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. No antibody- or assay-specific application protocols are associated with this small-molecule reagent. For synthetic transformations and stock-solution preparation, see the Reaction Conditions and Solvent Selection sections.
Biological Roles
This compound is a synthetic aromatic carboxylic acid bearing a para-acetyl group and is not known as a natural metabolite. No endogenous biological role is established.
General biochemical considerations (literature/general, non-clinical):
The benzoate motif is widely encountered in metabolism, where benzoic acid can be conjugated (e.g., to glycine). However, the para-acetyl functionality makes this molecule more hydrophobic and not a typical substrate for common benzoate-catabolizing enzymes.
Ionization: With a carboxyl pKa around ~4.3 (literature), the compound will be predominantly deprotonated at physiological pH, increasing aqueous compatibility if converted to a salt; the neutral ketone remains electrophilic but is significantly deactivated by resonance with the ring.
Assay use: In biochemical research, aryl acids like this may be used as reference substrates or haptens, or as intermediates en route to conjugates (e.g., linkers via amide formation). Any biological testing should be conducted under institutional approvals, and results interpreted strictly for research use.
No claims are made regarding pharmacology, toxicity thresholds, or therapeutic relevance; for hazard classification and exposure limits, consult the SDS.
Buffer Applications
4-Acetylbenzoic acid is not a dedicated buffering agent and is not commonly used to prepare pH buffer systems. While its carboxyl group has a pKa in the acidic range (literature ~4.3), standard laboratory buffers (acetate, citrate, phosphate, MES, etc.) are preferred for reproducibility and biological compatibility.
If dissolution in aqueous media is required, convert to the sodium/potassium salt with a stoichiometric base and use an appropriate established buffer to control pH.
Green Alternatives
While 4-acetylbenzoic acid is a solid reagent (the substance itself is not replaced), its processing can be greener via solvent and reagent choices.
Greener processing options (literature/general):
Solvents:
Prefer ethanol, isopropanol, ethyl acetate, or 2-MeTHF for recrystallizations and extractions instead of chlorinated solvents.
Replace DMF/NMP with acetonitrile, 2-MeTHF, CPME, or propylene carbonate when reaction compatibility allows.
Couplings/derivatizations:
Use EDC·HCl with catalytic DMAP in EtOAc or MeCN as alternatives to DIC/DMF; aqueous micellar catalysis (e.g., TPGS-750-M) can enable amide formation under milder, water-rich conditions.
Enzymatic esterifications in solvent-free or green solvents can reduce waste and hazards.
Workup and purification:
Aqueous bicarbonate/acid toggling to partition acid/base forms can reduce silica use. Crystallization-driven purifications lower solvent/energy footprints versus chromatography.
Greener: EtOAc, 2-MeTHF, acetonitrile, catalytic EDC in benign media; advantages: lower toxicity/worker exposure; tradeoffs: solubility differences, reaction rate changes.
Note: Verify solubility and reaction kinetics when switching solvents; minor base or temperature adjustments often restore performance.
Pharmaceutical Uses
No excipient or pharmacopeial status is specified for this item. 4-Acetylbenzoic acid is primarily used as a synthetic intermediate in research and development.
Formulation/manufacturing context (general):
Intermediate utility: The acid can be transformed into esters, amides, or acyl chlorides that serve as intermediates in active ingredient synthesis or in polymeric materials.
Impurity considerations: For GMP contexts, control of related substances such as 4-ethylbenzoic acid (from over-reduction), benzoic acid derivatives (from cleavage), or residual coupling reagents is important.
Analytical control: Identity/purity typically verified by NMR, IR (distinct dual carbonyl bands), HPLC/UPLC with UV detection (aromatic chromophore), and, where needed, GC-MS after derivatization of the acid.
Item-specific pharmacopeial compliance or excipient use: Not specified for this item; refer to CoA/Spec Sheet and your quality system requirements.
Physical Properties
Item-specific numerical specifications are not provided in the Product Data; consult the CoA/Spec Sheet for guaranteed values. Literature and general reference data for 4-acetylbenzoic acid are summarized below (for guidance only):
Appearance: Not specified for this item; refer to CoA/Spec Sheet.
Melting point: typically ~204–206 °C (literature, multiple sources)
Boiling point: not usually distilled; decomposes before boiling at atmospheric pressure (literature)
Density (solid): not commonly reported; depends on crystal form (literature)
pKa (carboxyl): ~4.3 (literature, similar to benzoic acid derivatives)
LogP (neutral acid): expected in the low-to-moderate range for aromatic carboxylic acids with a ketone; exact value varies by source (literature)
Solubility (qualitative, literature):
Water: low at neutral pH; solubility increases strongly in basic media via carboxylate formation (e.g., NaOH, carbonate).
Organic: soluble in polar organics (MeOH, EtOH, acetone, acetonitrile) and highly soluble in aprotic polar solvents (DMF, DMSO); sparing in nonpolar hydrocarbons.
UV characteristics: aromatic π→π* absorption typical of benzoates; precise UV cutoffs not specified for this item; refer to CoA/Spec Sheet.
Refractive index: not applicable to a crystalline solid.
Notes for practice (general): For analytical or stock solutions, dissolve in DMSO or DMF; for aqueous systems, prepare the sodium salt in situ with equimolar base to achieve high solubility.
Quality and Grades
Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.
Context for professional users (general guidance):
Research-grade vs. higher analytical grades: Research-grade 4-acetylbenzoic acid typically supports synthetic, materials, and method-development work. When sensitive applications (e.g., photophysics, trace-metal catalysis) demand tighter impurity control, look for specifications such as assay by HPLC/GC, water content by KF, and trace metals by ICP. For this SKU, such item-specific specifications are not provided here.
Stabilizers: None are typically required for this solid; absence/presence of stabilizers for this item is not specified.
UV/Chromatography considerations: If using as a calibration standard or for photometric analytics, source material with documented UV absorbance baseline and known extinction coefficients; for this item, numeric UV cutoff is not specified.
Batch documentation: Request CoA/Spec Sheet for actual lot assay, residual solvents, and impurity profile (e.g., 4-ethylbenzoic acid, 4-acetylbenzoate esters, or starting materials). Confirm identity by NMR/IR/MS as needed; the carbonyl stretches (~1680–1710 cm−1 ketone; ~1685–1725 cm−1 acid) and aromatic signals provide clear diagnostic features.
Practical tip: Recrystallization from ethanol/water or ethyl acetate/hexanes often affords high-purity material; validate purification choice by your method requirements.
Reaction and Applications
As a bifunctional aromatic building block, 4-acetylbenzoic acid is valuable in synthesis where orthogonal manipulation of an aryl carboxyl and an aryl methyl ketone is desired.
Representative uses (literature/general):
Carboxyl activation and derivatization:
Esterification (Fischer) to 4-acetylbenzoates under acid catalysis; enzymatic or Steglich (DCC/DMAP) alternatives when acid-sensitive partners are present.
Amide formation via EDC·HCl/HOBt or HATU in DCM/DMF, delivering para-acetylbenzamides while retaining the ketone.
Acid chloride formation (SOCl2, oxalyl chloride) enabling acylations with alcohols/amines.
Ketone transformations:
Oxime/hydrazone formation (hydroxylamine or hydrazines) for characterization or further rearrangements.
Selective reduction of the aryl ketone to the secondary alcohol with NaBH4 or catalytic hydrogenation, leaving the acid intact; further esterification/amidation provides diversified scaffolds.
Complete carbonyl reduction (Clemmensen or Wolff–Kishner) to 4-ethylbenzoic acid when an ethyl substituent is desired para to the acid.
Aldol-type condensations at the methyl ketone under strong base, affording chalcone-like systems (e.g., with aromatic aldehydes).
Ring functionalization:
Both carbonyls are meta-directing; electrophilic substitutions tend to occur at the 3-positions relative to each substituent, enabling predictable substitution patterns on the ring.
Materials/intermediates:
Serves as a precursor to polyesters, liquid-crystalline monomers, azo dye intermediates, and pharmaceutical intermediates where a para-acyl/acid motif is required.
Practical tips: Protect the acid as an ester when using strong bases on the ketone. Conversely, protect the ketone (e.g., as a ketal) if forcing acid chloride formation or other conditions risk ketone participation.
Reaction Conditions
General literature guidance for common transformations of 4-acetylbenzoic acid (actual conditions should be optimized):
Acid chloride formation: SOCl2 (3–5 eq) with catalytic DMF, 0–reflux (65–80 °C) 1–3 h; remove excess under reduced pressure. Protect ketone if sensitive downstream. Typical conversions: high.
Amide coupling: EDC·HCl (1.1–1.5 eq), HOBt or HOAt (0.1–1 eq), catalytic DMAP, base (DIPEA, 2–3 eq) in DCM or DMF, 0–25 °C, 2–16 h. Isolated yields: often 70–95% (literature ranges).
Fischer esterification: ROH (excess), catalytic conc. H2SO4 or p-TsOH, reflux 4–24 h; azeotropic water removal improves rates. Yields commonly 70–90%.
NaBH4 reduction of the ketone: MeOH, EtOH, or MeOH/THF at 0–25 °C, 0.5–2 h; affords 4-(1-hydroxyethyl)benzoic acid. Acid function generally survives; monitor for transesterification in alcohols.
Oxime formation: Hydroxylamine·HCl (1.1–1.5 eq), pyridine or NaOAc buffer, EtOH or MeOH, 25–60 °C, 2–6 h; typically high conversions.
Aldol condensation: Strong base (NaOMe/NaOEt, t-BuOK) in alcohol or THF, 0–reflux with aromatic aldehydes; protect acid (as ester) to improve yields and prevent salt formation.
Baeyer–Villiger oxidation (ketone → ester): mCPBA (1.5–2 eq) in DCM at 0–25 °C; evaluate chemoselectivity vs. acid.
Workup tips: Use bicarbonate/acid toggling to separate unreacted acid from neutral products. Recrystallization from EtOAc/hexanes or EtOH/H2O often gives analytically pure solids.
Safety and Handling
GHS classification, pictograms, and H-statements: Not specified for this item; refer to the product SDS for authoritative safety information.
General laboratory safety guidance for aromatic carboxylic acids with ketone functionality (informational):
Hazards: May cause irritation to eyes, skin, and respiratory tract as a fine organic powder. Dust may form combustible mixtures with air; avoid dust generation and ignition sources.
PPE: Wear lab coat, safety glasses, and appropriate chemical-resistant gloves (e.g., nitrile). Handle powders in a fume hood to minimize inhalation.
Incompatibilities: Strong oxidizers (risk of exothermic reaction); strong bases (salt formation and possible aldol-type reactions at the methyl ketone under strongly basic conditions); strong acids (may catalyze self- or cross-condensations of the ketone with nucleophiles). Avoid reducing agents that target the ketone unless intended.
First aid (overview; see SDS):
Inhalation: Move to fresh air; seek medical attention if symptoms persist.
Skin/eye contact: Rinse with water for 15 minutes; remove contaminated clothing; obtain medical advice if irritation continues.
Ingestion: Rinse mouth; do not induce vomiting; seek medical attention.
Fire-fighting: Use dry chemical, CO2, or foam. Thermal decomposition can release CO/CO2; firefighters should wear SCBA.
Handling/storage: Keep container tightly closed, dry, and well-ventilated. Minimize exposure to heat and light that could induce slow discoloration or degradation of carbonyl compounds. Always consult the SDS before use.
Solvent Selection
4-Acetylbenzoic acid is a moderately polar, hydrogen-bonding capable aromatic acid with an additional ketone. Solvent choice hinges on ionization state and downstream use.
Poorly soluble: alkanes (hexane, heptane), toluene at ambient (solubility improves when hot).
Aqueous systems: low solubility as the neutral acid near pH 7; readily soluble as its carboxylate above pH ~5.5 (e.g., Na+, K+ salts).
Typical selection strategies:
For analytical stock solutions: DMSO or DMF at 10–100 mg/mL; dilute into assay media last, or pre-neutralize to salt form for aqueous dosing.
For recrystallization: ethanol/water or ethyl acetate/hexanes provide good crystallization behavior and impurity rejection; adjust ratios by solubility curves.
For coupling reactions (amide/ester formation): DCM, DMF, THF, or acetonitrile are common; consider greener swaps such as EtOAc or 2-MeTHF where feasible.
For base-mediated condensations at the methyl ketone: alcohols (EtOH) or aprotic polar (DMF/DMSO) support solvating bases and nucleophiles.
When to choose alternatives:
If water compatibility is mandatory, form the sodium/potassium salt and work in buffered aqueous/MeOH mixtures.
If low-toxicity solvent is required, prefer ethanol or ethyl acetate over chlorinated solvents.
Note: Avoid highly basic aqueous media if preserving the ketone integrity is critical (enolization/condensation can occur).
Storage and Reconstitution
Storage conditions (item-specific): Room temperature (product data). Store tightly closed in a dry, well-ventilated place. Protect from prolonged exposure to moisture and strong light.
Shipping (item-specific): Shipped at ambient temperature (Normal; product data).
Stability (general): Aromatic carboxylic acids with ketones are typically stable for years when dry and sealed. Periodically check by NMR/IR/HPLC if using for analytical reference work.
Organic stocks: Dissolve in DMSO or DMF to 10–100 mg/mL; filter (0.22 µm) if needed. For less polar media, warm gently to aid dissolution (avoid overheating).
Aqueous use: Generate the sodium or potassium salt in situ with equimolar base (e.g., NaOH) to achieve high solubility; adjust pH with buffer.
Working solutions: Prepare fresh as needed to minimize hydrolysis/side reactions in strongly acidic/basic media.
Freeze–thaw: Not applicable to the dry solid. For DMSO/DMF stocks, aliquot and store desiccated to avoid water uptake; minimize freeze–thaw cycles if low-temperature storage is used.
For guaranteed specifications (assay, water, metals, residual solvents), and any lot-specific handling notes, consult the CoA/Spec Sheet.
Structure and Identity
A para-acylated benzoic acid combining a carboxylic acid and a methyl ketone on a benzene ring (para relationship).
InChIKey (item-specific): Not specified for this item; refer to CoA/Spec Sheet.
SMILES (literature): CC(=O)c1ccc(cc1)C(=O)O
Molecular formula (literature): C9H8O3
Molecular weight (literature): 164.16 g/mol
Structural features (descriptive):
Aromatic ring bearing two strong electron-withdrawing carbonyl substituents.
Para substitution pattern: the acetyl group (–COCH3) and carboxylic acid (–CO2H) are opposite each other on the ring.
Functional groups: carboxylic acid (acidic, can form salts/esters/amides) and aryl methyl ketone (electrophilic carbonyl; forms oximes/hydrazones; undergoes reductions and condensations).
Planar conjugation across the ring and both carbonyls; no stereocenters.
2D structure in words: A benzene ring with –CO2H at C1 and –COCH3 at C4 (para). The acid carbonyl and the ketone carbonyl are coplanar with the ring, enabling resonance withdrawal from the ring and directing meta in further electrophilic aromatic substitution.
Synthetic Utility
Functional group complementarity makes 4-acetylbenzoic acid a versatile bifunctional synthon.
Carboxyl group (–CO2H):
Readily converted to acid chlorides (SOCl2, oxalyl chloride) for subsequent esterification or amidation.
Direct couplings (EDC/HOBt, HATU, CDI) provide amides under mild conditions, often with the ketone untouched.
Esterification (Fischer, Steglich) introduces protecting or functional handles for further transformations.
Ketone (–COCH3):
Nucleophilic addition (NaBH4 → secondary alcohol; organometallic addition under controlled conditions if acid is protected or present as salt).
Derivatization (oximes, hydrazones) enabling tracers or further rearrangements.
Reductive transformations (Clemmensen/Wolff–Kishner) to para-ethylbenzoic acid; Baeyer–Villiger oxidation can access 4-(carboxymethyl)benzoic acid ester derivatives depending on conditions.
Enolate chemistry: Aldol condensations with aldehydes/ketones to build chalcone-like scaffolds; requires base and often protection of –CO2H.
Aromatic substitution profile: Dual carbonyl meta-directing effects guide further EAS to positions 3,5 relative to the acid/ketone.
Retrosynthetic value: Serves as a convergent node linking benzoic acid chemistry with aryl ketone elaboration, enabling orthogonal protection and stepwise diversification in medicinal chemistry and materials synthesis.
Target Specificity
Not applicable. This product is a small-molecule chemical reagent and does not possess biomolecular target specificity (no antigen/epitope, clone, or isotype).
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