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
Not applicable as a biological reagent. No validated protocols for WB, IHC, IF, or FC apply. For synthetic applications, see the Reaction Conditions and Synthetic Utility sections for representative laboratory procedures and setup guidance.
Biological Roles
This compound is a synthetic aromatic aldehyde/ketone and is not a native metabolite.
General biochemistry context (literature):
Aromatic aldehydes can undergo biotransformations such as aldehyde dehydrogenase-catalyzed oxidation to the corresponding carboxylic acids, and carbonyl reductase-mediated reduction to benzyl alcohol derivatives.
The presence of both an aldehyde and an aryl methyl ketone allows for multiple conjugation pathways with biological nucleophiles (e.g., Schiff base formation with amines), but such reactivity is nonspecific and underpins general irritancy/toxicity rather than a defined biological role.
Electron-withdrawing carbonyl substituents on benzene reduce electron density, which may affect nonspecific interactions with biomacromolecules; nonetheless, 3-acetylbenzaldehyde is primarily a laboratory chemical intermediate.
Applications in bioconjugation/chemical biology (methodological, not clinical):
The aldehyde can serve as a handle for reversible imine/oxime ligation with aminooxy or hydrazide probes under mild conditions, enabling temporary immobilization or tagging of synthetic constructs. Careful pH control (typically pH 4.5–6 for oximes) and use of anilinium catalysts can increase rates.
No specific physiological function or targeted biochemical pathway is associated with 3-acetylbenzaldehyde. All uses are for in vitro research or synthetic applications only.
Buffer Applications
Not typically applicable. 3-Acetylbenzaldehyde is not used as a buffering agent and does not form defined buffer systems. For aqueous work, select a buffer appropriate to your reaction (e.g., acetate, phosphate, citrate) and consider that aldehydes can react with primary amines in buffers (e.g., Tris, glycine), potentially consuming the reagent. Use amine-free buffers for oxime/hydrazone ligations.
Green Alternatives
Because 3-acetylbenzaldehyde is a building block (not a solvent), greener choices focus on solvent selection and catalytic methods that minimize waste while preserving chemoselectivity.
Greener solvent options (literature guidance):
Replace chlorinated solvents (e.g., DCM) with ethyl acetate, 2-MeTHF, CPME, or toluene where feasible.
Perform condensations in bio-derived ethanol or water/ethanol mixtures; many Knoevenagel/Claisen–Schmidt reactions proceed efficiently under aqueous ethanol with heterogeneous bases.
Comparative solvent considerations (general):
DCM: excellent for low-temperature Wittig; environmental concern (chlorinated). Substitute with toluene or CPME when possible.
THF: widely useful but peroxide-forming; 2-MeTHF offers similar polarity, higher boiling point, bio-based origin, and lower peroxide tendency.
DMF/DMSO: powerful polar aprotics but problematic in EHS; MeCN, propylene carbonate, or green amide alternatives (e.g., NBP, Cyrene where compatible) can be considered.
Catalysis and process intensification:
Use organocatalysts (e.g., proline, piperidine) in ethanol/water for condensations.
Drive equilibrium reactions by benign means (azeotropic water removal, molecular sieves) rather than stoichiometric dehydrating agents.
Workup/waste minimization:
Favor crystallization or trituration over extensive chromatography.
Use lower-toxicity derivatization reagents (e.g., hydroxylamine hydrochloride in ethanol) for analytical/derivatization steps.
Trade-offs: While greener solvents may slightly alter selectivity or rates, they often provide comparable yields with improved EHS profiles; confirm by small-scale screening.
Pharmaceutical Uses
Item-specific pharmacopeial status: Not specified for this item; refer to CoA/Spec Sheet.
Context in pharmaceutical R&D/manufacturing (general, non-clinical):
Synthetic intermediate: The meta-disposition of aldehyde and ketone groups enables divergent SAR exploration in aryl carbonyl motifs. It is commonly used to construct chalcones, stilbenes, and heterocycles that serve as discovery intermediates.
Process chemistry considerations: Chemoselective reductions and olefinations allow late-stage diversification under conditions compatible with sensitive functionalities. Protection of the aldehyde (as acetal) can be used to manipulate the ketone selectively.
Analytical handling: For GMP contexts, control of residual solvents, peroxides (if any solvents are peroxide-forming), and aldehyde content is critical. Impurities such as the corresponding benzoic acid derivative or self-condensation products should be monitored by HPLC/GC.
No therapeutic claims are made. This product is supplied strictly for research and laboratory use.
Physical Properties
Item-specific specs: Not specified for this item; refer to CoA/Spec Sheet.
Physical state: typically a pale yellow to colorless liquid or low-melting solid depending on purity and temperature.
Solubility: sparingly soluble in water; miscible with many organic solvents (e.g., ethanol, methanol, acetone, dichloromethane, toluene, ethyl acetate). Aromatic aldehydes/ketones are generally well soluble in medium-polar aprotic solvents.
Acidity/basicity: no Brønsted basic sites; aldehydic proton is weakly acidic; the methyl of the acetyl group is enolizable under basic/acidic conditions.
Partitioning: expected moderate hydrophobicity due to aryl core; polar functionalities (two carbonyls) enhance solubility in polar organics.
Stability: susceptible to self-condensation/polymerization under strong base or acid; aldehyde can oxidize to the corresponding acid and can form hydrates/acetals in protic media with acids.
Optical/refractive properties: aromatic carbonyls often show strong UV absorption in the 240–300 nm region (π→π*), and a lower-intensity n→π* band around 320–360 nm (literature, qualitative). Exact UV cutoff/ε: Not specified for this item; refer to CoA/Spec Sheet.
Note: Use these literature descriptors as guidance only; consult the CoA for any required numeric specifications such as BP, MP, density, refractive index, logP, pKa, water/peroxide content.
Quality and Grades
Item-specific grade/purity: Not specified for this item; refer to CoA/Spec Sheet.
What to expect from Aladdin Scientific for this class of reagent:
Identity confirmation typically by NMR and/or GC–MS/LC–MS; aldehyde functionality may be supported by IR (νC=O ~1690–1725 cm⁻¹; literature) and by derivatization (e.g., 2,4-DNP).
Residual solvent, water content, and stabilizer details are reported on the CoA when applicable. If low-peroxide or low-water specifications are critical for your synthesis, request a current CoA lot.
Stabilizers/inhibitors: None specified for this item. Many aromatic aldehydes are supplied neat under inert gas. If any inhibitor is used, it will be declared on the CoA, and may need to be removed before sensitive catalysis.
Use-case guidance by grade (general information):
Synthetic grade: typical for routine transformations (Wittig, oxime formation, condensations).
High-purity/low UV grade: preferred for photophysical work or trace-analysis; ensures minimized background in UV detection. Not specified for this item; refer to CoA/Spec Sheet.
QC notes:
Aldehyde value can drift by oxidation to the acid; confirm assay before precision reactions (e.g., Grignard additions). Our storage recommendation (2–8°C, argon) helps maintain stability.
Reaction and Applications
As a meta-disubstituted aryl aldehyde/aryl methyl ketone, 3-acetylbenzaldehyde is a versatile building block where chemoselectivity can be exploited between the more reactive aldehyde and the enolizable acetyl group.
Condensation chemistry: Knoevenagel and Claisen–Schmidt condensations with active methylene partners (malononitrile, ethyl cyanoacetate, acetophenones) to access cinnamylidene/benzylidene and chalcone-type scaffolds; base catalysts include piperidine, ammonium acetate, K2CO3, NaOH; often performed in EtOH, MeOH, or MeCN.
Carbon–carbon bond formation at the aldehyde: Wittig, Horner–Wadsworth–Emmons, and Julia–Kocienski olefinations; Barbier/Grignard additions to give secondary alcohols (strictly anhydrous, low temperature).
Oxime/hydrazone/Schiff bases: Reaction with hydroxylamine, hydrazines, and primary amines under mildly acidic catalysis; useful for ligand synthesis and as protecting/derivatization strategies.
Selective reductions/oxidations: Aldehyde to alcohol (NaBH4, catalytic transfer hydrogenation), or to acid (Oxone, TEMPO/bleach); chemoselective reductions that leave the aryl ketone intact achievable with careful reagent choice (e.g., NaBH4 reduces aldehyde faster than aryl ketone at 0–25°C).
Enolate chemistry at the acetyl group: α-halogenation, alkylation, Michael additions after enolization (LDA, NaOMe/MeOH), giving access to elaborated 1,3-dicarbonyl-like motifs on the aromatic ring.
Cross-couplings on the aryl ring (if halogenated derivatives are prepared) can be combined with the above carbonyl manipulations for modular assembly of complex targets.
Synthetic contexts:
Intermediates for dyes, photonic materials, and ligand frameworks where meta-separation of carbonyls tunes electronics and sterics.
Precursor to heterocycles (e.g., oxazoles, isoxazoles) via cyclodehydration of appropriate imine/oxime derivatives.
Note: Control moisture/oxygen; aldehydes are prone to oxidation/aldol side reactions.
Reaction Conditions
General literature guidance for common transformations of 3-acetylbenzaldehyde (not product specifications; optimize per substrate and scale):
Oxime formation (aldehyde):
Reagents: hydroxylamine·HCl (1.1–1.5 equiv), NaOAc (1.5–2 equiv) or pyridine as base.
Solvent: ethanol, methanol, or EtOH/H2O.
Conditions: 25–60°C, 1–4 h; drive to completion by slight heating and removal of water (molecular sieves optional).
Conditions: 0–25°C, 2–16 h; monitor by TLC/GC. Quench with aqueous NH4Cl; typical isolated yields often 60–90% depending on ylide stability (literature ranges).
Claisen–Schmidt/chalcone formation (enolate of acetyl vs aromatic aldehydes):
Base: NaOH (10–40% aq.) or K2CO3 in EtOH/aq. EtOH.
Conditions: 0–25°C addition, then 2–24 h at RT or mild reflux; precipitates often form on neutralization. Yields variable (50–95%) based on partner and conditions.
Selective reduction of aldehyde:
Reagent: NaBH4 (0.5–1.0 equiv) in MeOH or EtOH at 0–5°C to favor aldehyde reduction over aryl ketone.
Workup: quench with AcOH/H2O; extract with EtOAc.
α-Alkylation at acetyl methyl:
Base: LDA (1.1–1.5 equiv) in THF at −78 to −20°C; electrophile added dropwise. Alternatively, NaH/NaOMe for less hindered electrophiles.
Notes:
Maintain inert atmosphere as recommended (argon) to limit oxidation.
Drying: Use 3 Å molecular sieves for imine/oxime and Wittig steps; ensure solvents are anhydrous.
Monitor for side reactions: self-aldol or Cannizzaro is unlikely due to aryl ketone presence but aldol-type oligomerization can occur under strong base.
Safety and Handling
Item-specific hazard classification: Not specified for this item; refer to the SDS for authoritative GHS classification, H-statements, and pictograms.
General hazards (literature, for similar aryl aldehydes/ketones):
Irritant to skin, eyes, and respiratory tract; may cause sensitization in susceptible individuals.
Harmful if swallowed or inhaled; avoid aerosols/vapors.
Combustible organic liquid; keep away from ignition sources.
PPE and engineering controls:
Use chemical-resistant gloves (e.g., nitrile), lab coat, and splash goggles.
Handle in a fume hood; avoid breathing vapors.
Storage and incompatibilities:
Product data: Store at 2–8°C, argon charged. Ship on wet ice. Maintain tight closure and inert headspace to limit aerial oxidation.
Keep away from strong oxidizers (risk of rapid oxidation), strong bases/acids (risk of aldol/condensation or acetalization), and nucleophiles (formation of imines/oximes with amines/hydroxylamine).
Use amber containers or minimize light exposure to reduce photochemical degradation.
First-aid overview (consult SDS for full guidance):
Inhalation: Move to fresh air; seek medical attention if symptoms persist.
Skin/eye contact: Rinse with water for several minutes; remove contaminated clothing; obtain medical advice if irritation continues.
Ingestion: Rinse mouth; do not induce vomiting; seek medical attention.
Spill/fire response:
Absorb small spills with inert material; ventilate area; dispose per regulations.
For fire, use dry chemical, CO2, or foam; water spray to cool containers.
Stability note: Aldehydes can slowly oxidize; inerting with argon as supplied helps preserve assay.
Solvent Selection
3-Acetylbenzaldehyde is an aromatic bifunctional carbonyl compound; solvent choice is typically governed by desired chemoselectivity and reactivity of the aldehyde vs the aryl methyl ketone.
Solubility/miscibility (literature/general):
Miscible with most polar aprotic and medium-polar protic solvents (e.g., THF, MeCN, DCM, EtOAc, toluene, ethanol, methanol). Sparingly soluble in water.
Polarity considerations:
Moderate polarity due to two carbonyls; favors solvents that stabilize polar transition states without promoting side reactions (e.g., DCM or toluene for EAS; MeCN or THF for condensations; EtOH for Knoevenagel under basic catalysis).
Selection tips by transformation:
Oxime/imine formation: ethanol or methanol with a catalytic acid; remove water (Dean–Stark in toluene or add molecular sieves) to drive equilibrium.
Wittig/olefination at the aldehyde: dry THF, toluene, or DCM; rigorously anhydrous conditions for phosphonium ylides.
Claisen–Schmidt (chalcone synthesis) exploiting the acetyl methyl: ethanol, MeOH, or aqueous ethanol under base (NaOH, K2CO3); or non-protic solvents (THF/DMF) for stronger bases (LDA) to control enolate formation.
Electrophilic aromatic substitutions: use unreactive solvents like nitrobenzene, DCM, or acetic acid depending on the reagent; note both substituents are meta-directing/deactivating.
Practical note: Avoid strong protic acids if retention of the aldehyde is critical (acetalization/polymerization risk). Dry, oxygen-free solvents help limit oxidation and self-condensation.
Storage and Reconstitution
Storage (item-specific): Store at 2–8°C under argon (argon-charged). Ship on wet ice. Keep container tightly closed and headspace inert to minimize oxidation and self-condensation. Protect from light where feasible.
Form supplied: Neat liquid/solid (appearance not specified for this item; refer to CoA/Spec Sheet.). No reconstitution required.
Handling after opening:
Purge with argon or nitrogen after each use; recap promptly.
For long-term storage, consider aliquoting into amber vials to reduce air exposure and headspace oxygen.
If moisture is a concern for your application, store over inert desiccant in a sealed secondary container.
Stability notes (general): Aldehydes can slowly oxidize to acids; monitor by NMR/GC if material is stored for extended periods. If acid content increases, purification by distillation under reduced pressure or column chromatography may restore usability for sensitive reactions.
Freeze-thaw guidance: Not typically applicable. Avoid repeated warming/cooling cycles; maintain within 2–8°C range. If crystallization occurs at low temperature, redissolve gently at room temperature before use.
Compatibility: Avoid prolonged contact with strong acids/bases and primary amines in storage vessels (risk of acetal/imine formation). Refer to the SDS for detailed stability and incompatibility information.
Structure and Identity
Brief description: 3-Acetylbenzaldehyde is a meta-disubstituted benzene bearing an aldehyde (–CHO) and an acetyl ketone (–COCH3) on the aromatic ring in a 1,3-relationship, making it a bifunctional aryl aldehyde/aryl methyl ketone building block.
Item-specific (as provided):
CAS: 41908-11-6
InChIKey: 307622 (as listed by supplier)
SMILES: 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.
Literature/computed (for reference only; not item specifications):
Molecular formula (literature): C9H8O2
Molecular weight (literature): 148.16 g/mol
Exact mass (computed): 148.0524 Da
Typical SMILES (literature): CC(=O)c1cccc(C=O)c1 (denotes an m-disubstituted benzene bearing acetyl and formyl groups)
Structural features: One benzene ring; one aldehyde carbonyl (electrophilic, easily oxidized/reduced) and one aryl methyl ketone (enolizable, participates in aldol/condensation chemistry); no stereocenters.
2D description in words: A six-membered aromatic ring with the aldehyde group at position 1 and an acetyl (methyl ketone) group at position 3 (meta) relative to the aldehyde.
Synthetic Utility
Key functional groups and reactivity profile enable multiple orthogonal manipulations:
Aldehyde handle:
Highly chemoselective for nucleophilic additions (Wittig/HWE, cyanohydrin formation, Grignard/organolithium additions, reductive amination via imine formation and subsequent reduction). Protect as acetal (ethylene glycol, catalytic TsOH) when required.
Aryl methyl ketone handle:
Enolizable; participates in base- or acid-catalyzed condensations (Claisen–Schmidt), α-functionalizations (halogenation, alkylation), and can serve as a directing group after suitable activation in metalation chemistry.
Aromatic core (meta-disubstituted):
Both carbonyls are meta-directing and deactivating toward EAS, biasing further substitution to remaining meta positions. Metal-catalyzed C–H activation strategies may be used to functionalize positions otherwise deactivated to EAS.
Divergent synthesis strategies:
Sequential, chemoselective transformations (e.g., Wittig at –CHO → olefin, then α-alkylation at –COCH3) to build complexity without protecting groups.
Cyclization to heterocycles: Formation of oxazoles/isoxazoles via condensation with hydroxylamine/amide equivalents followed by cyclodehydration.
Retrosynthetic value:
As a convergent node: access from meta-directed acylation/formylation sequences (e.g., Friedel–Crafts acylation to install acetyl group, then formylation via Vilsmeier–Haack on deactivated ring, or vice versa using directed metalation tactics in modern routes).
Overall, 3-acetylbenzaldehyde serves as a versatile aryl carbonyl linchpin for constructing conjugated systems and heterocycles with meta-separated electronic effects.
Target Specificity
Not applicable. This product is a small-molecule chemical building block and is not an antibody, enzyme, or biological targeting reagent. No antigen/epitope or species reactivity applies.
Perguntas frequentes
What is the purity of this product?
This product is supplied at ≥95% purity (chemical assay). Lot-specific values are stated on the Certificate of Analysis.
How should this product be stored?
Store at 2–8 °C under argon. It is supplied under an argon blanket; reseal under inert gas after each use.
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 41908-11-6, the molecular formula is C9H8O2, and the molecular weight is 148.16 g/mol. InChIKey QVNFUJVNBRCKNJ-UHFFFAOYSA-N.
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