≥97% pour les flux de travail chromatographiques et analytiques sensibles nécessitant une interférence de ligne de base minimale.
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Stockage & expédition
Store at 2-8°C Expédition Wet ice. Consultez le COA spécifique au lot pour les spécifications exactes.
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Documents qualité
SDS, COA, fiche technique et fiche de spécifications disponibles au téléchargement. COA spécifique au lot accessible via la recherche par numéro de lot.
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Preuve documentaire
Cité dans 0 publications à comité de lecture couvrant la chromatographie, la synthèse organique et les réactions de couplage croisé.
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
No assay-specific protocols (e.g., WB, IHC, IF, FC) apply to this small-molecule reagent.
General laboratory usage suggestions (non-binding):
Stock solutions: Prepare at 10–100 mM in DMSO or acetonitrile; store aliquots at 2–8 °C protected from light. Allow to warm to room temperature before opening to minimize moisture ingress.
Reaction setup: For condensations, combine equimolar aldehyde and 2-acetylbenzothiazole in ethanol with catalytic piperidine; heat at 60–80 °C and monitor by TLC/HPLC. For oxime formation, add hydroxylamine·HCl and sodium acetate in ethanol and stir at ambient to 50 °C.
Analytics: Track by HPLC-UV (254–300 nm) or LC–MS. Record 1H/13C NMR to confirm formation of vinylic or imine protons in derivatives.
Biological Roles
This product is supplied strictly for research use; no medical or clinical use is intended or implied.
General context (literature; not product-specific):
Benzothiazole is a heteroaromatic motif found in various research probes, dyes, and enzyme ligands. Its electron-accepting character supports intramolecular charge-transfer when conjugated to electron donors (e.g., in styrylbenzothiazoles), enabling studies of membrane polarity and microenvironmental sensing.
2-Acetylbenzothiazole itself is a neutral aromatic ketone used primarily as a synthetic precursor. It does not serve as a biological buffer or nutrient. It may appear as a structural element in research compounds used to interrogate protein–ligand interactions or to modulate photophysical behavior in labeled systems.
Metabolic/biotransformation insights are limited for this specific ketone; as with many aromatic heterocycles, oxidative metabolism (ring or side-chain oxidation) and conjugation could occur in biological systems. Such information, when needed, should be sourced from primary ADME studies of the final research compound rather than this intermediate.
Handling in bioassays:
Prepare concentrated stocks in DMSO or acetonitrile; dilute into assay media to minimize solvent content (<0.5–1% v/v typical) while monitoring precipitation.
Verify compound stability under assay illumination if optical readouts are used; benzothiazole chromophores can absorb in the near-UV.
For any biological testing, consult institutional guidelines and perform appropriate hazard and waste assessments.
Buffer Applications
2-Acetylbenzothiazole is not a buffering agent and is not commonly used to prepare pH buffer systems. It lacks acid/base pairs in the physiological pH range and is only weakly enolizable under strong base.
Practical note: If dissolution into biological buffers is needed (e.g., for screening), prepare a concentrated stock in DMSO or acetonitrile and add to the buffer with vigorous mixing, keeping final cosolvent below assay tolerance limits.
For buffer preparation guidance, consider dedicated buffering agents (e.g., phosphate, HEPES, Tris) rather than this aromatic ketone.
Green Alternatives
While 2-acetylbenzothiazole itself is the target substrate, greener choices can be made for solvents, catalysts, and auxiliaries used with it.
Replace chlorinated solvents (DCM, CHCl3) with ethyl acetate, 2-MeTHF, CPME, or toluene when feasible.
Favor protic, bio-derived solvents (ethanol, isopropanol) for Knoevenagel/aldol condensations.
Avoid high-boiling polar aprotics (DMF/DMSO) at scale; consider MeCN or MeTHF for improved workup and lower EHS burdens.
Catalyst/base choices:
Use organocatalysts (piperidine, proline, ammonium acetate) or solid-supported bases (basic alumina) to minimize metal residues.
For oxime/hydrazone formation, catalytic acetic acid in ethanol is effective and lower impact than strong mineral acids.
Energy/time efficiency:
Employ solvent-free or neat grinding methods for aldehyde condensations where substrates are liquid/low-melting; microwave heating in ethanol can shorten reaction times and reduce energy consumption (literature precedents).
Performance: MeCN often faster; ethanol may require slightly elevated temperatures.
2-MeTHF/CPME vs. THF/DCM:
EHS: improved safety (lower peroxide tendency than THF; reduced chlorinated waste vs. DCM).
Performance: good for workups/crystallization; polarity slightly lower than THF, adjust bases accordingly.
Note: Select alternatives consistent with your process safety dossier and regulatory constraints; validate on target scale.
Pharmaceutical Uses
No excipient or pharmacopeial status is specified for this item; it is offered for research use only.
General (non-clinical) context:
2-Acetylbenzothiazole is used as a synthetic intermediate in discovery chemistry. Its reactivity (enolate formation, condensations, α-functionalization) enables access to heteroaromatic scaffolds that may be evaluated during lead identification and SAR campaigns.
It is not used as a buffering agent, preservative, or functional excipient in finished dosage forms.
If material is incorporated into GMP-related development workflows as a starting material or intermediate, ensure supplier qualification, impurity profiles, and residual solvent limits are defined. For this catalog item, specific GMP grade or compendial compliance is not specified; refer to CoA/Spec Sheet.
Handling in formulation research (if applicable):
Prepare solutions in pharmaceutically acceptable organic solvents (e.g., ethanol, PEGs) only for nonclinical studies; confirm solubility and stability by HPLC.
Avoid claims of therapeutic utility; all uses should remain within lab-scale research and development.
Physical Properties
Item-specific (from Product Data):
Appearance: Not specified for this item; refer to CoA/Spec Sheet.
Molecular weight: Not specified for this item; refer to CoA/Spec Sheet. (General literature: ~177.22 g/mol)
Literature/general reference values (non-spec; for planning only):
Physical state: typically a crystalline solid (aromatic ketone).
Melting point: commonly reported in the mid-50s °C range (e.g., ~54–58 °C; literature).
Boiling point: high-boiling aromatic ketone; values around ~300 °C at atmospheric pressure have been reported (literature). Distillation is not generally preferred; purification via recrystallization is typical.
Density: not widely tabulated; expect near 1.2 g/mL for analogous aromatic thiazole ketones (qualitative literature comparison; exact value not established for this item).
Refractive index: not applicable (solid); solutions may be characterized spectroscopically instead.
UV–Vis: strong π→π* absorption in near-UV due to benzothiazole chromophore (literature).
Solubility: sparingly soluble in water; soluble in common organic solvents (ethanol, methanol, acetone, acetonitrile, DMSO, DMF, THF, dichloromethane, toluene) (literature). Solubility increases with temperature and solvent polarity for the carbonyl-functionalized ring.
pKa: not applicable to the neutral ketone; the α-CH of the acetyl group is moderately acidic in strong base due to resonance with the carbonyl and heteroaromatic system (qualitative).
logP: expected moderate lipophilicity for benzothiazole ketones (literature qualitative; exact value not established).
Important: Numerical property values are not specified for this item; consult CoA/SDS and primary literature before critical process design.
Quality and Grades
Item-specific: Grade/purity not specified for this item; refer to CoA/Spec Sheet. No stabilizers or inhibitors are listed in the Product Data.
General guidance on quality for heteroaromatic building blocks:
Purity metrics: For condensation chemistry (e.g., formation of styrylbenzothiazoles, hydrazones/oximes), typical lab practice targets ≥95% purity by HPLC/GC with supporting NMR and MS. Trace acidic/basic impurities can catalyze side reactions in base- or acid-promoted condensations.
UV background: Benzothiazoles absorb in the near-UV; for photophysical studies or analytical quantification, low-UV-impurity material is preferred. HPLC-grade solvents and amber glass can minimize spectral baseline noise.
Water content: While ketones are less hygroscopic than amides or salts, water can affect base-catalyzed condensations (Knoevenagel/aldol) and oxime formation kinetics. Karl Fischer specifications, when provided, help ensure reproducibility. For this item, specific water limits are not specified; refer to CoA/Spec Sheet.
Metals/ions: Typically not relevant unless the material is produced via metal-catalyzed routes; residual Pd/Cu/Ni can poison subsequent catalytic steps. For this item, metal limits are not specified; refer to CoA/Spec Sheet.
Lot traceability: Verify lot-specific characterization (1H/13C NMR, HRMS, HPLC/GC, melting point). For solid aromatic ketones, a sharp and literature-consistent melting point supports identity.
If you require a particular grade (e.g., ≥98% GC, low water, or catalyst-screened), contact us for available specifications or a custom lot.
Reaction and Applications
2-Acetylbenzothiazole is a versatile building block; the conjugated methyl ketone adjacent to a benzothiazole ring undergoes enolization and nucleophile/electrophile chemistry, enabling efficient access to functional dyes and heteroaromatics.
Carbon–carbon bond formation (literature):
Knoevenagel/aldol condensations: With aromatic aldehydes (e.g., benzaldehydes), delivers (E)-2-styrylbenzothiazoles (benzothiazolyl enones/alkenes), widely studied as push–pull chromophores. Catalysts: piperidine, pyrrolidine, ammonium acetate, or basic alumina; solvents: EtOH, iPrOH, MeCN. Typical yields: moderate to high.
Claisen–Schmidt variants: Under basic conditions (NaOH/EtOH), the methyl ketone couples with aryl aldehydes; control over E/Z via temperature and catalyst loading.
Carbon–heteroatom derivatization:
Oxime/hydrazone formation with hydroxylamine or hydrazines in alcohols under acid catalysis; provides analytical derivatives and synthetic handles.
α-Halogenation (Br2, NBS) at the acetyl methyl affords 2-(haloacetyl)benzothiazoles, enabling substitution with amines/thiols to access amide/thiolated derivatives.
Ring-directed reactivity (general):
The benzothiazole ring can act as a ligand or electron-accepting moiety; the 2-acyl substituent modifies ring electronics, often enhancing ICT in downstream styryl derivatives (basis of many benzothiazole dyes and probes).
Materials and sensing (non-clinical, research use only):
Precursor to styrylbenzothiazoles and related donor–acceptor systems for fluorescence studies, solvatochromic probes, and model push–pull frameworks.
Practical tips:
Drying: For base-catalyzed condensations, dry solvent and glassware improve rates and selectivity.
Workup: Condensation products often crystallize on cooling; ethanol or ethyl acetate/hexane systems give clean isolations.
Analysis: Strong UV absorbance; HPLC-UV (254–300 nm) and LC–MS provide robust tracking of reactions and purity.
Reaction Conditions
General literature guidance for common transformations of 2-acetylbenzothiazole (non-binding; optimize for your substrates):
Knoevenagel/Claisen–Schmidt condensation with aromatic aldehydes:
Typical conditions: 2-acetylbenzothiazole (1.0 equiv), aldehyde (1.0–1.2 equiv), catalytic piperidine (5–20 mol%) or ammonium acetate (0.5–1.0 equiv), solvent EtOH or MeCN (0.1–0.5 M), 50–80 °C, 1–6 h.
Expected outcome: (E)-styrylbenzothiazoles in 60–95% yield; crystallization from EtOH common.
Oxime formation:
Hydroxylamine hydrochloride (1.2–1.5 equiv), NaOAc (1.5–2.0 equiv), EtOH or MeOH (0.1–0.3 M), 20–60 °C, 1–3 h. Workup by dilution with water and filtration/extraction; typical yields 70–95%.
α-Bromination of the acetyl group:
NBS (1.05–1.2 equiv) or Br2 (1.05–1.1 equiv), solvent acetic acid, DCM, or MeCN; 0–25 °C; catalytic acid (AcOH) if needed. Monitor by TLC/HPLC; quench with sodium bisulfite; yields often 65–90%.
Reduction of the carbonyl (where compatible):
NaBH4 in MeOH/THF at 0–25 °C can reduce the ketone to the corresponding secondary alcohol; ring stability generally maintained. Workup with aqueous NH4Cl; yields vary.
Purification and analysis:
Many products crystallize; else, use flash chromatography (hexanes/EtOAc or toluene/EtOAc gradients). Monitor by UV (254–300 nm). LC–MS provides rapid confirmation of mass and purity.
Notes:
Avoid strong mineral bases in protic solvents at high temperatures to limit side reactions (e.g., ring opening or over-condensation).
Scale-up: ensure heat removal and control of exotherms during halogenations/condensations; implement in-line quench and antioxidant strategies as needed.
Safety and Handling
Item-specific hazard data (from Product Data):
Signal word: Not specified for this item; refer to SDS.
H-statements: Not specified for this item; refer to SDS.
GHS classification/pictograms: Not specified for this item; refer to SDS.
General safety guidance for aromatic heterocycles and ketones (literature/industry practice; not product-specific):
Expected hazards: May cause skin/eye irritation and respiratory tract irritation; harmful if swallowed. Avoid dust formation. Handle under adequate ventilation.
PPE: lab coat, safety glasses or chemical splash goggles, and appropriate chemical-resistant gloves (e.g., nitrile). Use a fume hood when weighing, transferring, or heating.
Incompatibilities: strong oxidizing agents; strong bases/acids may induce condensation, hydrolysis, or ring activation reactions. Avoid halogenating agents unless intended (α-halogenation can occur at the acetyl methyl).
Thermal/chemical stability: Typically stable under ambient conditions; avoid prolonged heating above the melting point and minimize exposure to strong light/UV during extended storage to preserve chromophoric integrity.
First aid (overview; follow institutional SOPs):
Inhalation: move to fresh air; seek medical attention if symptoms persist.
Skin/eye contact: rinse thoroughly with water for at least 15 minutes; remove contaminated clothing; seek medical attention if irritation persists.
Ingestion: rinse mouth; do not induce vomiting; obtain medical advice.
Spills: Collect solids by gentle sweeping; avoid dust; for solutions, absorb with inert material. Dispose according to local regulations.
Always consult the product SDS for authoritative hazard classification, exposure limits, and emergency procedures.
Solvent Selection
2-Acetylbenzothiazole is a moderately polar aromatic ketone and dissolves well in many organic solvents. Solvent choice should consider reaction type (nucleophilic addition/condensation vs. electrophilic functionalization) and downstream isolation.
Poor solubility: water; alkanes at room temperature.
Dielectric environment: polar aprotic media (DMF, DMSO, MeCN) enhance base-mediated enolate chemistry; protic alcohols (EtOH, iPrOH) support Knoevenagel/aldol with organic base catalysts.
Selection by application:
Aldol/Knoevenagel-type condensations with aldehydes: ethanol or 2-propanol (catalytic piperidine or ammonium acetate) for greener profiles; DMF/MeCN for challenging substrates.
Oxime/hydrazone formation: ethanol/MeOH with AcOH catalyst; or MeCN with catalytic acid for water-sensitive partners.
α-Halogenation (bromination/chlorination) at the acetyl group: glacial acetic acid, chloroform, or CCl4 (legacy) have literature precedence; modern choices favor DCM or MeCN under controlled conditions.
Metal-catalyzed downstream couplings of derived enones: toluene, dioxane, MeTHF, or CPME can be effective, depending on catalyst system.
Small comparison (general):
Ethanol: green, inexpensive, easy workup; may promote reversible imine/oxime exchange in water-rich systems.
MeCN: excellent for rate and selectivity in condensations; less green, requires waste controls.
DMSO/DMF: maximal solubility; challenging removal; consider for small-scale discovery only.
For analytical sample prep, DMSO or acetonitrile stock solutions are convenient; dilute with MeOH/MeCN for LC methods.
Storage and Reconstitution
Item-specific (from Product Data):
Storage conditions: Store at 2–8 °C.
Shipped: on wet ice.
Appearance: Not specified for this item; refer to CoA/Spec Sheet.
General handling and reconstitution (literature/industry practice):
Solid handling: Allow container to reach room temperature before opening to prevent condensation. Minimize headspace exposure; reseal promptly.
Solution preparation: Dissolve in DMSO, acetonitrile, ethanol, methanol, acetone, THF, DCM, or ethyl acetate. For biological assays, prepare concentrated stocks in DMSO or MeCN and dilute into buffer/media with vigorous mixing; verify absence of precipitation.
Light/moisture: Store in tightly closed amber glass to minimize UV exposure; keep desiccated if long-term storage is anticipated.
Stability: Aromatic ketones are generally stable at 2–8 °C. Avoid prolonged heating above the melting point and strong acids/bases unless required by the protocol.
Freeze–thaw: If storing as solution, aliquot to avoid repeated freeze–thaw cycles; inspect for crystallization or degradation before use.
For definitive shelf life, impurity limits, and recommended retest intervals, consult the lot-specific CoA/Spec Sheet and SDS. Research use only.
Structure and Identity
A heteroaromatic ketone featuring a benzothiazole ring substituted at the 2-position by an acetyl group (methyl ketone). The fused benzene–thiazole system provides a rigid, planar π-framework; the thiazole ring contains one ring nitrogen and one ring sulfur.
Item-specific (from Product Data):
Product name: 2-acetylbenzothiazole
CAS: 1629-78-3
CID: 539568
InChIKey (as provided): 110574
Storage: 2–8 °C; shipped on wet ice
Literature/computed (typical reference values; not specs for this item):
Molecular formula: C9H7NOS (benzothiazole core + acetyl at C2)
Functional groups: aryl thiazole (benzothiazole) and aryl methyl ketone (acetyl).
Ring system: fused benzene–thiazole (benzothiazole), aromatic and planar; substitution at the 2-position (alpha to ring N) by COCH3.
Electronic characteristics: the carbonyl is conjugated to the benzothiazole ring, enabling enolization at the methyl and facilitating Knoevenagel/aldol-type condensations. The ring N/S contribute to coordination and charge delocalization in downstream derivatives (e.g., styrylbenzothiazoles, cyanine-like dyes).
Notes: Item-specific identifiers beyond those listed under Product Data are not specified for this item; refer to CoA/Spec Sheet for definitive identity attributes (e.g., exact elemental analysis, spectral data).
Synthetic Utility
Key functional elements of 2-acetylbenzothiazole—an activated methyl ketone conjugated to an electron-accepting benzothiazole ring—make it a flexible synthon.
Enolate chemistry:
Base-promoted enolization at the acetyl methyl enables C–C bond formation with aldehydes (Knoevenagel/Claisen–Schmidt-type condensations), often delivering (E)-alkenylbenzothiazoles with high selectivity.
Michael donor/acceptor tuning: The benzothiazole ring biases electron density, facilitating formation of push–pull enones useful as intermediates in further cycloadditions or reductions.
Carbonyl derivatizations:
Oxime and hydrazone formation provides handles for further transformations (e.g., Beckmann-type rearrangements on oximes; Wolff–Kishner or Clemmensen reductions on the ketone in precursor stages—subject to heteroaromatic compatibility).
α-Halogenation (NBS/Br2) affords haloacetyl derivatives that undergo SN2 with amines/thiols to furnish amide/thiol-extended frameworks.
Ring-functionalization strategies (general):
Electrophilic substitution on the benzothiazole benzene ring (e.g., nitration, halogenation) can be executed on the parent or on styryl derivatives, bearing in mind directing effects and deactivation by the 2-acyl substituent.
Quaternization at ring nitrogen (on benzothiazoles generally) forms benzothiazolium salts used to generate cyanine-like dyes; the 2-acyl substituent can modulate stability and reactivity in such sequences.
Retrosynthetic value:
Serves as a convergent junction between benzothiazole cores and aryl/heteroaryl aldehydes, enabling rapid library synthesis of conjugated dyes and ligands.
Practical note: Maintain anhydrous, oxygen-moderated conditions for sensitive base-mediated condensations, and select greener solvents (EtOH, MeCN, MeTHF) when feasible.
Target Specificity
Not applicable. This product is a small-molecule building block, not an antibody, enzyme, or affinity reagent. No antigen/epitope, species reactivity, clone, or isotype information applies.
Foire aux questions
What is the purity of this product?
This product is supplied at ≥97% purity (chemical assay). Lot-specific values are stated on the Certificate of Analysis.
How should this product be stored?
Store at 2–8 °C. Refrigerated storage is required to maintain the specified shelf life.
How is this product shipped?
This product ships chilled on wet ice. Unpack on arrival and transfer it to the storage condition stated above.
What are the CAS number, molecular formula and molecular weight?
The CAS Number is 1629-78-3, the molecular formula is C9H7NOS, and the molecular weight is 177.23 g/mol. InChIKey GSTOPVGJHLPSBJ-UHFFFAOYSA-N.
What documentation is provided?
Available product documentation, including Certificates of Analysis (COA), Safety Data Sheets (SDS), and specification sheets, is shown in the product document area. Document availability and access follow the current site policy.
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