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 assay or bioanalytical application protocols are provided for this item in the Product Data. As a chemical reagent/solvent, typical "protocols" correspond to reaction procedures (see Reaction Conditions and Synthetic Utility sections). For handling and preparative use, consult the SDS and standard organic synthesis references.
Biological Roles
Item-specific biological data are not provided for this product.
General context (literature):
4-Nonanone is a simple aliphatic ketone with no known endogenous role in human biochemistry. It may occur as a minor volatile organic compound in environmental or industrial contexts.
Metabolism (general): aliphatic ketones can undergo NAD(P)H-dependent reduction to secondary alcohols via ketoreductases, followed by phase I oxidation or conjugation. Oxidative pathways (ω- and β-oxidation of side chains after reduction) are common in microbial systems.
Interactions: functions as a hydrogen-bond acceptor; can partition into lipid phases due to hydrophobic chains. This may influence environmental bioaccumulation potential, which generally scales with logP; however, specific bioconcentration data for 4-nonanone should be consulted from environmental databases.
Research use only: no medical, diagnostic, or dietary use is intended or implied.
Buffer Applications
Not typically applicable. 4-Nonanone is a hydrophobic organic ketone and is not used to prepare aqueous buffer systems. For experimental planning, consider its role as a reaction solvent or organic extractant rather than a buffering component.
Green Alternatives
Sustainability considerations revolve around volatility, toxicity, and origin. 4-Nonanone has lower volatility than light ketones, reducing VOC emissions, but remains a petroleum-derived solvent. Greener choices may be preferable depending on the application.
Potential alternatives (general comparison):
| Solvent | Boiling point (lit.) | Polarity profile | Green notes |
|---|---|---|---|
| 2-MeTHF | ~80 °C | Ether, moderately polar | Biomass-derived, forms fewer peroxides than THF; lower bp eases removal.
| CPME | ~106 °C | Ether, low/mod. polarity | Low peroxide tendency, hydrophobic, good azeotrope behavior.
| Ethyl acetate | ~77 °C | Ester, polar aprotic | Readily biodegradable, widely accepted as green.
| Propylene carbonate | ~242 °C | Highly polar aprotic | Low vapor pressure, recyclable; may be too polar for some solutes.
| 4-Heptanone (as alt. ketone) | ~145–150 °C | Ketone, mid polarity | Lower bp than 4-nonanone; less energy to remove.
Tradeoffs:
Lower-bp solvents simplify workup but may change reaction selectivity/solubility.
Ethers (2-MeTHF/CPME) offer greener credentials but different polarity and potential reactivity; verify catalyst compatibility.
Propylene carbonate is very polar and high-boiling—excellent for minimizing VOCs but can be difficult to remove and may not dissolve highly nonpolar substrates.
Optimization tips:
Screen using small-scale solubility/reactivity tests; target minimal solvent volumes and recycling where possible.
Consider life-cycle impacts and waste streams; closed-loop recovery can make high-bp solvents more sustainable.
Pharmaceutical Uses
Item-specific pharmacopeial status or excipient designation is not provided for this product.
General formulation/process context (literature):
Aliphatic ketones may serve as process solvents or crystallization media in API manufacturing where higher boiling points and moderate polarity are beneficial. 4-Nonanone’s relatively high bp can support controlled cooling crystallizations or high-temperature transformations.
Due to limited water miscibility, phase-separation driven workups are feasible. Residual solvent limits, extractables/leachables, and impurity carryover must be controlled; consult ICH Q3C and internal specifications if considering for process development.
Not a typical listed pharmacopeial excipient; qualification would require comprehensive safety, residual solvent, and impurity assessments specific to the process and region.
No therapeutic or clinical claims are made; product is for research and laboratory use only.
Physical Properties
Item-specific (Product Data):
Appearance: Not specified for this item; refer to CoA/Spec Sheet.
Molecular Formula: Not specified for this item; refer to CoA/Spec Sheet.
Molecular Weight: Not specified for this item; refer to CoA/Spec Sheet.
Literature/Reference properties (for general guidance; not specifications for this item):
Typical boiling point: ~190–195 °C (literature, atmospheric pressure)
Typical melting point: approximately −30 to −40 °C (literature)
Density (20 °C): ~0.81–0.83 g/mL (literature)
Refractive index nD20: ~1.418–1.422 (literature)
Water solubility: very low (insoluble to slightly soluble; on the order of a few g/L or less) (literature)
Solubility: miscible with many organic solvents (alcohols, ethers, esters, hydrocarbons, chlorinated solvents) (literature)
LogP (octanol/water): ~2.7–3.0 (literature estimate for C9 ketones)
Vapor pressure: low to moderate for a C9 ketone (literature)
Dielectric constant: expected low-to-moderate for a simple ketone, lower than acetone and MEK, higher than alkanes (literature trend)
Structural/physicochemical notes (general):
The central carbonyl imparts modest polarity and hydrogen-bond acceptor capability; no hydrogen-bond donor sites.
Volatility substantially lower than C3–C5 ketones, providing a higher-boiling, mid-polarity medium.
Typical IR: strong C=O stretch near 1715–1725 cm−1 (literature). Typical 13C NMR: carbonyl near 205–215 ppm; alpha-methylene ~40–45 ppm (literature).
Quality and Grades
Item-specific (Product Data):
Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.
Stabilizers/Inhibitors: Not specified for this item; refer to CoA/Spec Sheet.
Guidance on grades (general information):
Typical solvent/reagent designations include: Technical (process use), Reagent/ACS (meets ACS specifications), HPLC/GC grade (low nonvolatile residue and low UV background), Anhydrous grades (controlled water content for moisture-sensitive chemistry). Specifics must be confirmed on the item’s CoA.
For chromatography use, low UV absorbance and low peroxide/aldehyde impurities are often important. For moisture-sensitive enolate chemistry, anhydrous specification and Karl Fischer water content are critical. Since no item-specific numbers are provided here, please verify water content, acidity/alkalinity, and trace metals on the CoA as needed.
Practical implications:
Ketone solvents can carry residual aldol-condensation byproducts or higher-boiling congeners; distillation and GC purity profiles matter when used as a reaction medium or analyte matrix.
If a stabilizer is present (none is specified here), understand its impact on downstream reactions (e.g., base-catalyzed steps).
Reaction and Applications
As a simple dialkyl ketone, 4-nonanone is both a useful solvent and a versatile substrate in carbonyl chemistry (general literature guidance):
As a substrate:
Reduction to secondary alcohol: NaBH4 or catalytic hydrogenation affords 4-nonanol with high chemoselectivity for C=O.
Complete deoxygenation to hydrocarbon: Wolff–Kishner or Clemmensen reductions convert the ketone to n-nonane (conditions dependent).
Baeyer–Villiger oxidation: with peracids (e.g., m-CPBA) yields the symmetrical ester n-butyl n-butyrate due to equal migratory aptitude of the two n-butyl groups.
Enolate/aldol chemistry: deprotonation at the α-positions (e.g., LDA, NaHMDS) enables alkylation, acylation, or aldol reactions. Base strength/temperature controls mono- vs. over-alkylation.
Halogenation: α-halogenation under acidic (Br2/Cl2) or basic conditions gives alpha-halo ketones, useful electrophiles for further elaboration.
As a solvent or cosolvent:
High-boiling, aprotic, and relatively inert under neutral conditions; suitable for elevated-temperature reactions where protic solvents would be problematic.
Can stabilize polar transition states modestly via carbonyl dipole; often paired with bases for condensations, or with catalysts for transfer hydrogenation.
Practical tips:
Control base-promoted self-condensation at elevated temperatures; keep strong base concentration low and temperatures moderated unless condensation is desired.
Dry solvent for moisture-sensitive enolate chemistry; rigorously exclude air/moisture when using strong bases or air-sensitive catalysts.
Monitor by GC due to convenient bp separation from many low boilers.
Reaction Conditions
General literature guidance for typical transformations of 4-nonanone (not item-specific specifications):
Reduction to 4-nonanol:
NaBH4: MeOH/EtOH or IPA, 0–25 °C, 0.5–4 h; quench with water; typical high yields for simple dialkyl ketones.
Catalytic hydrogenation: Raney Ni, Pd/C, or Pt/C, H2 (1–5 bar), RT–50 °C, several hours; monitor to avoid over-reduction.
Baeyer–Villiger oxidation to n-butyl n-butyrate:
m-CPBA (1.1–1.5 eq), DCM or CHCl3, 0 °C to RT, 2–16 h; Na2CO3 wash to remove acids. Alternative: peracetic acid in AcOH, controlled addition and cooling.
Enolate generation and alkylation:
LDA (1.05–1.2 eq) in THF, −78 °C to −40 °C, then add electrophile (alkyl halide); warm to 0–25 °C. For thermodynamic control, employ weaker base (NaHMDS) and higher temperatures.
α-Halogenation:
NBS (1.0–1.2 eq) with catalytic acid or radical initiator; solvent: CCl4/CH2Cl2 or acetonitrile; 0–25 °C; monitor to avoid polyhalogenation.
Aldol/self-condensation (if desired):
NaOH or t-BuOK (5–20 mol%), toluene or solvent-free, 60–120 °C; remove water to drive equilibrium; can lead to higher C–C coupled products then dehydration.
Solvent notes:
4-Nonanone can be a reaction medium at reflux (~190–195 °C, literature); ensure materials compatibility and appropriate reflux setup.
Adjust conditions to substrate scope and safety; verify on small scale before scale-up.
Safety and Handling
Item-specific (Product Data):
GHS Classification: Not specified for this item; refer to SDS.
Signal Word: Not specified for this item; refer to SDS.
H-Statements: Not specified for this item; refer to SDS.
Pictograms: Not specified for this item; refer to SDS.
Storage Conditions: Room temperature; shipped under normal conditions.
Research Use Note: For research use only.
General safety information for aliphatic ketones (literature/good practice; consult SDS for this product):
Expected hazards: flammable liquid and vapor; may cause eye/skin irritation; inhalation of vapors may cause drowsiness or dizziness for some ketones. Always verify with the specific SDS.
PPE: safety glasses or goggles, lab coat, nitrile gloves. Use in a fume hood to control vapors.
Handling: keep away from heat/sparks/open flames. Ground/bond containers during transfer. Use only non-sparking tools.
Incompatibilities: strong oxidizers (risk of exotherm), strong reducing agents, alkali metals. Ketones can undergo aldol condensation under strong base.
First aid overview (non-authoritative): fresh air for inhalation exposure; rinse with water for eye/skin contact; obtain medical attention if symptoms persist. For ingestion, do not induce vomiting; seek medical attention. Follow SDS guidance.
Spill response: absorb with non-combustible material (vermiculite, sand), collect for disposal. Ventilate area. Eliminate ignition sources.
Fire-fighting: alcohol-resistant foam, dry chemical, CO2. Cool containers with water spray.
Always defer to the product’s SDS for definitive hazard classification, exposure limits, and emergency measures.
Solvent Selection
4-Nonanone is a mid-polarity, high-boiling aliphatic ketone. While not as common as acetone or MEK, it can serve as a less-volatile reaction or extraction medium.
Polarity and miscibility (literature/general):
Polarity: aprotic, hydrogen-bond acceptor only; polarity lower than acetone/MEK, higher than hydrocarbons.
Miscibility: miscible with most organic solvents (ethers, esters, alcohols, aromatics, chlorinated solvents); very limited solubility in water.
Boiling range: ~190–195 °C (literature), enabling elevated-temperature operations versus lighter ketones.
When to choose 4-nonanone:
As a higher-boiling alternative to 2-butanone/acetone for reactions benefiting from sustained reflux near ~190 °C without extreme pressures.
For extractions where a less-volatile organic phase is desired to minimize solvent losses.
As a medium-polarity solvent that can dissolve both nonpolar substrates and some polar organics due to the carbonyl’s acceptor capacity.
Comparisons (general):
Versus acetone/MEK: much higher bp, lower volatility; slower evaporation; typically lower polarity; reduced water miscibility.
Versus hydrocarbons (hexane/toluene): offers carbonyl H-bond acceptor character that can enhance solubility of modestly polar solutes.
Versus 2-heptanone/4-heptanone: similar behavior with somewhat higher bp and lower volatility.
Practical notes:
Drying: molecular sieves (3Å or 4Å) or distillation over drying agents; avoid strong base if aldol self-condensation is a concern.
Compatibility: generally compatible with common elastomers and PTFE; check for long-term swelling with certain plastics.
Storage and Reconstitution
Item-specific (Product Data):
Storage Conditions: Room temperature
Shipped In: Normal
General guidance for ketone solvents/reagents:
Store tightly sealed in a cool, well-ventilated area away from ignition sources and strong oxidizers.
Protect from moisture and strong bases if extended storage at elevated temperature is possible, to minimize self-condensation.
If ultra-dry solvent is required for enolate chemistry, dry before use (e.g., 3Å/4Å molecular sieves, freshly activated), and handle under inert gas. No reconstitution is needed for neat liquid; if supplied in sealed bottles, open under a fume hood.
After opening, record the open date and, for sensitive applications, periodically verify purity/water content by GC/KF as needed.
Stability:
Aliphatic ketones are generally stable under ambient laboratory conditions. Avoid prolonged exposure to light/heat and avoid contact with reactive metals or reducing agents.
Refer to the product CoA and SDS for any lot-specific storage notes or stabilizers. Product is for research use only.
Structure and Identity
Brief: 4-Nonanone (nonan-4-one) is a symmetrical, linear aliphatic ketone featuring a central carbonyl flanked by two n-butyl groups.
Item-specific (Product Data):
SKU: N158991
Product Name: 4-Nonanone
CAS: 4485-09-0
Storage Conditions: Room temperature
Shipped In: Normal
Research Use Note: For research use only
InChIKey (as provided): 352946 (note: this is not in standard InChIKey format; see literature identifiers below)
SMILES: Not specified for this item; refer to CoA/Spec Sheet.
Molecular Formula: Not specified for this item; refer to CoA/Spec Sheet.
Molecular Weight: Not specified for this item; refer to CoA/Spec Sheet.
Literature/Computed (for reference; not item-specific specifications):
Structural motif: one trigonal-planar ketone carbonyl (sp2 C=O) at the 4-position; two linear n-butyl chains; overall acyclic, achiral, and highly conformationally flexible.
2D description (words): a nine-carbon chain with a carbonyl at the center (C4). Counting from either terminus (C1–C9), the carbonyl carbon is C4, giving a symmetric backbone: CH3–CH2–CH2–C(=O)–CH2–CH2–CH2–CH3.
Notes:
No stereocenters; no tautomers of consequence under neutral conditions. Weakly polar due to the carbonyl; otherwise hydrophobic alkyl envelope.
For authoritative identity matching of this specific lot, please refer to the product CoA/SDS and spectral data where available.
Synthetic Utility
4-Nonanone is a symmetrical dialkyl ketone (di-n-butyl ketone) offering classic carbonyl reactivity and strategic value in synthesis (general literature guidance):
Functional group behavior:
Carbonyl (C=O): electrophilic; engages in nucleophilic additions (hydrides, organometallics), reductions (to 4-nonanol), and oxidations (Baeyer–Villiger to n-butyl n-butyrate).
α-Positions: mildly acidic C–H; enol/enolate formation under acid/base catalysis enables aldol, Michael-type, and alkylation chemistry.
Named/typical transformations:
Baeyer–Villiger oxidation → symmetric ester (n-butyl n-butyrate) due to identical n-butyl groups.
Wolff–Kishner/Clemmensen reductions → deoxygenation to n-nonane.
Enolate alkylation (LDA/NaHMDS) → α-alkylated ketones for building complexity; subsequent oxidation or reduction diversifies functionality.
α-Halogenation (NBS/Br2) → alpha-bromo ketones for substitution/elimination cascades.
Aldol condensations → higher carbon frameworks; careful base control needed to avoid self-condensation unless desired.
Retrosynthetic/strategic notes:
The symmetry simplifies product distributions in BV oxidations and certain cleavage pathways.
As a mid-polar solvent, it can also double as medium in transformations that tolerate ketones (avoid with strong nucleophiles that attack the carbonyl).
Practical considerations:
Exclude moisture/oxygen when generating enolates. Control temperature to favor kinetic vs. thermodynamic enolates. Monitor by GC/GC–MS.
Target Specificity
Not applicable. This product is a small-molecule aliphatic ketone, not a biological targeting reagent (e.g., antibody, probe, or inhibitor). No antigen/epitope specificity data are relevant.
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