|
HS Code |
949120 |
| Chemical Formula | C15H10N2S |
| Molar Mass | 246.32 g/mol |
| Appearance | Solid (usually) |
| Physical State | Solid at room temperature |
| Melting Point | Data may vary, check specific sources |
| Boiling Point | Data may vary, check specific sources |
| Solubility In Water | Low solubility in water |
| Solubility In Organic Solvents | May be soluble in some organic solvents like DMSO, DMF |
| Color | Color may vary, often appears as a colored solid |
| Odor | Odorless or very faint odor |
| Stability | Stable under normal conditions, but may react under certain chemical environments |
As an accredited 2-(1H-Indol-3-Yl)-Benzothiazole factory, we enforce strict quality protocols—every batch undergoes rigorous testing to ensure consistent efficacy and safety standards.
| Packing | 10 grams of 2-(1H - Indol - 3 - Yl) - Benzothiazole in a sealed, chemical - resistant vial. |
| Shipping | 2-(1H - Indol - 3 - Yl) - Benzothiazole is shipped in accordance with strict chemical safety regulations. It's packaged securely to prevent damage and leakage, transported by approved carriers for chemical goods. |
| Storage | 2-(1H - Indol - 3 - Yl) - Benzothiazole should be stored in a cool, dry place away from direct sunlight. Keep it in a tightly sealed container to prevent moisture absorption and contact with air, which could potentially lead to degradation. Store it separately from incompatible substances, in a well - ventilated area to minimize the risk of fumes accumulation. |
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Impregnation of analytical-grade cellulose filter paper with a 2-(1H-indol-3-yl)-benzothiazole solution in anhydrous tetrahydrofuran and ethyl acetate (4:1 v/v) at a functional loading of 0.03–0.07 mg/cm² yields a turn-off fluorescent test strip sensitive to Cu²⁺ in aqueous samples at pH 5.8–7.2. The manufacturing line operates with a slot-die coater configured at 3.5 m/min web speed through a 55 °C forced-air drying tunnel, after which the master roll is immediately slit and pouch-sealed under nitrogen with 20 g of silica gel desiccant per 100 strips to mitigate humidity-induced photobleaching. During scale-up runs on a Kroenert PAK 410 pilot coater, batch-to-batch fluorescence intensity variance remained within ±7 % when precursor solution viscosity was controlled to 4.2 ± 0.1 mPa·s and ambient relative humidity maintained below 38 %. The strips exhibit a Stern-Volmer quenching constant of 1.8 × 10⁴ M⁻¹ for Cu²⁺, with a detection limit calculated at 1.2 ppb per the 3σ/m criterion referenced in ASTM E2144-11. Quality control for export batches requires compliance with ISO 17381:2012 (selection and validation of rapid test methods for water quality) and documentation that the substrate has been produced under ISO 9001:2015 certified management. The end product is a ready-to-use test strip card sealed in aluminum trilaminate pouches for field detection of copper contaminants in electronics manufacturing wastewater.
Live-cell imaging workflows utilizing 2-(1H-indol-3-yl)-benzothiazole as a mitochondrial membrane-potential indicator require rigorous exclusion of serum-borne esterases that can cleave the benzothiazole ring in the presence of high-protein media; a pre-conjugated BSA-tracer prepared via EDAC/NHS coupling at a dye-to-protein ratio of 4:1 and diluted to a working concentration of 50–200 nM in phenol red-free DMEM achieves a signal-to-noise ratio exceeding 15:1 on a spinning-disc confocal system with 405 nm excitation and 60×/1.42 NA oil-immersion objective. The staining protocol mandates a 37 °C, 5% CO₂ incubation for 45 minutes, followed by three washes with pre-warmed Hank’s balanced salt solution; omission of the final wash step consistently generates diffuse cytoplasmic background that masks cristae-level resolution. Under continuous illumination at 1.5 mW/cm² for 120 seconds, photobleaching remains below 22%, a threshold verified across 12 independent HeLa cell preparations, yet exposure to ambient oxygen without the antioxidant ascorbate (added at 0.1 mM) accelerates signal decay by a factor of 1.8. Cytotoxicity assessed per ISO 10993-5:2009 indicates IC₅₀ > 100 μM after 24-hour exposure, placing the product in the low-toxicity category suitable for research-grade live-cell reagents. The final product format is a 1 mM anhydrous DMSO stock solution in amber ampules, packed under argon in secondary containment meeting IATA PI 650 for transport. What Limits the External Quantum Efficiency of Indolylbenzothiazole-Based Emitters in Solution-Processed Phosphorescent OLEDs?Emission in the deep-red region (λ_EL = 638 ± 4 nm) is obtained when 2-(1H-indol-3-yl)-benzothiazole is doped at 3.0 wt% into a mixed host of mCP and 30 wt% OXD-7, with the layer deposited inside a nitrogen-filled glovebox (H₂O < 0.1 ppm, O₂ < 0.5 ppm) via spin-coating from chlorobenzene at 1200 rpm and baked at 100 °C for 20 minutes to reduce pinhole density. The primary processing conflict arises from the compound’s sublimation onset temperature of 218 ± 3 °C at 10⁻⁶ mbar; attempts to thermally evaporate at source temperatures above 240 °C induce partial decomposition and a drift in deposition rate monitored on an INFICON quartz crystal microbalance, forcing the adoption of solution-processing as the sole viable route for fabrication. In a 10 cm² test pixel on an ITO/PEDOT:PSS anode, the external quantum efficiency plateaus at 4.8% at 3 mA/cm², after which triplet-triplet annihilation drives a roll-off to 3.1% at 50 mA/cm²; this behavior has been mapped in a Keithley 2400 source meter coupled with a calibrated integrating sphere per IEC 62341-5-1. The operational lifetime (LT₅₀) at 1000 cd/m² initial luminance is recorded at 820 hours under constant current driving, limited by electromer formation that is accelerated when the host matrix contains residual chloride above 5 ppm. Conformity to IEC 62341-1-1:2019 mandates testing for chromaticity shift (Δu’v’ < 0.01 after 500 hours) and compliance with RoHS 2011/65/EU for cadmium-free display components. Terminal goods are sealed glass-encapsulated OLED panels integrated into automotive dashboard indicators and wearable biometric monitors. Fabrication of a distributed fiber-optic mercury sensor array involves covalent bonding of 2-(1H-indol-3-yl)-benzothiazole-5-carboxylic acid to amine-terminated silica fiber tips via EDC/HOBt carbodiimide chemistry at a loading of 0.8 ng/cm², followed by rigorous washing in acetonitrile to remove physisorbed species that otherwise contribute a background fluorescence drift of 2.3% per minute. Long-term drift tests conducted over 720 hours on a 16-channel array submerged in synthetic freshwater at 23 ± 1 °C show a sensitivity retention of 94% when the probe is overcoated with a sol-gel layer derived from tetraethoxysilane hydrolysed at pH 4.0; uncoated tips lose 41% of initial response within the same period. Under flow-injection analysis conditions with a peristaltic pump delivering sample at 0.8 mL/min and pH buffered to 6.8, the sensor achieves a Stern-Volmer constant of 2.3 × 10⁴ M⁻¹ for Hg²⁺, a 90% response time of 3.8 seconds, and a reversible signal recovery to 97% upon flushing with 10 mM EDTA. Cross-sensitivity to Ag⁺ and Pb²⁺ is suppressed to below 6% relative error by the incorporation of a 25 μm-thick Nafion™ cation-exchange barrier dip-coated prior to the sol-gel layer. Validation against ISO 5667-1:2020 sampling protocols and IEC 61757-1:2023 ensures the device meets the conformity requirements for in-line water quality monitoring in chlor-alkali plant effluent streams. The final product is a factory-calibrated probe assembly delivered with a factory-stored calibration curve embedded in the microcontroller of the interrogation unit. Accelerated Weathering Crack Onset in Thin-Section PP Tapes Under 0.25 wt% Indolyl-Benzothiazole StabilizationMelt-blending of the heterocyclic stabilizer with polypropylene homopolymer (MFI 3.2 g/10 min at 230 °C/2.16 kg) is performed on a co-rotating twin-screw extruder with L/D = 40 and medium shear screw profile, where the compound is metered via a loss-in-weight side feeder at zone 7 to limit total residence time above 220 °C to under 42 seconds. This configuration is dictated by a sharp process window: differential scanning calorimetry traces place the onset of thermal degradation at 277 °C under nitrogen, yet at screw speeds exceeding 350 rpm, friction-induced temperature spikes of 12–15 °C above the barrel setpoint are routinely recorded in zone 5 of a Leistritz ZSE 27 MAXX extruder, causing stabilizer loss of 8–11% as confirmed by UV-Vis assay of pellet extracts. The recommended addition range of 0.15–0.35 wt% is thus laterally fed rather than pre-blended, and a nitrogen blanket at 2.5 L/min is maintained over the feeder hopper to suppress oxidative yellowing during processing. Tapes drawn at 6:1 stretch ratio to a thickness of 45 μm and exposed in a Xenon-arc weatherometer per ISO 4892-3:2016 cycle A2 (with 0.55 W/m² at 340 nm) exhibit a 60% gloss retention after 2400 kJ/m² radiant exposure, versus 22% for an unstabilized control; however, when the same formulation is combined with a secondary hindered amine light stabilizer (HALS) at 0.1 wt%, a synergistic jump to 78% gloss retention is recorded, accompanied by a delay in crack onset from 1600 kJ/m² to 3400 kJ/m². Conversely, co-addition of amine-based process aids must be avoided because nucleophilic attack on the benzothiazole ring at melt temperatures opens a de-activation pathway that reduces the effective absorber concentration by 27% within the first 48 hours of accelerated aging as tracked by carbonyl index growth per ASTM D5576. The final woven fabric or woven tape product is deployed as FIBC bulk bags and outdoor furniture webbing, where REACH Annex XVII compliance and extractables below the 10 mg/dm² overall migration limit for food-contact applications (simulated per EN 1186-1) open routes into indirect food packaging. When Indole-Benzothiazole Is Used as a Molecular Scaffold in the Synthesis of Dual EGFR/Src Kinase InhibitorsThe convergent synthetic route requires 2-(1H-indol-3-yl)-benzothiazole to be N-alkylated with 1-bromo-3-chloropropane in the presence of cesium carbonate (2.5 eq) in anhydrous dimethylformamide at 60 °C for 18 hours under argon, achieving a typical isolated yield of 71–76% after flash chromatography. The subsequent Suzuki-Miyaura coupling at the indole C-2 position with a pre-formed pinacol boronate ester demands a catalyst loading of Pd(PPh₃)₄ at 1.3 mol% and aqueous Na₂CO₃ (2 M) in dioxane at 85 °C for 12 hours, with strict exclusion of oxygen to prevent Pd black formation that contaminates the active pharmaceutical ingredient (API) beyond the permitted residual metal limit of 10 ppm palladium per ICH Q3D guidelines. Process analytical technology (PAT) implemented on a 100 L Hastelloy reactor tracks the disappearance of the benzothiazole-CH₂Cl intermediate via in-line Raman at 1550 cm⁻¹, enabling a crystallization trigger when the peak area falls below 0.5% of initial intensity. The recrystallized API batch must meet ≥ 99.8% HPLC purity with total related substances < 0.15% as per Ph. Eur. 2.2.29, and residual solvent limits for DMF < 880 ppm and dioxane < 380 ppm per ICH Q3C Class II thresholds. A major process stability issue emerges during storage: the unmilled API loses 0.3% potency per month at 25 °C/60% RH due to benzothiazole ring hydrolysis, necessitating double-blister packaging with aluminum foil and a desiccant canister to achieve 24-month shelf life as required by ICH Q1A(R2). The terminal dosage form is a hard gelatin capsule containing 50 mg or 150 mg of the micronized inhibitor, manufactured in an ISO 8 cleanroom under FDA 21 CFR Part 211 conditions and labelled for the treatment of advanced non-small-cell lung cancer as a third-line oral therapy. |
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2-(1H-Indol-3-yl)-benzothiazole (IUPAC: 3-(1,3-benzothiazol-2-yl)-1H-indole) is a heteroaromatic fluorophore constructed from a benzothiazole ring fused at the 2-position to the 3-carbon of indole. The molecule exhibits excited-state intramolecular proton transfer (ESIPT) across the indole N–H••N benzothiazole hydrogen bond, yielding a large Stokes shift typically exceeding 140 nm. In crystalline form, it displays a melting point range of 248–252 °C and a molecular weight of 250.32 g·mol⁻¹. The compound is supplied as a pale yellow microcrystalline powder with purity verified by HPLC at ≥98.5% (area%) using a C18 column and acetonitrile/water gradient elution. Storage under argon at 2–8 °C and protection from light are mandatory to prevent photo-oxidative degradation of the indole ring. The product grade IBT-98 is intended for use as a fluorescent molecular rotor, a pharmaceutical intermediate, and a building block for donor-acceptor conjugated polymers.
| Parameter | Value | Analytical Method |
|---|---|---|
| Appearance | Pale yellow powder | Visual (QCL-03-011) |
| Melting point | 248–252 °C | Differential scanning calorimetry, 10 K·min⁻¹, N₂ |
| Purity (HPLC) | ≥98.5% area% | HPLC-UV at 254 nm, C18, acetonitrile/water |
| Excitation λmax (MeOH) | 342 ± 3 nm | Fluorescence spectrophotometry, 10 µM |
| Emission λmax (MeOH) | 498 ± 4 nm | Fluorescence spectrophotometry, 10 µM |
| Solubility in DMSO | ≥25 mg·mL⁻¹ | Gravimetric, 25 °C |
| Residual solvents | ≤0.1% ethanol, ≤0.05% ethyl acetate | Headspace GC-FID (Ph. Eur. 2.4.24) |
| Water content | ≤0.5% | Karl Fischer coulometry (ISO 760:1978) |
When embedded into 1,2-dipalmitoyl-sn-glycero-3-phosphocholine (DPPC) vesicles, the fluorophore partitions into the gel-phase bilayer interior with a measured partition coefficient log P of 3.8 ± 0.2. The tautomer emission intensity at 495 nm is highly sensitive to the phase transition temperature (41.4 °C for pure DPPC). Below the transition, the enol emission band (350–380 nm) is suppressed by a factor of 6.2 relative to the keto tautomer band, whereas above the phase transition the keto/enol intensity ratio collapses to 1.3. This ratiometric response enables membrane fluidity mapping without the need for a second reference dye. One documented limitation is the loss of ESIPT in vesicles composed of > 40 mol% cholesterol, where increased free volume disrupts the intramolecular hydrogen bond network, causing the quantum yield to drop below 0.02 and rendering the probe unusable. All fluorescence lifetime measurements were acquired with a time-correlated single-photon counting system (TCSPC, pulsed laser diode 375 nm, IRF 120 ps).
In non-polar media the enol tautomer dominates, yielding a sharp absorbance peak at 355 nm. When evaluating the compound as a micro-viscosity sensor in lubricant basestocks, rotational correlation times derived from fluorescence anisotropy decay in polyalphaolefin PAO-6 at 40 °C increase from 0.12 ns (hexane) to 1.47 ns, correlating with a kinematic viscosity of 32.5 cSt (ASTM D445). The quantum yield enhancement ratio (ΦPAO-6/Φhexane) reaches 3.8 under these conditions, calibrated against quinine sulfate in 0.1 M H₂SO₄ (Φ = 0.546 at 25 °C). Above 80 °C, thermal deactivation pathways compete, and the normalized intensity declines by 14% per 10 K increment. This imposes a practical upper operating temperature for viscosity sensing of 100 °C in sealed cells. Data for ester-based basestocks show a positive deviation from the Förster–Hoffmann linear calibration curve at viscosities above 50 cSt, attributed to aggregation-induced emission contributions, which complicates quantitation and requires a polynomial correction model.Blends of 2-(1H-indol-3-yl)-benzothiazole with poly(methyl methacrylate) (PMMA, Mw = 120,000 g·mol⁻¹) were prepared via solution casting from tetrahydrofuran. At dopant concentrations below 0.3 wt%, the emission spectrum is dominated by the structured enol band at 371 nm (FWHM 32 nm), indicating molecular dispersion. At loadings between 0.5 and 1.5 wt%, a red-shifted aggregate band emerges at 517 nm with a lifetime component of 2.3 ns (amplitude-weighted). This dual emission degrades the chromatic purity required for blue-emitting OLEDs, restricting the usable doping window to ≤0.25 wt% in polyfluorene host matrices. Parallel experiments with 2-(2′-hydroxyphenyl)benzothiazole (HBT) show aggregate emission onset only above 1.0 wt% in PMMA, highlighting that the indole derivative has a lower threshold for aggregation due to reduced steric hindrance around the single bond connecting the two aromatic systems. Twin-screw extrusion compounding (Coperion ZSK 26, L/D = 40, 200 rpm, barrel temperature 230 °C) caused a 7% reduction in fluorescence intensity of the IBT-98/PMMA strand compared to the solution-cast film, attributed to partial thermal isomerization detected by HPLC. Pre-drying of the polymer at 80 °C for 4 h under vacuum (−0.08 MPa) and operation at ≤225 °C mitigated the intensity loss to ≤2.5%.
Electrochemical impedance spectroscopy on X65 pipeline steel coupons in NACE TM-0169 solution (1 M HCl, unstirred, 25 °C) reveals that the charge transfer resistance increases from 32 Ω·cm² (blank) to 587 Ω·cm² at 150 mg·L⁻¹ of the inhibitor. This corresponds to a corrosion current density reduction from 985 µA·cm⁻² to 47 µA·cm⁻² and an inhibition efficiency of 95.2%, calculated according to ASTM G106-89. The adsorption follows the Langmuir isotherm with a linear regression coefficient R² of 0.9991 and a Gibbs free energy of adsorption ΔGads of −38.2 kJ·mol⁻¹, suggesting mixed physisorption and chemisorption through the indole π-system and benzothiazole nitrogen lone pair. Weight-loss measurements conducted per ASTM G31-72 (immersion 24 h, 25 °C) confirm an efficiency of 94.8% at the same concentration. A critical operational boundary is the rapid desorption above 60 °C: at 70 °C the efficiency falls to 43%, making the inhibitor unsuitable for hot acid pickling lines or high-temperature wellbore acidizing treatments. Additionally, the compound is incompatible with chloride-containing brines at pH > 9, where deprotonation of the indole N–H promotes oxidative coupling and loss of solubility.
Regioselective halogenation at the 5-position of the indole ring (electrophilic substitution with N-bromosuccinimide in DMF at 0 °C) proceeds with a yield of 72–78% after column chromatography (silica gel, hexane/ethyl acetate 4:1 v/v). The 5-bromo derivative undergoes Suzuki–Miyaura cross-coupling with phenylboronic acid pinacol ester under standard catalytic conditions (Pd(PPh₃)₄ 5 mol%, K₂CO₃, dioxane/water, 90 °C, 12 h) to provide the biaryl adduct in 81% isolated yield. This intermediate serves as a precursor for kinase inhibitor scaffolds. A key advantage over the 2-(4-aminophenyl)benzothiazole analogue is the absence of a primary aromatic amine, which eliminates the requirement for continuous nitrogen blanketing during long-term storage; IBT-98 exhibits <0.3% degradation after 12 months at −20 °C in amber glass, while the amine-containing analogue darkens and forms oligomeric species within 8 weeks under identical conditions. The indole N–H functionality also permits selective N-alkylation with propargyl bromide (1.2 eq., K₂CO₃, DMF, 25 °C) in 91% yield, enabling click chemistry conjugation for targeted drug delivery applications. Published data for the anti-proliferative activity of the parent compound against HeLa and MCF-7 cell lines is limited to preliminary MTT assays that indicate IC₅₀ values in the 15–30 µM range, placing it as a moderate cytostatic agent requiring structural optimization before lead development.
| Feature | 2-(1H-Indol-3-yl)-benzothiazole | 2-(2′-Hydroxyphenyl)-benzothiazole (HBT) | 2-Mercaptobenzothiazole (MBT) |
|---|---|---|---|
| Proton transfer donor | Indole N–H (pKₐ ~13) | Phenolic O–H (pKₐ ~9.2) | Thiol S–H (pKₐ ~6.9) |
| ESIPT Stokes shift | 140–155 nm | 150–170 nm | Not applicable |
| Primary application | Fluorescent rotor, intermediate | Optical brightener, photostabilizer | Vulcanization accelerator |
| Aggregation-induced emission onset | ~0.5 wt% in PMMA | ~1.0 wt% in PMMA | Poorly emissive in solid state |
| Corrosion inhibition (1 M HCl) | 95.2% at 150 mg·L⁻¹ | Not reported as inhibitor | 92–96% at 200 mg·L⁻¹ |
| Synthetic versatility | Halogenation, N-alkylation, Suzuki | Limited to O-acylation, sulfonation | Metal complexation, disulfide formation |
| Long-term stability | > 12 months under argon at −20 °C | > 12 months under argon at −20 °C | Hygroscopic, requires desiccation |
Processing on a multi-kilogram scale via one-pot condensation of 2-aminothiophenol with indole-3-carboxaldehyde in polyphosphoric acid at 130–140 °C is established, with recrystallization from 95% ethanol yielding product IBT-98. The crude yield before purification is typically 82–87%, dropping to 68% after double recrystallization required to meet fluorescence-grade purity. Batch-to-batch variation in the trace metal profile (iron levels > 2 ppm can quench fluorescence) is controlled by implementing a 0.5 µm in-line filtration step and chelating resin treatment of the recrystallization solvent. For polymer fiber spinning trials using wet-spinning into a coagulation bath of DMF/water at 15 °C, the dopant remains molecularly dispersed at draw ratios up to 4:1, provided the bath water content is kept below 25 vol% to prevent premature phase separation and aggregate formation that would diminish the keto emission band.