This compound belongs to the class of organic compounds known as alkyl-phenylketones. These are aromatic compounds containing a ketone substituted by one alkyl group, and a phenyl group.
External Descriptors
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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 biological assay protocols (WB, IHC, IF, FC, etc.) apply to this chemical building block. For synthetic applications, see Reaction Conditions and Synthetic Utility for representative procedures and adapt them to your laboratory’s standards.
Biological Roles
This product is supplied strictly for research and laboratory use; no biological or clinical claims are made.
General chemical biology context (literature/general):
Methoxy-substituted aryl ketones are common motifs in natural product fragments and can serve as precursors to polyphenolic systems via O-demethylation, enabling study of phenolic oxidation states and redox behavior in model systems.
The aryl–ketone chromophore affords UV detectability, which can be useful in analytical method development (e.g., HPLC-UV internal standards) for biochemical assays, provided compatibility is confirmed.
After structural modification (e.g., conversion to chalcones or stilbenes), derivatives may serve as chemical probes in enzymology or materials in affinity platforms; such applications pertain to derivatives and should be validated independently.
No inherent role in metabolism or signaling is established for 2′,4′,5′-trimethoxyacetophenone itself. Any biological interactions would be emergent properties of specific derivatives and experimental contexts.
Buffer Applications
Not a buffering agent. 2′,4′,5′-Trimethoxyacetophenone lacks acid–base pairs in the physiological pH range suitable for buffering. For biochemical work, use conventional buffer systems (e.g., phosphate, TRIS, HEPES) and dissolve this compound in a compatible co-solvent (DMSO, ethanol, or minimal organic) if needed before dilution into buffered media.
Green Alternatives
While this item is a solid building block (not a solvent), many of its common transformations and purifications involve organic solvents and reagents. Greener choices can often be implemented without compromising performance.
Greener solvent swaps (literature best practices):
Replace DCM/chloroform with: EtOAc, 2-MeTHF, CPME, or toluene where polarity allows. For workups, MTBE or CPME often give superior phase splits vs. THF/Et2O.
Replace hexanes with heptane or cyclohexane (lower volatility/benzene content) for chromatography and crystallizations.
For aldol/Claisen–Schmidt condensations: Ethanol or water/ethanol mixtures (with phase-transfer catalysts) can reduce solvent hazard.
Reagent considerations:
Baeyer–Villiger: Use percarbonate/H2O2 systems under catalysis rather than mCPBA when compatible.
O-Demethylation: Consider catalytic hydrogenolysis (e.g., Pd/C under H2 with appropriate directing groups) or bio-based demethylating strategies where applicable; classical BBr3/HI are effective but hazardous and generate halogenated waste.
Comparison snapshot:
THF vs 2-MeTHF: similar enolate chemistry performance; 2-MeTHF is biomass-derived, less miscible with water (simplifies isolation), and has a higher boiling point, aiding solvent recovery.
Waste minimization:
Favor crystallization over silica chromatography where feasible.
Apply solvent recycling and distillation; select higher-boiling, recoverable solvents (e.g., toluene, 2-MeTHF) when appropriate.
Pharmaceutical Uses
Item-specific regulatory/excipient status: Not specified for this item; refer to CoA/Spec Sheet.
General formulation/manufacturing context (no therapeutic claims):
2′,4′,5′-Trimethoxyacetophenone is primarily a synthetic intermediate used in fine chemical and medicinal chemistry research. Its aryl–ketone core enables elaboration to libraries of enones, alcohols, and acids for SAR campaigns.
Not known as a pharmacopeial excipient. If considered for process development, impurity profiles, residual solvents, and polymorph control should be established under appropriate quality systems.
Analytical methods: HPLC-UV with C18 columns typically provide robust assay/impurity tracking due to the aromatic UV chromophore; confirmation by 1H/13C NMR and HRMS is standard.
Physical Properties
Item-specific specifications: Not specified for this item; refer to CoA/Spec Sheet.
Literature/general data (for planning only; verify against primary sources before use):
Phase at ambient conditions: typically a crystalline solid for many trimethoxyacetophenone isomers; solubility characteristics below are consistent with that assumption.
Solubility: expected to be sparingly soluble in water; freely soluble in common organic solvents (e.g., dichloromethane, chloroform, ethyl acetate, acetone, acetonitrile, methanol, ethanol, THF) due to the combination of an aromatic ring, methoxy groups, and a ketone (general chemistry expectation).
Polarity/logP: aromatic ketone with three methoxy substituents typically exhibits moderate lipophilicity with enhanced polarity vs. unsubstituted acetophenone (qualitative).
UV characteristics: conjugated aryl–ketone chromophore typically absorbs in the near-UV (approx. 240–290 nm) with a weaker n→π* band at longer wavelengths; methoxy substituents bathochromically shift π→π* bands (literature expectation).
Practical notes for handling (general):
The electron-rich ring can lead to noticeable UV absorbance; useful for HPLC/UV monitoring.
Recrystallization often feasible from ethanol, isopropanol, or ethyl acetate/hexanes mixtures; optimal solvent must be established empirically for the specific lot.
Thermal behavior (mp/bp) and density are not provided here; consult curated databases or the CoA for exact values before process design.
Quality & Grades
Item-specific quality/grade: Not specified for this item; refer to CoA/Spec Sheet.
Guidance on grades (general):
Research grade aromatic building blocks are typically supplied with an assay by HPLC/GC/NMR and identity confirmed by NMR/IR/MS. If “>98%” or similar assay is required for sensitive applications (e.g., asymmetric catalysis, materials templating), confirm on the CoA.
Low-residual-solvent specifications, metal content, water content (Karl Fischer), and stabilizers are sometimes listed for solvent products; for solid aryl ketones like this, metal/water limits are generally not standardized unless stated. Where absent, assume standard research-grade controls only.
UV cutoffs and LC baseline specifications (HPLC grade) are solvent-specific and do not apply here.
Stabilizers/antioxidants: None specified for this item. If a stabilizer is present in a different catalog listing, it will be explicitly declared on the label/CoA.
Lot-specific documentation: For precise assay, residuals, and impurity profiles, consult the lot CoA and/or Spec Sheet.
Reaction & Applications
As an electron-rich, polysubstituted acetophenone, 2′,4′,5′-trimethoxyacetophenone is a versatile building block for aromatic and carbonyl chemistry.
Carbonyl transformations (literature/general):
Aldol/Claisen–Schmidt condensations with aromatic or aliphatic aldehydes to produce chalcones and related enones; base-promoted in EtOH/MeOH or under phase-transfer catalysis.
Baeyer–Villiger oxidation to the corresponding aryl acetate (using peracids or mCPBA), enabling subsequent hydrolysis to phenols or rearranged products.
Reductions: NaBH4 or catalytic hydrogenation to form the secondary alcohol (1-(2,4,5-trimethoxyphenyl)ethanol); further hydrogenolysis can adjust side-chain oxidation state.
Alpha-functionalization: Halogenation (NBS/Br2), oxidation to acids (via haloform or direct oxidation), or formation of enolates for subsequent C–C bond formations (e.g., alkylation, Michael additions).
Aromatic ring chemistry:
O-Demethylation with BBr3, AlCl3/thiols, or HI to access polyhydroxyacetophenone analogs (regioselective demethylation often occurs first at the ortho-methoxy group; literature-dependent).
Electrophilic substitutions (nitration, sulfonylation) are influenced by the methoxy activators; careful control is required to avoid over-substitution.
Materials/synthetic contexts:
Useful synthon in the preparation of methoxy-rich aryl enones, ligands, and intermediates for fragrance, dye, and fine chemical pathways.
Practical tips:
For base-mediated condensations, ensure rigorous exclusion of water when strong bases are used; methoxy groups are base-stable but demethylation can occur under forcing nucleophilic conditions.
For BBr3 demethylations, temperature control (−78 to 0 °C) and slow addition reduce poly-demethylation and side reactions.
Reaction Conditions
The following are general, literature-style conditions often applied to aryl methyl ketones of this type. They are provided for planning and must be optimized for this substrate.
Typical: 1–2 equiv aldehyde, 20–50 mol% NaOH or KOH in EtOH or MeOH, 0–25 °C, 2–24 h. Alternative: Piperidine-catalyzed in EtOH; or solvent-free grinding with base.
Outcome: trans-enone in moderate to high yields; electron-rich ring accelerates condensation.
O-Demethylation:
BBr3 (1–3 equiv per OMe) in dry DCM, −78 to 0 °C, 1–6 h; quench with MeOH/H2O → polyphenols. HI (57%) reflux can also demethylate but is harsher. Regioselectivity may favor ortho-OMe.
Reduction of carbonyl:
NaBH4 (1.1–1.5 equiv) in MeOH/EtOH at 0–25 °C, 0.5–2 h → secondary alcohol. For stereochemical control in subsequent steps, consider CBS reduction on derived aryl ketones.
Catalytic hydrogenation (H2, Pd/C, EtOH) can reduce both C=C of chalcones and the carbonyl if over-reduced; monitor closely.
Baeyer–Villiger oxidation:
mCPBA (1.2–1.5 equiv) in DCM, 0–25 °C, 2–16 h → aryl acetate; or H2O2 with catalytic acids in greener solvents (EtOAc, MeCN) as an alternative.
Alpha-halogenation:
NBS (1.1–1.2 equiv) with catalytic acid or via enolization in CCl4/MeCN/DCM, 0–25 °C; or Br2 in AcOH. Followed by nucleophilic substitution to diversify the side chain.
Workup/purification:
Typical aqueous quench, extraction into EtOAc/DCM, brine wash, drying (Na2SO4/MgSO4), and silica gel chromatography or crystallization.
All conditions should be validated on small scale and adapted to this substrate’s specific reactivity.
Safety & Handling
Item-specific GHS details: Not specified for this item; refer to SDS.
General laboratory safety guidance for aryl ketones (informational; defer to SDS for authoritative data):
Likely hazards: May cause eye/skin irritation and respiratory tract irritation if dusts or aerosols are generated. Combustible organic solid; avoid ignition sources and dust accumulation.
PPE: Safety glasses or goggles, lab coat, appropriate chemically resistant gloves (e.g., nitrile). Use in a fume hood to minimize inhalation exposure, especially during weighing, transfers, or when heating.
Incompatibilities: Strong oxidizing agents (risk of exotherm), strong reducing agents (may reduce carbonyl), strong bases/acids under heating (possible side reactions or hydrolysis of methoxy groups under forcing conditions). Avoid brominating/halogenating agents unless intended, as activated rings may undergo EAS.
First aid (overview): If inhaled—move to fresh air. Skin/eye contact—rinse with water for at least 15 minutes; remove contaminated clothing. If ingested—rinse mouth; seek medical advice. In all cases, consult the SDS and obtain medical attention as needed.
Fire safety: Use CO2, dry chemical, or foam extinguishers. Combustion can produce CO/CO2 and irritant organics.
Waste: Collect organic waste in appropriate halogenated/non-halogenated containers according to solvent use. Do not discharge to drains.
Always consult the specific SDS for this product and your institutional EHS procedures.
Solvent Selection
This product is a small-molecule solid (aromatic ketone), not a solvent. However, solvent choice is important for its handling, purification, and reactions.
General solubility/miscibility profile (literature/experience-based):
Moderate to low solubility: toluene, hexanes/Heptane (may be useful for antisolvent crystallizations when paired with EtOAc/EtOH).
Very low solubility: water.
Selection tips by task:
Recrystallization: Start screens with EtOAc/hexanes, IPA/water, EtOH/water, or toluene/EtOAc. Balance solubility contrast and oiling-out risk.
Chromatography: Normal phase—elute with hexanes/EtOAc gradients; the polar carbonyl and methoxy groups typically require 20–60% EtOAc. For greener options, use cyclopentyl methyl ether (CPME) or toluene/EtOAc.
Reactions involving enolate chemistry: Use dry, aprotic solvents (THF, 2-MeTHF, DME) with controlled base additions.
Electrophilic aromatic substitutions: Solvents like DCM, nitrobenzene, or acetic acid may be chosen depending on electrophile and catalyst.
Comparison note:
THF vs 2-MeTHF: 2-MeTHF offers better phase separation and a greener profile; both solvate enolates well.
Storage & Reconstitution
Item-specific storage: Room temperature (per Product Data). Protect from moisture and excessive heat. Store tightly closed in a dry, well-ventilated place.
Shipped in: Not specified for this item; refer to CoA/Spec Sheet.
Appearance: Not specified for this item; refer to CoA/Spec Sheet.
General handling guidance:
Keep container tightly sealed to prevent uptake of moisture and odors. Although methoxy-substituted aryl ketones are typically stable, minimize prolonged exposure to light and air to avoid slow oxidation or discoloration.
If solidification/oiling occurs during storage, gently warm and seed, or recrystallize from a suitable solvent system to restore handling quality.
Solution preparation:
Prepare stock solutions in dry organic solvents (e.g., DMSO, MeOH, EtOH, DCM, THF) as needed. Filter through a PTFE syringe filter for analytical use.
For long-term solution storage, prefer amber vials under inert gas at low temperature to mitigate degradation; verify stability by HPLC before critical use.
Stability: No formal shelf-life or stability data are specified for this item; consult the lot CoA or perform fit-for-purpose QC (NMR/HPLC) prior to scale-up or sensitive applications.
Structure & Identity
A trimethoxy-substituted aromatic methyl ketone: 1-(2,4,5-trimethoxyphenyl)ethan-1-one (commonly, 2′,4′,5′-Trimethoxyacetophenone).
Item-specific (from Product Data):
SKU: T468872
Product Name: 2′,4′,5′-Trimethoxyacetophenone
CAS: 1818-28-6
PubChem CID: 74560
InChIKey (as provided): 112095
Storage: Room temperature
Research Use: For research use only
Literature/computed identity (for reference; not a product specification):
Core structural features: an acetophenone (aryl–CO–CH3) with three methoxy groups at the 2′, 4′, and 5′ positions on the phenyl ring. The 2D structure is a benzene ring bearing an acetyl group para-to one methoxy and flanked by adjacent methoxy groups, creating an electron-rich aromatic system with an ortho-methoxy that can influence conformation via weak intramolecular interactions.
SMILES: Not specified for this item; refer to CoA/Spec Sheet.
Stereochemistry: None (achiral small molecule).
Synthetic Utility
Key functional elements: one aromatic ketone (Ar–CO–Me) and three anisole-type methoxy substituents (electron-donating, ortho/para-directing).
Retrosynthetic value:
Readily formed by Friedel–Crafts acylation of 1,3,4-trimethoxybenzene with acetylating agents (e.g., AcCl/AlCl3 or Ac2O/BF3·OEt2) under regioselective conditions (literature precedent), giving access to this specific substitution pattern.
Divergent synthesis opportunities:
Enone formation (Claisen–Schmidt) → access to highly substituted chalcones/enones that can cyclize to flavanones/aurones or undergo Michael additions.
Alpha-chemistry of the ketone: enolate trapping with electrophiles (alkyl halides, carbonyls), enabling side-chain diversification.
Redox interconversions: reduction to secondary alcohol; oxidation to acid or alpha-halo ketones; Baeyer–Villiger to aryl acetates.
O-Demethylation → polyphenolic acetophenones for subsequent etherification, acylation, or metal chelation chemistries.
Protecting-group logic:
Methoxy groups act as permanent electron donors; if phenols are desired later, selective demethylation strategies can be staged after C–C bond formations to exploit enhanced ring activation.
Cross-coupling compatibility:
Although lacking a halogen handle, the aromatic core can be halogenated (e.g., NBS/NCS or electrophilic halogenation) at activated positions, enabling subsequent Suzuki/Heck/Sonogashira couplings from derived aryl halides.
Target Specificity
Not an antibody, enzyme, or biological targeting agent. No target specificity information applies to this small-molecule reagent. For intended chemical transformations, refer to Synthetic Utility and Reaction Conditions.
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