This compound belongs to the class of organic compounds known as pyridines and derivatives. These are compounds containing a pyridine ring, which is a six-member aromatic heterocycle which consists of one nitrogen atom and five carbon atoms.
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.
Zertifikate (CoA, COO, BSE/TSE und Analyse-Diagramm)
C of A & Other Certificates(BSE/TSE, COO):
Analytical Chart:
Chemische und physikalische Eigenschaften
Molekulargewicht
205.340 g/mol
XLogP3
5.200
Hydrogen Bond Donor Count
0
Hydrogen Bond Acceptor Count
1
Rotatable Bond Count
8
Exact Mass
205.183 Da
Monoisotopic Mass
205.183 Da
Topological Polar Surface Area
12.900 Ų
Heavy Atom Count
15
Formal Charge
0
Complexity
133.000
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
Lösungsrechner
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Application Protocols
No assay-specific or bioanalytical application protocols are provided for this small-molecule reagent.
General laboratory usage notes (literature/best practice):
Handling: Transfer under inert atmosphere if water- or air-sensitive reagents are present in the same operation; the compound itself is typically air-stable.
Solution preparation: Prepare stock solutions in toluene, THF, DCM, or acetonitrile as appropriate for your reaction; record exact concentration gravimetrically for reproducibility.
Workup: For reactions in which the base/ligand is not consumed, remove by extraction into organic phase and, if necessary, silica or alumina plug with basic modifier.
Analytical: For GC, use a polar or mid-polar column if resolution of positional isomers is required; for HPLC, add 0.1% TEA to mobile phase to reduce tailing on silica-based columns.
For validated methods (e.g., in-process controls or release testing), develop and qualify protocols specific to your matrix and performance criteria.
Biological Roles
Item-specific biological function data: Not specified for this item; research use only.
General/biochemical context (literature):
3-Nonylpyridine is a synthetic hydrophobic pyridine derivative with no established physiological role. Unlike pyridine motifs found in natural cofactors (e.g., nicotinamide in NAD+/NADP+), the C9 alkyl substituent confers strong hydrophobicity and reduces aqueous compatibility.
Protonation state: At acidic pH, the molecule forms a pyridinium cation; such cationic amphiphiles can associate with lipid membranes or micelles in model systems. This property may be leveraged in studies of phase behavior or ion-pair extraction, but it does not imply biological activity or safety.
Biotransformation (conceptual): N-oxidation and oxidative chain shortening are common metabolic themes for tertiary nitrogen heterocycles and long-chain alkanes, respectively; however, specific metabolic pathways and rates for 3-nonylpyridine have not been characterized in detail in the open literature.
Important: No medical, diagnostic, or therapeutic uses are implied. This product is supplied strictly for laboratory research and development by trained professionals.
Buffer Applications
3-Nonylpyridine is not used as a buffering agent. Its low water solubility and hydrophobic nature make it unsuitable for preparing aqueous buffers or maintaining pH in biochemical assays.
If a basic nitrogen is needed in aqueous systems, conventional buffer systems (e.g., phosphate, Tris, HEPES, MOPS) are recommended depending on the target pH range.
For biphasic or nonaqueous systems requiring a basic heteroaromatic, 3-nonylpyridine can serve as a hydrophobic base or ligand in the organic phase; consult the Reaction & Applications and Solvent Selection sections for more relevant guidance.
Green Alternatives
Sustainability considerations for using 3-nonylpyridine (general literature guidance):
Role and substitution potential:
If used primarily as a base/ligand, consider less toxic and more biodegradable alternatives where feasible (e.g., bio-derived N-heterocycles or amine bases) recognizing that coordination behavior and hydrophobic partitioning may not translate directly.
If serving as a hydrophobic additive or phase modifier, evaluate renewable solvents or surfactant systems (e.g., 2-MeTHF, CPME, anisole, limonene) to reduce reliance on chlorinated solvents during processing.
Process-intensity improvements:
Employ solvent selection guides (ACS GCI, CHEM21) to replace DCM/DCE with greener media (e.g., EtOAc, Me-THF, CPME) for N-oxidation or quaternization where compatible.
Use catalytic oxidants (H2O2 with suitable catalysts) instead of stoichiometric peracids for N-oxide formation, when selectivity allows.
Implement continuous flow for exothermic quaternizations, improving heat transfer and minimizing solvent volumes.
Comparison snapshot (illustrative; not product specs):
2-MeTHF/CPME as processing solvents: bio-based (2-MeTHF), lower toxicity profiles, ease of workup with aqueous phases, suitable for organometallics.
Waste and EHS:
Segregate basic nitrogen-containing organics; consider acid-neutralization before aqueous disposal in accordance with local regulations.
Prefer solvent recovery (distillation) given the compound’s high boiling point and stability.
Pharmaceutical Uses
Item-specific pharmacopeial/excipient status: Not specified for this item; refer to CoA/Spec Sheet.
General considerations (non-clinical, research/manufacturing context only):
3-Nonylpyridine is not a common pharmaceutical excipient. Its potential roles in process development could include:
Research intermediate: as a building block en route to quaternary pyridinium salts or piperidine derivatives used as specialty materials.
Phase modifier: hydrophobic nitrogen heterocycles can sometimes modulate extraction or crystallization behavior in process screens, though this is highly application-specific.
Regulatory: No established monographs in major pharmacopeias are known for this specific isomer; any GMP use would require full characterization and justification.
No therapeutic or clinical claims are made or implied. Use is restricted to research and development by qualified personnel.
Physical Properties
Item-specific specifications (for this catalog lot):
Appearance: Not specified for this item; refer to CoA/Spec Sheet.
Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.
Literature/general properties for 3-alkylpyridines (contextual, not product specs):
Physical state: Typically a colorless to pale yellow oily liquid for long-chain (C≥7) alkylpyridines; viscosity increases with chain length.
Volatility: High-boiling, low vapor pressure relative to pyridine; nonyl substitution significantly elevates boiling point and reduces odor volatility.
Solubility: Expected low solubility in water; good solubility in nonpolar and moderately polar organic solvents (e.g., hexanes, toluene, ether, chlorinated solvents, esters). Protonated (pyridinium) forms are water-insoluble without counterion tailoring.
Basicity: Pyridine nitrogen pKaH typically ~5.2 (literature for unsubstituted pyridine); alkyl substitution modestly perturbs basicity. In neutral water, remains predominantly unprotonated; in acidic media forms the corresponding pyridinium salt.
Partitioning: Long C9 chain implies high hydrophobicity (high logP relative to pyridine; qualitative statement, literature trend).
Refractivity/density: Increases with chain length; exact values for the 3-nonyl isomer are not widely standardized in open literature.
Do not treat the above as specifications. For exact BP/MP, density, refractive index, or UV cutoff of this item, consult the CoA/Spec Sheet for SKU N1257922.
Quality and Grades
Item-specific quality information:
Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.
Guidance on quality considerations for 3-nonylpyridine (general):
Identity & isomerism: Confirm substitution pattern (3-isomer) by 1H/13C NMR; long-chain alkyl signals (multiplets ~1.2–1.4 ppm) and terminal methyl (~0.85–0.90 ppm) should be evident, along with characteristic pyridine ring protons (typically 7–9 ppm, solvent-dependent).
Purity measures: For chromatographic or kinetic work, GC or GC–MS is often preferred due to volatility and UV properties; HPLC-UV can be used but note pyridine absorbance at 254 nm.
Trace impurities: Typical impurities may include positional isomers (2- or 4-nonylpyridine), unreacted pyridine or nonanol/olefin precursors, and oxidative byproducts. Where low UV background or trace metal specifications are critical, request an application-specific grade.
Stabilizers: Alkylpyridines generally do not require stabilizers. If present, stabilizers will be listed on the CoA and may impact downstream reactions (e.g., acid scavenging or coordination chemistry). None are specified for this item.
Documentation: For method validation, obtain the lot-specific CoA detailing assay, identification, and residual solvent profile. If you require low water content, request Karl Fischer data for the lot, as hydrophobic high-boiling liquids can still retain trace moisture.
Reaction and Applications
This long-chain alkylpyridine serves as a versatile hydrophobic heteroaromatic base, ligand, and building block.
Representative research applications (literature/general):
Ligand/heteroaromatic base: The pyridine nitrogen can coordinate to transition metals (e.g., Pd, Ni, Cu) and modulate catalyst microenvironments via the C9 hydrophobe, benefiting biphasic or micellar systems.
Quaternization to ionic liquids/surfactants: Alkylation at the ring nitrogen (e.g., with alkyl halides or sulfates) furnishes 3-nonylpyridinium salts. Choice of counterion (e.g., BF4−, PF6−, NTf2−) tunes melting point and hydrophobicity for phase-transfer or ionic-liquid media.
N-Oxidation: Treatment with peracids (mCPBA) or H2O2/AcOH affords the N-oxide, enabling subsequent rearrangements (e.g., Boekelheide) or as a polarity-switching handle.
Directed metalation/functionalization: Lithiation at 2- or 4-positions under strong base (e.g., n-BuLi, TMP-based bases) allows introduction of electrophiles; the 3-nonyl group biases regioselectivity compared with unsubstituted pyridine.
Hydrogenation: Catalytic hydrogenation of the ring yields the corresponding piperidine derivative (useful for surfactant-like tertiary amines upon further functionalization).
Side-chain modification: Radical halogenation/oxidation at benzylic-like positions is limited (chain is aliphatic without benzylic activation), but terminal functionalization can be introduced via hydroboration–oxidation after olefin installation or via C–H activation methodologies.
Practical notes:
Basicity of the ring can inhibit acid-catalyzed steps; transient protonation or protection (N-oxide) can be strategic.
In chromatographic separations, use basic modifiers (e.g., 0.1–1% NEt3) to minimize tailing.
Remove residual pyridine-like odor by high-vacuum stripping at mild heat; avoid extended high temperatures to prevent oxidative discoloration.
Reaction Conditions
General literature-guidance for common transformations of 3-alkylpyridines (adapt to your substrate and scale; not item-specific specs):
N-Quaternization (to pyridinium salts):
Reagents: Alkyl bromides/iodides, dialkyl sulfates, or alkyl triflates.
Solvents: Acetonitrile, acetone, nitromethane, or neat conditions.
Conditions: RT to reflux (e.g., 20–80°C) for 2–24 h; monitor by 1H NMR or LC-MS. Isolate salts by precipitation with ether or by solvent swap.
N-Oxidation (to pyridine N-oxide):
Reagents: mCPBA (1.1–1.5 equiv) in DCM at 0–25°C; or H2O2 (30%) in AcOH or MeOH with catalytic tungstate.
Notes: Control exotherm; avoid over-oxidation of side chain. Typical times 1–6 h.
Directed metalation/functionalization (2- or 4-position):
Base: n-BuLi or s-BuLi with TMEDA or LiTMP.
Solvent: Dry THF or Et2O.
Temperature: −78 to −40°C, then add electrophile (e.g., DMF, CO2, alkyl halides). Quench carefully.
Halogenation via N-oxide route:
Convert to N-oxide, then treat with POCl3/PCl5 or PBr3 to obtain 2-halo derivatives; further cross-coupling under Pd catalysis.
Catalytic hydrogenation (ring saturation):
Catalyst: Pd/C, PtO2, or Raney Ni.
Solvent: EtOH, iPrOH, or AcOH.
Conditions: 1–10 bar H2, 25–80°C; monitor to avoid over-reduction or chain cleavage.
Typical yields vary with substrate and conditions; consult primary literature and perform small-scale optimization before scale-up.
Safety and Handling
Item-specific hazard data (from Product Data):
Signal Word: Not specified for this item; refer to SDS.
H-Statements: Not specified for this item; refer to SDS.
GHS Classification: Not specified for this item; refer to SDS.
Pictograms: Not specified for this item; refer to SDS.
General safety guidance for alkylpyridines (literature/ best practice; defer to SDS for authoritative data):
Hazards: Pyridine derivatives are typically harmful if inhaled, swallowed, or upon skin contact and can cause eye/skin irritation. High-boiling organics may present combustible liquid hazards.
PPE: Use appropriate lab PPE—lab coat, safety glasses or goggles, and chemical-resistant gloves (e.g., nitrile). Avoid inhalation of vapors/aerosols; handle in a fume hood.
Incompatibilities: Strong oxidizers; strong acids will form pyridinium salts (exotherm possible on neutralization). Avoid contact with alkali metals and strong reducing agents.
First aid (overview; follow SDS):
Inhalation: Move to fresh air; seek medical attention if symptoms persist.
Skin contact: Wash with soap and water; remove contaminated clothing.
Eye contact: Rinse cautiously with water for several minutes; seek medical advice if irritation continues.
Ingestion: Rinse mouth; do not induce vomiting; seek medical attention.
Spills: Contain with inert absorbent; collect in appropriate waste. Prevent entry into drains.
Fire-fighting: Use foam, dry chemical, or CO2. Cool containers with water spray.
Always consult the product-specific SDS before use. Research use only.
Solvent Selection
Applicability: 3-Nonylpyridine is typically used as a reagent/ligand/building block rather than as a bulk solvent. This section focuses on dissolving and handling it in typical reaction media.
Polarity and miscibility (literature/general):
Hydrophobic, high-boiling liquid; miscible with nonpolar and moderately polar organics (hexanes, toluene, ethers, esters, chlorinated solvents). Poorly soluble in water at neutral pH; forms insoluble pyridinium salts in strong acid unless the counterion promotes solubility.
Selection guidance:
For organometallic and coupling chemistry: Dry THF, MTBE, toluene, CPME, or 2-MeTHF provide good solvency while allowing low-temperature operations.
For electrophilic N-oxidation or N-alkylation: Chlorinated solvents (DCM/DCE), acetonitrile, acetone, or nitromethane are commonly used depending on reagent choice.
For purification: Normal-phase silica chromatography elution can require nonpolar to mid-polar eluents (hexanes/EtOAc or toluene/EtOAc); the basic nitrogen may tail—add 0.1–1% TEA or use basic alumina.
Comparison notes (literature trends):
Versus shorter-chain alkylpyridines (e.g., propyl-, butyl-): nonyl exhibits lower volatility and higher hydrophobicity; choose when phase separation or hydrophobic interactions are desired.
Versus pyridine: markedly less polar and far less water soluble; choose when reduced miscibility with aqueous phases is preferred.
Always verify solvent compatibility with reagents/catalysts in your specific protocol.
Storage and Reconstitution
Item-specific storage and shipping (from Product Data):
Storage Conditions: Room temperature.
Shipped In: Normal.
General handling and stability guidance:
Container: Store in a tightly closed, chemically compatible container (amber glass recommended) to minimize oxidative discoloration and adsorption into plastics due to hydrophobicity.
Atmosphere: Typically air-stable; for long-term storage, a dry, inert atmosphere (e.g., nitrogen) is beneficial to limit moisture uptake and oxidation.
Light: Protect from excessive light/UV to prevent slow oxidation or discoloration.
Shelf life: Not specified for this item; refer to CoA/Spec Sheet. Inspect periodically for changes in color or precipitation of impurities.
Reconstitution/solution preparation:
Solubility: Readily soluble in common organic solvents (e.g., hexanes, toluene, ethers, chlorinated solvents, esters). Poorly soluble in water.
Preparing stock solutions: Use anhydrous solvents when relevant to moisture-sensitive applications. Record mass and volume to establish accurate concentrations; filter through PTFE syringe filters (0.45 µm) if particulate matter is suspected.
Freeze–thaw: Not typically frozen; if a solution is stored cold, allow to warm to ambient and mix thoroughly to redissolve any phase-separated components.
Always consult the product’s CoA and SDS for lot-specific recommendations. Research use only.
Structure and Identity
3-Nonylpyridine is a monoalkylated pyridine featuring a linear C9 alkyl chain at the 3-position of the ring. The molecule combines a basic heteroaromatic nitrogen with a hydrophobic tail, yielding amphiphilic behavior under acidic conditions.
Item-specific identifiers (from Product Data):
SKU: N1257922
CAS: 108123-63-3
CID: 13816259
InChIKey: 265431 (as provided)
SMILES: Not specified for this item; refer to CoA/Spec Sheet.
Molecular formula (monosubstituted 3-nonyl isomer): C14H23N (literature)
Molecular weight: ~205.35 g/mol (literature, calculated from C14H23N)
Core functional group: pyridine ring (sp2 aromatic N-heterocycle) with a 3-position n-nonyl substituent (–(CH2)8–CH3)
Bronsted basic site: ring nitrogen; can be protonated to form the pyridinium salt.
2D structural description (literature):
Six-membered aromatic ring with one ring nitrogen (position 1).
The nonyl chain is attached at ring carbon C3 (meta to the ring nitrogen), extending as a linear saturated hydrocarbon chain of nine carbons.
No stereocenters; conformational flexibility resides in the alkyl chain.
Note: Where discrepancies exist between public databases and the product label, defer to the item’s CoA/SDS provided by Aladdin Scientific.
Synthetic Utility
Functional handles and reactivity (literature/general):
Ring nitrogen (N):
Lewis base/ligand for transition metals; can modulate catalyst environment and solvation.
Quaternization to form pyridinium salts (ionic liquids, surfactants, or phase-transfer agents), with counterion selection tuning physical properties.
N-oxidation to pyridine N-oxide enables further rearrangements (e.g., Boekelheide) and polarity inversion.
Aromatic ring (positions 2,4,5,6 available):
Directed metalation (e.g., with s-BuLi/TMEDA or TMP-bases) for electrophile trapping at 2- or 4-positions.
Electrophilic halogenation/nitration is generally poor for pyridines; prefer halogenation via directed methods or through N-oxide activation.
Cross-coupling: After halogenation (e.g., 2-bromo- or 4-bromination), Suzuki, Negishi, or Buchwald–Hartwig (for amination) transformations allow elaboration.
Side chain (n-nonyl):
Inert saturated chain provides hydrophobicity; terminal functionalization can be accessed via radical bromination (with care for selectivity), or by installing an olefin (e.g., via dehydrogenation or cross-metathesis on derived substrates) followed by hydrofunctionalization.
Strategic uses:
Provide a hydrophobic “handle” to bias phase behavior, enabling extraction or separations of pyridinium derivatives.
Build amphiphiles by combining N-quaternization with tailored counterions to produce room-temperature ionic liquids or surfactant-like salts.
Purification tip: Basic stationary phases or adding amine modifiers mitigate tailing during column chromatography.
Target Specificity
This product is a small-molecule chemical reagent and does not have biological target specificity in the sense of antibodies, enzymes, or nucleic acid probes.
Antigen/epitope, clone, isotype, or species reactivity: Not applicable.
For information on coordination to metal centers or roles as a ligand/base in catalysis, refer to the Reaction & Applications and Synthetic Utility sections.
Häufig gestellte Fragen
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.
How should this product be stored?
Store at room temperature.
How is this product shipped?
This product ships under standard ambient conditions. No temperature-controlled packaging is required.
What are the CAS number, molecular formula and molecular weight?
The CAS Number is 108123-63-3, the molecular formula is C14H23N, and the molecular weight is 205.34 g/mol. InChIKey ORKUMIPWDRAQES-UHFFFAOYSA-N.
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.
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