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 assay protocols (e.g., WB, IHC, IF, FC) are associated with this small-molecule reagent. For practical use, refer to Reaction Conditions, Synthetic Utility, and Reaction & Applications for guidance on employing the compound in organic synthesis.
Biological Roles
This product is intended for research and laboratory use only.
General note: Octafluoroacetophenone is a synthetic, perfluorinated aryl ketone with no known natural biological role or occurrence in metabolic pathways.
Biochemistry context (literature/general):
Perfluorinated aromatics are generally xenobiotic to biological systems and resist metabolic oxidation/hydrolysis due to strong C–F bonds.
The aryl ketone functionality can participate in noncovalent interactions (e.g., dipolar interactions) in model studies of binding, but such uses are physical-organic probes rather than biological roles.
Caution: Avoid extrapolating any biochemical observations to clinical or therapeutic contexts. No medical or clinical claims are made or implied.
Buffer Applications
Not typically applicable. Octafluoroacetophenone is a hydrophobic, perfluorinated aryl ketone and is not used as a buffering agent or pH control component. For relevant practical guidance, see Reaction & Applications and Synthetic Utility for its role as a reagent/substrate in organic synthesis.
Green Alternatives
Fluorinated organics can pose environmental persistence concerns. Selection should weigh performance against EHS impact and downstream life-cycle considerations.
Environmental/EHS considerations (general):
Per- and polyfluorinated aromatics are typically persistent and resistant to biodegradation. Minimize release, use closed systems, and implement effective waste capture.
Possible alternative building blocks (context-dependent):
Cons: Aryl ring not activated for SNAr; different reactivity profile—may require metal-catalyzed halogenation/activation steps.
Trifluoroacetophenone (partially fluorinated):
Pros: Retains some electron-withdrawing character with fewer C–F bonds; may reduce persistence relative to perfluoroaryl systems.
Cons: Lacks pentafluorophenyl activation; SNAr on aryl ring generally not accessible.
Pentafluorobenzoyl chloride (if acyl-transfer is the goal):
Pros: Efficient acylating agent; can be used catalytically in peptide coupling methodologies (e.g., PFBCl protocols).
Cons: Corrosive, lachrymatory; still fluorinated and requires careful handling.
Small comparison (general; not product specifications):
Octafluoroacetophenone: maximally activates aryl ring for SNAr; non-enolizable; high persistence.
Less-fluorinated ketones: reduced EHS burden but different reactivity—may necessitate alternative routes (e.g., halogenation then cross-coupling).
Strategy: If a perfluoroaryl handle is not essential to the end product, redesign the route to avoid persistent fluorinated intermediates and adopt greener solvents (e.g., 2-MeTHF, CPME) and catalytic conditions.
Pharmaceutical Uses
No therapeutic or clinical uses are claimed. Any utilization would be in the context of research or process development chemistry.
Potential roles in pharmaceutical R&D (general):
Synthetic intermediate: The pentafluorophenyl unit enables late-stage diversification via SNAr to build libraries of aryl ethers, thioethers, and anilines for SAR studies.
Reagent/substrate in methodology development: Non-enolizable ketone useful for benchmarking nucleophilic addition conditions without competing enol chemistry.
Regulatory notes: Not a pharmacopeial excipient. If considered for GMP-related applications (e.g., as an intermediate), require full impurity profiling, residual solvent assessment, and appropriate clearance of fluorinated residues per internal and regulatory standards.
Physical Properties
Item-specific specifications are not provided in the Product Data. Do not use the values below as product specifications; consult the CoA/Spec Sheet for this specific lot.
From Product Data:
Appearance: Not specified for this item; refer to CoA/Spec Sheet.
Storage conditions: Room temperature (as provided)
Literature/typical properties for octafluoroacetophenone (reference only):
State: typically a colorless to pale liquid (literature/general)
Molecular weight: ~264.06 g/mol (literature)
Molecular formula: C8F8O (literature)
Density: often higher than nonfluorinated analogs of similar size due to fluorination (literature trend)
Boiling point, melting point, refractive index, UV cutoff, water content, residual metals: Not specified here; consult primary literature or supplier CoA for exact values.
Solubility: generally low in water; miscible with many polar aprotic and nonpolar organic solvents (literature generalization for perfluoroaryl ketones)
LogP: expected elevated relative to acetophenone due to extensive fluorination; exact value not compiled here (literature trend)
Not provided for this item; refer to CoA/Spec Sheet where applicable:
Water content, stabilizers, inhibitor content
Peroxide levels
Heavy metal limits
UV-Vis absorbance profile for HPLC/UV applications
Quality and Grades
Grade/purity: Not specified for this item; refer to CoA/Spec Sheet.
Appearance: Not specified for this item; refer to CoA/Spec Sheet.
Guidance for interpreting common grades (general):
Research grade: Suitable for most synthetic, materials, and analytical workflows. Review impurity profile if using in sensitive catalysis or materials doping.
HPLC/UV grade (if applicable): Tight control of UV-Vis absorbance and volatile/nonvolatile residues; preferred for trace analysis. For fluorinated ketones, background at deep UV can vary—verify against your detector wavelength.
Anhydrous/Water content: Not specified for this item. If moisture-sensitive transformations (e.g., strong base-promoted SNAr) are planned, consider drying over molecular sieves or distilling under inert atmosphere as appropriate to your internal SOPs.
Batch-specific documents:
Certificate of Analysis (CoA) and/or Specification Sheet will state assay method, purity, water, residual solvents, stabilizers/inhibitors (if any), and recommended storage. For regulated or high-precision work, request and retain these documents.
Reaction and Applications
Octafluoroacetophenone is a versatile, strongly deactivated aryl ketone useful for installing functionality on the pentafluorophenyl ring via nucleophilic aromatic substitution (SNAr) and for carbonyl-based transformations without complications from enolization.
Key application families (literature/general):
SNAr on pentafluorophenyl: The carbonyl (–COCF3) acts as a strong –M/–I director that activates the ring toward nucleophilic attack, particularly at para and ortho positions. Nucleophiles include amines, alkoxides/phenoxides, thiolates, and some carbon nucleophiles under strong conditions.
Nucleophilic addition to the carbonyl: Organomagnesium/organolithium reagents add to the ketone to give tertiary alcohols; the absence of α-H (CF3) prevents enolization and aldol-type side reactions.
Reductive transformations: Carbonyl reduction (e.g., NaBH4, hydrosilanes with catalysts) affords the corresponding secondary alcohol; chemoselectivity must account for potential defluorination under strong conditions.
Electrophile trapping: The electron-poor aryl can undergo metal-catalyzed couplings after targeted SNAr to introduce leaving groups (e.g., convert to aryl ethers/aryl thioethers, then cross-couple).
Photochemical/physical: Highly fluorinated aryl ketones often show distinct n→π* transitions; they may serve as sensitizers or probes in physical organic studies (application-specific literature).
Practical notes:
Maintain dry, oxygen-free conditions for strong nucleophiles/bases; adventitious moisture suppresses SNAr and consumes reagents.
For SNAr, cesium carbonate or potassium carbonate in DMF/DMSO/MeCN often improves rates; phase-transfer strategies can help less soluble nucleophiles.
Monitor for regioisomer formation in SNAr; directing effects of the carbonyl and reaction temperature/base strength influence selectivity.
Reaction Conditions
The following are general, literature-style guidelines for common transformations of perfluoroaryl ketones. They are not product specifications and should be adapted/validated for the intended substrate and scale.
SNAr on the pentafluorophenyl ring:
Solvents: DMF, DMSO, NMP, MeCN (dry).
Bases: K2CO3, Cs2CO3, NaH, or t-BuOK depending on nucleophile strength.
Nucleophiles: amines, alkoxides/phenoxides, thiolates; thiolates often react fastest.
Temperatures: 25–120 °C; elevated temperatures accelerate substitution and influence regioselectivity.
Notes: Use excess nucleophile or base to drive reaction; monitor by 19F NMR to track site-selective substitution.
Nucleophilic addition to the carbonyl:
Reagents: RMgX or RLi for C–C bond formation; NaBH4 or hydrosilanes (with catalysts) for reduction to alcohols.
Solvents: Dry ethers (THF, 2-MeTHF, MTBE) or hydrocarbons (toluene) depending on reagent solubility.
Temperature: −78 to 25 °C for organometallic additions; 0 to 25 °C for hydride reductions (method-dependent).
Notes: The CF3 group stabilizes the carbonyl; use stoichiometry and temperature control to avoid over-reduction or side reactions; quench carefully to avoid HF formation if any defluorination occurred.
Workup and analysis:
Quench under cooled, controlled conditions; avoid strong acids that could generate HF.
Analyze by 19F NMR and GC/LC; perfluoroaryl patterns give distinct multiplets useful for regiochemical assignment.
Safety and Handling
Always handle according to your institutional EHS procedures and the product SDS.
From Product Data:
Storage conditions: Room temperature
Shipped in: Normal
GHS/Signal word/H-statements/Pictograms: Not specified for this item; refer to SDS.
General safety considerations for perfluorinated aryl ketones (literature/general):
Hazards: Many aryl ketones can cause eye/skin irritation and may be harmful if inhaled or ingested. Perfluorinated organics can have unique toxicological profiles; avoid aerosol formation and inhalation of vapors.
Thermal stability: Fluorinated ketones are often thermally stable; avoid excessive heating and ignition sources. Combustion or high-temperature decomposition may release corrosive/toxic HF and perfluoroisobutylene-like fragments—use appropriate fume hood and avoid exposure to heat/open flames.
Incompatibilities: Strong bases and strong nucleophiles can promote nucleophilic aromatic substitution on the pentafluorophenyl ring; strong reducing agents may attack the carbonyl. Avoid contact with alkali metals, strong bases, and strong oxidizers unless intended.
PPE: Safety glasses or goggles, lab coat, and appropriate chemical-resistant gloves (e.g., fluoroelastomer or laminated barrier gloves for extended contact); use in a certified chemical fume hood.
First aid (overview; defer to SDS):
Inhalation: Move to fresh air, keep at rest; seek medical attention if symptoms persist.
Skin/eye contact: Rinse with water for at least 15 minutes; remove contaminated clothing; seek medical advice.
Ingestion: Rinse mouth; do not induce vomiting; seek medical attention.
Waste: Collect as halogenated organic waste; do not release to the environment. Follow local regulations.
Solvent Selection
Octafluoroacetophenone is primarily a synthetic building block/reagent rather than a bulk solvent. However, understanding its solvation behavior aids in reaction planning.
Polarity and interactions (general):
The carbonyl group provides dipolar character and H-bond acceptor capability; the extensive fluorination lowers polarizability and increases density relative to hydrocarbon analogs.
Typically low water solubility but good solubility in polar aprotic media (DMF, DMSO, MeCN) and common organics (EtOAc, CH2Cl2, toluene) (literature/general).
When to use/choose around it:
As a substrate in SNAr on the pentafluorophenyl ring, choose polar aprotic solvents (DMF/DMSO/NMP/MeCN) to favor nucleophilic displacement and solubilize inorganic bases.
For carbonyl additions (e.g., Grignard/organolithium), use ethers (THF, MTBE, 2-MeTHF) under strictly anhydrous conditions. The substrate is non-enolizable, simplifying chemoselectivity.
Comparison to alternatives (general):
Versus acetophenone: far more electron-poor aryl ring, enabling SNAr; typically more volatile and denser.
Versus trifluoroacetophenone: stronger ring deactivation with pentafluoroaryl, enhancing SNAr at para/ortho positions.
Note: Selection of the reaction solvent should be based on the intended transformation; this compound itself is not generally employed as a chromatography-grade solvent.
Storage and Reconstitution
From Product Data:
Storage conditions: Room temperature
Shipped in: Normal
General guidance (literature/practice):
Store tightly sealed under ambient conditions away from strong bases, strong oxidizers, and sources of ignition. Protect from moisture ingress if using in base-sensitive SNAr chemistry; consider storing under dry nitrogen for long-term stability.
Container compatibility: Fluorinated organics are generally compatible with borosilicate glass and PTFE-lined caps. Avoid elastomers that may swell (test case-by-case).
Reconstitution: Not applicable; supplied neat. If solidifies at lower temperatures (if applicable), gently warm to ambient and homogenize before use.
Handling before critical reactions: If water content is a concern, dry over 3 Å molecular sieves or pass through a short plug of activated alumina; verify by Karl Fischer if required by SOP.
Stability: Fluorinated aryl ketones are typically stable under ambient light and temperature. Always consult the current CoA/SDS for lot-specific stability and handling notes.
Research Use Note: For research use only.
Structure and Identity
Octafluoroacetophenone is a fully fluorinated aryl ketone: a pentafluorophenyl ring bonded to a trifluoroacetyl group (perfluoroaryl–CO–CF3). The ring is electron-poor and highly deactivated toward electrophilic aromatic substitution, while the carbonyl is non-enolizable due to the CF3 group.
Item-specific identifiers (from Product Data):
SKU: O343160
CAS: 652-22-2
InChIKey: Not specified for this item; refer to CoA/Spec Sheet.
SMILES: Not specified for this item; refer to CoA/Spec Sheet.
Literature identity data (for the named compound; for reference only):
Core structural features: one aryl ketone (C=O) directly attached to a pentafluorophenyl ring; no stereocenters; no enolizable hydrogens at the α-position (CF3).
2D structural description (general):
Carbonyl carbon double-bonded to oxygen; carbonyl carbon also bonded to a quaternary carbon bearing three fluorines (CF3). The carbonyl carbon’s sp2 bond connects to the ipso carbon of a hexagonal aromatic ring bearing fluorine substituents at all remaining positions (five ring-bound F atoms).
Synthetic Utility
Functional features and reactivity (literature/general):
Strongly electron-withdrawing aryl system:
Pentafluorophenyl ring is highly activated toward SNAr. Typical nucleophiles (RO−, RS−, R2NH) can replace F, often with para selectivity relative to the carbonyl. Stepwise substitution allows multi-functional patterns.
Non-enolizable ketone center:
The CF3-substituted carbonyl lacks α-hydrogens, preventing enolization/tautomerization. This simplifies chemoselectivity in base and avoids aldol-type side pathways. Suitable for benchmarking hydride additions or carbon–carbon additions.
Transformations and derivatizations:
Reduction to alcohols (NaBH4, catalytic hydrosilylation) yielding tertiary carbinols bearing CF3 and perfluoroaryl motifs.
Grignard/organolithium additions to the carbonyl to install alkyl/aryl groups; subsequent defluorinative steps (if desired) can remodel the aryl ring.
Sequential SNAr to introduce heteroatom substituents, then cross-coupling (e.g., Suzuki on introduced aryl halides after further functionalization), enabling modular assembly.
Electrophilic acyl transfer is not a primary feature (it is a ketone, not an acyl chloride), but the carbonyl can engage in oxime/hydrazone formation for protection or further transformation.
Retrosynthetic value:
Provides a perfluoroaryl handle for SNAr-driven diversification, orthogonal to classical EAS strategies. Useful in routes where electron-poor aryls or CF3-bearing tertiary alcohols are targets.
Target Specificity
Not applicable. This product is a small-molecule aryl ketone and is not an antibody, protein, or nucleic acid reagent. No antigen/epitope or species reactivity is relevant.
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