This compound belongs to the class of organic compounds known as trifluoromethylbenzenes. These are organofluorine compounds that contain a benzene ring substituted with one or more trifluoromethyl groups.
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.
Certificados (CoA, COO, BSE/TSE y tabla de análisis)
C of A & Other Certificates(BSE/TSE, COO):
Analytical Chart:
Propiedades químicas y físicas
Peso molecular
242.240 g/mol
XLogP3
3.000
Hydrogen Bond Donor Count
0
Hydrogen Bond Acceptor Count
4
Rotatable Bond Count
1
Exact Mass
242.092 Da
Monoisotopic Mass
242.092 Da
Topological Polar Surface Area
17.100 Ų
Heavy Atom Count
17
Formal Charge
0
Complexity
267.000
Isotope Atom Count
0
Defined Atom Stereocenter Count
0
Undefined Atom Stereocenter Count
0
Defined Bond Stereocenter Count
0
Undefined Bond Stereocenter Count
0
The total count of all stereochemical bonds
0
Covalently-Bonded Unit Count
1
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Application Protocols
No application protocols (e.g., WB, IHC, IF, FC) are applicable to this small-molecule reagent.
General laboratory usage suggestions:
Analytical stock solutions: Prepare at 10–100 mM in DMSO or MeCN; store aliquots to minimize freeze–thaw and moisture exposure. Verify solution stability by LC or NMR over your intended use period.
Purification: Normal-phase silica using hexanes/EtOAc or DCM/MeOH systems; consider reverse-phase C18 for highly lipophilic impurity profiles.
Characterization: 1H/13C NMR (aromatic signals and carbonyl at ~200 ppm), 19F NMR (singlet for CF3), HRMS, and HPLC purity.
For specialized transformations, see the Reaction Conditions and Synthetic Utility sections.
Biological Roles
This compound is a synthetic small molecule and is not known as a natural metabolite, cofactor, or biopolymer building block.
Biochemical relevance (general): Aryl ketones can serve as hydrophobic fragments in medicinal chemistry programs. The para-CF3 group often increases metabolic stability and membrane permeability of derived scaffolds (literature trend), but this product itself is provided strictly for research use as a chemical intermediate.
Reactivity in biological settings: The carbonyl can form reversible adducts (Schiff bases after derivatization to imine) with primary amines, but such transformations typically require dehydrating conditions not found physiologically.
Assay considerations: Strong aromatic UV absorption enables straightforward detection by HPLC-UV. High lipophilicity suggests potential for protein binding and partitioning into lipid phases in experimental systems; account for nonspecific binding in biochemical assays.
No specific enzymatic targets, transporters, or pathways are attributed to this compound. If used in probe development, evaluate off-target interactions, plasma protein binding, and microsomal stability empirically.
Research Use Note: For research use only (Product Data). No medical or clinical applications are intended or supported.
Buffer Applications
This product is a hydrophobic aryl ketone and is not used as a buffering agent. It lacks acid–base pairs suited for maintaining pH in aqueous media.
For aqueous work involving this molecule (e.g., analytical assays), choose a standard buffer (phosphate, acetate, HEPES) suitable for the biological or analytical system, and dissolve the compound first in a miscible organic co-solvent (DMSO, MeCN, EtOH) before dilution into buffer to avoid precipitation.
No buffer recipes are specific to this compound.
Green Alternatives
Greener practice focuses on solvent and reagent choices, as the molecule itself is a specialty building block.
DCM → Ethyl acetate or 2-MeTHF for extractions and chromatography (check selectivity/solubility).
Chloroform → Cyclopentyl methyl ether (CPME) or toluene.
Replace conventional ethers:
THF → 2-MeTHF (renewable, higher boiling point, improved stability to peroxide formation vs THF; still monitor for peroxides).
Polar aprotic replacements:
DMF/DMAc/NMP → MeCN, sulfolane, or propylene carbonate when compatible with the chemistry.
Small comparison (general):
2-MeTHF: bio-based, water-lean phase separations, good for enolates; may swell elastomers and has odor considerations.
EtOAc: readily biodegradable, easy workups; lower polarity than DCM can alter chromatographic resolution.
CPME: broad liquid range, low peroxide formation; may provide slower reaction rates for some nucleophilic substitutions vs THF.
Process suggestions:
Use catalytic rather than stoichiometric reagents where feasible (e.g., catalytic hydrogenation vs metal hydrides).
Implement telescoped steps (e.g., in situ oxime formation/reduction) to reduce solvent exchanges.
Evaluate solvent recovery (toluene, EtOAc, MeCN) and minimize halogenated waste.
Pharmaceutical Uses
No pharmacopeial monograph or excipient role is indicated for this item. It is offered as a research chemical building block.
Potential role (general, non-clinical): Intermediate for synthesis of arylcyclohexyl derivatives, where the para-CF3 aryl group provides lipophilicity and electron withdrawal. Such transformations are confined to R&D; no claims are made for therapeutic use.
Formulation context (analytical or screening samples): For in vitro screening, prepare stock solutions in DMSO or MeCN due to poor water solubility; filter through 0.2 μm PTFE before use to remove particulates. Assess stability upon dilution into aqueous media (precipitation risk).
All uses are for research and laboratory development only, not for human or veterinary applications (Product Data: Research Use Only).
Physical Properties
Item-specific specifications are not provided in the Product Data. Where useful, general/literature or computed values are noted and clearly labeled.
Appearance: Not specified for this item; refer to CoA/Spec Sheet.
Molecular formula (literature/computed): C13H13F3O
Melting point: Not specified for this item; refer to CoA/Spec Sheet.
Boiling point: Not specified for this item; refer to CoA/Spec Sheet.
Density: Not specified for this item; refer to CoA/Spec Sheet.
Refractive index: Not specified for this item; refer to CoA/Spec Sheet.
pKa (enolization, literature trend): Typical cyclic aryl ketones exhibit α-C–H pKa in the high teens to low 20s in DMSO; exact value not determined for this structure.
Partition behavior (literature expectation): High hydrophobicity due to aryl + CF3; expected poor water solubility and good solubility in common organic solvents (EtOAc, DCM, THF, MeCN, toluene, alcohols). Verify experimentally.
UV characteristics (literature expectation): Aromatic π–π* absorption near 200–220 nm and ~254–270 nm; ketone n→π* around 300 nm of low intensity. Exact cutoffs not established for this item.
Note: For chromatography and method development, determine actual solubility, retention, and UV response empirically with your solvent system. Consult the CoA/SDS for definitive product-specific physical data.
Quality and Grades
Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.
In the absence of an explicit grade, users should verify application suitability via CoA data (assay, chromatographic purity profile, residual solvents, identified impurities) and, where relevant, by running an incoming QC (e.g., 1H/13C NMR, LC/HPLC purity, HRMS).
Guidance on common grades (general knowledge):
Analytical/AR grade: Suitable for most synthetic applications; impurity profiles controlled but not necessarily optimized for chromatographic transparency.
HPLC grade (for solvents): Low UV absorbance and particle content; not applicable to this solid reagent but relevant for mobile phases when analyzing it.
Bio/Pharm grades: Focus on endotoxin/bioburden and residuals; typically not applicable to small-molecule building blocks unless specified.
If stabilizers or inhibitors were present, they would be listed on the CoA. None are indicated in the Product Data for this item.
Recommendation: For sensitive enolate chemistry or stereoselective reductions, consider confirming base-neutral impurity levels (acids, amines, water) and trace metals if using catalytic processes. Request lot-specific CoA for exact specifications.
Reaction and Applications
As a para-CF3–substituted aryl cyclohexanone, this building block is valuable in discovery and process chemistry where a lipophilic, electron-withdrawing aryl motif is desired.
Key application areas (general/literature):
Enolate chemistry: α-Functionalization via LDA, LiHMDS, NaH, or KHMDS to access α-alkylated, α-aryl, or α-heteroatom derivatives. The CF3-aryl group stabilizes adjacent negative charge inductively, often improving enolate formation control.
Aldol and related condensations: Cross-aldol with aldehydes/ketones; intramolecular variants to form bicyclic frameworks. Subsequent dehydration affords α,β-unsaturated ketones (enones) for conjugate additions.
Reductions: Chemoselective reduction to the secondary alcohol (NaBH4, Luche, catalytic hydrogenation). Over-reduction (to cyclohexyl) typically requires harsher conditions.
Oxime/hydrazone formation and reductive amination: Carbonyl derivatization (HONH2, hydrazines); imine formation followed by hydrogenation introduces amino functionality at the carbonyl carbon.
Baeyer–Villiger oxidation: Conversion to ε-lactones using peracids or m-CPBA; electronic effects of CF3-aryl can influence migratory aptitude.
Photoredox/EDA strategies: Aryl CF3 contributes to photophysical properties; ketone can participate in α-alkylation under photocatalysis (literature precedent for aryl ketones).
Cross-coupling (indirect): After α-halogenation, engage in C–C bond construction (e.g., enol triflate formation → Pd-catalyzed Suzuki/Negishi coupling to elaborate enone scaffolds).
Practical tips:
Thoroughly dry solvents and bases for enolate chemistry; control temperature (−78 to 0 °C) to favor kinetic vs thermodynamic enolates.
The CF3 group increases lipophilicity; expect enhanced retention in RP-LC and higher solubility in aromatic solvents.
Reaction Conditions
General literature guidance for aryl cyclohexanone transformations; optimize for your substrate and scale.
Enolate formation/alkylation:
Base/solvent: LDA or LiHMDS in THF/2-MeTHF at −78 to −20 °C. Typical times 0.5–2 h for enolate generation; electrophile addition 0.5–2 h. Quench with NH4Cl.
Selectivity: Lower temps favor kinetic α-alkylation; higher temps/longer times may lead to equilibration.
Aldol condensations:
Conditions: NaOH, K2CO3, or secondary amines (enamine route) in EtOH, MeOH, or THF. 0–25 °C for aldol step; 40–80 °C for dehydration.
Workup: Aqueous acid quench; silica or recrystallization purification.
NaBH4/Luche reductions:
Solvent: MeOH, EtOH, or THF/H2O; 0–25 °C, 0.5–2 h. Cerium(III) chloride (Luche) improves chemoselectivity in the presence of conjugated systems.
Reductive amination:
Imine formation with amine + Ti/iPrOH or molecular sieves; reduction with NaBH3CN (pH 5–6) or H2/Pd-C (1–3 bar). 0–25 °C, 2–16 h.
Baeyer–Villiger oxidation:
Reagent: m-CPBA (1.2–2.0 equiv) in DCM at 0–25 °C, 2–24 h; or peracetic acid. Monitor for over-oxidation; neutralize acids in workup.
Enol triflation/cross-coupling:
Formation: LiHMDS, then N-phenyltriflimide or Tf2O in THF at −78 to −40 °C.
Coupling: Pd(0) catalyst (e.g., Pd2(dba)3/XPhos) in toluene/THF, base (K3PO4/Cs2CO3), 60–100 °C, 2–16 h.
Yields are substrate- and condition-dependent; consult primary literature and run small-scale scouts before scale-up.
Safety and Handling
Safety details are not specified in the Product Data; consult the SDS for authoritative information. The guidance below reflects general practices for aryl ketones containing a trifluoromethyl group.
GHS/CLP classification: Not specified for this item; refer to SDS.
Signal word / H-statements / pictograms: Not specified for this item; refer to SDS.
General handling recommendations (good laboratory practice):
PPE: Lab coat, safety glasses or splash goggles, and appropriate chemical-resistant gloves (e.g., nitrile). Use within a fume hood to minimize inhalation of vapors or aerosols during weighing or solvent handling.
Incompatibilities: Avoid strong oxidizers and strong bases in storage. Under reactive conditions, carbonyl compounds may form imines/oximes/hydrazones; segregate from reactive amines/hydrazines if undesired.
Thermal stability: Aryl ketones are generally stable at ambient temperature; avoid excessive heat and ignition sources. No known peroxide-formation hazard (unlike ethers), but observe standard solvent safety.
Spill/cleanup: Absorb small spills with inert material (vermiculite, silica). Collect for disposal in halogenated-organics or general organics waste stream per your local procedures.
First aid (overview): Inhalation—move to fresh air; Skin—wash with soap/water; Eye—rinse with water for several minutes; Ingestion—rinse mouth; seek medical attention as per SDS recommendations.
Waste: Dispose as organic laboratory chemical waste; fluorinated aromatics may require incineration compliant with local regulations.
Always defer to the product’s SDS and your institutional EHS guidance.
Solvent Selection
This compound is an aryl–alicyclic ketone with high hydrophobicity (CF3-phenyl substituent). It is typically soluble in common organic solvents and poorly soluble in water.
Polarity class (general): Moderately polar functional group (ketone) on a largely nonpolar framework; overall behavior is nonpolar to moderately polar.
Limited: Hexanes/heptane (may be soluble warm or with co-solvent).
Poor: Water.
Chromatography: Silica gel elution typically requires 5–30% EtOAc in hexanes or 1–10% MeOH in DCM depending on polarity of impurities. Aromatic UV handles enable 254 nm detection.
Crystallization/recrystallization: Mixed solvents such as EtOAc/hexanes, toluene/hexanes, or IPA/water (with antisolvent) are common starting points; confirm solubility curves experimentally.
Comparison and selection tips:
Choose THF or 2-MeTHF for base-mediated enolate chemistry (good solvation; 2-MeTHF offers greener profile).
Use toluene or EtOAc for greener workups; EtOAc simplifies aqueous separations.
For analytical LC, MeCN/water or MeOH/water gradients with 0.1% acid modifier often provide sharp peaks; confirm stability against modifiers (TFA/formic/acetic acid).
Shipped in: Not specified for this item; refer to CoA/Spec Sheet.
Appearance: Not specified for this item; refer to CoA/Spec Sheet.
Recommendations (general best practice for aryl ketones):
Store tightly closed in a dry place, protected from excessive heat and direct sunlight. Use desiccant if ambient humidity is high.
If long-term storage is planned, consider amber glass to limit photolysis of aromatic ketones and maintain in secondary containment to prevent solvent odor absorption.
Avoid prolonged exposure to strong bases/acids in storage; keep separate from oxidizers.
Reconstitution/solution preparation:
Dissolve in common organic solvents (e.g., DCM, THF/2-MeTHF, EtOAc, MeCN, toluene, alcohols, or DMSO) as compatible with your application. Poorly soluble in water; use a co-solvent for aqueous systems.
Filter solutions through PTFE (0.2–0.45 μm) prior to analytical use.
For assay stocks (e.g., 10–100 mM in DMSO/MeCN), prepare aliquots and store capped under inert headspace if possible; minimize freeze–thaw.
Always refer to the lot-specific CoA/SDS for definitive handling and storage details.
Structure and Identity
A para-trifluoromethyl–substituted aryl–cyclohexanone combining a lipophilic CF3-phenyl ring with a cyclohexanone core.
Product Name (catalog): 4-(4-(Trifluoromethyl)phenyl)cyclohexanone
CAS: 40503-94-4 (Product Data)
CID: 18400217 (Product Data)
InChIKey (as provided): 313629 (Product Data)
SMILES: Not specified for this item; refer to CoA/Spec Sheet.
Molecular formula (literature/computed from name): C13H13F3O
Core: Cyclohexanone ring (six-membered alicyclic ketone) with a carbonyl at C1.
Substitution pattern: A para-(trifluoromethyl)phenyl group bonded at the 4-position of the cyclohexanone (1,4-disubstitution on the ring relative to the carbonyl).
Functional groups: Aryl ring (phenyl) bearing a strong –CF3 group at the para position; cyclic ketone (C=O).
Electronic characteristics: The aryl CF3 is a powerful σ-withdrawing and lipophilicity-enhancing substituent; the carbonyl is enolizable at the α-positions on the cyclohexanone ring.
Stereochemistry: No stereogenic centers in the idealized chair conformer; conformational isomerism (chair/boat) possible, with the aryl substituent typically favoring an equatorial orientation in the lowest-energy chair (literature, conformational analysis).
Synthetic Utility
Functional group set: a cyclic ketone adjacent to a para-CF3 phenyl substituent.
Transformations (literature/general):
α-Functionalization via enol(ate):
Alkylation (primary halides), acylation (acid chlorides/anhydrides), and electrophilic trapping (silylation, halogenation). Use LDA/LiHMDS at −78 to −20 °C for kinetic control.
Formation of enol triflates for subsequent Pd-catalyzed cross-coupling to build substituted enones or dienones.
Carbonyl chemistry: Oximes/hydrazones (HONH2/hydrazines), Wolff–Kishner or Clemmensen conditions for deoxygenation (substrate compatibility must be assessed due to CF3-aryl stability).
Reductive amination: Introduces aminoalkyl groups at the carbonyl carbon; commonly NaBH3CN or catalytic hydrogenation used after imine formation.
Baeyer–Villiger oxidation: Access to lactones enabling ring-expanded or functionalized products for polymer or agrochemical leads.
Conjugate chemistry: Aldol → enone → 1,4-addition of nucleophiles (cuprates, organozincs, organoboron under Pd). The CF3 aryl can modulate Michael acceptor reactivity through inductive effects.
Photoredox α-alkylation: Exploits ketone α-C–H activation under photocatalysis to couple with electron-deficient partners (general precedent for aryl ketones).
Strategic value: The CF3 substituent is a persistent handle that elevates lipophilicity and can tune pKa/logP in downstream analogs—useful in medicinal chemistry SAR campaigns.
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 data are associated with this item.
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