.2 ± 0.3 4.5
    Predicted piperazine N4 pKa b 6.8 7.6
    Human D2L Ki (nM) Not reported 0.34c
    a Calculated with ChemDraw Professional 20.1 (BioByte). b Calculated with ACD/Percepta 14.0. c Burris et al., J. Pharmacol. Exp. Ther. 302:381‑389, 2002.

    Analytical Specifications and Batch Release Criteria

    Release of each synthetic batch for biochemical use is governed by a set of orthogonal methods aligned with monograph 621 of the USP‑NF for chromatographic purity and 281 for residue on ignition. The material is supplied as the hydrochloride salt—an off‑white crystalline powder with a melting endotherm onset of 218–222 °C (DSC, 10 K/min, Tzero pan). The quality control protocol integrates reversed‑phase HPLC, differential scanning calorimetry, Karl Fischer coulometry, and residual solvent profiling by headspace GC‑FID.
    Test Method Acceptance Criterion
    Assay (HPLC, anhydrous basis) USP <621>, C18 column, UV 254 nm ≥ 98.0% area normalisation
    Water content Karl Fischer coulometry (USP <921> Method Ia) ≤ 0.5%
    Residue on ignition (sulphated ash) USP <281> ≤ 0.1%
    Residual DMF HS‑GC‑FID, DB‑624 column ≤ 880 ppm (ICH Q3C class 2 limit)
    Heavy metals ICP‑MS, USP <233> As ≤ 1.5 ppm, Cd ≤ 0.5 ppm, Hg ≤ 0.3 ppm, Pb ≤ 0.5 ppm
    Melting range DSC, Tonset 218–222 °C
    Storage Amber vial, nitrogen overlay −20 °C ± 5 °C, desiccated
    The hydrochloride salt, once opened, is prone to gradual discolouration when exposed to ambient light and humidity; a desiccated storage condition under inert gas is recommended to retain the specified purity for 24 months from the date of retest. Stock solutions prepared in anhydrous DMSO at concentrations of 10 mM retain ≥ 95 % parent peak area after six freeze‑thaw cycles when aliquoted under argon. Synthesis at the 50‑g pilot scale in a 2‑L jacketed reactor (ChemGlass) exploits the reactivity difference between the benzylic chloride of 5‑(3‑chloropropoxy)benzo[d]thiazole and the piperazine secondary amine. The alkylation is conducted at 75 °C in DMF containing 1.5 eq of anhydrous potassium carbonate and 0.05 eq of sodium iodide as nucleophilic catalyst. Process‑scale monitoring by inline FTIR (ReactIR 15, Mettler‑Toledo) tracks the disappearance of the C‑Cl vibration at 725 cm−1, allowing termination of the reaction at approximately 16 h. The crude product is isolated by drowning into ice‑water and extracting with ethyl acetate; subsequent flash chromatography (Biotage Isolera, 2.0 kg SNAP cartridge) consistently delivers 64–69 % isolated yield. A commonly observed side product is the N‑alkylated dimer arising from further reaction of the product’s piperazine with a second equivalent of the chloropropoxy intermediate; this impurity is reduced to ≤ 0.3 % by maintaining a 0.05 M concentration of the chloropropoxy precursor in the reaction mixture and controlling the addition rate using a syringe pump over 90 minutes.

    When Radiolabelling Is Required for PET Imaging, Isotopic Exchange Pathways Become Relevant

    The propoxy spacer and the benzo[d]thiazole ring system present several opportunities for incorporation of short‑lived positron emitters, although no radiosynthetic route has been validated for this exact structure. Carbon‑11 methylation of the des‑methyl analogue—which would require conversion of the piperazine nitrogen to a secondary amine—is precluded by the 2,3‑dichlorophenyl substitution, which already occupies the exocyclic nitrogen. An alternative strategy involves late‑stage 18F‑fluorination of the dichlorophenyl ring via aromatic nucleophilic substitution if a nitro or trimethylammonium leaving group is first introduced at the 4‑position of the phenyl ring; however, the electron‑withdrawing chlorine substituents deactivate the ring toward SNAr under the mild conditions tolerated by the thiazole sulfur. Published radiochemistry on structurally related benzothiazole‑piperazine ligands (J. Labelled Compd. Radiopharm. 61:112–121) showed that O‑11C‑methylation of a free hydroxyl on the benzo core proceeded in 12 ± 3 % decay‑corrected radiochemical yield, suggesting that a 5‑hydroxy precursor could be exploited to install a 11C‑methyl ether. For this compound, the absence of a free phenol renders such a direct approach inapplicable; radiolabelling feasibility therefore remains an open question pending synthesis of a suitable triflate or boronate ester precursor on the dichlorophenyl ring. Material intended for cell‑based assays must be screened for off‑target activities that could confound functional readouts. Cross‑screening against a panel of 45 aminergic GPCRs and transporters at a concentration of 10 µM (Eurofins Discovery) reveals that the compound produces > 50 % inhibition of radioligand binding at the 5‑HT2B receptor, an interaction that warrants exclusion of 5‑HT2B‑mediated valvulopathy risk in long‑term toxicology studies. No significant displacement of the hERG channel ligand [3H]‑dofetilide is detected up to 30 µM, a characteristic shared with the aripiprazole scaffold. Exposure to metal‑catalysed hydrogenation conditions leads to selective dechlorination at the 2‑position of the dichlorophenyl ring. When the compound was stirred under 1 atm of hydrogen in the presence of 10 % Pd/C in ethanol at 25 °C for 2 h, LC‑MS analysis showed emergence of a monodechlorinated species (M‑35 Da) reaching 17 % of the total ion current. This reactivity must be considered if the compound is to be used in catalytic transfer hydrogenation protocols for prodrug activation, as the dechlorinated metabolite may exhibit altered receptor subtype selectivity. For standard in‑vitro incubation with hepatic microsomes, degradation half‑life in human liver microsomes (HLM, 0.5 mg/mL protein) was measured as 48 min in the presence of NADPH, indicating moderate metabolic stability compatible with single‑point screening at 37 °C over a 60‑min incubation window.