4,5-Dihydroisothiazole 1,1-Dioxide

4,5-Dihydroisothiazole 1,1-Dioxide


    • Product Name 4,5-Dihydroisothiazole 1,1-Dioxide
    • Alias Isothiazolidine 1,1-dioxide
    • Einecs EINECS 238-012-6
    • Mininmum Order 25g
    • 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

    877773

    Molecular Formula C3H5NO2S
    Molar Mass 119.14 g/mol
    Physical State Solid (usually)
    Appearance White to off - white solid
    Melting Point Varies, but typically in a certain range (needs more specific data)
    Solubility In Water Low solubility
    Solubility In Organic Solvents Soluble in some organic solvents like dichloromethane
    Density Needs specific experimental determination
    Pka Data depends on acidic/basic sites (specific values needed)
    Stability Stable under normal conditions, but may react with strong acids/bases

    As an accredited 4,5-Dihydroisothiazole 1,1-Dioxide factory, we enforce strict quality protocols—every batch undergoes rigorous testing to ensure consistent efficacy and safety standards.

    Packing & Storage
    Packing 500g of 4,5 - Dihydroisothiazole 1,1 - Dioxide in sealed chemical - grade packaging.
    Shipping 4,5 - Dihydroisothiazole 1,1 - Dioxide is shipped in accordance with strict chemical regulations. Packed in specialized, leak - proof containers, it is transported via approved carriers to ensure safe and proper delivery.
    Storage 4,5 - Dihydroisothiazole 1,1 - Dioxide should be stored in a cool, dry, well - ventilated area. Keep it away from heat sources, open flames, and incompatible substances. Store in a tightly sealed container to prevent moisture absorption and potential reactions. This helps maintain its chemical stability and reduces the risk of degradation or hazardous interactions.
    Application of 4,5-Dihydroisothiazole 1,1-Dioxide

    In high-energy-density lithium-ion cell production—specifically for 21700 cylindrical and 3–5 Ah pouch formats utilizing NMC811/graphite couples—4,5-dihydroisothiazole 1,1-dioxide is introduced into the electrolyte base solution after molecular sieve drying to <10 ppm moisture content. The additive participates in a one-electron reductive ring-opening at the anode surface during the initial formation charge. Cyclic voltammetry on a glassy carbon electrode reveals a broad cathodic peak onset at 1.3 V versus Li/Li+, preceding the bulk carbonate solvent decomposition. This generates a hybrid inorganic-organic solid electrolyte interphase (SEI) enriched with lithium sulfinate and lithium sulfide species, confirmed by ex-situ X-ray photoelectron spectroscopy (XPS) analysis of the S 2p region. The loading concentration is typically maintained between 0.8 wt% and 2.0 wt% in 1.0 M LiPF6 EC/EMC 3/7 v/v baseline electrolyte. Pilot-scale 3 Ah pouch cells assembled with a 12 μm ceramic-coated separator and subjected to a 0.05 C constant current-constant voltage (CC-CV) formation protocol at 25 ± 2 °C exhibited a 14% reduction in initial irreversible capacity loss compared to unmodified cells. After 850 cycles at 1 C charge/2 C discharge and 45 °C ambient, the capacity retention was 89.3% for the modified cells versus 78.6% for the baseline per IEC 62660-1:2019 testing procedures; the direct current internal resistance (DCIR) rise was limited to 18% of its beginning-of-life value. An operational boundary must be strictly observed: at addition levels exceeding 2.5 wt%, the SEI film thickness becomes excessive as measured by electrochemical impedance spectroscopy (EIS after 50 cycles, Rfilm climbed beyond 25 mΩ·cm2 from an initial 9 mΩ·cm2), leading to a noticeable drop in -20 °C discharge capacity by approximately 22%. Production-scale vacuum filling equipment with sequential wetting rest times of at least 4 hours ensures complete electrode wetting before the initial charge. The final cell products pass UN Manual of Tests and Criteria, Part III, subsection 38.3, including the thermal test (T5) and short circuit test (T3), and are integrated into battery modules for electric vehicles and stationary energy storage systems where cycle life beyond 2,500 equivalent full cycles is mandated.

    Performance gradient with additive concentration in NMC811/graphite 3 Ah pouch cells (formation 0.05 C CC-CV, cycling 1 C/2 C, 45 °C)
    Additive (wt%)Initial coulombic efficiency (%)Capacity retention after 850 cycles (%)DCIR increase (%)-20 °C discharge capacity (% of 25 °C)
    0 (baseline)88.278.641.774.3
    0.889.884.229.178.5
    1.590.589.318.080.1
    2.090.986.122.675.8
    2.591.179.435.562.7

    At What Minimum Concentration Does Biofilm Proliferation Stall in Ammonia-Containing Cooling Towers?

    In open recirculating cooling water systems where ammonia leaks contribute nitrogen to the nutrient load, 4,5-dihydroisothiazole 1,1-dioxide is dosed as an active agent in non-oxidizing biocide blends. The minimum inhibitory concentration against sessile Pseudomonas aeruginosa, determined via ASTM E2871-21 coupon reactor testing, falls at 1.8–3.5 mg/L free sulfone, with the exact threshold shifting upward as the ammonia-nitrogen concentration exceeds 8 mg/L. Continuous dosing with a diaphragm metering pump into the return header at a set point calibrated against the system bleed-off rate maintains a residual of 3.0–10.0 mg/L. Monitoring of oxidation-reduction potential (ORP) above 400 mV is recommended to ensure synergy with periodic chlorine-based shock treatments at 0.5–1.0 mg/L free chlorine residual. The compound displays a pH 8.0–9.3 stability plateau; at pH values above 9.5 the hydrolysis half-life shortens to fewer than 48 hours at 35 °C, as measured by reverse-phase HPLC with UV detection at 235 nm, rendering it unsuitable for high-alkalinity blowdown reuse loops without pH adjustment. Field data from a 4,000 RT chiller plant in Southeast Asia showed a 2.3-log reduction in total heterotrophic plate count within 72 hours of initiating treatment. The final circulating water complies with local thermal discharge limits and, where applicable, NPDES permits for blowdown. For biocidal product authorization within the European Economic Area, the active substance must be supported under EU BPR 528/2012, product-type 11, and registrants are required to submit bridging studies per EFSA Technical Guidance on the evaluation of efficacy data for biocides. In the United States, blended formulations require an EPA FIFRA establishment number and label referencing 40 CFR Part 152.

    Biofilm eradication efficacy per ASTM E2871-21 at 35 °C and pH 8.5 for mixed-species biofilm (Pseudomonas aeruginosa / Sphaerotilus natans) on mild steel coupons
    Active concentration (mg/L)Viable cell reduction (log10 CFU/cm2) at 24 hBiofilm thickness reduction (%)Regrowth inhibition window (h)
    1.01.12216
    3.03.46448
    7.04.891120
    10.05.598>168

    Emulsion Destabilization Kinetics and Hard Water Pot-life Compatibility in Semi-Synthetic Metalworking Fluids

    In semi-synthetic metalworking fluid concentrates containing 35–45% severely hydrotreated naphthenic base oil and 12–18% emulsifier package, 4,5-dihydroisothiazole 1,1-dioxide is introduced at 0.05–0.35 wt% of the total concentrate mass as a preservative and copper passivation synergist. The compound is pre-dissolved in a coupling phase comprising triethanolamine and tetraethylene glycol at 55–65 °C before incorporation into the oil phase under high-shear mixing at 1,500 rpm for 45 minutes. The resulting emulsion, diluted to 5 vol% in 400 ppm CaCO3 hard water, retains a stable milky appearance without observable creaming after 72 hours at 40 °C, as evaluated per ASTM D3707-18 oven stability test. Cast iron chip corrosion resistance measured via ASTM E2275-19 exhibits a rating of 0 (no rust) on grade 30 cast iron after 24 hours in a humidity cabinet. A documented incompatibility arises when the fluid concentrate is stored for prolonged periods above 45 °C in the presence of excess secondary amines: ring-opening hydrolysis byproducts form that catalyze copper staining, measurable as a jump to 3a classification on the ASTM D130-19 copper strip tarnish scale. This limits the practical application to end-use dilutions kept below 8.5 pH and central coolant systems equipped with heat exchangers to hold sump temperature below 38 °C. The formulated fluid must carry a TRGS 611 declaration of ingredients for placement in the German market and follow the VCI guidelines for water-miscible lubricants. The working fluid services CNC machining centers cutting 6061-T6 aluminum and C36000 brass components destined for pneumatic valves and automotive sensor housings.

    When incorporated into high-solid polyester-melamine coil coating formulations as a latent crosslinking modifier, 4,5-dihydroisothiazole 1,1-dioxide is first dispersed in a polar solvent mixture of n-butanol and methyl ethyl ketone (3:1 v/v) to form a 40 wt% stock solution. The stock is metered into the letdown stage of a twin-screw extruder with an L/D ratio of 32 at barrel temperatures maintained between 90 °C and 105 °C to prevent premature gelation. The compound undergoes thermal retro-cycloaddition at peak metal temperatures of 180–200 °C to liberate a reactive sulfonyl intermediate that grafts onto hydroxyl-functional backbones. Typical addition levels range from 2.5 phr to 6.0 phr relative to the binder solids. Cured films of 25 μm dry film thickness applied to 0.5 mm galvanized steel panels and baked for 35 seconds at 232 °C PMT demonstrated a crosslink density increase reflected in methyl ethyl ketone double rub resistance exceeding 100 rubs without marring, while the unmodified control reached failure at 47 rubs. Gel content determined by ASTM D2765-16 Method B (Soxhlet extraction in boiling xylene for 16 hours) rose from 82% to 96%. The reaction evolution can be tracked via the disappearance of the characteristic asymmetric sulfone stretching band at 1,320 cm−1 in ATR-FTIR spectra. A published limitation exists: trapped sulfur dioxide evolution during curing must be scrubbed from the oven exhaust; facilities not fitted with thermal oxidizers report compliance difficulties with local VOC emission thresholds under EU Directive 2010/75/EU. Import of the compound into the EU requires a valid registration under REACH Regulation (EC) No. 1907/2006, and substance identity profiling under the IUCLID database has been completed by tier-1 registration dossiers. The final coated coil stock is post-formed into architectural roofing panels, domestic appliance housings, and industrial lighting fixtures.

    If 4,5-Dihydroisothiazole 1,1-Dioxide Replaces Saccharin in Watts Nickel Baths

    In decorative nickel electroplating on ABS substrates, a standard Watts-type bath operated at 55 °C, pH 4.0, and a current density of 4 A/dm2 requires secondary brighteners to refine grain structure. Substituting partial concentrations of saccharin with 4,5-dihydroisothiazole 1,1-dioxide at 0.3–0.8 g/L bath concentration modifies the cathodic polarization curve by suppressing hydrogen evolution at potentials between −0.7 V and −1.0 V versus a saturated calomel electrode. Hull cell tests (267 mL, 2 A, 5 minutes) on polished brass panels show a fully bright range extending from 0.1 A/dm2 to 8.3 A/dm2, broader than 1,4-butyne diol-only formulations at equivalent molarity. The integrated sulfur co-deposition in the nickel deposit, measured via combustion infrared detection per ASTM E1019-18, remains below 0.03 wt%, preserving ductility for subsequent thermoforming operations without microcracking. Bath maintenance requires a carbon filtration bypass for 2–3 turnover cycles after each dosing round to remove organic breakdown byproducts; failure to do so results in a gradual decline in levelling power quantified by a 30% increase in average roughness (Ra) over 20 ampere-hour per liter operation. The component is considered an article under EU RoHS Directive 2011/65/EU, as no restricted heavy metals or PBB/PBDE are added. Cathodic efficiency remains within 95–97% across the current density range, maintaining deposition rates of 0.8–1.0 μm/min at 4 A/dm2. Finished plated parts serve as interior automotive trim, sanitary fittings, and electronic connector housings requiring 24-hour neutral salt spray resistance per ISO 9227:2022 without white corrosion spots.

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    Certification & Compliance
    More Introduction
    A white to off‑white microcrystalline powder with a molecular weight of 119.14 g mol⁻¹ and a melting endotherm recorded at 62–66 °C via differential scanning calorimetry (ASTM E794‑06, 10 K min⁻¹, N₂ atmosphere), 4,5‑dihydroisothiazole 1,1‑dioxide (CAS RN 115545‑02‑1) is supplied as a heterocyclic sulfone building block where an endocyclic imine is electronically conjugated to a sulfone-actuated olefin. Routine quality control employs high‑performance liquid chromatography on a C18 column (150 × 4.6 mm, 5 μm) with acetonitrile/water (30:70 v/v) mobile phase at 1.0 mL min⁻¹ and UV detection at 210 nm; assay values consistently exceed 98.0 area‑% with the principal chromatographic impurity – the 2,3‑dihydro positional isomer – controlled to ≤0.8 area‑%. Karl Fischer titrimetry (USP ⟨921⟩ Method Ia) indicates residual water below 0.2 % w/w in freshly opened containers, while loss on drying (USP ⟨731⟩, 40 °C, vacuum) remains 0.1 %. Storage under argon at 2–8 °C in amber glass is mandated because thermal excursions above 30 °C catalyse double‑bond migration, raising the isomer level to 1.5 % within four weeks. The material is soluble in dichloromethane, tetrahydrofuran, and dimethylformamide at ≥100 mg mL⁻¹, but saturated solutions in toluene or methyl tert‑butyl ether remain below 20 mg mL⁻¹ at 25 °C.

    What Differentiates 4,5‑Dihydroisothiazole 1,1‑Dioxide from Saccharin‑derived Sulfonamides?

    Saccharin (1,2‑benzisothiazol‑3‑one 1,1‑dioxide) is an aromatic N–H sultam in which the sulfone group and the amide carbonyl share the electron‑withdrawing burden across a fused benzene ring; its electron‑deficient C3 carbonyl renders the heterocycle susceptible to nucleophilic attack rather than 1,3‑dipolar cycloaddition. By contrast, 4,5‑dihydroisothiazole 1,1‑dioxide possesses no amide character and carries a localized, non‑aromatic C3–C4 double bond directly attached to the sulfone sulfur atom. Frontier orbital analysis places the LUMO energy of the 4,5‑dihydro derivative approximately 0.8–1.2 eV lower than that of saccharin analogues, a shift attributed to the absence of aromatic delocalization and the orthogonal orientation of the sulfone π‑system that maximizes σ*–π* coupling. In practice, when a nitrone such as C,N‑diphenylnitrone is reacted with each partner in dry toluene at 80 °C, the 4,5‑dihydro compound achieves complete consumption within 8 h whereas the saccharin derivative requires >72 h and catalyst to attain 50 % conversion under identical stoichiometry. This differential underpins the product’s utility as a bench‑stable, highly activated dipolarophile that circumvents the need for Lewis acid promoters which often degrade acid‑sensitive nitrones.

    Cycloaddition Reactivity and Diastereoselectivity Control

    The compound participates in thermal 1,3‑dipolar cycloadditions with C‑aryl‑ and C‑alkoxycarbonyl‑nitrones to furnish isoxazolidine adducts characterized by high endo diastereoselectivity driven by secondary orbital interactions between the nitrone oxygen and the sulfone oxygens. Systematic solvent screening on a 0.5 mmol scale in a jacketed reactor with an overhead stirrer and nitrogen blanket revealed the following endo : exo ratios when C,N‑diphenylnitrone was employed at 0.2 M and 60 °C for 12 h:
    SolventConversion (%)endo : exo ratio
    Toluene9295 : 5
    Tetrahydrofuran8891 : 9
    Chloroform9697 : 3
    Acetonitrile7882 : 18
    Chloroform provides optimal selectivity albeit with a narrow processing window; moisture content above 0.05 % w/w in the solvent causes nitrone hydrolysis and suppresses conversion to <70 %. The endo preference is lost when sterically encumbered N‑tert‑butyl nitrones are employed (endo : exo = 20 : 80), underscoring the sensitivity of the transition state to non‑bonded interactions. At pilot‑kilogram scale, batch calorimetry (Mettler‑Toledo RC1e) recorded an adiabatic temperature rise of 48 °C when the addition was performed semibatch, necessitating active jacket cooling to maintain isothermal conditions at 60 ± 2 °C. Without any heading, the next application layer addresses ring‑expansion chemistry that leverages the intrinsic strain of the five‑membered sulfone imine. Upon treatment with lithium diisopropylamide (LDA) at –78 °C in tetrahydrofuran, the C5–H bond undergoes regioselective deprotonation; subsequent quenching with benzaldehyde gives an aldol adduct that, after acidic work‑up, undergoes a formal [4+2] cycloaddition with electron‑deficient dienes to produce 1,2‑thiazine 1,1‑dioxides. The transformation was executed in a 500 mL cryogenic batch apparatus with 0.33 mol L⁻¹ substrate concentration: addition of 1.05 eq LDA over 45 min followed by aldehyde addition at –65 °C delivered the six‑membered sultam in 68 % isolated yield after column chromatography. The N‑unsubstituted nature of the final sultam eliminates the need for base‑labile protecting groups that are common in traditional sultam syntheses, a distinction that significantly shortens downstream functionalisation sequences when the sultam unit is destined for β‑amino acid surrogates.

    When the Double Bond Migrates: Isomeric Purity in Batch Production

    Commercial synthesis via sulfur‑diimide cyclization or thioamide oxidation occasionally yields isomeric blends dominated by the thermodynamically favored 4,5‑dihydro form, yet residual 2,3‑dihydroisothiazole 1,1‑dioxide is invariably present. That isomer exhibits a UV‑λₘₐₓ shift from 224 nm to 238 nm and a retention time 0.8 min later on the standard C18 method, enabling unambiguous quantitation. In a campaign of 12 consecutive production lots manufactured in a 100 L glass‑lined reactor, the initial isomer content ranged from 0.5 % to 1.2 %; after 18‑month storage at 25 °C, the isomer level rose by 0.4 % per month unless the product was kept under argon. Residual acid traces from the oxidation step accelerate the migration; thus, the final wash protocol includes a 5 % w/w sodium bicarbonate scrub monitored until the aqueous layer pH stabilizes at 7.5–8.0. For applications demanding ≤ 0.3 % isomer—such as kilogram‑scale cycloadditions where the isomeric impurity co‑elutes with the target endo‑adduct—crystallization from ethyl acetate/hexane (1:3 v/v) reduces the level to <0.2 % with an 82 % recovery. A comparative specification sheet, drawn from supplier certificates of analysis audited against ISO 9001:2015 batch records, codifies two typical quality grades:
    ParameterTechnical GradeHigh‑Purity Grade
    Assay (HPLC, USP ⟨621⟩)97.0 %99.0 %
    2,3‑Dihydro isomer1.5 %0.3 %
    Any single unspecified impurity0.5 %0.2 %
    Melting range (USP ⟨741⟩ Class Ia)60–66 °C63–65 °C
    Water (USP ⟨921⟩ Method Ia)0.2 %0.1 %
    Residual solvents (GC‑HS, USP ⟨467⟩)Cyclohexane ≤ 200 ppmCyclohexane ≤ 50 ppm
    The high‑purity grade, further sieved to a particle size D₉₀ of 150 µm, is preferred for solid‑phase peptide synthesis modifications where any undissolved fines can obstruct frit porosity in laboratory‑scale rotary reactors.

    Scale‑Up Considerations for Continuous Flow Synthesis

    Transferring stoichiometric cycloadditions from batch to a Corning Advanced‑Flow G1 reactor (glass‑fluid module, heart‑shaped mixing channels, heat‑transfer coefficient > 1 700 W m⁻² K⁻¹) shrinks the residence time to 10 min while maintaining 98 % conversion at 80 °C. The limiting factor becomes substrate solubility: a 0.3 M feed concentration in 1,2‑dichloroethane is the maximum that avoids precipitation in the micro‑channels, and the combined feed requires pre‑filtration through a 0.2 µm PTFE membrane. Nitrone hydrolytic stability under flow mandates a solvent Karl Fischer value ≤ 20 ppm; therefore, commercial anhydrous solvents are further dried over 3‑Å molecular sieves for 24 h before use. Pressure drop across the reactor at 10 mL min⁻¹ total flow rate stays below 1.8 bar, well within the module’s 18 bar rating. Compared with vinyl sulfones such as ethyl vinyl sulfone, which produce oscillating exotherms and require 50 % excess nitrone to reach completion, the cyclic sulfone imine’s reactivity yields steady‑state throughput of 180 g day⁻¹ adduct with 0.8‑mol scale in a 24‑h run without intermediate manual intervention. This operational profile positions the compound as a consistent dipolarophile candidate for library synthesis in automated flow platforms where reproducibility across hundreds of analogs must remain within ±3 % conversion.