This compound belongs to the class of organic compounds known as phenothiazines. These are polycyclic aromatic compounds containing a phenothiazine moiety, which is a linear tricyclic system that consists of a two benzene rings joined by a para-thiazine ring.
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.
1.Jie Chen, Zexiao Cheng, Yaqi Liao, Lixia Yuan, Zhen Li, Yunhui Huang. (2022) Selection of Redox Mediators for Reactivating Dead Li in Lithium Metal Batteries. Advanced Energy Materials, 12 (40):(2201800). [PMID:][10.1002/aenm.202201800]
2.Haoyuan Yin, Haijun Chi, Zhuye Shang, Ali Qaitoon, Jianfei Yu, Qingtao Meng, Zhiqiang Zhang, Hongmin Jia, Run Zhang. (2021) Development of a new water-soluble fluorescence probe for hypochlorous acid detection in drinking water. Food Chemistry: Molecular Sciences, [PMID:35415634][10.1016/j.fochms.2021.100027]
3.Su Yi, Zheng Zefei, Sun Lingjie, Sun Wenzhe, Zhang Yongqi, Liu Huapeng, Yang Chenfei, Li Shouzhen, Wang Miaoyu, Chen Xing, Ding Shuaishuai, Yang Fangxu, Zhang Xiaotao. (2025) Broadband-absorbing structurally distorted cocrystal with enhanced nonradiative decay for solar interfacial water evaporation. Science China-Materials, [PMID:][10.1007/s40843-025-3563-0]
4.Rongfeng Yang, Fan Wang, Wan-er Cui, Wei Chen, Tianyu Lei, Dongjiang Chen, Dongxu Chen, Li Xia, Chi Zhang, Kaijun Cheng, Runyi Dai, Yichao Yan, Xiaobin Niu, Yin Hu. (2025) Regenerative redox mediator for the suppression of dead lithium for lithium sulfur pouch cell. Energy Storage Materials, [PMID:][10.1016/j.ensm.2025.104030]
5.Haiyan Ma, Yuyao Li, Xianjing Zhang, Ling Yan, He Gao, Lan Liu, Longbin Xu. (2025) A phenothiazine-based fluorescent probe for ultrafast and selective hypochlorous acid detection with hydrogel-integrated smartphone readout. SPECTROCHIMICA ACTA PART A-MOLECULAR AND BIOMOLECULAR SPECTROSCOPY, [PMID:41202412][10.1016/j.saa.2025.127114]
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Recensioni
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Application Protocols
No item-specific tested application protocols are provided for this reagent. Refer to the Reaction & Applications and Reaction Conditions sections for literature-style setup guidance (e.g., photoredox donor use, electrochemical mediation, directed lithiation chemistry).
General example workflows (literature, non-binding)
Photoredox sacrificial donor screen: Prepare 0.05 M substrate in MeCN, add 1 mol% acridinium photocatalyst, 1–2 equiv 10-methylphenothiazine, irradiate with 450 nm LEDs under air, monitor by LC–MS.
Electrochemical mediation: 10 mM mediator in MeCN/0.1 M TBAPF6, cyclic voltammetry scan 0 to +1.2 V vs SCE, assess reversibility and follow-up controlled potential electrolysis as needed.
These are illustrative only. Optimize conditions for your specific system and consult the CoA/SDS for handling limits.
Biological Roles
This product is intended for research use only. No medical or clinical claims are made.
General biochemical context (literature)
Phenothiazine is a privileged scaffold in medicinal chemistry; N-substitution modulates electronic properties and lipophilicity. While many phenothiazine derivatives exhibit biological activities, 10-methylphenothiazine here is considered as a chemical reagent and redox mediator rather than a bioactive agent.
Redox behavior: The capacity of phenothiazines to reversibly form radical cations underlies their use as electron shuttles in biochemical model systems and as probes in oxidative stress studies in vitro.
Spectroscopic probes: The persistent radical cation of phenothiazines exhibits characteristic UV–vis/NIR absorption bands; in biochemical settings this has been used to monitor electron-transfer events in model membranes or proteins (literature), but application requires careful control to avoid nonspecific oxidation.
Practical guidance
Aqueous compatibility is limited due to hydrophobicity; use co-solvents (DMSO, MeCN) for in vitro assays, maintaining low final organic content.
Avoid interpreting any observation as therapeutic relevance; for mechanistic biochemical experiments, include appropriate redox and solvent controls.
Item-specific biological roles are not provided; consult the literature if you plan exploratory mechanistic studies.
Buffer Applications
Not typically applicable. 10-Methylphenothiazine is a neutral, hydrophobic organic reagent and does not function as a buffering agent. It has poor water solubility and lacks a conjugate acid/base pair in the physiological pH range suitable for buffering.
For experiments requiring this compound in aqueous systems, consider:
Preparing concentrated stocks in DMSO, DMF, or MeCN and diluting into buffer to ≤1–2% organic content.
Using surfactants or cyclodextrins if higher apparent solubility is required (evaluate for your assay).
Refer instead to the Solvent Selection and Reaction & Applications sections for practical usage guidance.
Green Alternatives
Context: 10-Methylphenothiazine is a high-performance organic redox mediator/electron donor. Greener choices focus on solvent selection, alternative donors with lower environmental impact, and process intensification.
Greener solvents (literature)
2-Methyltetrahydrofuran (2-MeTHF): biomass-derived, lower peroxide tendency than THF; suitable for many ET-mediated reactions.
Anisole or toluene: aromatic, lower toxicity than chlorinated solvents; transparent enough for many visible-light photoredox reactions.
Dimethyl carbonate (DMC) or propylene carbonate: benign profiles; useful in electrochemistry depending on conductivity and potential window.
Alternative organic donors (literature comparison)
5,10-Dihydrophenazine/phenoxazine derivatives: similar redox performance; often accessible from commodity anilines/quinones.
Ascorbate or Hantzsch ester: biodegradable hydride/electron donors for some photoredox manifolds.
Small comparison (illustrative; literature)
MeCN vs 2-MeTHF: MeCN offers wider potential window and salt solubility for CV; 2-MeTHF is greener and suitable for many photoredox reactions, though polarity is lower.
DCM vs anisole: DCM maximizes solubility and ease of removal; anisole avoids chlorinated waste and supports high-temperature or LED-driven processes.
Process strategies
Flow photochemistry improves photon economy and reduces solvent inventories.
Electrochemical oxidation of the donor can replace stoichiometric chemical oxidants, reducing waste.
Select green options that maintain required redox potential and kinetics; validate by small-scale screening.
Pharmaceutical Uses
No medical or clinical claims. This product is for research use only.
Intermediate/scaffold: Phenothiazines constitute a core chemotype in numerous drug discovery programs. 10-Methylphenothiazine can serve as a synthetic intermediate for structure–activity exploration (e.g., further substitution at 3,7-positions or N-derivatization) during medicinal chemistry campaigns.
Analytical reference: May be used as a reference material for method development in LC–UV/LC–MS for phenothiazine-related impurities or degradants in manufacturing research.
Materials interfaces: In device-related pharmaceutical analytics (e.g., photostability testing), phenothiazine scaffolds are sometimes used as redox/photostability probes; applications require risk assessment and are not therapeutic.
Regulatory notes
Pharmacopeial status: Not specified for this item; refer to CoA/Spec Sheet and applicable pharmacopeias if intended for regulated workflows.
Residual solvent/metals: For cGMP or GLP-adjacent research, request detailed impurity profiles (ICP-MS, GC residuals) if relevant.
All uses must remain within preclinical research, method development, or materials evaluation contexts.
Physical Properties
Item-specific specifications
Appearance: 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.
Melting point, boiling point, density, refractive index, UV cutoff, water/peroxide/metal content: Not specified for this item; refer to CoA/Spec Sheet.
Literature/general values (for context only; not product specifications)
Empirical formula: C13H11NS (literature)
Formula weight: ~213.30 g/mol (literature)
Physical form: typically an off-white to pale-yellow crystalline solid (literature)
Solubility profile: sparingly soluble in water; freely soluble in common organic solvents such as dichloromethane, chloroform, THF, toluene, acetonitrile, ethyl acetate, DMF, and DMSO (literature)
Acid–base behavior: tertiary anilide-like nitrogen (non-basic in water; can be protonated in strong acids); no ionizable groups in neutral water (literature)
Redox: readily forms a persistent radical cation upon one-electron oxidation; reversible waves observed in cyclic voltammetry (literature). Half-wave potentials reported for N-aryl/N-alkyl phenothiazines are commonly E1/2 ~ +0.6 to +0.9 V vs SCE, medium dependent (literature)
Practical notes
Being aromatic and hydrophobic, dissolution is fastest in moderately polar aprotic media (MeCN, DCM) or aromatic solvents (toluene). Gentle warming and sonication help achieve homogeneous solutions. Always verify exact properties for your lot on the CoA.
Quality and Grades
Item-specific quality information
Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.
Stabilizers/Inhibitors: Not specified for this item; refer to CoA/Spec Sheet.
How to interpret potential grades (general guidance)
Research/Technical grade: Suitable for most synthetic, materials, and analytical method-development work. Impurities may include residual solvents, trace metals, or low-level oxidized congeners (e.g., sulfoxide). Verify by NMR/LC–MS as needed.
High-purity/98–99% grade: Useful for mechanistic studies, electrochemistry, and photoredox benchmarking where background reactivity must be minimized. Typically associated with tighter limits on UV-absorbing impurities and peroxides.
HPLC grade (if offered): Not about chromatographic performance of the solid per se, but implies stringent control of UV-absorbing/fluorescent impurities that might interfere with detection.
Redox sensitivity: Trace oxidation to sulfoxide/sulfone or formation of colored radical cations can occur upon light/air exposure. Light-protected, desiccated storage helps preserve assay.
Metals: For photoredox/electrochemistry, low metal background is desirable; if critical, request ICP data.
Identity/assay confirmation: 1H/13C NMR (diagnostic N–CH3 singlet), HRMS, and melting point are common. For photoredox applications, cyclic voltammetry can benchmark the oxidation potential.
Always rely on the item’s CoA/Spec Sheet for definitive grade, assay, and impurity limits for your lot.
Reaction and Applications
Use domains (literature/general)
Redox mediator/electron donor: 10-Methylphenothiazine readily undergoes reversible one-electron oxidation to a persistent radical cation, making it a potent organic reductant in photoredox and electrochemical systems.
Photoredox catalysis: Serves as a sacrificial donor or co-catalyst in oxidative quenching cycles with acridinium, porphyrin, or iridium photocatalysts. Facilitates C–O, C–N, and C–C bond formations via radical pathways.
Organocatalyst analog: N-alkyl phenothiazines are used as electron-transfer mediators for dehalogenations, hydrodehalogenations, and radical polymerizations under visible light.
Materials: Precursor and dopant for hole-transport layers; building block for donor–acceptor polymers and electroactive dyes.
Synthetic intermediate: Platform for further substitution at 3,7-positions (via directed lithiation or electrophilic substitution) and N-oxidation to access sulfoxide/sulfone derivatives.
Practical tips (literature)
Exclude oxygen/moisture for reductive transformations; for oxidative quenching cycles trace O2 may be tolerated or even required for catalyst turnover—optimize case-by-case.
Light: Blue to violet LEDs (390–455 nm) commonly used; monitor for photo-bleaching and radical cation accumulation (color change).
Drying: If needed, dry from toluene or azeotrope with acetonitrile; store under inert gas in amber containers.
Note: The above are literature-based application domains; verify conditions with small-scale trials for your specific system.
Reaction Conditions
General guidance compiled from literature for phenothiazine-based systems; verify experimentally for your target transformation.
Photoredox electron-donor applications
Typical solvent: MeCN, DCM, or 2-MeTHF; 0.01–0.1 M substrate.
Light source: 390–455 nm LEDs; 5–40 mW/cm².
Catalyst: Often paired with acridinium photocatalysts (1–2 mol%) in oxidative quenching cycles; 10-methylphenothiazine 1–3 equiv as sacrificial donor or 5–20 mol% as co-catalyst.
Atmosphere: Air or O2 sometimes assists re-oxidation; inert atmosphere for highly reducing manifolds.
Temperature: Ambient; mild heating (30–40 °C) can improve rates.
Electrochemistry (mediated oxidations/reductions)
Solvent/electrolyte: Anhydrous MeCN with 0.1 M TBAPF6.
Electrode setup: Glassy carbon working, Pt counter, Ag/AgCl or Ag/Ag+ reference.
Potential: Oxidation onset typically +0.6 to +0.9 V vs SCE for N-alkyl phenothiazines (medium dependent).
Directed lithiation and electrophile trapping
Base: s-BuLi or n-BuLi with TMEDA at −78 to −40 °C.
Quench: CO2, DMF, electrophiles (RX, RCHO, RCOCl) to install 3,7-substituents.
Solvent: THF or 2-MeTHF; rigorously anhydrous.
Expected outcomes (illustrative)
Many photoredox couplings furnish 50–90% yields depending on substrate electronics.
These parameters are literature norms and not product specifications.
Safety and Handling
Authoritative safety information resides in the SDS; consult it before use.
Item-specific hazard data
GHS classification, pictograms, signal word, H-statements: Not specified for this item; refer to SDS.
Storage: Protected from light; Room temperature; Desiccated; Cool (per Product Data). Shipped under normal conditions.
General handling guidance (literature/general)
Potential hazards: Aromatic heterocycles may cause irritation to skin, eyes, or respiratory tract. Dust may be combustible in air. Phenothiazine scaffolds can undergo photo-oxidation; protect from light to minimize degradation.
PPE: Use lab coat, safety glasses, and appropriate chemically resistant gloves. Handle powders in a fume hood to avoid dust inhalation.
Incompatibilities: Strong oxidizers (can induce rapid oxidation to radical cations or sulfoxides); strong acids may lead to protonation and enhanced solubility; strong bases and alkylating agents can further functionalize the nitrogen or rings.
First aid overview: If inhaled—move to fresh air; seek medical attention if symptoms persist. Skin/eye contact—rinse with plenty of water for at least 15 minutes; remove contaminated clothing. If ingested—rinse mouth; do not induce vomiting; seek medical attention. Refer to SDS for detailed measures.
Fire safety: Use CO2, dry chemical, or foam. Combustion may produce SOx/NOx—firefighters should wear self-contained breathing apparatus.
Waste disposal: Treat as organic hazardous waste; follow institutional and local regulations.
Solvent Selection
Compound class: hydrophobic, conjugated heteroaromatic amine (tertiary), neutral in water; strong π-system and moderate polarizability.
General solubility/miscibility (literature trends)
Poorly soluble: water and aqueous buffers at neutral pH.
Selection guidance by application
Photoredox catalysis/electron-transfer studies: MeCN is often preferred for high dielectric constant and transparency; DCM/CHCl3 offer good solubility and rapid mass transfer. For greener choices, see 2-MeTHF or anisole when compatible with light transmission and kinetics.
Electrochemistry: Anhydrous MeCN with 0.1 M TBAPF6 or similar electrolyte offers wide potential windows and good conductivity.
Synthesis and N-functionalization: THF, DMF, or toluene depending on base and electrophile; DCM for electrophilic aromatic substitutions.
Quick comparison (literature)
MeCN: polar aprotic, excellent for CV and photochemistry; dissolves salts and the substrate.
DCM: non-protic, good solubility; easy removal; limited for strongly basic conditions.
THF/2-MeTHF: good for metalation and organometallic steps; 2-MeTHF provides greener profile with similar solvation.
Toluene/anisole: aromatic, high boiling; useful for thermal reactions and greener photoredox alternatives.
Note: Verify actual solubility and stability in your chosen solvent experimentally and consult the CoA for any solvent-related restrictions.
Container: Store in a tightly sealed amber vial within a desiccator or low-humidity cabinet. Consider inert gas backfill (argon or nitrogen) to minimize air oxidation.
Light/air sensitivity: Phenothiazine cores can undergo photo-oxidation; minimize exposure during weighing and solution prep.
Reconstitution and solution handling (literature/general)
Solvents: Prepare stock solutions in dry MeCN, DCM, THF, toluene, DMF, or DMSO as appropriate. Typical concentrations: 10–100 mM for photoredox/electrochemistry; adjust to solubility.
Filtration: If particulate is present, clarify through a PTFE syringe filter (0.2–0.45 µm).
Stability: Solutions are generally stable for hours to days under inert atmosphere and subdued light; colored solutions may indicate radical cation formation. For extended storage, keep aliquots in amber vials at 2–8 °C under inert gas and verify by LC–MS/NMR before use.
Freeze–thaw: For DMSO or DMF stocks, avoid repeated freeze–thaw; prepare single-use aliquots.
Always refer to the CoA/SDS for any lot-specific stability information or restrictions beyond the general guidance above.
Structure and Identity
Brief overview: 10-Methylphenothiazine is an N-methylated phenothiazine, a tricyclic, electron-rich heteroaromatic containing both sulfur and nitrogen in the central ring. The 10-position corresponds to the ring nitrogen; methylation there increases electron-donor strength and alters redox behavior relative to phenothiazine.
Item-specific identifiers (from Product Data)
SKU: M157970
CAS: 1207-72-3
CID: 71015
InChIKey: 308772 (as provided)
SMILES: Not specified for this item; refer to CoA/Spec Sheet.
Literature/computed identifiers and descriptors (non-specification)
Common name: 10-Methylphenothiazine (N-methylphenothiazine)
Molecular formula (literature): C13H11NS
Molecular weight (literature): ~213.30 g/mol
Example SMILES (literature): CN1c2ccccc2Sc2ccccc21
Core features: Tricyclic phenothiazine system; 1 ring nitrogen (sp2), 1 thioether sulfur; N-methyl substituent at the bridgehead (10-position); fully conjugated polycyclic aromatic.
2D structure description (literature)
Two benzene rings fused to a central six-membered heterocycle that contains one nitrogen and one sulfur at opposite bridgehead positions. The nitrogen bears a methyl substituent (–CH3) projecting pseudo-axially from the tricycle. Aromaticity extends across the framework, enabling reversible one-electron oxidation to a persistent radical cation in many media.
Note: Where item-specific identifiers are not provided above, consult the product’s CoA/Spec Sheet for definitive structural descriptors for this specific lot.
Synthetic Utility
Functional handles and reactivity (literature/general)
Tertiary amine (aromatic): Undergoes quaternization, N-oxidation, or reductive alkylation to diversify electronic properties. N-methyl is robust under many conditions but can be further functionalized (e.g., N-oxide formation).
Electron-rich aromatic rings: Amenable to electrophilic aromatic substitution (EAS), especially at 3,7-positions; sulfoxidation/sulfonylation at sulfur is also accessible.
Directed metalation: Lithiation at 3,7-positions (e.g., with s-BuLi/TMEDA at low temperature) followed by trapping with electrophiles affords a broad array of substituted phenothiazines.
Named/representative transformations (literature)
Oxidative couplings: Photoredox or electrochemical cross-couplings using the phenothiazine radical cation to initiate C–C or C–N bond formation.
Buchwald–Hartwig/Chan–Lam: Post-functionalization of halo-phenothiazines prepared from 10-methylphenothiazine.
Sulfur functionalization: Controlled oxidation to sulfoxide/sulfone adjusts photophysical and redox properties.
Retrosynthetic value
10-Methylphenothiazine serves as a convergent node: the N-methyl protects and tunes redox, while ring positions can be elaborated to donor–acceptor motifs, fluorophores, or hole-transport monomers. Its robust framework tolerates a variety of bases, oxidants, and catalytic systems, making it a versatile starting point for heteroaromatic libraries and materials components.
Target Specificity
Not applicable. This product is a small-molecule chemical reagent, not a biological macromolecule or affinity reagent. No antigen/epitope targets, clone information, or species reactivity apply.
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