This compound belongs to the class of organic compounds known as benzothiazoles. These are organic compounds containing a benzene fused to a thiazole ring (a five-membered ring with four carbon atoms, one nitrogen atom and one sulfur atom).
External Descriptors
Not available
1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.
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Application Protocols
Not applicable as an assay reagent with standardized biological protocols.
General lab use examples (literature/guidance)
Electrophilic sulfenylation screening: Prepare 0.1 M enolate solution in dry THF at −78 °C; add 1.2 equiv of reagent in THF/DCM dropwise; warm to 0 °C and quench; analyze by LC–MS.
Radical thiol–ene model: Combine alkene (1.0 equiv), reagent (1.2 equiv), AIBN (10 mol%) in toluene; heat to 80 °C under N2 for 2–4 h; monitor by GC/LC–MS.
Item-specific validated protocols and dilutions: Not specified for this item; refer to CoA/Spec Sheet and primary literature.
Biological Roles
This product is a synthetic organic reagent and is not intended for biological use in living systems.
Literature/General context
Benzothiazole frameworks appear in diverse bioactive molecules, and disulfides are central to protein structure; however, 4-(2-benzothiazolyldithio)morpholine is a laboratory reagent, not a biological metabolite.
Disulfide exchange chemistry can be leveraged in biomimetic materials and dynamic covalent systems, but such applications typically require carefully chosen solvents, pH, and reducing environments incompatible with most biological assays.
Practical note
If exploring disulfide exchange with peptides/proteins, ensure compatibility: this reagent is hydrophobic and generally requires organic media or biphasic systems; it may modify cysteine residues non‑selectively. For biological/biochemical work, specialized water‑soluble disulfide transfer reagents are often preferred.
Item-specific biochemical data (binding targets, transport, metabolism): Not specified for this item; refer to primary literature and SDS.
Buffer Applications
Not typically applicable.
4-(2-Benzothiazolyldithio)morpholine is not used as a buffering agent and does not form a defined conjugate acid/base pair suitable for maintaining pH in aqueous systems.
For aqueous work, select established buffers (e.g., phosphate, HEPES, Tris) appropriate to your target pH and ionic strength.
Green Alternatives
Context
Disulfide‑based benzothiazole reagents are effective sulfenylating agents but often rely on chlorinated solvents and can pose aquatic toxicity concerns.
Greener choices and strategies (literature/general)
Alternative reagents: Use less toxic sulfenylating agents where feasible (e.g., S‑sulfinyl reagents or thiocarbonyl transfer agents) that avoid benzothiazole residues; consider dimethyl disulfide (DMDS) or elemental sulfur/S8 with catalysts for C–S formation, acknowledging different selectivities.
Solvent optimization: Replace DCM/CHCl3 with ethyl acetate, 2‑MeTHF, cyclopentyl methyl ether (CPME), or MeCN when compatible with the mechanism. Aqueous micellar media (TPGS‑750‑M) can enable some C–S couplings at room temperature.
Catalysis and energy input: Photoredox or electrochemical initiation of S–S cleavage can reduce need for thermal input or stoichiometric initiators; flow photochemistry improves safety and scalability.
Waste minimization: Design reactions to produce removable/benign leaving groups; plan for benzothiazole‑containing waste segregation and treatment.
Comparison (indicative trade‑offs)
2‑MeTHF/CPME vs DCM: lower toxicity and better sustainability metrics, but may alter rates/selectivity; ensure anhydrous grade for enolate chemistry.
Elemental sulfur routes: excellent atom economy; typically require catalysts and may have narrower substrate scope vs electrophilic disulfides.
Item-specific environmental metrics (E-factor, solvent recommendations, toxicity data): Not specified for this item; refer to SDS/CoA.
Pharmaceutical Uses
Not typically applicable as a pharmaceutical excipient.
Literature/General context
While morpholine and benzothiazole moieties appear in some drug substances, 4-(2-benzothiazolyldithio)morpholine is a laboratory reagent. It is not described in common pharmacopeial monographs as an excipient.
In process chemistry research, disulfide reagents may be explored for chemoselective sulfur incorporation or protecting‑group strategies; such investigations remain at research scale unless specifically validated.
Regulatory note
For any work related to GMP or clinical development, only use materials with appropriate pharmacopeial grade and documentation. For this item, grade/purity: Not specified for this item; refer to CoA/Spec Sheet.
Physical Properties
Item-specific (from Product Data)
Appearance: Not specified for this item; refer to CoA/Spec Sheet.
Literature/General (typical for benzothiazolyl disulfide derivatives; confirm experimentally)
Phase: Typically isolated as a solid organic compound.
Solubility: Often soluble in chlorinated and aromatic solvents (e.g., dichloromethane, chloroform, toluene) and moderately in acetone/ethyl acetate; limited solubility in water due to hydrophobic benzothiazole and disulfide. Exact solubilities are system- and sample-dependent.
Partitioning: Disulfide/benzothiazole motifs generally confer moderate hydrophobicity; logP expected to be positive (literature trend for related benzothiazole disulfides). Quantitative logP for this exact compound: Not specified for this item; refer to CoA/Spec Sheet.
pKa: The morpholine nitrogen is a tertiary amine (conjugate acid pKa typically ~8.3–8.6 for morpholine, literature). However, when embedded in a disulfide, basicity and protonation behavior can shift; measure under your conditions.
UV-Vis: Benzothiazole chromophore absorbs in the near‑UV; precise λmax/ε for this item are not specified; refer to CoA/Spec Sheet.
Melting/boiling point, density, refractive index: Not specified for this item; refer to CoA/Spec Sheet.
Practical notes
Drying prior to use is recommended (vacuum over P2O5 or in a desiccator) to ensure reproducible reactivity. Avoid strong reducing environments during handling to prevent disulfide cleavage.
Quality and Grades
Item-specific (from Product Data)
Grade/purity: Not specified for this item; refer to CoA/Spec Sheet.
General guidance for this compound class
Typical quality descriptors you may encounter for heteroaromatic disulfides include: synthetic grade (suitable for general organic synthesis), reagent grade (meets common impurity thresholds), and specialized grades (e.g., “low‑UV” for chromatography or “metal‑screened” for catalysis). The absence of a stated grade means selection should be guided by your application’s tolerance for trace acids/bases, residual solvents, or sulfur oxidation byproducts.
Stabilizers: This class generally does not require added stabilizers if stored properly. If stabilizers or inhibitors are present, they will be declared on the CoA/Spec Sheet and may affect highly sensitive reactions (e.g., radical chemistry). For this item, stabilizers: Not specified for this item; refer to CoA/Spec Sheet.
Quality control: For disulfides, identity/purity is commonly supported by 1H/13C NMR, IR (S–S stretch often weak), HRMS, and HPLC/GC purity. Trace analyses such as water content (Karl Fischer), residual solvents, and peroxide content may be reported. Specific numeric limits for this item: Not specified for this item; refer to CoA/Spec Sheet.
Fit for purpose: For electrophilic sulfenylation or radical generation, low peroxide/over‑oxidized sulfur (sulfoxide/sulfone) levels are preferred; for polymer/rubber studies, ash/metal content can be relevant. Verify with the CoA for your lot.
Reaction and Applications
Literature/General applications for benzothiazolyl disulfide reagents (extend to this morpholine disulfide analogue)
Electrophilic sulfenylation: Transfers a benzothiazolylthio (BtS–) or related thio fragment under Lewis or Brønsted acid activation to nucleophiles (enolates, silyl enol ethers, electron‑rich aromatics), forming C–S bonds with high chemoselectivity. The morpholine linkage can modulate reactivity and solubility relative to purely aryl–aryl disulfides.
Radical chemistry: Homolytic S–S cleavage (thermal, photochemical, or initiator‑mediated, e.g., AIBN/peroxide or photoredox) generates thiyl radicals that participate in anti‑Markovnikov hydro(thio)functionalization of alkenes/alkynes, thiol–ene additions, and intramolecular cyclizations.
Thiol–disulfide exchange: Under basic or nucleophilic conditions, reacts with thiols to form mixed disulfides or to install benzothiazolylthio protecting groups; useful in stepwise disulfide construction and protein‑mimetic materials chemistry (in organic media).
Sulfur donation in materials: Benzothiazole‑based disulfides are widely used in vulcanization research as accelerators/sulfur donors. This morpholine variant provides different processing characteristics (e.g., activation temperature, dispersion) for academic formulation studies.
Oxidative coupling of thiols: Functions as a mild oxidant to convert RSH to RSSR while incorporating or transferring a benzothiazolylthio motif under certain conditions.
Practical tips
Control the redox environment; trace reducing agents can deactivate electrophilic sulfenylations by premature S–S cleavage.
For enolates, pre‑cool (0 to −78 °C) to enhance regioselectivity; quench cautiously to avoid over‑sulfenylation.
Remove benzothiazole byproducts by acidic washes or silica gel chromatography; monitor for sulfoxide/sulfone impurities.
Reaction Conditions
Literature/General guidance (adjust to your substrate and scale)
Electrophilic sulfenylation of enolates/silyl enol ethers:
Solvent: DCM, MeCN, or THF (anhydrous).
Base/activation: LDA or LiHMDS for enolate generation (−78 to 0 °C), or TMS enol ethers with Lewis acid (e.g., BF3·OEt2) at −20 to 25 °C.
Stoichiometry: 1.0–1.5 equiv reagent; slow addition to control exotherm.
Workup: Aqueous quench then acidic wash to remove benzothiazole residues; silica gel purification.
Catalyst: Brønsted or Lewis acid (TFA, BF3·OEt2); 0–25 °C.
Typical times: 0.5–6 h; monitor by TLC/LC–MS.
Radical additions/cyclizations:
Initiation: AIBN (5–10 mol%) with PhSH or thermal initiator; or blue LED photoredox (e.g., Ir(ppy)3 0.5–1 mol%).
Solvent: Toluene, DCM, or MeCN; 25–80 °C (thermal) or ambient (photoredox).
Atmosphere: Inert (N2/Ar) to suppress oxidative side reactions.
Thiol–disulfide exchange:
Base: Triethylamine or DBU (5–20 mol%) in DCM/MeCN at 0–25 °C.
Provides mixed disulfides; control equivalents to avoid scrambling.
Outcomes
Yields in literature for analogous benzothiazolyl disulfides are commonly good to excellent (50–90%) with proper control of moisture and temperature. Exact yields for this specific item/substrate set will vary; verify with small‑scale trials.
Item-specific optimized conditions: Not specified for this item; refer to primary literature and your internal method development.
Safety and Handling
Item-specific (from Product Data)
GHS classification, signal word, hazard statements, pictograms: Not specified for this item; refer to SDS.
Storage conditions: Room temperature.
Shipping: Normal.
Literature/General safety guidance (not a substitute for SDS)
Likely hazards for benzothiazole–disulfide chemistries include skin/eye irritation, skin sensitization, and aquatic toxicity. Avoid inhalation of dusts and contact with skin/eyes.
PPE: Use lab coat, chemical‑resistant gloves (e.g., nitrile), and splash goggles. Handle in a fume hood to minimize inhalation exposure.
Incompatibilities: Strong reducing agents (e.g., DTT, TCEP, NaBH4) can cleave the disulfide; strong oxidants may over‑oxidize sulfur to sulfoxides/sulfones. Avoid prolonged contact with bases/acids that could promote decomposition or ring opening.
Thermal considerations: Disulfides may decompose upon overheating to release sulfur species; avoid sources of ignition and high temperatures.
First aid (overview): If on skin, wash with soap and water; if in eyes, rinse cautiously with water for several minutes and seek medical attention; if inhaled, move to fresh air; if ingested, rinse mouth and seek medical advice. Provide SDS to responders.
Environmental: Prevent release to waterways. Collect spills with inert absorbent; dispose as hazardous waste according to local regulations.
Always consult the product’s SDS for authoritative, item‑specific hazard and response information.
Solvent Selection
Literature/General guidance for this compound class
Polarity/miscibility: The benzothiazole–disulfide core is hydrophobic, while morpholine contributes some polarity. Expect poor water solubility but good solubility in moderately polar aprotic and nonpolar organic solvents (e.g., dichloromethane, chloroform, ethyl acetate, acetone, toluene). Alcohols may be usable but can participate in side reactions under strongly electrophilic conditions.
Dielectric considerations: Reactions involving ionic or polar transition states (e.g., sulfenylation of enolates) often proceed well in MeCN, DCM, THF, or 1,2‑dichloroethane. Radical or thermal processes are commonly conducted in toluene, chlorobenzene, or DCM.
Dryness: Keep solvents anhydrous for base‑mediated or moisture‑sensitive transformations (e.g., enolate chemistry) to avoid hydrolysis or competitive protonation.
When to choose this reagent vs alternatives
Compared to dialkyl disulfides, benzothiazolyl disulfides are more electrophilic and can act as better sulfenylating agents, enabling milder conditions.
Relative to N‑sulfenylated sulfenamides (e.g., MBT sulfenamides), the morpholine disulfide can offer different solubility and leaving‑group behavior; selection depends on substrate compatibility and desired rate.
Quick comparison (literature trends)
DCM/MeCN: good for electrophilic sulfenylations and polar mechanisms.
Toluene/PhCl: useful for radical or thermal homolysis regimes.
THF/Et2O: suited to base‑generated enolates; ensure dryness.
Item-specific solvent specs (solubility numbers, UV cutoff, water content): Not specified for this item; refer to CoA/Spec Sheet.
Storage and Reconstitution
Item-specific (from Product Data)
Storage conditions: Room temperature.
Shipped in: Normal.
General handling guidance for disulfide reagents
Keep container tightly closed in a dry, well‑ventilated place. Store in original container or amber glass to minimize light exposure that might promote homolysis.
Protect from strong reducing/oxidizing agents. Avoid prolonged exposure to elevated temperatures.
If solidifies or forms clumps, gently break up under inert atmosphere; do not grind vigorously if dust formation is a concern.
Reconstitution: If supplied as a solid and solution is desired, dissolve in an appropriate anhydrous organic solvent (e.g., DCM, MeCN, THF, toluene) at the required concentration. Filter if necessary to remove particulates.
Stock solutions: Prepare fresh when possible. For short‑term storage, keep sealed under inert gas at 2–8 °C or room temperature depending on solvent stability; avoid prolonged storage in protic solvents.
Item-specific details (hydration state, stabilizers, solution shelf life): Not specified for this item; refer to CoA/Spec Sheet.
Molecular formula: Not specified for this item; refer to CoA/Spec Sheet.
Molecular weight: Not specified for this item; refer to CoA/Spec Sheet.
SMILES: Not specified for this item; refer to CoA/Spec Sheet.
Literature/General description of structure
Core features: a fused bicyclic heteroaromatic benzothiazole ring (benzene fused to thiazole) tethered through a disulfide linkage (–S–S–) to a morpholine ring (a six‑membered heterocycle containing one O and one tertiary amine N).
Functional groups: heteroaromatic thiazole sulfur and nitrogen, an aryl–sulfur bond, a disulfide moiety (RSSR), and a tertiary amino ether ring (morpholine). No stereogenic centers are expected.
2D topology (in words): the benzothiazole ring bears a thio substituent at the 2‑position that is connected via a disulfide bridge to sulfur bound at the 4‑position of morpholine, which is opposite the ring oxygen.
Notes
Disulfide-containing benzothiazole derivatives are commonly used as electrophilic sulfenylating reagents and sulfur donors; the morpholine fragment modulates polarity and reactivity relative to dialkyl or diaryl analogs.
Synthetic Utility
Literature/General utility of benzothiazolyl disulfides; applicable principles to this morpholine derivative
C–S bond formation: Acts as an electrophilic sulfur source for alpha‑sulfenylation of carbonyl compounds, sulfenylation of indoles/anilides, and dearomative or heteroaromatic functionalizations. The benzothiazolylthio unit is a classic leaving group that can be displaced under mild conditions.
Protecting/activating group chemistry: Installation of the benzothiazolylthio (BtS) group on sulfur or nitrogen can serve as a removable activating handle for subsequent cross‑couplings or nucleophilic substitutions; reductive or nucleophilic removal regenerates the parent thiol/amine.
Radical cascades: Under photoredox or thermal conditions, S–S scission delivers thiyl radicals enabling thiol–ene/yne additions and intramolecular cyclizations; the benzothiazole fragment stabilizes the radical and influences selectivity.
Disulfide engineering: Enables stepwise construction of asymmetrical disulfides by exchange with thiols, useful in polymer/materials modification and probe assembly.
Leaving‑group economy: Benzothiazole byproducts are often easily separated by acid extraction or chromatography, aiding purification.
Strategic considerations
Choice of base and solvent is key for enolate sulfenylations (e.g., LDA/THF or silyl enol ethers in DCM with Lewis acids). For electron‑rich arenes/heteroarenes, mild Lewis acids (e.g., BF3·OEt2) or Brønsted acids can promote electrophilic substitution.
Monitor for over‑oxidation (sulfoxide/sulfone) and control temperature to preserve disulfide integrity.
Target Specificity
Not applicable.
This product is a small‑molecule reagent, not a biological targeting agent or antibody. No antigen/epitope specificity, clone, or isotype information applies to this item.
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