This compound belongs to the class of organic compounds known as ketones. These are organic compounds in which a carbonyl group is bonded to two carbon atoms R2C=O (neither R may be a hydrogen atom). Ketones that have one or more alpha-hydrogen atoms undergo keto-enol tautomerization, the tautomer being an enol.
External Descriptors
Oxygenated hydrocarbons
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
No application assays (e.g., WB, IHC, IF, FC) are relevant to this small-molecule reagent. For laboratory use, follow the Reaction Conditions and Synthetic Utility sections for procedural guidance. If using as an analytical standard, develop method-specific protocols (e.g., GC-FID, GC–MS, HPLC) with appropriate calibration and derivatization if needed (oxime/2,4-DNP), validated to your matrix.
Biological Roles
Applicability note: 4-Undecanone is a simple aliphatic ketone used as a chemical building block. It has no established intrinsic biological role in cellular pathways.
General biochemical context (literature-based, not product-specific)
Linear aliphatic ketones of medium-to-long chain length can occur at low levels among volatile organic compounds from biological or environmental processes, but 4-undecanone itself is not a canonical metabolite.
In biological assays, such hydrophobic ketones may act as inert organic phase components or hydrophobic carriers, but this is application- and matrix-dependent and must be validated experimentally.
Reactivity considerations in bio-context: the carbonyl group can form Schiff-base adducts with primary amines only after prior conversion to imines/oximes under dehydrating conditions; such chemistry does not typically occur spontaneously in aqueous physiological environments.
Use constraints
For research use only. Not intended for diagnostics, therapeutics, or ingestion.
If your project requires biocompatibility or defined biological activity, consider validated biochemicals or excipients and perform appropriate toxicity and compatibility testing.
Buffer Applications
This compound is a hydrophobic aliphatic ketone and does not function as a buffer or pH control agent. It has no defined pKa in the physiological range relevant to buffering capacity.
For pH control, consider dedicated buffer systems (e.g., phosphate, Tris, HEPES) and refer to those reagents’ specific guidance. For this product, the most relevant sections are Reaction & Applications, Synthetic Utility, and Reaction Conditions.
Green Alternatives
Context: 4-Undecanone is primarily a reagent rather than a process solvent. Greener choices concern both the reaction medium and alternative substrates when feasible.
Greener solvent choices (when 4-undecanone is not the substrate/limiting reagent)
Replace aromatic or chlorinated solvents with bio-based ethers (e.g., 2-MeTHF) or cyclopentyl methyl ether (CPME) for many enolate or carbonyl reactions.
For extractions, ethyl acetate or methyl tert-butyl ether can substitute more hazardous solvents while maintaining partitioning efficiency.
For hydrogenations and reductions, consider green alcohols (ethanol, isopropanol) as solvents and hydrogen donors (transfer hydrogenation) where compatible.
Tradeoffs and considerations
2-MeTHF/CPME offer lower toxicity and better sustainability profiles but may alter enolate formation equilibria and reaction rates relative to THF/toluene.
High-boiling hydrophobic media (like 4-undecanone if used as solvent) complicate solvent recovery; switching to lower-boiling, recyclable solvents improves energy efficiency.
If the synthetic target tolerates positional isomers, bio-derived 2-undecanone (commercially available from natural sources) may be considered as an alternative substrate; verify regioselectivity requirements first.
Comparison snapshot (qualitative)
THF vs 2-MeTHF: similar coordinating ability; 2-MeTHF is more hydrophobic, partially water-immiscible, and often easier to separate; both form peroxides—test and inhibit as needed.
Toluene/DCM vs EtOAc/CPME: greener options reduce halogenated waste and aromatic emissions while maintaining workable solvation for nonpolar substrates.
Always validate green substitutions via small-scale trials to confirm selectivity and yield.
Pharmaceutical Uses
No item-specific pharmacopeial grade or excipient status is provided for this listing.
General formulation/manufacturing context (not product-specific)
4-Undecanone is primarily a synthetic intermediate in research/manufacturing settings rather than a common pharmaceutical excipient.
Potential roles in process chemistry include serving as a carbonyl building block for generating long-chain alcohols, amines, or esters via reduction, reductive amination, or Baeyer–Villiger oxidation, respectively.
Due to its high boiling point and hydrophobicity, it is seldom used as a primary process solvent but may appear as a reaction participant in multiphase or high-temperature steps.
Compliance notes
If use in regulated manufacturing is contemplated, establish a full quality profile (impurities, residual solvents, elemental impurities) and verify conformance to internal specifications, as no compendial monograph is assumed.
Ensure removal to below acceptable residual levels if used as a process intermediate or solvent-like medium, documented by appropriate analytical methods (GC-FID/GC-MS).
This product is supplied strictly for research use only and is not intended for human or veterinary applications.
Physical Properties
Item-specific specifications
Appearance: Not specified for this item; refer to CoA/Spec Sheet.
Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.
Typical physical state: Colorless to pale yellow liquid (literature, for linear C11 ketones).
Molecular formula: C11H22O (literature)
Molecular weight: 170.29 g/mol (literature)
Boiling point: Reported for positional isomers in the range ~220–235 °C at 1 atm; 4-undecanone is expected in this range (literature, consult specific data sources before process design).
Melting point: Often below 0 °C for mid-chain methyl ketones; specific value for 4-undecanone not widely tabulated (literature).
Density: Approximately 0.82–0.84 g/mL at 20–25 °C for similar C11 ketones (literature estimates; verify experimentally).
Refractive index (nD20): Typically ~1.420–1.430 for C11 aliphatic ketones (literature).
Vapor pressure: Low at ambient temperature relative to short-chain ketones (literature trend).
Solubility: Low in water; miscible with nonpolar/aprotic organics such as hexanes, toluene, ethers, and chlorinated solvents (literature).
LogP: Expected >3 owing to C11 hydrophobic chain (literature trend for aliphatic ketones).
Practical notes
High-boiling, hydrophobic ketone; behaves as a nonpolar organic phase component.
Verify key parameters (bp, density, refractive index) on the CoA before scale-up or analytical qualification.
Quality & Grades
Item-specific details
Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.
Interpretation guidance (general)
For carbonyl building blocks like 4-undecanone, grade typically reflects limits on non-volatile residue, carbonyl purity (GC area %), water content (Karl Fischer), and trace acids/bases.
If offered as synthetic/HPLC grade, expectations include:
Tight GC purity (e.g., ≥98–99% area by GC) with low homologs/isomers.
Controlled UV absorbance at analytical wavelengths for chromatographic uses.
Low water to support moisture-sensitive reactions (enolate, organometallic additions).
Stabilizers: Aliphatic ketones normally do not require stabilizers; if any inhibitor is present, consult CoA for identity and removal (e.g., passage through basic alumina) before sensitive chemistry.
What to verify on receipt (best practices)
Inspect CoA for: assay method (GC/FID), residual solvents, water, and any specific impurities (e.g., aldol dimers/condensation byproducts).
Confirm physical constants (refractive index, density) to fingerprint identity.
If using in enolate chemistry, consider an additional drying step and verification of water by KF.
Note: In the absence of an explicit grade on this listing, treat as a research reagent and qualify internally for critical applications.
Reaction & Applications
This compound is a versatile aliphatic methyl ketone. While this listing includes no manufacturer application notes, chemists commonly leverage the following transformations (literature-based):
Carbonyl additions
Grignard/organolithium additions to form tertiary alcohols after workup. Control temperature (−78 to 0 °C) to minimize side reactions and enolization.
Hydride reductions (NaBH4, LiAlH4, catalytic hydrogenation) afford the corresponding secondary alcohol (4-undecanol). Selectivity and over-reduction depend on reagent choice.
Enolate chemistry
Formation of kinetic or thermodynamic enolates (e.g., LDA, NaHMDS, NaOEt) enabling alkylation (mono- vs poly-alkylation control via base, temperature, and equivalents) and aldol condensations with aldehydes.
Haloform-like oxidations are not applicable (non-methyl at carbonyl), but alpha-halogenation under NBS/Br2 is feasible.
Derivatizations
Oxime/hydrazone formation (NH2OH, DNPH) for characterization or further transformations (e.g., Wolff–Kishner to hydrocarbon, or reductive cleavage).
Baeyer–Villiger oxidation with peracids to the corresponding long-chain ester (migration favors the more substituted/longer side; verify regiochemistry experimentally).
Times: 0.5–4 h enolate generation; 1–6 h alkylation. Typical isolated yields: 60–85% depending on sterics/leaving group.
Reduction to alcohol
NaBH4 in MeOH/EtOH at 0–25 °C, 1–2 h; quench with NH4Cl. Catalytic hydrogenation (H2, 1–5 bar) over Raney Ni or Pd/C, rt–50 °C, 1–6 h. Yields often 80–95%.
Reductive amination
Amine + ketone with NaBH3CN or H2/Raney Ni in MeOH/EtOH; pH control with AcOH; 20–40 °C, 2–16 h. Typical yields 70–90%.
Baeyer–Villiger oxidation
mCPBA (1.2–1.5 equiv) in DCM at 0–25 °C, 2–12 h, or peracetic acid in AcOH. Monitor for regioisomeric esters; silica plug removes acids.
Grignard/organolithium addition
RMgX or RLi (1.2–2.0 equiv) in Et2O/THF, −78 to 0 °C; aqueous NH4Cl workup. Avoid over-addition by temperature control. Yields 65–90%.
Workup and purification
Given the high bp, consider silica gel chromatography or short-path distillation under high vacuum (≤1–2 mbar). Co-evaporate with a low-bp solvent for efficient removal.
Note: Conditions above are representative ranges drawn from standard aliphatic ketone chemistry; verify experimentally for 4-undecanone and your substrate set.
Safety & Handling
Authoritative safety data must be obtained from the SDS for this specific lot.
Item-specific hazard information
Signal word: Not specified for this item; refer to SDS.
H-statements: Not specified for this item; refer to SDS.
GHS classification/pictograms: Not specified for this item; refer to SDS.
General safety considerations for aliphatic ketones (literature-based, not item-specific)
Flammability: Mid-/high-boiling ketones are typically combustible liquids; avoid ignition sources. Flash points increase with chain length; consult SDS for the exact value.
Exposure hazards: May cause skin/eye irritation and respiratory irritation at elevated vapor concentrations. Use only with adequate ventilation.
Peroxide formation: Aliphatic ketones are not strong peroxide formers (unlike ethers), but routine peroxide testing is prudent only if solvent use and storage are prolonged under air and light.
Incompatibilities: Strong oxidizers, strong bases or acids (can catalyze aldol/condensation), reducing agents (for carbonyl reduction). Avoid reactive metals if water/acid is present.
PPE and hygiene
Wear safety glasses, lab coat, and nitrile gloves; use splash goggles/face shield for larger transfers.
Employ local exhaust (fume hood) when heating or handling on scale.
First aid (general)
Inhalation: Move to fresh air; seek medical attention if symptoms persist.
Skin/eye contact: Rinse with water for at least 15 minutes; remove contaminated clothing.
Ingestion: Rinse mouth; do not induce vomiting; seek medical advice.
Spill/Fire response
Small spills: Absorb with inert material (vermiculite), collect as organic waste.
Fire: Use dry chemical, CO2, or foam; water spray for cooling. Refer to SDS for specifics.
Solvent Selection
Applicability note: 4-Undecanone is more commonly used as a hydrophobic reagent/building block than as a bulk solvent. However, understanding its solvent-like behavior helps in reaction planning and workup.
Polarity class: Low to moderate polarity, aprotic; much less polar than short-chain ketones (e.g., acetone, MEK) due to the long alkyl chain.
Dielectric behavior: Lower effective polarity than acetone; behaves similarly to other high-boiling aliphatic ketones (e.g., diisobutyl ketone).
When to use/avoid
Use when a reagent-like aliphatic ketone is desired in a two-phase system (e.g., for selective partitioning) or as a substrate-compatible medium for ketone transformations at elevated temperature.
Avoid as a solvent for highly polar substrates/ionic reactions; substitute with polar aprotics (DMF/DMSO/MeCN) when needed.
Workup considerations
Due to a high boiling point, removal may require rotary evaporation at elevated bath temperature and/or high vacuum; consider co-evaporation with a low-boiling solvent.
Its hydrophobicity aids liquid–liquid extraction from aqueous media.
Comparison snapshot (literature, qualitative)
4-Undecanone vs acetone: much less polar, far higher bp, better for nonpolar matrices; poorer for dissolving salts.
4-Undecanone vs toluene: similar hydrophobicity, but 4-undecanone has a reactive carbonyl which may participate in side reactions under basic conditions.
Storage & Reconstitution
Item-specific storage/shipping
Storage conditions: Room temperature (per Product Data). Protect from moisture and strong oxidants.
Shipped in: Normal conditions (per Product Data).
General handling guidance
Keep container tightly closed in a cool, well-ventilated area. For long-term storage, minimizing air exposure helps limit slow aldol-type self-condensation.
If ultra-dry material is required for base- or organometallic-mediated reactions, dry over 3 Å molecular sieves or distill under reduced pressure immediately before use.
Reconstitution
Not applicable; supplied neat as a liquid reagent. If solidification occurs at low temperature, gently warm to ambient and mix to homogeneity.
Stability notes (literature/general)
Aliphatic ketones are generally stable under neutral conditions. Avoid prolonged exposure to strong bases/acids or elevated temperatures to prevent condensation.
For analytical identity checks over time, monitor GC purity and refractive index; any significant drift may indicate contamination or degradation.
Always refer to the product CoA and SDS for definitive storage and stability instructions.
Structure & Identity
Brief overview: 4-Undecanone is a linear aliphatic methyl ketone (C11) with the carbonyl at the 4-position along the chain; it is a hydrophobic, non-protic, aprotic organic compound useful as a building block in enolate and carbonyl chemistry.
Item-specific identifiers (from Product Data)
SKU: U162909
Product name: 4-Undecanone
CAS: 14476-37-0
InChIKey: Not specified for this item; refer to CoA/Spec Sheet.
SMILES: Not specified for this item; refer to CoA/Spec Sheet.
Literature/computed identifiers (for reference only; not item specification)
Molecular formula (literature): C11H22O
Molecular weight (literature): 170.29 g/mol
Preferred SMILES (literature): CCC(=O)CCCCCCC
InChIKey (literature): Typically a 27-character hashed key; consult databases (e.g., PubChem CID 84467) for the canonical value.
Structural features (general description)
Functional group: ketone (aliphatic, methyl ketone) at C4.
Carbon skeleton: unbranched C11 chain; the carbonyl carbon is flanked by a propyl group (C3) and a heptyl group (C7).
Stereochemistry: None (achiral, no stereocenters).
2D depiction in words: a straight chain where the fourth carbon (counting from one end) bears the carbonyl (C=O); no additional substituents or rings.
Category path: 全部 / 可售 / 化学和生化试剂
Note: All item-critical identifiers should be confirmed on the product CoA/Spec Sheet prior to regulated use.
Synthetic Utility
Key functional elements
Ketone carbonyl (C=O) enables nucleophilic additions, reductions, condensations, and rearrangements.
Alpha positions (both sides) are enolizable, allowing controlled enolate chemistry with base.
Representative transformations (literature)
Enolate generation and alkylation: LDA or NaHMDS in THF/2-MeTHF at −78 to −20 °C for kinetic control; NaOEt/NaH in alcohols or toluene for thermodynamic control. Subsequent alkylation with alkyl halides yields α-substituted ketones.
Aldol/Claisen-type condensations: Self- and cross-aldol with aldehydes/ketones; control self-condensation by using preformed enolates and low temperatures.
Nucleophilic additions: RMgX/RLi reagents afford tertiary alcohols; Cu-catalyzed 1,4-additions are not applicable (no conjugation) but cuprates can still add to the carbonyl under certain conditions.
Reductive chemistry: NaBH4 for selective C=O reduction to 4-undecanol; catalytic hydrogenation (Raney Ni, Pd/C) suitable on scale. Reductive amination installs long-chain amines efficiently.
Baeyer–Villiger oxidation: mCPBA or peracetic acid delivers a long-chain ester; migratory aptitude typically favors the more substituted/longer chain side—determine regioisomer outcome analytically.
Derivatization for analytics: Oximes, 2,4-DNP hydrazones improve detectability and aid characterization by melting point/LC.
Strategic value
Serves as a C11 hydrophobic synthon that can be stepped up/down in oxidation state or leveraged to introduce stereocenters at α-carbons during enolate alkylation.
Target Specificity
Not applicable. This product is a small-molecule aliphatic ketone and is not an antibody, enzyme, or affinity reagent. No target, epitope, clone, or species reactivity is defined.
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