This compound belongs to the class of organic compounds known as aryl alkyl ketones. These are ketones have the generic structure RC(=O)R', where R = aryl group and R'=alkyl 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 validated bioassay protocols.
No tested biological applications or dilutions are provided in the Product Data for this small-molecule reagent.
General laboratory usage notes
For synthetic transformations, typical procedures follow standard organic methodologies (see Reaction Conditions tab). For analytical use, prepare stock solutions in suitable solvents (e.g., acetonitrile, methanol, DMSO) and filter through 0.2 µm PTFE prior to HPLC/LC–MS.
Always confirm identity and purity of working solutions by NMR/LC–MS before use in critical experiments.
Biological Roles
Item-specific biological roles
Not specified for this item; this product is supplied strictly for research use.
General biochemical context (informational; no clinical/physiological claims)
Furan-containing small molecules are prevalent as synthetic intermediates and motifs in probe and ligand design due to their electron-rich heteroaromatic ring, which can participate in π-stacking and hydrogen-bond-acceptor interactions.
The aryl-ketone functionality can engage in reversible interactions with proteins (e.g., as a hydrogen-bond acceptor) and serves as a handle for derivatization into alcohols, imines, or enones that may be screened in chemical biology.
Metabolic tendencies (general): Aryl ketones may undergo phase I reduction or oxidation and phase II conjugations (glucuronidation/sulfation) in biological systems. Furan rings can be susceptible to oxidative bioactivation by certain P450 enzymes in vivo, but applicability to this specific compound and conditions should be experimentally verified and is outside the scope of this listing.
Use guidance
Any biological testing should be conducted under appropriate approvals and containment, with analytical confirmation of identity and purity for the test article. No medical, diagnostic, or therapeutic use is intended or implied.
Buffer Applications
Not typically applicable.
2-Hexanoylfuran is a hydrophobic organic building block, not a buffering agent. It lacks acid/base pairs suitable for maintaining pH in aqueous systems.
For aqueous work, dissolve in a miscible organic co-solvent (e.g., DMSO, ethanol) before dilution into buffered media if needed for assays. Select buffer systems (phosphate, HEPES, MES) according to your biological or analytical application; this compound does not contribute to buffering capacity.
Green Alternatives
Context
2-Hexanoylfuran is an organic building block; the “green” discussion centers on solvent/process choices rather than on the molecule itself.
Greener solvent choices (general guidance)
Replace dichloromethane/chloroform with ethyl acetate, cyclopentyl methyl ether (CPME), toluene, or dimethyl carbonate when feasible.
For reductions and enolate chemistry, 2-MeTHF or CPME can often substitute for THF and MTBE, offering higher boiling points and bio-based origins (2-MeTHF) with improved safety profiles.
For chromatographic purification, consider heptane/ethyl acetate in place of hexane/ethyl acetate to reduce low-boiling hydrocarbon use.
Comparison snapshot (general)
DCM vs EtOAc: EtOAc is biodegradable, lower toxicity, and non-halogenated; polarity often adequate for extractions and chromatography.
THF vs 2-MeTHF/CPME: Similar solvating power; greener options have better peroxide stability profiles than THF but still require periodic testing.
Acetonitrile vs MeCN alternatives: If water tolerance permits, ethanol or isopropanol may be used for imine formations or recrystallizations; assess selectivity impacts.
Process considerations
Catalysis: Favor catalytic hydrogenation or transfer hydrogenation over stoichiometric metal hydrides when compatible.
Oxidations: Use oxygen or H2O2-based systems under catalysis (Baeyer–Villiger, aerobic oxidations) to reduce waste versus peracids.
Energy: Exploit microwaves or flow chemistry to reduce reaction times and improve heat/mass transfer, lowering energy use.
Pharmaceutical Uses
Item-specific pharmacopeial status/uses
Not specified for this item; no excipient or compendial status provided.
General formulation/manufacturing context
2-Hexanoylfuran may serve as a synthetic intermediate or reference standard in medicinal chemistry and process development due to its handle-rich functionality (aryl ketone) and heteroaromatic core. It is not offered as a drug or excipient.
The ketone can be diversified to libraries of derivatives (oximes, hydrazones, reduced alcohols, enones), enabling SAR exploration around a furan scaffold in discovery workflows.
For handling in formulation research settings: prepare stock solutions in suitable organic solvents (DMSO, ethanol) and evaluate solubility/compatibility with excipients if used as an intermediate in pre-formulation studies. Ensure all uses remain within research contexts and not for human or veterinary application.
Physical Properties
Item-specific specifications
Not specified for this item; refer to CoA/Spec Sheet.
General/literature expectations for 1-(furan-2-yl)hexan-1-one (for context only; verify experimentally)
Physical state: typically a colorless to pale yellow liquid for mid-chain acylfurans due to lowered melting points from the flexible alkyl chain.
Volatility: substantially less volatile than short-chain acylfurans (e.g., 2-acetylfuran) owing to increased molecular weight and polarizability.
Solubility profile: expected to be sparingly soluble in water; freely miscible with common organic solvents (ethers, esters, aromatics, chlorinated solvents, alcohols). No numeric solubilities are assigned for this specific item.
Density/refractive index: aryl ketones of similar size often have densities near or slightly above that of water and elevated refractive indices relative to hydrocarbons; no item-specific values are available.
pKa/logP: the carbonyl is non-ionizable under neutral conditions; the compound is hydrophobic with a moderate-to-high logP typical of C10 aryl ketones; no specific values are assigned here.
Practical notes (general)
The conjugated carbonyl may show a characteristic IR C=O stretch around 1665–1685 cm−1 (conjugated ketone; literature range) and strong UV absorption in the near-UV owing to the furan chromophore and enone-like conjugation.
Quality and Grades
Item-specific grade/purity
Not specified for this item; refer to CoA/Spec Sheet for assay, impurity profile, and any stabilizers.
Guidance on grades (general)
Research grade: Suitable for most synthetic and analytical research uses; verify trace impurity tolerances if using in sensitive catalysis or materials applications.
HPLC/UV grade (if offered): Emphasizes low UV-absorbing impurities and particulates; useful when the compound is used as a reference or when monitoring UV-active reactions. Not specified for this item.
Stabilizers: Not specified for this item. Acylfurans generally do not require stabilizers, but storage under inert gas can help preserve color and purity over time.
Quality control considerations for 2-hexanoylfuran (general)
Identity confirmation: 1H/13C NMR (diagnostic furan protons near 6.2–7.6 ppm; carbonyl ~190–200 ppm), IR (conjugated C=O), GC–MS/LC–MS (M+ at m/z 166 for C10H14O2; literature), and HPLC purity.
Trace impurities to watch: residual starting acid chlorides/acids, over-acylated byproducts, peroxides (rare, more common in ethers than in acylfurans), and oligomers from acid-catalyzed processes. Confirm by CoA/SDS for this specific lot before use in critical applications.
Reaction and Applications
Manufacturer applications
Not provided in Product Data.
General synthetic and application landscape for 2-acylfurans
Building block: 2-Hexanoylfuran is a versatile heteroaryl ketone used as a synthon in heterocycle elaboration, materials motifs, and flavor/fragrance research contexts (no end-use claims here). The conjugated aryl ketone undergoes a broad range of carbonyl transformations.
Nucleophilic additions/reductions: NaBH4 or catalytic hydrogenation reduces the ketone to the corresponding secondary alcohol; selective reduction can be tuned by solvent/catalyst choice.
Oxime/hydrazone formation: Reaction with hydroxylamine or hydrazines under mild acid catalysis affords imine derivatives, useful for characterization or further transformations.
Wittig/olefination: Conversion to the corresponding alkene provides styryl-like furan derivatives, extending conjugation.
Baeyer–Villiger oxidation: Insertion adjacent to the carbonyl affords furan-2-yl alkyl esters; choice of peracid or catalytic system controls selectivity.
Enolate chemistry: The α-methylene of the hexanoyl side chain can be deprotonated (e.g., with LDA) for aldolizations or alkylations; protect furan under strongly basic conditions.
Electrophilic substitution on furan: While the carbonyl deactivates somewhat, C-5 remains the most activated site for EAS; directed metalation strategies (TMP-bases) can also be used with care.
Practical tips
Avoid strong mineral acids that can open or polymerize the furan ring. Maintain anhydrous conditions for base-mediated steps. Monitor by UV-active TLC (furan/ketone chromophores).
Reaction Conditions
General literature guidance (verify experimentally for your system)
Reductions: NaBH4 (MeOH, EtOH, or THF, 0–25 C) typically reduces the ketone selectively to the secondary alcohol. For chemoselectivity in presence of other carbonyls, use catalytic hydrogenation (Pd/C, H2, 1–5 bar, RT–40 C) or borane reagents.
Oxime formation: Hydroxylamine hydrochloride (1.2–2.0 equiv) with pyridine or NaOAc in EtOH/MeOH or aqueous EtOH, 25–60 C, 1–6 h. Monitor by TLC/HPLC.
Wittig/HWE olefination: Generate ylide or phosphonate carbanion at 0 C to RT in THF or toluene; typical bases: n-BuLi, NaH, or KHMDS. Reaction temperatures −78 to 25 C depending on selectivity.
Enolate chemistry: LDA (1.1–1.5 equiv) in THF at −78 to −40 C, then electrophile addition; quench at low temperature to preserve furan integrity. Alternative softer bases (DBU) can mediate milder α-functionalizations.
Baeyer–Villiger oxidation: mCPBA (1.2–2.0 equiv) in DCM at 0–25 C or catalytic systems with H2O2 in fluorinated/alcoholic media; watch for furan oxidation—use buffered conditions and low temperatures.
Electrophilic substitutions on furan: Use mild Lewis acids and low temperatures to avoid ring opening; C-5 substitution is typical.
Workup/purification
Standard aqueous workups; avoid prolonged acidic washes. Purify by silica gel chromatography (hexanes/EtOAc). Compound is UV-active; use 254 nm detection.
Expected yields
Many of the above transformations report moderate to high yields in the literature for analogous acylfurans; optimize per substrate and scale.
Safety and Handling
Item-specific hazard data
Signal word, H-statements, GHS classification, pictograms: Not specified for this item; refer to SDS.
General safety considerations for acylfurans and aryl ketones (informational; defer to SDS)
Likely hazards: May cause skin/eye irritation and respiratory tract irritation. Avoid inhalation of vapors and contact with skin or eyes.
PPE: Use lab coat, safety goggles, and appropriate chemically resistant gloves (e.g., nitrile). Employ in a fume hood to control vapors and ensure good ventilation.
Incompatibilities: Avoid strong oxidizers (risk of exothermic oxidation), strong acids (which can catalyze polymerization or ring-opening of furan) and strong bases (which can promote aldol/self-condensation or furan degradation).
Fire safety: Organic liquid; keep away from ignition sources. Use CO2, dry chemical, or foam extinguishers as appropriate.
First aid (overview): If on skin, wash with soap and water. If in eyes, rinse cautiously with water for several minutes and remove contact lenses if present; seek medical attention if irritation persists. If inhaled, move to fresh air. If ingested, rinse mouth; do not induce vomiting; seek medical attention.
Handling tips: Minimize exposure to air and light to reduce slow oxidative discoloration; keep containers tightly closed. Always consult the official SDS for authoritative hazard and response information.
Solvent Selection
Applicability
As a moderately nonpolar, UV-active aryl ketone, 2-hexanoylfuran dissolves well in many organic solvents. Solvent choice will typically be driven by reaction type or analytical method rather than by solubility constraints.
Expected miscibility: high in ethers (THF, MTBE, CPME), esters (EtOAc), aromatics (toluene), halogenated solvents (DCM, CHCl3), and alcohols. Sparingly soluble in water.
Selection tips by task
Synthesis: For enolate chemistry or reductions, use dry ethereal solvents (THF, CPME, 2-MeTHF) or toluene; for acylations or oxime formation, alcohols or acetonitrile may be suitable.
Purification: Normal-phase silica gel using hexanes/EtOAc or toluene/EtOAc gradients typically affords good resolution for acylfurans. For prep HPLC, acetonitrile–water with a small acid modifier may be used; ensure the compound’s low water solubility is accommodated.
Spectroscopy: CDCl3 or DMSO-d6 for NMR; IR neat or in CH2Cl2.
Comparison (general)
Versus shorter acylfurans (e.g., 2-acetylfuran): less volatile, more lipophilic; choose higher boiling solvents and slightly stronger eluents in chromatography.
Versus highly polar ketones: fewer hydrogen-bonding interactions; nonpolar eluents are usually effective.
Storage and Reconstitution
Item-specific storage
Storage: Room temperature (as provided in Product Data). Protect from light and moisture; keep tightly sealed.
Shipping: Normal conditions.
General handling and stability
Keep in amber bottles or away from direct light to minimize slow oxidative discoloration. Store under inert gas (nitrogen/argon) if long-term storage is anticipated to limit oxidation of the furan ring.
Avoid strong acids/bases and oxidizing agents during storage; these can promote degradation (ring opening/polymerization or side-chain reactions).
If solidification occurs at low temperature, gently warm to ambient and mix thoroughly before use.
Reconstitution/solution preparation
Solubility: Readily soluble in common organic solvents (e.g., DCM, EtOAc, toluene, THF, MeOH, EtOH); sparingly soluble in water. For aqueous applications, pre-dissolve in a miscible organic co-solvent (e.g., DMSO or ethanol) before dilution.
Recommended stock solutions: 0.1–1.0 M in anhydrous solvent, stored in tightly capped vials at room temperature or refrigerated if required by your application. Minimize headspace and consider aliquoting to reduce air exposure.
Shelf life
Not specified for this item; refer to CoA/Spec Sheet and monitor by periodic NMR/LC–MS for long-term projects.
Structure and Identity
Item-specific (from Product Data)
Product name: 2-Hexanoylfuran (SKU H339726)
CAS: 14360-50-0
InChIKey (as provided): 446945
Storage: Room temperature; shipped under normal conditions
Research use: For research use only
Computed/literature identifiers and features (general/reference)
Conjugation: carbonyl conjugated to the furan ring, enabling resonance stabilization and electrophilicity at the carbonyl carbon; furan ring is electron-rich and susceptible to electrophilic substitution at C-5.
2D arrangement (textual): Five-membered O-containing ring with the carbonyl directly bonded at ring position 2; the carbonyl connects to a linear n-hexyl chain (–CO–(CH2)4–CH3). No stereocenters present.
Synthetic Utility
Reactivity highlights (general)
Carbonyl chemistry: The conjugated ketone readily forms imines/oximes, undergoes nucleophilic additions (e.g., NaBH4 reduction to secondary alcohols), and participates in olefination reactions (Wittig/HWE) to furnish alkenes conjugated to furan.
Enolization: The α-CH2 of the hexanoyl chain can be deprotonated (LDA, LiHMDS) to form enolates for aldol, Claisen-type condensations, or α-alkylations/sulfenylations; protect or consider the furan’s sensitivity under strong base.
Electrophilic aromatic substitution: Furan remains reactive at C-5; acyl substitution at C-2 is directing/deactivating but still allows further functionalization.
Oxidative transformations: Baeyer–Villiger oxidation gives furan-2-yl hexanoates; selective oxidations on the side chain can also be achieved under mild conditions.
Strategic value
As a 2-acylfuran, it is a convergent node between heteroaromatic chemistry and carbonyl-based diversification, enabling rapid scaffold hopping.
In retrosynthesis, it dissects to furan and a hexanoyl equivalent (e.g., hexanoyl chloride or anhydride), typically accessed by Friedel–Crafts acylation or acylation of metallated furan.
Analytical handles
Strong UV activity for TLC/HPLC monitoring; characteristic NMR and IR signals aid rapid tracking during multi-step sequences.
Target Specificity
Not applicable.
This product is a small-molecule chemical building block, not a biological macromolecule or affinity reagent. No antigen/epitope specificity, clone, isotype, or species reactivity applies.
Item-specific target data are not provided.
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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.
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.
Products are supplied to verified businesses, institutions, and qualified professionals for research and development use only. Not for use in humans, animals, diagnosis, or therapy.
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