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
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 vendor-tested biological or analytical application protocols are provided for this item in the Product Data.
General laboratory usage examples (non-validated; literature-style starting points):
Stock solution preparation: Dissolve to 10–100 mM in DMSO or DMF. Filter through 0.22 µm PTFE if needed. Store aliquots under inert gas, protected from moisture.
Recrystallization: Dissolve in hot ethanol (or EtOH/H2O). Cool slowly to room temperature, then in an ice bath to maximize crystal quality. Collect by vacuum filtration and dry under reduced pressure.
Oxime synthesis (analytical derivative): Dissolve substrate in EtOH, add hydroxylamine HCl (1.2–1.5 equiv) and NaOAc (2–3 equiv). Stir at 60–78 °C for 1–2 h. Cool, dilute with water, collect precipitated oxime, wash, and dry.
These examples are for experienced users to adapt and optimize. For validated, application-specific protocols, consult the literature or develop in-house SOPs.
Biological Roles
Item-specific biological data: Not specified for this item; refer to literature if needed.
General context (biochemistry/chemical biology perspective; no clinical claims):
4'-Acetamidoacetophenone is a small aromatic amide/ketone not known as a natural metabolite. It serves primarily as a synthetic intermediate or probe scaffold rather than a biological ligand.
Structural motifs: The acetanilide moiety is a classic protecting group and appears in numerous laboratory reagents; related acetanilides are found in some industrial chemicals and legacy analgesic scaffolds, though this specific compound is not established as a bioactive agent.
Reactivity considerations in biological media: The amide is usually stable under physiological pH; the ketone can form reversible Schiff bases with primary amines (e.g., lysine) under dehydrating conditions, but such reactions are slow in aqueous neutral buffers without catalysis.
ADME-relevant features (conceptual): Moderate aromaticity with dual carbonyls suggests limited aqueous solubility and potential for plasma protein binding via hydrogen bonding and π-stacking, typical of aryl amide/ketones. These are general trends and not measurements for this item.
Applications in chemical biology:
Can be used as a starting point for derivatization into fluorescent or affinity probes by converting the ketone to oxime/imine linkers or by deprotecting to the aniline for further conjugation.
All biological discussions here are general and for research planning; no medical or diagnostic use is implied.
Buffer Applications
This compound is not a buffering agent and does not form a defined conjugate acid–base pair with practical pKa values near physiological ranges. Consequently, it is not typically used to prepare buffers or as a buffering component in biochemical assays.
Practical guidance:
If dissolution in aqueous buffers is required for assays, prepare a concentrated stock in DMSO, DMF, or ethanol, then dilute into the target buffer with vigorous mixing to avoid precipitation. Keep final cosolvent content low (commonly ≤1–2% v/v) to minimize biological assay interference.
Adjust pH of the buffer independently with appropriate buffering systems (e.g., phosphate, HEPES, acetate) rather than relying on this compound to influence pH.
For buffer compatibility, evaluate solubility and stability empirically under your specific ionic strength, pH, and temperature conditions.
Green Alternatives
Sustainable choices relate mainly to solvent and reagent selection when using 4'-acetamidoacetophenone. The molecule itself is a stable, reusable intermediate; improvements typically focus on process mass intensity and safer auxiliaries.
Replace chlorinated solvents with ethyl acetate, 2-MeTHF, or cyclopentyl methyl ether (CPME) where feasible for workups, recrystallizations, and some reactions.
Prefer ethanol over methanol for recrystallization and condensations when solubility allows; both water-miscible and lower toxicity profile for ethanol.
Use acetonitrile or 2-MeTHF instead of THF/DMF where process and EHS constraints favor them; validate kinetics and selectivity.
Illustrative comparison (general):
Ethanol vs. Methanol: Comparable polarity; ethanol has better EHS profile and lower toxicity but may require higher temperature for dissolution.
2-MeTHF/CPME vs. THF: Ethers with higher boiling points and improved peroxide resistance; better phase separation in extractions; however, solubility profiles differ and costs may be higher.
EtOAc vs. DCM: EtOAc is biodegradable and less hazardous; note higher boiling point and different polarity may affect reaction rates.
Reagent choices:
For reductions, consider catalytic hydrogenation (H2/Pd) or transfer hydrogenation (isopropanol/Raney Ni) as alternatives to metal hydrides when chemoselectivity permits.
For alpha-halogenation, NBS in greener solvents can replace Br2 in chlorinated media.
Process tips:
Favor crystallization-based purifications over chromatography to reduce solvent use.
Apply solvent recovery and drying reuse where compatible with quality requirements.
Pharmaceutical Uses
Item-specific pharmacopeial status or excipient role: Not specified for this item; refer to CoA/Spec Sheet if applicable.
General, non-clinical context:
4'-Acetamidoacetophenone is primarily a research chemical and synthetic intermediate. The acetanilide group can function as a protecting group for anilines in multistep preparations during medicinal chemistry campaigns.
Formulation relevance: As a crystalline aromatic solid with limited aqueous solubility, it is not typically employed as an excipient. When used in discovery settings, it is commonly dosed as a solution in DMSO or formulated with cosolvents/surfactants for in vivo models in preclinical research (outside the scope of this product’s intended use).
Process chemistry relevance: The scaffold can be elaborated into more complex pharmacophores by transformations at the ketone (e.g., reductive amination, oxime ether formation) or after deprotection of the aniline for further coupling.
Compliance note:
This product is labeled “For research use only.” It is not intended for human or veterinary use, API manufacture, or clinical applications.
Physical Properties
Item-specific specifications: Not specified for this item; refer to CoA/Spec Sheet.
Literature/general properties (for planning only; verify for your application):
Physical state: Typically an off-white crystalline solid (literature reports for this structure); actual appearance for this item is not specified.
Melting point: Commonly reported in the high 160s °C range for the para isomer, depending on purity/polymorph (literature).
Boiling point: Not typically distilled; decomposition may precede boiling under ambient pressure (literature expectation for aromatic amide/ketone solids).
Solubility: Sparingly soluble in water; readily soluble in polar organic solvents such as ethanol, methanol, acetonitrile, DMSO, and DMF (literature). Solubility increases with gentle heating.
Acid–base behavior: Amide N is weakly basic and weakly acidic; no useful buffering capacity near neutral. Ketone is neutral; no protolytic behavior (general organic chemistry knowledge).
LogP/logS: Aromatic amide/ketones tend to have moderate lipophilicity; specific values for this compound vary by source and are not provided here (literature trend only).
Spectral features: Expected strong IR bands near ~1650–1680 cm−1 (amide C=O) and ~1680–1710 cm−1 (aryl ketone C=O), plus N–H stretch ~3300 cm−1 (literature generalization).
Always confirm key physical parameters for your lot via the CoA or your own QC prior to process design.
Quality & Grades
Item-specific quality details:
Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.
Appearance: Not specified for this item; refer to CoA/Spec Sheet.
Packaging and handling specifics from Product Data:
Storage Conditions: Room temperature, Argon charged. An argon headspace minimizes oxidative and moisture exposure, helping maintain assay and color for aromatic amide/ketone solids over long-term storage.
Shipped In: Normal conditions (no cold pack indicated).
Guidance on grades (general information; not item-specific):
Research/technical grade solids are commonly suitable for synthesis, screening, and method development. When UV-transparent or LC/MS applications are planned, higher-purity grades or additional purification may be desirable to minimize baseline noise.
HPLC grade and spectrophotometric grade refer to solvent products; for solids, vendors may specify assay, residual solvents, and trace metals. Since these are not specified here, confirm fitness-for-use by CoA or in-house QC as needed.
Recommendations:
If trace metal content, water content, or organic impurity profile are critical, request the lot-specific CoA. Do not assume values that are not provided. Where necessary, perform recrystallization or preparative purification prior to demanding applications.
This product is labeled “For research use only.” Not for human or veterinary use.
Reaction & Applications
Representative applications (literature/general; expand as appropriate for your program):
Protect–deprotect strategies: The acetamido group functions as a protecting group for the para aniline of p-aminoacetophenone. Hydrolysis (acidic or basic, typically reflux) regenerates the aniline for further functionalization (e.g., diazotization, coupling).
Carbonyl derivatization: The aryl methyl ketone readily forms oximes and hydrazones (e.g., with hydroxylamine or 2,4-DNP) and engages in imine formation/reductive amination with primary amines under standard conditions.
Alpha-functionalization: Benzylic activation adjacent to the carbonyl enables halogenation (e.g., NBS or Br2 in AcOH), sulfonylation, or enolate chemistry (Claisen, aldol) to introduce side-chain diversity.
Reduction chemistry: Selective reduction of the ketone to the corresponding secondary alcohol (NaBH4, catalytic hydrogenation) can be performed while retaining the amide. More forcing conditions can reduce the amide if desired.
Cross-coupling after deprotection: Deprotected p-aminoacetophenone can be converted to aryl halides or diazonium salts for Suzuki, Sonogashira, or Buchwald–Hartwig sequences. Starting from the acetamide can improve handling during upstream steps.
Cyclization/heterocycle construction: Condensation with bifunctional partners (e.g., amidines, hydrazides) can lead to imidazole, quinazolinone, or related ring systems using the ketone and/or amide as handles.
Practical notes:
Maintain anhydrous conditions when base-mediated enolate chemistry is intended; moisture suppresses enolization.
The acetanilide attenuates ring activation relative to a free aniline, often improving selectivity against overreaction in electrophilic steps.
The argon-charged packaging is compatible with standard inert-atmosphere workflows.
Reaction Conditions
General literature conditions (verify and optimize for your system):
Hydrolysis (deprotection of acetanilide):
Basic: 1–2 M NaOH or KOH in EtOH/H2O (1:1 to 3:1), reflux 2–6 h, then acidify to precipitate p-aminoacetophenone. The aryl ketone typically survives these conditions.
Acidic: 6–12 M HCl aqueous, reflux 2–8 h; isolate by basification and extraction. Acidic conditions can lead to some ketone hydration; monitor by TLC/LC.
Oxime formation (ketone to oxime): Hydroxylamine hydrochloride (1.2–1.5 equiv) with pyridine or NaOAc base in EtOH or MeOH, 20–78 °C, 1–4 h. Typical isolated yields: good to excellent for aryl methyl ketones.
Reductive amination: Primary amine (1.1–1.5 equiv), NaBH3CN or NaBH(OAc)3 in MeOH, EtOH, or DCE with acetic acid as promoter; 0–25 °C for imine formation, then room temp to reflux, 2–18 h.
Selective ketone reduction: NaBH4 in MeOH/EtOH at 0–25 °C affords secondary alcohol; catalytic hydrogenation (H2, Pd/C, 1–3 bar) can also reduce the ketone selectively under mild conditions.
Alpha-bromination: NBS (1.1 equiv) with catalytic acid or irradiation in solvent such as AcOH or MeCN; 0–25 °C to reflux, monitor to avoid overbromination.
Enolate chemistry: LDA or NaHMDS in THF or THF/hexamethylphosphoramide alternatives at −78 to 0 °C enables aldol/Claisen-type couplings; quench with electrophile (e.g., aldehydes, esters). Ensure rigorously anhydrous conditions.
Notes:
Solvent choice impacts rates/selectivity; see Solvent Selection. Use inert atmosphere to match the product’s argon packaging and to minimize oxidation during basic or high-temperature steps.
Always monitor by TLC/LC–MS and adjust equivalents/temperature to accommodate your scale and impurity profile.
Safety & Handling
Item-specific hazard information (from Product Data):
GHS 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 considerations for aromatic amide/ketone solids (literature/good practice):
Expected hazards: Low to moderate acute toxicity by ingestion/inhalation/skin contact is typical for similar compounds; dust may cause irritation to eyes, skin, and respiratory tract. Avoid generating dust and inhalation.
PPE: Use safety glasses or goggles, lab coat, and appropriate chemical-resistant gloves (e.g., nitrile). Work in a fume hood when weighing or dissolving.
Handling: Prevent dust formation. Use clean, dry tools. Keep container tightly closed under an inert atmosphere as supplied.
Incompatibilities: Strong oxidizers may react with aromatic organics. Concentrated acids/bases can hydrolyze the acetanilide at elevated temperature. Avoid strong reducing agents for carbonyl safety.
Thermal stability: Amides and aryl ketones are generally stable at ambient conditions; avoid excessive heating as decomposition may occur before boiling.
First aid (overview; defer to SDS): Move exposed person to fresh air after inhalation; rinse skin with water after contact; flush eyes with water for several minutes and remove contact lenses; seek medical attention if symptoms persist.
Spill response: Avoid dust. Sweep up carefully or use HEPA vacuum; place in suitable container for disposal per local regulations.
Always consult the product SDS for authoritative hazard and response guidance. Research use only.
Solvent Selection
Compound type and polarity (general):
4'-Acetamidoacetophenone is an aromatic amide/aryl methyl ketone. It is moderately polar and hydrogen-bond donating (amide N–H) and accepting (amide and ketone C=O).
Water: Sparingly soluble at ambient temperature; solubility increases on warming.
Polar protic: Good solubility in ethanol and methanol; useful for recrystallization and derivatizations (e.g., oxime formation).
Polar aprotic: Readily soluble in DMSO and DMF; soluble in acetonitrile. These facilitate coupling and condensation reactions.
Moderately polar ethers/esters: Soluble in ethyl acetate; limited to moderate solubility in THF depending on temperature.
Selection guidance:
For analytical sample prep: DMSO or DMF stock solutions with subsequent dilution into acetonitrile/water blends are common.
For recrystallization: Ethanol or ethanol–water mixtures often provide clean crystallization for para-acylated anilides; ethyl acetate/hexanes can also be tuned for purity versus recovery.
For reactions sensitive to water: Use dry polar aprotic solvents (DMF, DMSO, MeCN) and maintain inert atmosphere, aligning with the argon-charged packaging.
Comparison (typical substitutes):
Ethanol vs. methanol: Ethanol is a greener, less toxic choice with slightly lower solvating power; methanol may dissolve more at room temperature.
DMF vs. DMSO: DMF offers lower viscosity and is advantageous for acylation/coupling; DMSO provides broader solvency but can complicate workup.
Always verify solubility for your lot and application before scale-up.
Storage & Reconstitution
Item-specific storage and logistics (from Product Data):
Storage Conditions: Room temperature, Argon charged. Keep the container tightly closed. Maintain the inert headspace by promptly resealing after opening.
Shipped In: Normal conditions (no special temperature control indicated).
General guidance for this compound class:
Protect from excessive humidity and prolonged exposure to air to minimize potential discoloration or surface oxidation of aromatic solids.
If long-term storage after opening is anticipated, consider transferring to a dry, inert-atmosphere vial (argon or nitrogen) with desiccant present in the secondary container.
Reconstitution: For solution preparation, use anhydrous solvents (e.g., DMSO, DMF, ethanol). Warm gently and sonicate if needed to aid dissolution; avoid overheating. Filter if particulate persists.
Stability in solution: Stock solutions in dry DMSO/DMF are typically stable for weeks at 2–8 °C or at −20 °C under inert gas and protected from light (literature practice). Prepare fresh solutions if precipitation or discoloration is observed.
Freeze–thaw: For solution stocks, aliquot to avoid repeated freeze–thaw cycles, which can introduce moisture and promote degradation.
Research use only. Consult the CoA and SDS for any lot-specific stability, purity, and safety information not provided here.
Structure & Identity
Item-specific (from Product Data):
SKU: A151745
Product Name: 4'-Acetamidoacetophenone
CAS: 2719-21-3
PubChem CID: 75937
InChIKey: 396001 (as provided)
SMILES: Not specified for this item; refer to CoA/Spec Sheet.
Core scaffold: A para-disubstituted benzene ring bearing two carbonyl-derived functionalities.
Functional groups: An aryl methyl ketone (–CO–CH3) and a para acetanilide (–NH–CO–CH3) on the ring. The amide N is typically secondary (–NH–) and conjugated to the ring; the ketone is benzylic.
2D description: A benzene ring with an acetyl group at the 1-position and an acetamido group at the 4-position (para to each other), giving a symmetric para substitution pattern without stereocenters.
Stereochemistry: None (achiral). No E/Z or axial chirality.
Computed/literature identifiers (for context; verify before use):
Empirical formula (literature): C10H11NO2
Molecular weight (literature): ~177.20 g/mol
Notes:
The item-specific SMILES and exact identifiers beyond what is listed are not provided in the Product Data. Consult the CoA/Spec Sheet for definitive structure strings used for this lot.
Synthetic Utility
Functional group leverage:
Amide (acetanilide): Serves as a protecting group for the para aniline. Stable to many electrophilic aromatic substitutions and mild bases; cleavable under acidic (HCl, H2SO4) or basic (NaOH, KOH) hydrolysis at reflux. Enables staged synthesis where free aniline would be overreactive.
Aryl methyl ketone: Benzylic acidity allows enolate/enol chemistry. Readily participates in oxime/hydrazone formation, reductive amination, and selective carbonyl reductions.
Strategic uses (literature/general):
Divergent synthesis: From a common stock, branch to (a) p-aminoacetophenone via deacetylation, then to azo dyes, ureas, or Buchwald–Hartwig products; or (b) side-chain elaborations via aldol/Claisen condensations at the methyl ketone.
Chemoselectivity: Optimize conditions to reduce the ketone while preserving the amide (NaBH4, catalytic hydrogenation) or to deprotect the amide without affecting the ketone (aqueous acid/base). Protective group orthogonality is advantageous in multistep routes.
Late-stage functionalization: The para arrangement reduces directing-group complications. After aniline deprotection, diazotization enables Sandmeyer-type substitutions to diversify aryl substituents.
Purification and handling:
Often crystallizable from ethanol or EtOAc/hexanes, enabling scalable purification with minimal chromatography.
Compatible with inert-atmosphere techniques as supplied (argon charged), reducing discoloration during heated steps.
Overall, 4'-acetamidoacetophenone is a versatile, manageable building block bridging protected aniline chemistry with benzylic ketone reactivity.
Target Specificity
This section is primarily applicable to biological macromolecules (e.g., antibodies, enzymes, ligands with defined biological targets). As a small-molecule building block, 4'-acetamidoacetophenone does not have item-specific target, antigen, or isotype information.
Item-specific data: Not specified for this item; refer to CoA/Spec Sheet if any biological binding data are provided for a particular application.
For chemoproteomic or probe-development contexts, any “specificity” would derive from derivatives made from this scaffold rather than the parent compound itself.
Frequently Asked Questions
What is the purity of this product?
This product is supplied at ≥98% purity (chemical assay). Lot-specific values are stated on the Certificate of Analysis.
How should this product be stored?
Store at room temperature under argon. It is supplied under an argon blanket; reseal under inert gas after each use.
How is this product shipped?
This product ships under standard ambient conditions. No temperature-controlled packaging is required.
What are the CAS number, molecular formula and molecular weight?
The CAS Number is 2719-21-3, the molecular formula is C10H11NO2, and the molecular weight is 177.2 g/mol. InChIKey WECHHDJTILFYQT-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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