3-Cyclopentylpyridine - ≥95% , CAS No.79134-68-2

CAS: 79134-68-2 Cat. No.: C1258555 Fórmula: C₁₀H₁₃N Peso molecular: 147.22

GRADE & PURITY ≥95%

Storage

Room temperature

Shipped In

Normal

Specifications

Especificaciones y pureza

≥95%

Condiciones de almacenamiento de almacenamiento

Room temperature

Enviado en

Normal

Pureza

≥95%

Nombres e identificadores

Sonrisas canónicas

C1CCC(C1)C2=CN=CC=C2

IUPAC Name

3-cyclopentylpyridine

InChIKey

WSAFCRLBAFJPTN-UHFFFAOYSA-N

INCHI

1S/C10H13N/c1-2-5-9(4-1)10-6-3-7-11-8-10/h3,6-9H,1-2,4-5H2

Peso molecular

147.22

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organoheterocyclic compounds
    • Clase Pyridines and derivatives

• Kingdom: Organic compounds
• Superclass: Organoheterocyclic compounds
• Clase: Pyridines and derivatives
• Subclass: Not available
• Intermediate Tree Nodes: Not available
• Direct Parent: Pyridines and derivatives
• Alternative Parents: Heteroaromatic compounds Azacyclic compounds Organonitrogen compounds Hydrocarbon derivatives
• Molecular Framework: Aromatic heteromonocyclic compounds
• Substituents: Pyridine - Heteroaromatic compound - Azacycle - Organic nitrogen compound - Hydrocarbon derivative - Organonitrogen compound - Aromatic heteromonocyclic compound
• Descripción: 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

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

Propiedades químicas y físicas

• Peso molecular: 147.220 g/mol
• XLogP3: 2.800
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 1
• Exact Mass: 147.105 Da
• Monoisotopic Mass: 147.105 Da
• Topological Polar Surface Area: 12.900 Ų
• Heavy Atom Count: 11
• Formal Charge: 0
• Complexity: 116.000
• 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 validated bioassay protocols (e.g., WB, IHC, IF, FC) are associated with this small-molecule reagent. For synthetic use, refer to the Reaction Conditions and Synthetic Utility sections for general guidance and adapt to your specific method.

Biological Roles

This compound is a synthetic heteroaromatic and is not known to have endogenous biological roles.

• General information (literature)

  • Pyridine rings are common motifs in bioactive small molecules. Alkyl substitution at the 3-position modulates lipophilicity and basicity (conjugate acid pKa typically mid-5s), influencing membrane permeability and binding to acidic sites.
  • As a neutral base, the free pyridine can coordinate to metal centers or be protonated under physiological-like acidic conditions, forming pyridinium salts that are more water-soluble.

• Experimental considerations

  • For biochemical assays, confirm absence of reactive impurities (e.g., peroxides, acids) that could confound results.
  • Solubilization often requires a co-solvent (DMSO, MeCN) or conversion to a pyridinium salt for aqueous work.

No medical/clinical claims are made; this material is supplied strictly for research and laboratory use.

Buffer Applications

Not typically used as a buffering agent. As a weak base, 3-cyclopentylpyridine (conjugate acid pKa generally in the mid-5 range for 3-alkylpyridines, literature) does not provide practical buffering capacity in common laboratory pH windows.

• Practical note: If aqueous handling is required, transient protonation to a pyridinium salt can aid extraction or crystallization, but this is not a defined buffer system. For buffering needs, use established systems (e.g., phosphate, acetate, HEPES) matched to the target pH.

Green Alternatives

While 3-cyclopentylpyridine itself is a target/building block rather than a solvent, greener choices can be applied in its preparation and use.

• Solvent considerations (literature guidance)

  • Replace chlorinated solvents (DCM, CHCl3) with ethyl acetate, Me-THF, CPME, or 2-propanol where feasible (e.g., for extractions, N-oxidation workups, and hydrogenations).
  • For hydrogenations, ethanol or isopropanol are preferable to DMF/MeOH in many catalytic systems; water/EtOH mixtures may be viable with appropriate catalysts.

• Oxidants/reductants

  • N-oxidation: Use urea–hydrogen peroxide (UHP) or H2O2/acetic acid systems under controlled conditions as alternatives to m-CPBA; assess selectivity and safety.
  • Reductions: Employ catalytic hydrogenation (H2) rather than stoichiometric hydrides when ring reduction is desired; choose reusable supported catalysts.

• Energy and safety

  • Leverage continuous-flow for exothermic steps (e.g., oxidations, quaternizations) to improve heat/mass transfer and reduce solvent volumes.
  • Use solvent-recycling and in-process base washes to minimize waste salts.

• Tradeoffs

  • Greener solvents can alter rates/selectivity (e.g., Me-THF may solubilize peracids differently vs DCM). Catalyst activity and product isolation may demand iterative optimization.

Comparison snapshot (general)

• DCM: excellent solubility/phase behavior; environmental concerns → consider EtOAc/CPME.
• MeOH: good H2 solubility; toxicity concerns → consider EtOH/iPrOH.
• DMF/DMSO: powerful media; difficult removal → consider MeCN/Me-THF where compatible.

Pharmaceutical Uses

No pharmacopeial monograph or excipient designation is provided for this item. It is not supplied as a dosage-form component.

• Research/manufacturing context (general)
  • Employed as a synthetic intermediate or heteroaryl scaffold in discovery chemistry to tune physicochemical properties (lipophilicity, basicity) of lead series.
  • Conversion to 3-cyclopentylpiperidine via catalytic hydrogenation can deliver saturated amine motifs frequently encountered in fine chemicals.
  • Formation of pyridinium salts may be useful for phase-transfer or to generate crystalline derivatives for purification.

All uses are for research and laboratory synthesis only; no therapeutic or clinical claims are made.

Physical Properties

• Item-specific specs (from Product Data)

  • Appearance: Not specified for this item; refer to CoA/Spec Sheet.
  • Molecular Weight: Not specified for this item; refer to CoA/Spec Sheet.
  • Storage conditions: Room temperature (provided)

• Literature/computed (general reference; not item-specific)

  • Molecular formula: C10H13N (computed from structure)
  • Molecular weight: ~147.22 g/mol
  • Physical state: typically a colorless to pale yellow liquid for many C-alkylpyridines of similar size; solidification possible at lower temperatures depending on purity (literature trend)
  • Basicity: pKa of conjugate acid for 3-alkylpyridines is commonly ~5.3–5.7 in water at 25 °C
  • LogP: 3-alkyl substitution increases hydrophobicity versus pyridine; estimated logP for C10 alkylpyridines is in the ~2–3 range (literature trend, method-dependent)
  • Solubility: low in water; miscible with common organic solvents (alcohols, ethers, chlorinated solvents, hydrocarbons) typical for alkylpyridines
  • Refractive index/density/boiling point: Specific values for this item are not provided here; consult primary databases or the CoA for exact specifications.

Notes: Any precise numerical property required for method development (e.g., GC method temperature, refractive index for purity checks) should be verified against the item’s CoA/Spec Sheet to ensure alignment with the supplied batch.

Quality and Grades

• Item-specific grade/purity: Not specified for this item; refer to CoA/Spec Sheet.

• Guidance on typical grades for this compound class (general information)

  • Neat reagent grade: Suitable for most synthetic applications including N-oxidation, quaternization, or hydrogenation to piperidine derivatives. Verify GC/HPLC area percent and water content if critical.
  • High-purity (GC ≥99%) or Low-UV grades: Preferred for photophysical measurements or when used as an internal standard/ligand in catalysis. Low-UV grades minimize baseline noise in LC detection.
  • Stabilizers: Not commonly added to alkylpyridines; if any stabilizer or inhibitor is present, it will be stated on the CoA. Absence/presence of stabilizers can affect downstream reactions involving strong electrophiles.

• What to check on receipt

  • Identity confirmation (1H/13C NMR: pyridine ring signals and cyclopentyl aliphatic envelope; MS m/z ~147 [M+H]+ expected for C10H13N, literature)
  • Volatile impurities by GC; water by Karl Fischer if moisture-sensitive transformations are planned
  • Peroxide test not generally applicable (non-ether), but check for oxidative impurities if stored long-term.

Rely on the specific batch CoA/Spec Sheet for definitive grade, assay, and impurity limits.

Reaction and Applications

3-Cyclopentylpyridine is a versatile heteroaromatic building block featuring a Lewis-basic nitrogen and a hydrophobic cycloalkyl substituent.

• Representative transformations (literature)

  • N-oxidation: Formation of 3-cyclopentylpyridine N-oxide with peracids (e.g., m-CPBA). The N-oxide can serve as a directing group for subsequent functionalization or be reduced back to the pyridine.
  • Quaternization: Alkylation (e.g., MeI, BnBr) affords pyridinium salts, useful phase-transfer reagents or precursors to N-ylides.
  • Catalytic hydrogenation: Reduction of the pyridine ring to the corresponding 3-cyclopentylpiperidine under H2 (Pd/C, PtO2, or Raney Ni), a valuable intermediate for fine-chemical synthesis.
  • Directed ortho-functionalization: Strong base (e.g., s-BuLi/TMEDA) enables lithiation at positions adjacent to N, enabling electrophile trapping (halogenation, formylation) on suitably protected systems.
  • Electrophilic activation at nitrogen: N-oxides enable rearrangements (e.g., Boekelheide) to install oxygen at the ring methyl equivalents (adapted for substituted systems, literature).
  • C–H activation/cross-coupling: While the parent lacks a halogen handle, pre-activation (e.g., via N-oxide or C–H activation methods) can introduce cross-coupling partners.

• Utility and context

  • Ligand/auxiliary: The pyridyl nitrogen coordinates to transition metals, modulating reactivity in stoichiometric or catalytic settings.
  • Polarity tuning: The cyclopentyl substituent boosts lipophilicity relative to pyridine, useful in SAR campaigns and material applications.

• Practical notes

  • Drying: Pass through basic alumina or dry over molecular sieves to remove trace water and acids prior to moisture-sensitive steps.
  • Protonation state: Control with acid/base to tune extraction and crystallization (free base vs pyridinium salt).

Reaction Conditions

General literature guidance for common transformations involving 3-alkylpyridines; optimize for this substrate.

• N-oxidation to N-oxide

  • Reagents: m-CPBA (1.1–1.5 equiv) in DCM or MeCN; 0–25 °C, 0.5–3 h.
  • Workup: aqueous Na2CO3/NaHCO3 wash to remove acids; silica plug. Typical isolated yields: 70–95% (substrate-dependent).

• Quaternization (N-alkylation)

  • Reagents: MeI, MeOTf, BnBr, or dialkyl sulfates; solvent MeCN, acetone, or neat; 25–80 °C, 2–24 h.
  • Notes: Counterion affects crystallinity and isolation; choose for downstream steps.

• Hydrogenation to piperidine

  • Catalyst: 5–10% Pd/C or Raney Ni; H2 3–30 bar; solvent EtOH, iPrOH, or AcOH; 25–80 °C, 2–16 h.
  • Caution: Control to avoid N-dealkylation or ring opening of cyclopentyl under harsh conditions.

• Directed ortho-lithiation

  • Base: s-BuLi (1.1–1.5 equiv) ± TMEDA in THF/toluene; −78 to −40 °C, 0.5–2 h; trap with electrophiles (I2, DMF, Me3SiCl).
  • Notes: Protect from proton sources; quench carefully; subsequent cross-coupling after halogenation.

• Cross-coupling (if pre-halogenated)

  • Suzuki: Pd(PPh3)4 (1–3 mol%), base (K2CO3), solvent dioxane/H2O or toluene/EtOH/H2O, 60–100 °C.
  • Negishi/Kumada: organozinc/magnesium cyclopentyl partners under Pd/Ni; anhydrous, 0–80 °C.

Yields and conditions vary by substrate and scale. Conduct small-scale optimization and monitor by GC/HPLC/NMR.

Safety and Handling

• 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 alkylpyridines (literature/good practice)

  • Hazards: Many alkylpyridines are irritants to skin, eyes, and respiratory tract and may be harmful if swallowed. Avoid inhalation of vapors and contact with skin/eyes. Some members have combustible vapors; keep away from ignition sources until exact flash point is confirmed from the SDS.
  • PPE: lab coat, safety glasses or splash goggles, and appropriate chemical-resistant gloves (e.g., nitrile). Use in a fume hood.
  • Incompatibilities: strong oxidizers (risk of exotherm/oxidation), strong acids (exothermic protonation; potential salt formation), and strong bases for prolonged contact with air-sensitive metals (can coordinate and alter reactivity). Avoid reactive acylating/alkylating agents unless intended.
  • First aid (overview; defer to SDS): move to fresh air if inhaled; rinse cautiously with water for eye/skin contact; remove contaminated clothing; seek medical attention if symptoms persist.
  • Spill/cleanup: absorb with inert material (vermiculite, sand), collect in a sealable container. Prevent entry into drains. Ventilate area.
  • Fire-fighting: use dry chemical, CO2, or foam. Combustion may produce NOx and carbon oxides.

Always consult the product-specific SDS prior to use for authoritative classification and response guidance.

Solvent Selection

This product is a heteroaromatic reagent/substrate rather than a laboratory solvent. Solvent selection focuses on choosing media for its reactions, purifications, and analyses.

• Miscibility and polarity (general trends for alkylpyridines)

  • Low water solubility; good solubility in ethers (THF, MTBE), alcohols (MeOH, EtOH), aprotic polar solvents (MeCN, DMF, DMSO), chlorinated solvents (DCM, chloroform), and aromatics (toluene).
  • The basic nitrogen can coordinate or be protonated; highly acidic solvents (TFA, formic acid) will form pyridinium salts and alter reactivity/solubility.

• Choosing a medium by transformation

  • N-oxidation: DCM, CHCl3, or MeCN at 0–25 °C (m-CPBA or peracids), buffering with Na2CO3 to control exotherm (literature).
  • Quaternization (N-alkylation): polar aprotic (MeCN, acetone) or neat alkyl halide; heating accelerates.
  • Catalytic hydrogenation to piperidine: alcohols (EtOH/iPrOH) or acetic acid; heterogeneous catalysts (Pd/C, Raney Ni) (literature).
  • Metalation/SEAr on pyridine ring is limited; directed ortho-lithiation uses hydrocarbon/ether mixtures (toluene/THF) at −78 to −40 °C with strong bases (literature).

• Small comparison (selection rationale)

  • DCM vs MeCN: DCM enhances solubility, easy workup; MeCN is polar and greener but may coordinate to catalysts.
  • Toluene vs THF: toluene preferred for high-temp and hydrophobicity; THF for low-temp organometallics.

Confirm solvent compatibility with the specific catalyst/reagent system and with any downstream analytical methods.

Storage and Reconstitution

• Item-specific storage and shipping (from Product Data)

  • Storage: Room temperature
  • Shipped: Normal

• General handling

  • Store tightly closed in a cool, dry, well-ventilated place away from strong oxidizers and strong acids.
  • If long-term storage is planned, consider storing under inert gas to minimize oxidative discoloration and moisture uptake; include a desiccant in secondary containment.
  • Warm to ambient temperature before opening to avoid condensation. If crystallization occurs upon cooling, gently warm and mix to re-homogenize.

• Reconstitution

  • Supplied neat; no reconstitution required. For solution preparation, common concentrations are 0.1–1.0 M in dry organic solvents (e.g., DCM, MeCN, THF, toluene) depending on application. Use anhydrous solvents for moisture-sensitive transformations.

• Stability notes (general)

  • Alkylpyridines are typically stable at ambient conditions. Avoid prolonged exposure to light and air if ultra-low impurity levels are critical. Verify assay periodically by GC or NMR if stored for extended periods.

Always defer to the product’s CoA and SDS for definitive storage constraints and compatibility.

Structure and Identity

A cycloalkyl-substituted heteroaromatic: 3-Cyclopentylpyridine is a pyridine ring bearing a cyclopentyl group at the 3-position (meta to the ring nitrogen). The ring nitrogen is sp2-hybridized and capable of coordination and protonation.

• Item-specific identifiers (from Product Data)

  • SKU: C1258555
  • CAS: 79134-68-2
  • InChIKey: 406603 (as provided)
  • SMILES: Not specified for this item; refer to CoA/Spec Sheet.

• Computed/literature identity (for general reference; not item-specific specifications)

  • Typical molecular formula (literature/computed): C10H13N
  • Typical molecular weight (literature/computed): ~147.22 g/mol
  • 2D structural description: a six-membered aromatic pyridine ring (positions numbered with N at position 1). A saturated five-membered cyclopentyl ring is attached at ring position 3 via a C–C bond. No stereocenters are present. Functional groups: aromatic heterocycle (pyridine), saturated carbocycle (cyclopentyl).

• Structural features of note

  • Lewis basic ring nitrogen (can be protonated, quaternized, or coordinated to metals)
  • Benzylic-type activation patterns absent (cyclopentyl is fully saturated and attached directly to the aromatic carbon)
  • Potential for directed ortho-metalation adjacent to N under strong base conditions (literature) due to pyridyl directing effects.

Synthetic Utility

Key reactive site is the pyridine nitrogen; the ring carbons are relatively deactivated to electrophiles but can be engaged via directed or metal-catalyzed strategies.

• Transformations (literature)

  • N-centered chemistry: quaternization (alkyl/arylalkyl halides), acylation (to N-acylpyridinium), and N-oxidation (m-CPBA, H2O2 systems). N-oxides open routes to rearrangements (e.g., Boekelheide) enabling C–O installation on the ring.
  • Ring reductions: catalytic hydrogenation to piperidine derivative (Pd/C, PtO2, Raney Ni) under H2; partial reductions may require precise control to avoid over-reduction.
  • Directed ortho-functionalization: s-BuLi/TMEDA or LiTMP at low temperature to install halogens, formyl, or silyl groups adjacent to N; subsequent cross-couplings (Suzuki, Negishi) possible after introduction of a halide/triflate.
  • C–H activation: use of transient directing strategies (via N-oxide or pyridinium) enables late-stage functionalization (borylation, arylation) under Ir/Rh/Pd catalysis.
  • Cyclopentyl modification: oxidation at tertiary C–H positions is limited; radical-mediated functionalization on the cycloalkyl ring can be explored with photoredox or peroxide initiators.

• Retrosynthetic value

  • Readily assembled from 3-halopyridines via cross-coupling with cyclopentylmetal reagents (e.g., Suzuki with cyclopentylboronates, Negishi with cyclopentylzinc reagents).
  • Alternative routes include Minisci-type alkylation of protonated pyridine using cyclopentyl radicals (photoredox or Ag/H2O2 initiation), delivering 3-substitution under controlled conditions.

Target Specificity

Not applicable. This product is a small-molecule heteroaromatic reagent and is not an antibody, protein, or targeted biological reagent. No antigen, clone, isotype, or species reactivity information applies.

Preguntas frecuentes

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 79134-68-2, the molecular formula is C10H13N, and the molecular weight is 147.22 g/mol. InChIKey WSAFCRLBAFJPTN-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.