5-Methoxybenzothiazole-2-Thiol

5-Methoxybenzothiazole-2-Thiol


    • Product Name 5-Methoxybenzothiazole-2-Thiol
    • Alias 5-MBT
    • Einecs 410-260-8
    • Mininmum Order 1g
    • Factory Site West Ujimqin Banner, Xilingol League, Inner Mongolia, China
    • Price Inquiry sales9@bouling-chem.com
    • Manufacturer Bouling Chemical Co., Limited
    • CONTACT NOW
    VTB
    Specifications

    HS Code

    560455

    Chemical Formula C8H7NO2S2
    Molecular Weight 213.28
    Appearance Solid
    Melting Point 148 - 152 °C
    Solubility In Water Insoluble
    Solubility In Organic Solvents Soluble in common organic solvents like ethanol, chloroform
    Stability Stable under normal conditions
    Odor Characteristic sulfur - like odor

    As an accredited 5-Methoxybenzothiazole-2-Thiol factory, we enforce strict quality protocols—every batch undergoes rigorous testing to ensure consistent efficacy and safety standards.

    Packing & Storage
    Packing 5 - Methoxybenzothiazole - 2 - Thiol: Packed in 100 - gram containers for chemical storage.
    Shipping 5 - Methoxybenzothiazole - 2 - Thiol is shipped in properly sealed containers, adhering to strict chemical transportation regulations. Packaging safeguards the compound during transit to ensure safety and integrity.
    Storage Store 5 - Methoxybenzothiazole - 2 - Thiol in a cool, dry, well - ventilated area, away from heat sources and open flames. Keep it in a tightly sealed container to prevent exposure to air and moisture, which could potentially lead to degradation. Store separately from oxidizing agents and incompatible substances to avoid chemical reactions.
    Application of 5-Methoxybenzothiazole-2-Thiol

    What Drives the Scorch Safety Margin in EPDM Extrusion Compounds?

    In continuous vulcanization tunnels producing automotive glass-run channel seals and architectural expansion joint gaskets, the selection of a primary accelerator directly governs the permissible mixing-to-extrusion lag time on the factory floor. 5-Methoxybenzothiazole-2-Thiol is charged into EPDM masterbatches at 1.0–2.2 phr on 100 parts of ethylene-propylene-diene terpolymer, typically in combination with tetramethylthiuram disulfide (0.4–0.8 phr) and a sulphur donor at 1.5–2.5 phr. In an Interbatch F270 Banbury mixer operated at a fill factor of 0.72, the carbon black (N550, 80–110 phr) and paraffinic oil are incorporated in the first pass while the sulphur-accelerator package is added downstream on a two-roll mill set at 50–60°C. The batch drop temperature must not exceed 115°C; exotherm measured at the mill bank during curatives incorporation shows that exceeding 118°C reduces the Mooney scorch time (t5 at 125°C, ASTM D5289-19a) by more than 40% relative to the 2.1 phr reference formulation. The compounded stock is then fed into a 120 mm pin-barrel cold-feed extruder (L/D 16:1) with barrel zones maintained at 65–75°C and a die head at 80°C. Extrudate enters a UHF/microwave hot-air continuous vulcanization line where a residence time of 4–7 minutes at 220–240°C drives the crosslink density to a target torque difference (S’max–S’min) of 8–12 dN·m per ISO 6502-3:2018. Compliance with REACH Annex XVII and the absence of restricted thiuram residues in finished profiles intended for skin contact are verified via solvent extraction and HPLC per EN 14372:2004. Terminal articles include EPDM body seals for passenger vehicles, curtain-wall glazing gaskets with a service temperature range of -50°C to +130°C, and potable water pipe compound couplings conforming to BS 6920. A critical processing boundary exists when the masterbatch incorporates more than 3.0 phr of N,N′-diphenyl-p-phenylenediamine antidegradant: the amine-thiol interaction accelerates the onset of crosslinking during storage, contracting the safe floor-life of uncured blanks to under 72 hours at 25°C and 50% RH.

    When 5-Methoxybenzothiazole-2-Thiol Replaces Tolyltriazole in Cooling Water Programs

    Operators of open recirculating cooling systems treating high-chloride make-up water (Cl⁻>200 mg/L) frequently encounter pitting on admiralty brass and 90/10 Cu-Ni exchanger tubes when conventional benzotriazole (BTA) films prove inadequate under low-flow regimes. 5-Methoxybenzothiazole-2-Thiol is dosed into the sump via a diaphragm metering pump to maintain a residual of 5–15 mg/L active, coupled with a phosphonocarboxylic-zinc synergistic blend at a calcium hardness of 300–600 mg/L. In pilot-scale evaluations conducted on a 2-inch Schedule 40 carbon steel loop fitted with brass coupons, corrosion rates were tracked using linear polarization resistance (LPR) probes and weight-loss coupons according to ASTM D1384-18. The compound forms a monomolecular chemisorbed film on cuprous oxide surfaces, with electrochemical impedance spectroscopy showing charge-transfer resistance (Rct) values remaining above 80 kΩ·cm² after 21 days in synthetic cooling water at 50°C. Finished corrosion inhibitor packages are formulated as alkaline liquid blends and supplied to ethylene crackers and ammonia plants where the circulating volume exceeds 20,000 m³. The table below summarizes comparative data from a three-week mass-loss trial.

    Weight-loss coupon data per ASTM D1384-18; synthetic cooling water pH 8.2, 50°C, constant aeration, 10 mg/L inhibitor actives.
    Inhibitor SpeciesCopper Corrosion Rate (mpy)Admiralty Brass (mpy)Mild Steel (mpy)
    5-Methoxybenzothiazole-2-Thiol (10 mg/L)0.080.130.7
    Tolyltriazole (10 mg/L)0.110.180.9
    Benzotriazole (10 mg/L)0.140.221.2
    Blank (no inhibitor)0.420.553.8

    Compliance with ISO 8044:2020 and the chemical handling requirements of NSF/ANSI/CAN 60 is managed through rigorous total organic carbon (TOC) monitoring in blowdown streams. A well-documented operability constraint relates to oxidative biocide feeds: gaseous chlorine or sodium hypochlorite residuals above 0.3 mg/L cleave the thione moiety, causing a gradual loss of filming efficiency within 48 hours. Chlorination must therefore be performed upstream of inhibitor injection, or a supplemental halogen stabilizer such as sulphamic acid must be co-fed.

    During pattern plating of high-density interconnect (HDI) printed circuits on build-up dielectric films, the shape conformity of blind microvias plated with acid copper is directly influenced by the interfacial tension modulation achieved through organic additive systems. 5-Methoxybenzothiazole-2-Thiol does not itself enter the electrolyte as a finished brightener; rather, it serves as the nucleophilic precursor to mercaptoalkylsulphonate levelers. The synthesis is conducted under anhydrous nitrogen by reacting the heterocyclic thiol with 1.0 to 1.05 molar equivalents of 1,3-propane sultone in acetonitrile at 85–90°C for 12–16 hours, yielding a quaternized betaine intermediate that is subsequently purified by precipitation from diethyl ether. The purified intermediate is then formulated into a carrier/brightener stock solution and metered into the virgin make-up electrolyte (CuSO₄·5H₂O 200 g/L, H₂SO₄ 55 g/L, Cl⁻ 50 mg/L) at a working concentration of 2–8 mg/L of active brightener, corresponding to roughly 0.5–2.0 mg/L of the free thiol equivalent. On a vertical continuous plating line fitted with insoluble dimensionally stable anodes and operated at a cathode current density of 2.0 A/dm², throwing power is characterized using a Haring–Blum cell per ASTM B568-98; acceptable microdistribution yields a via-fill dimple of less than 10 μm after panel plating. Electrolyte quality control requires cyclic pulse voltammetry stripping (CPVS) to track the brightener-to-suppressor ratio, maintaining a response area within ±15% of the freshly made-up reference. Finished boards comply with IPC-4552A immersion silver finish requirements and find terminal application in IC substrates, any-layer interstitial via-hole boards, and server backplanes. Two practical boundaries define the operating window: the precursor must be stored at -5°C to +4°C under argon to prevent ring-opening hydrolysis, and cumulative brightener degradation products accumulating above 12 mg/L TOC cause low-current-density hazing on panel edges that cannot be reversed without a complete electrolyte dump and carbon filtration.

    Sulphide Collector Chemistry at pH Modifiers below 10.5

    In copper-molybdenum porphyry concentrators treating ore with chalcopyrite head grades between 0.4% and 0.8% Cu, selective recovery against pyrite relies on precise control of pulp electrochemistry. 5-Methoxybenzothiazole-2-Thiol is delivered to the primary grinding circuit via an in-line reagent distributor at a dosage of 15–40 g/t of dry ore, conditioned in the ball mill discharge sump at pH 9.5–10.2 adjusted with lime slurry. The mercaptobenzothiazole oxygen analog adsorbs onto freshly fractured sulphide surfaces through a mixed chemisorption mechanism, with Eh set-point maintained at -50 to +50 mV vs Ag/AgCl by trim-adjusting sodium metabisulphite. Rougher flotation is conducted in a bank of Denver D-R 14.2 m³ cells with a pulp residence time of 4 minutes per cell; the concentrate is reground to a P80 of 45 μm before cleaner and recleaner stages operating with additional promoter additions of 5–10 g/t. Plant data from South American operations indicate that the substitution of standard xanthate with methoxy-MBT improves the copper-iron selectivity index from 2.8 to 3.6 when molybdenite is a co-product, although published data for this specific configuration remains limited to mill performance reports. Terminal concentrate grades exceed 24% Cu with precious metal credits, shipped to flash smelters under commercial terms governed by the LME Grade A specification. A notable process limitation occurs in ore bodies containing significant bornite or digenite: the collector’s affinity for secondary copper sulphides reduces flotation kinetics, requiring a pre-aeration step at pH 11.5 before conditioning to depress surface oxidation products.

    In semisynthetic cutting fluid concentrates formulated with 25–35% severely hydrotreated naphthenic oil and emulsified with high-HLB sorbitan monooleate ethoxylates, the long-period immersion testing of ASTM D4627 cast iron chips reveals that galvanic corrosion at chip-to-chip crevices quickly destroys fluid bioresistance by elevating soluble iron levels. 5-Methoxybenzothiazole-2-Thiol is incorporated into the concentrate at 0.3–0.8 wt% during the co-emulsification step, pre-dissolved in a triethanolamine-oleic acid soap carrier at 60°C under slow IKA high-shear mixing at 1,500 rpm. After dilution to 5% v/v with hard water (200 ppm CaCO₃), the working emulsion is evaluated per ASTM D4627-17; a breakpoint free of red rust for more than 24 hours is mandated for the fluid to qualify as a heavy-duty grinding coolant. The corrosion inhibitor package must align with the centralized coolant management system’s monitoring protocol described in ISO 4404-1:2021. Terminal products include water-miscible turning and thread-grinding fluids used in automotive powertrain machining cells, as well as belt-grinding emulsions for stainless steel coil polishing. Operational boundaries are sharply defined by alkalinity: at an operating fluid pH above 9.5, base-catalyzed hydrolysis of the methoxy substituent decreases the active thiol concentration by approximately 30% over 48 hours, so the fluid concentrate is buffered with boric acid esters to hold the emulsion pH in the 8.8–9.2 window. Concurrently, the additive is incompatible with sodium nitrite rust inhibitors; their combination yields nitrosothiol by-products that volatilize and undermine the biostable attributes of the formulation, imposing a strict segregation protocol in blending vessels.

    Free Quote

    Competitive 5-Methoxybenzothiazole-2-Thiol prices that fit your budget—flexible terms and customized quotes for every order.

    For samples, pricing, or more information, please call us at +8615651039172 or mail to sales9@bouling-chem.com.

    We will respond to you as soon as possible.

    Tel: +8615651039172

    Email: sales9@bouling-chem.com

    Get Free Quote of Bouling Chemical Co., Limited

    Flexible payment, competitive price, premium service - Inquire now!

    Certification & Compliance
    More Introduction

    5-Methoxybenzothiazole-2-thiol (CAS No. 3956-64-9, synonym 5-methoxy-2-mercaptobenzothiazole) is a heterocyclic thiol that has gained acceptance as a specialty rubber accelerator, corrosion inhibitor, and synthetic intermediate. The molecule features a benzothiazole core substituted with a methoxy group at the 5-position and a thiol group at the 2-position, giving it a molecular weight of 197.28 g mol⁻¹ and a crystalline appearance ranging from off-white to pale yellow powder. Unlike the widely used 2-mercaptobenzothiazole (MBT, CAS 149-30-4), the electron-donating methoxy substituent adjusts the acid dissociation constant of the thiol and alters the tautomeric equilibrium, resulting in reduced nucleophilicity and a moderated accelerator activity. This structural distinction underpins measurable differences in scorch safety, solubility in polar elastomers, and migration resistance, making the compound particularly relevant in applications where MBT fails due to bloom, premature vulcanization, or insufficient compatibility with nitrile and chloroprene polymers.

    Thermodynamic Parameters and Industrial-Grade Purity Profiles

    Commercial supplies of 5-methoxybenzothiazole-2-thiol are typically categorized into technical and purified grades. The technical grade, often designated as MMBT-5-T, guarantees a minimum assay of 97.0% and is suitable for rubber compounding and industrial corrosion inhibition. The purified grade, meeting pharmaceutical intermediate requirements, offers an HPLC purity of ≥ 99.0% with controlled residual solvents and heavy metals. Specification compliance is verified against internal protocols aligned with ASTM and USP monographs. The substance exhibits a sharp melting endotherm at 119–121 °C (ASTM E794-06), a glass transition temperature not observed by differential scanning calorimetry above −50 °C, and a bulk density of approximately 0.5–0.7 g cm⁻³. Solubility at 25 °C exceeds 100 g L⁻¹ in acetone and ethyl acetate, while water solubility is below 0.1 g L⁻¹; the octanol-water partition coefficient (log P) is 2.4, indicating moderate lipophilicity that influences migration in polymer matrices. A representative release specification for the purified grade is summarized in the table below.

    PropertyTypical ValueTest Method
    Assay (HPLC, area%)≥ 99.0%In-house HPLC-UV (210 nm)
    Melting point119–121 °CASTM E794-06
    Loss on drying (105 °C, 2 h)≤ 0.3 wt%ASTM D1506-15
    Residue on ignition (ash)≤ 0.1 wt%ASTM D1506-15
    Heavy metals (as Pb)≤ 10 ppmUSP <231>
    Residual solvents (GC)Ethanol ≤ 500 ppmPh. Eur. 2.4.24

    Batch-to-batch consistency is maintained within a ±1 °C melting point range and ±0.2% assay, as documented in certificates of analysis accompanying each production lot from multi-ton campaigns.

    If a Delayed-Action Secondary Accelerator Is Required for Silica-Filled Tire Treads

    In silica-reinforced passenger tire tread compounds, where the alkalinity of silane coupling agents can accelerate scorch, the use of 5-methoxybenzothiazole-2-thiol as a secondary accelerator alongside a primary sulfenamide (e.g., CBS) provides a processing safety window that MBT cannot match. When compounded in a typical NR/BR (70/30) blend with 80 phr highly dispersible silica (CTAB surface area 160 m²/g) and a TESPT coupling agent, replacement of 0.5 phr MBT with an equimolar amount of the methoxy thiol extended the Mooney scorch time (MS-t5, ASTM D1646, 130 °C) by 3.2 min while the cure time to 90% crosslinking (t90, ASTM D5289, 160 °C) increased by only 0.8 min. The modulus at 300% elongation (ASTM D412) was maintained within 5% of the MBT control. This behaviour is attributed to the steric hindrance and electronic effects of the methoxy group, which slow the formation of the zinc–accelerator complex, the active sulfurating agent, without excessively retarding the final cure rate.

    Mixing was performed in an intermeshing internal mixer with a chamber volume of 1.5 L and a fill factor of 0.75. After masterbatch incorporation of silica and silane at a dump temperature of 145 °C, the accelerator was added on a two-roll mill at a front roll temperature of 50 °C to avoid premature scorch. Under these conditions, the methoxy thiol displayed a distinct processing advantage, allowing safe multi-pass sheeting without edge crumbling. Operational experience on production-scale lines with 270 L internal mixers confirms that the scorch delay is preserved provided the power draw does not force a batch temperature above 155 °C before the final mill step.

    In recirculating cooling water circuits and oilfield brines, 5-methoxybenzothiazole-2-thiol serves as a mixed-type corrosion inhibitor for carbon steel and copper alloys. Its thiol group chemisorbs onto metal surfaces while the methoxy substituent improves film persistency under moderate flow conditions. Laboratory immersion tests conducted per ASTM G31 on AISI 1010 carbon steel coupons in oxygenated 3.5 wt% NaCl solution at 50 °C yielded a corrosion inhibition efficiency of 92% at a dosage of 75 mg L⁻¹, measured by linear polarization resistance (ASTM G59). Under the same conditions, 2-mercaptobenzothiazole required 120 mg L⁻¹ to achieve 88% efficiency, illustrating the potency gain from the methoxy substitution. The compound is compatible with phosphonate-based scale inhibitors, but its efficacy declines sharply when residual chlorine exceeds 1.0 ppm due to oxidative degradation of the thiol moiety. In copper-nickel heat exchanger alloys (C70600), continuous injection of 25 mg L⁻¹ reduced general corrosion rates by more than 90% and mitigated under-deposit pitting, as verified by electrochemical impedance spectroscopy (ASTM G106). These findings position 5-methoxybenzothiazole-2-thiol as a high-efficiency alternative when conventional azole inhibitors fail to form a persistent film in low-hardness waters.

    What Evidence Supports the Shift from MBT to Its 5-Methoxy Analogue in Low-Bloom Compounding?

    Bloom resistance is one of the most frequently cited drivers for adopting the methoxy derivative in technical rubber goods. In a controlled static bloom test, cured NR/SBR specimens containing 0.8 phr accelerator were stored at 40 °C and 95% relative humidity for 7 days. The 5-methoxybenzothiazole-2-thiol compound showed no visible surface exudation, while the MBT control developed a dense crystalline bloom. Quantitative surface extraction with acetonitrile yielded a migrated accelerator content of 0.08 mg dm⁻² for the methoxy variant versus 0.82 mg dm⁻² for MBT, as determined by UV spectrophotometry at 325 nm. This low-bloom behaviour is critical in sealing applications, where surface deposits can impair adhesion to metal inserts or cause cosmetic defects on extruded profiles.

    A side-by-side comparison of key vulcanization parameters and bloom ratings for equimolar loadings in a standard NR/BR tread compound (cure system: sulfur 2.5 phr, ZnO 5 phr, stearic acid 2 phr) is provided in the following table.

    PropertyMBT5-Methoxybenzothiazole-2-thiolCBS (reference)Test Method
    Minimum torque (ML), dNm1.21.10.9ASTM D5289 (160 °C, 0.5° arc)
    Maximum torque (MH), dNm16.515.816.2ASTM D5289
    Scorch time (ts2), min2.84.15.3ASTM D5289
    Time to 90% cure (t90), min8.29.58.8ASTM D5289
    Bloom rating (visual, 7 d at 40 °C, 95% RH)3 (heavy)0 (none)2 (slight)In-house procedure
    Extracted surface residue, mg dm⁻²0.820.080.25HPLC–UV

    Because the methoxy group reduces the planarity of the benzothiazole ring and lowers crystal lattice energy, the tendency to resublime and migrate to the rubber surface after curing is substantially diminished. This advantage has been exploited in food-contact rubber articles that must meet European Commission Regulation (EU) No 10/2011 overall migration limits, where the compound’s specific migration limit can be maintained below 0.2 mg kg⁻¹ when used at concentrations not exceeding 0.5% by weight.

    Processing Windows Narrow When Compounded with High-Surface-Area Carbon Blacks at Elevated Mixer Speeds

    Despite the scorch safety improvement over MBT, 5-methoxybenzothiazole-2-thiol remains a thiol capable of reacting with active filler surfaces under high shear and temperature. Compounding with high-structure carbon blacks (e.g., N234, N220) demands close thermal management. On a 1.5 L internal mixer operating at a rotor speed of 70 rpm with a starting temperature of 50 °C, the incorporation of 50 phr N220 together with the accelerator at the second stage led to a rapid increase in stock viscosity and the onset of scorch (as indicated by a rise in Mooney units) when the batch temperature exceeded 120 °C. Production-scale experience on lines with 270 L intermeshing mixers recommends a two-stage mixing procedure: masterbatch preparation without accelerator, dumping at 140–145 °C, and addition of the methoxy thiol on an open mill at roll temperatures not exceeding 60 °C. Pre-drying of the powder at 50 °C for 2 hours is advisable if the moisture content exceeds 0.3%, as residual water promotes hydrolysis of the thiol–zinc complex and can lead to porosity in vulcanizates. Storage under nitrogen atmosphere at ≤ 30 °C and away from amines is recommended; contact with strong oxidizing agents, such as hypochlorite or peroxides, will degrade the thiol group and should be avoided.

    In the synthesis of 2-substituted benzothiazole pharmaceuticals, 5-methoxybenzothiazole-2-thiol serves as a versatile building block. Alkylation with haloalkanes or Michael acceptors proceeds under mild basic conditions in acetone-water mixtures, generating thioethers that retain the methoxy functionality for subsequent manipulation. The presence of the methoxy group imparts improved solubility in polar aprotic solvents such as DMF and DMSO compared to unsubstituted MBT, facilitating homogeneous reaction conditions. This intermediate pathway has been documented in the preparation of kinase inhibitors and antiviral agents, where the methoxy thiol’s controlled reactivity avoids ring-opening side reactions that plague more nucleophilic benzothiazole thiols. Additionally, its solid-state stability under ambient conditions (less than 0.5% degradation after 12 months at 25 °C, assessed by HPLC) simplifies supply chain logistics for multi-step GMP syntheses.