Nonadecan-9-one - ≥98% , CAS No.75030-48-7

CAS: 75030-48-7 Cat. No.: N404810 Formula: C₁₉H₃₈O Molecular Weight: 282.51

GRADE & PURITY ≥98%

Synonyms

9-Nonadecanone

Storage

Room temperature

Specifications

Synonyms

9-Nonadecanone

Specifications & Purity

≥98%

Storage

Room temperature

Purity

≥98%

Names and Identifiers

Pubchem Sid

504763059

Pubchem Sid Url

https://pubchem.ncbi.nlm.nih.gov/substance/504763059

Canonical Smiles

CCCCCCCCCCC(=O)CCCCCCCC

IUPAC Name

nonadecan-9-one

InChIKey

GDEBLWVCYHWUDN-UHFFFAOYSA-N

INCHI

1S/C19H38O/c1-3-5-7-9-11-12-14-16-18-19(20)17-15-13-10-8-6-4-2/h3-18H2,1-2H3

Isomeric SMILES

CCCCCCCCCCC(=O)CCCCCCCC

Molecular Weight

282.51

Reaxy-Rn

1708680

Reaxys-RN_link_address

https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=1708680&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organic oxygen compounds
    • Class Organooxygen compounds
      • Subclass Carbonyl compounds

• Kingdom: Organic compounds
• Superclass: Organic oxygen compounds
• Class: Organooxygen compounds
• Subclass: Carbonyl compounds
• Intermediate Tree Nodes: Not available
• Direct Parent: Ketones
• Alternative Parents: Organic oxides Hydrocarbon derivatives
• Molecular Framework: Aliphatic acyclic compounds
• Substituents: Ketone - Organic oxide - Hydrocarbon derivative - Aliphatic acyclic compound
• Description: 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: Not available

Data sources

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.

DOI: 10.1186/s13321-016-0174-y

Chemical and Physical Properties

• Melt Point(°C): 51 °C
• Molecular Weight: 282.500 g/mol
• XLogP3: 8.100
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 16
• Exact Mass: 282.292 Da
• Monoisotopic Mass: 282.292 Da
• Topological Polar Surface Area: 17.100 Ų
• Heavy Atom Count: 20
• Formal Charge: 0
• Complexity: 198.000
• 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

Application Protocols

Not applicable. No antibody or bioassay-specific protocols are associated with this small-molecule ketone.

• Tested applications, recommended dilutions, positive controls: Not applicable.

For chemical transformations and analytical use, refer to the Reaction Conditions and Solvent Selection sections.

Biological Roles

• Item-specific biological data: Not specified for this item; refer to literature if required for contextual background.

• General/literature context

  • Long-chain aliphatic ketones can occur as minor constituents in natural waxes and cuticular lipids across plants and insects, arising from fatty acid/aldehyde oxidation pathways. Specific occurrence and abundance for nonadecan-9-one are not established here.
  • Due to high hydrophobicity and low volatility, such ketones primarily partition into lipid phases and hydrophobic matrices rather than aqueous environments.
  • They are often used as inert hydrophobic standards or probes in partitioning and sorption studies, and as substrates for generic carbonyl-transforming enzymes in biochemical method development (e.g., oxime formation for derivatization), without implying biological activity.

No clinical or therapeutic functions are claimed; this product is intended strictly for research use.

Buffer Applications

This compound is a nonpolar organic ketone and is not used to prepare aqueous buffer systems.

• Practical note
  • Insolubility in water precludes typical buffer roles (pH control, electrophoresis). For work requiring aqueous environments, consider forming emulsions, using co-solvents (e.g., <10% DMSO or ethanol), or encapsulation vehicles to introduce trace amounts for assays.
  • For pH-dependent derivatizations of the carbonyl (e.g., oxime formation), perform in biphasic or mixed organic/aqueous systems with appropriate acid/base catalysis.

Green Alternatives

This product is a hydrophobic ketone building block rather than a volatile solvent. “Green” considerations focus on choosing greener reagents and media when using it in synthesis or analysis.

• Solvent choices (greener options; literature/general)

  • Preferred: Heptane or cyclohexane over chlorinated solvents for nonpolar handling; 2-MeTHF or CPME as ether alternatives to diethyl ether/THF where compatible.
  • Avoid when possible: Dichloromethane and chloroform for routine dissolution; replace with toluene/heptane/ethyl acetate if performance allows.

• Oxidation/reduction alternatives

  • Baeyer–Villiger: Use H2O2 with a solid acid catalyst or enzyme (BV monooxygenases) in place of mCPBA, recognizing trade-offs in rate and selectivity.
  • Reduction: Catalytic hydrogenation (H2/Pd, H2/Ru) or transfer hydrogenation can replace stoichiometric metal hydrides to reduce waste.

• Workup and waste

  • Minimize halogenated waste; perform liquid–liquid separations with greener solvent pairs (e.g., heptane/EtOAc/brine) where feasible.
  • Recover and recycle high-boiling nonpolar solvents (toluene, xylene) via distillation when compatible with purity requirements.

• Comparison snapshot (general)

  • DCM vs heptane: Heptane reduces halogenated waste and toxicity; DCM offers stronger solvency but higher EHS burden.
  • THF vs 2-MeTHF: 2-MeTHF is biomass-derived and forms fewer peroxides; check solubility and reaction rates for enolate chemistry before switching.

Pharmaceutical Uses

No pharmacopeial or excipient status is provided for this item.

• Item-specific status

  • Pharmacopeia/monograph listing: Not specified for this item; refer to regulatory databases if needed.
  • Intended use: For research use only (per Product Data).

• General context (non-clinical)

  • Long-chain ketones may be evaluated in formulation research as hydrophobic components or model lipophiles in permeability and partition studies, but they are not typical pharmaceutical excipients.
  • If used in pre-formulation studies, ensure grade and impurity profiles meet the study’s analytical requirements and that suitable non-toxic carriers are selected.

No medical, clinical, or therapeutic claims are made for this product.

Physical Properties

Item-specific numerical specifications are not provided. Do not use these values as product specifications.

• Provided for this item

  • 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/general expectations (for context only; not product specifications)

  • Physical state: long-chain aliphatic ketones of this size are typically low-melting solids or viscous liquids near ambient temperature; low volatility.
  • Solubility: expected to be practically insoluble in water; freely soluble in nonpolar and moderately polar organic solvents (e.g., hexanes, heptane, toluene, diethyl ether, dichloromethane).
  • Density: anticipated close to that of long-chain hydrocarbons (less than water) (literature, qualitative).
  • LogP: high (strongly hydrophobic; logP >> 4) (literature, qualitative).
  • Odor: faint waxy/ketonic typical of long-chain ketones (literature, qualitative).

• Use notes (general)

  • Handle as a hydrophobic, low-volatility organic compound; gentle warming may aid dissolution in nonpolar solvents.
  • For exact physical constants (mp, bp, refractive index, UV cutoff, water/peroxide ppm, metal content): Not specified for this item; refer to CoA/Spec Sheet.

Quality & Grades

• Item-specific quality information

  • 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)

  • Research grade: Suitable for most synthetic and analytical R&D tasks; typical impurities may include traces of isomeric ketones, residual hydrocarbons, or oxidation products.
  • High-purity/GC grade: Lower nonvolatile and UV-absorbing impurities; preferred for analytical calibration and trace analysis.
  • Synthesis building-block grade: Emphasis on carbonyl integrity (low acid content), low water, and low residual solvents to support moisture-sensitive steps (e.g., enolate chemistry).

• What to check on the CoA/Spec Sheet

  • Identity: GC/MS or NMR match; IR with strong C=O band near ~1715 cm−1 (literature) for aliphatic ketones.
  • Assay/GC area% and limits for related substances (e.g., positional isomers, unreacted n-alkanes).
  • Residual solvents/water: Karl Fischer and headspace GC (if relevant to your application).
  • Stabilizers: Presence/absence and type, if any; these can affect downstream catalysis.

Select a grade aligned with your application (analytical vs. preparative vs. materials). For unspecified items, request the latest CoA/SDS for decision-making.

Reaction & Applications

Nonadecan-9-one is a representative mid-chain aliphatic ketone useful as a building block and model substrate in carbonyl chemistry and materials-oriented research.

• Typical reaction families (literature/general)

  • Nucleophilic additions/reductions: NaBH4 or catalytic hydrogenation to give the secondary alcohol (nonadecan-9-ol); selective hydrosilylation with metal catalysts.
  • Oxime/hydrazone formation: Reaction with hydroxylamine or hydrazines for derivatization or GC/MS stabilization of the carbonyl.
  • Baeyer–Villiger oxidation: Peracids (e.g., mCPBA) or H2O2-based systems convert the ketone to the corresponding long-chain ester; migration preferences follow typical BV rules.
  • Enolization/α-functionalization: LDA, LiHMDS, or KOtBu generate the enolate for alkylation, acylation, or aldol-type reactions (the long alkyl chains bias solubility toward hydrocarbon solvents).
  • Acyl anion equivalents: Umpolung strategies (e.g., thioacetalization followed by lithiation) enable carbon–carbon bond formation.

• Application contexts

  • Hydrophobic materials and surface science: Model compound for studying wettability, partitioning, and nonpolar matrix effects in coatings or lubricant-related systems.
  • Analytical method development: GC/LC method suitability studies for nonpolar ketones; reference in derivatization workflows (oximes, DNPH analogs where applicable to ketones).
  • Synthetic intermediate: Gateway to amphiphiles via selective reduction, oxidation, or α-functionalization to introduce polar handles at a defined interior position.

• Practical tips

  • Dry conditions improve outcomes for strong-base enolate chemistry; employ rigorously anhydrous solvents and inert atmosphere.
  • Gentle heating can aid dissolution prior to reaction; avoid excessive temperatures near strong oxidants.
  • For BV oxidations, control exotherm due to high organic content; phase-transfer or biphasic systems can improve handling of long-chain substrates.

Reaction Conditions

The following are literature-style general conditions for typical transformations of long-chain aliphatic ketones like Nonadecan-9-one; they are guidance only and not item specifications.

• Reduction to secondary alcohol

  • Reagents: NaBH4 (1.1–2.0 equiv) in MeOH/EtOH or THF; 0–25°C; 0.5–4 h. Quench with water, work up, purify by silica gel (hexanes/EtOAc).
  • Alternative: Catalytic hydrogenation (H2, 1–5 bar) with Raney Ni or Pd/C in i-PrOH or EtOAc at 25–60°C.

• Oxime formation (derivatization)

  • Hydroxylamine hydrochloride (1.2–2.0 equiv), pyridine or NaOAc buffer; EtOH or EtOH/H2O; 25–60°C; 1–6 h.

• Baeyer–Villiger oxidation

  • mCPBA (1.2–1.5 equiv), DCM or CHCl3, 0–25°C; 2–16 h; monitor by TLC/GC. Greener option: H2O2 (30%) with catalytic acid in toluene/acetonitrile biphasic system, 25–50°C.

• Enolate alkylation

  • Base: LDA or LiHMDS (1.1–1.5 equiv) in THF or THF/toluene; −78 to −20°C; then add alkyl halide (1.2–2.0 equiv). Quench at −78 to 0°C, standard aqueous workup.

• Hydrazone/Wolff–Kishner (decarbonylation to hydrocarbon segment)

  • Form hydrazone (hydrazine, trace acid, EtOH or toluene), then heat with strong base (KOH) and high-boiling solvent (DEG) at elevated temperatures; observe appropriate safety protocols.

• Workup/purification tips

  • Due to hydrophobicity, use nonpolar eluents (hexanes/toluene). For viscous oils, reduce pressure and gentle warming to remove solvent; low-temperature crystallization from heptane may assist isolation if solid.

Safety & Handling

Safety classifications specific to this catalog item are not provided.

• GHS/CLP for this item

  • Signal word: Not specified for this item; refer to SDS.
  • Hazard statements: Not specified for this item; refer to SDS.
  • GHS classification and pictograms: Not specified for this item; refer to SDS.

• General hazards (literature/general)

  • Long-chain aliphatic ketones are typically combustible organic liquids/low-melting solids with low acute toxicity but can cause irritation on contact or inhalation of mists/vapors.
  • Low volatility reduces inhalation risk at room temperature; mist generation or heating can increase exposure.

• PPE and handling (best practice)

  • Wear safety glasses, lab coat, and suitable chemical-resistant gloves (e.g., nitrile). Work in a fume hood when weighing, transferring, or heating.
  • Avoid breathing vapors/aerosols; prevent prolonged skin contact.

• Incompatibilities and reactivity (general)

  • Strong oxidizers (risk of exothermic reactions).
  • Very strong bases can promote enolization/condensation.
  • Generally stable; unlike ethers, simple ketones are not prone to hazardous peroxide formation under normal storage.

• First-aid overview (consult SDS for details)

  • Skin/eye contact: Rinse with water for several minutes; remove contaminated clothing. Seek medical attention if irritation persists.
  • Inhalation: Move to fresh air; seek medical attention if symptoms occur.
  • Ingestion: Rinse mouth; do not induce vomiting; seek medical attention.

Always consult the official SDS for authoritative, item-specific safety guidance.

Solvent Selection

As a highly hydrophobic, long-chain aliphatic ketone, Nonadecan-9-one dissolves best in low- to mid-polarity organic media.

• Polarity/miscibility profile (literature/general)

  • Water: essentially insoluble.
  • Excellent solvents: n-hexane, heptane, iso-octane, cyclohexane, toluene, xylene, diethyl ether, methyl tert-butyl ether (MTBE), dichloromethane, chloroform.
  • Moderate solvents: THF, ethyl acetate, acetonitrile (warming may be needed).
  • Poor solvents: alcohols with high water content; DMF/DMSO may dissolve but are often unnecessary for nonpolar systems.

• Selection guidance by task

  • Spectroscopy/GC: Hexanes or isooctane are common carriers for GC-FID; toluene for NMR if aromatic background is acceptable; CDCl3 for 1H/13C NMR (literature practice).
  • Crystallization/recrystallization: Use a nonpolar solvent (hexane/heptane) with gentle warming; slow cooling to induce crystallization if solid at room temp.
  • Reactivity (e.g., reductions, oxime formation): Ethanol/IPA, toluene, or DCM depending on reagent system; ensure the reagent is compatible with the solvent’s polarity and boiling range.

• Quick comparison (general)

  • Hexanes vs toluene: Hexanes maximize hydrophobic solubility and low boiling for easy removal; toluene offers higher bp for elevated-temperature reactions and better solvency for reagents.
  • DCM vs ether: DCM offers strong dissolving power and easy workup; ether provides a more benign polarity for moisture-sensitive base chemistry.

Storage & Reconstitution

• Storage conditions (item-specific)

  • Store at room temperature (per Product Data). Protect from strong oxidizers and ignition sources. Keep container tightly closed in a dry, well-ventilated place.

• Stability (general)

  • Long-chain saturated ketones are generally stable under ambient laboratory conditions. Avoid prolonged exposure to strong light/heat and air-borne contaminants to minimize slow oxidation.

• Reconstitution/handling (general)

  • Supplied neat. No reconstitution is required. If solid or highly viscous at room temperature, gently warm (e.g., 30–40°C water bath) to facilitate transfer.
  • To prepare solutions, dissolve in a suitable organic solvent such as hexanes, heptane, toluene, diethyl ether, or dichloromethane. For analytical work, use anhydrous, high-purity solvents.

• Shipping

  • Shipped In: Not specified for this item; refer to CoA/Spec Sheet.

• Freeze–thaw guidance

  • Not applicable to neat small molecules; if stored at lower temperatures for viscosity management, avoid condensation ingress by equilibrating to room temperature before opening.

Always consult the latest CoA and SDS for item-specific guidance on stability and handling.

Structure & Identity

Nonadecan-9-one is a long-chain aliphatic ketone featuring a single internal carbonyl embedded in a C19 saturated hydrocarbon backbone.

• Item-specific identifiers (from Product Data)

  • SKU: N404810
  • CAS: 75030-48-7
  • PubChem CID: 4561408
  • InChIKey: 98921 (as provided)

• Core identifiers (literature/general)

  • Preferred name: Nonadecan-9-one (systematic: nonadecan-9-one)
  • Molecular formula: C19H38O (literature)
  • Molecular weight: ~282.50 g/mol (literature)
  • SMILES: CCCCCCCC(=O)CCCCCCCCCC (literature; linear C8–C(=O)–C10)

• Structural features (general description)

  • Functional group: one internal ketone (aliphatic) at the C9 position counted from one terminus.
  • Saturation: fully saturated (no C=C).
  • Topology: extended linear hydrocarbon on both sides of the carbonyl; highly flexible, nonpolar chain.
  • Stereochemistry: none (achiral); carbonyl sp2 center flanked by sp3 carbons.

• 2D structure in words (general)

  • An 8-carbon n-alkyl segment attached to the carbonyl carbon on one side and a 10-carbon n-alkyl segment on the other: Octyl–CO–Decyl.

Synthetic Utility

The internal carbonyl of Nonadecan-9-one enables a range of carbonyl and α-carbon transformations while preserving a long, inert hydrocarbon scaffold.

• Functional group reactivity (literature/general)

  • Carbonyl electrophilicity: supports nucleophilic additions (hydrides, organometallics) to give the corresponding C9 secondary alcohol or tertiary alcohols (with R–M reagents).
  • Oxime/hydrazone/semicarbazone formation: useful for purification, characterization, or further transformations (e.g., Wolff–Kishner on hydrazones to install an internal methylene).
  • Baeyer–Villiger oxidation: affords long-chain esters which can be hydrolyzed to fatty alcohol/acid derivatives with a defined chain split.
  • α-Functionalization: Enolate generation (LDA, LiHMDS) enables alkylation, acylation, or aldol-type couplings; kinetic vs thermodynamic enolate control is achievable by base, temperature, and solvent.

• Retrosynthetic value

  • Serves as a platform for constructing amphiphiles (introducing polar groups at C9) or branching via α-alkylation, creating defined internal functionality in otherwise inert alkyl chains.

• Practical considerations

  • Solubility often favors hydrocarbon or ether solvents; strong bases require rigorously anhydrous conditions and inert atmosphere.
  • The long alkyl chains can slow diffusion; extended reaction times or slight heating may be beneficial.

Target Specificity

Not applicable. This product is a small-molecule ketone and is not an antibody, protein, or assay reagent with biological target specificity.

• Item-specific antigen/epitope/clone/isotype data: Not applicable.