2-(4-Chlorophenyl)-4-methylpyridine - ≥95% , CAS No.23182-19-6

CAS: 23182-19-6 Cat. No.: C1039232 Fórmula: C₁₂H₁₀ClN Peso molecular: 203.67 PubChem CID: 11593656

GRAU & PUREZA ≥95%

Storage

Room temperature

Especificações

Especificações e pureza

≥95%

Condições de armazenamento de armazenamento

Room temperature

Pureza

≥95%

Nomes e identificadores

Sorrisos canónicos

CC1=CC(=NC=C1)C2=CC=C(C=C2)Cl

IUPAC Name

2-(4-chlorophenyl)-4-methylpyridine

InChIKey

SSFODIIQDZBJKU-UHFFFAOYSA-N

INCHI

1S/C12H10ClN/c1-9-6-7-14-12(8-9)10-2-4-11(13)5-3-10/h2-8H,1H3

SMILES isoméricas

CC1=CC(=NC=C1)C2=CC=C(C=C2)Cl

PubChem CID

11593656

Peso molecular

203.67

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organoheterocyclic compounds
    • Classe Pyridines and derivatives
      • Subclass Phenylpyridines

• Kingdom: Organic compounds
• Superclass: Organoheterocyclic compounds
• Classe: Pyridines and derivatives
• Subclass: Phenylpyridines
• Intermediate Tree Nodes: Not available
• Direct Parent: Phenylpyridines
• Alternative Parents: Methylpyridines Chlorobenzenes Aryl chlorides Heteroaromatic compounds Azacyclic compounds Organonitrogen compounds Organochlorides Hydrocarbon derivatives
• Molecular Framework: Aromatic heteromonocyclic compounds
• Substituents: 2-phenylpyridine - Methylpyridine - Chlorobenzene - Halobenzene - Aryl chloride - Aryl halide - Monocyclic benzene moiety - Benzenoid - Heteroaromatic compound - Azacycle - Organohalogen compound - Organonitrogen compound - Hydrocarbon derivative - Organic nitrogen compound - Organochloride - Aromatic heteromonocyclic compound
• Descrição: This compound belongs to the class of organic compounds known as phenylpyridines. These are polycyclic aromatic compounds containing a benzene ring linked to a pyridine ring through a CC or CN bond.
• 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

Propriedades químicas e físicas

• Peso molecular: 203.670 g/mol
• XLogP3: 3.500
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 1
• Exact Mass: 203.05 Da
• Monoisotopic Mass: 203.05 Da
• Topological Polar Surface Area: 12.900 Ų
• Heavy Atom Count: 14
• Formal Charge: 0
• Complexity: 175.000
• 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 building block. For synthetic applications, refer to the Reaction Conditions and Synthetic Utility sections for general guidance.

Biological Roles

This compound is a synthetic heteroaryl–aryl scaffold and does not have a known intrinsic biological role.

• General considerations (literature/general)
  • The pyridine motif is prevalent in bioactive small molecules due to its hydrogen-bond acceptor ability and tunable basicity; however, this specific chlorinated biaryl is best regarded as a research intermediate or ligand rather than a biomolecule.
  • Metal coordination via the pyridine nitrogen can be leveraged to create metal–ligand probes or complexes for biochemical studies (e.g., photophysics, sensing) after appropriate derivatization; any biological testing should be performed under institutional approvals.
  • Hydrophobicity and aryl chloride functionality suggest low aqueous solubility; salt formation (pyridinium) can improve handling in biological assay media, but evaluate compatibility.

No medical or clinical claims are made. For research use only (per Product Data).

Buffer Applications

Not typically applicable. 2-(4-Chlorophenyl)-4-methylpyridine is a non-buffering, weakly basic heteroaromatic building block, not a dedicated buffer component. If increased aqueous solubility is needed for handling, temporary protonation to the pyridinium salt (with compatible acids) can aid transfers, but conventional biological buffer systems (e.g., phosphate, HEPES) should be used for pH control.

Green Alternatives

• Considerations for greener practice (general)
  • Solvent selection: Replace chlorinated solvents with greener options where feasible (e.g., 2-MeTHF or CPME instead of THF/toluene blends; water/ethanol biphasic for Suzuki with micellar catalysis).
  • Catalysis: Employ highly active Pd catalysts/ligands that operate at lower loadings and temperatures for aryl chloride activation (e.g., XPhos- or BrettPhos-derived systems), reducing energy and Pd usage.
  • Bases: Favor inorganic bases with lower hazard (K2CO3, K3PO4) and water as co-solvent for couplings, rather than strong alkoxides, where reactivity allows.
• Comparison snapshot (general)
  • Traditional approach: Aryl chloride coupling in dioxane or toluene at 100–120 °C with 2–5 mol% Pd.
  • Greener approach: Micellar aqueous Suzuki (e.g., TPGS-750-M or similar surfactants) at 40–70 °C with 0.1–0.5 mol% Pd, ethanol/water or water as medium; reduced solvent footprint and improved safety.
• Feedstock/functional handle alternatives
  • If aryl chloride reactivity is limiting, consider preparing/using the corresponding boronate, pinacol boronate (Bpin), or aryl triflate intermediate to enable milder couplings; weigh trade-offs in atom economy and waste.
• Waste minimization
  • Plan telescoped sequences (e.g., one-pot metalation–coupling) to reduce solvent exchanges. Capture and recycle Pd where infrastructure allows.

Pharmaceutical Uses

• Role in pharma workflows (general)
  • Best viewed as a synthetic intermediate or scaffold used in discovery chemistry and process development. The para-aryl chloride enables late-stage diversification to explore SAR around a 2-phenylpyridine core.
  • Potential roles include: intermediate toward ligands, catalysts, or materials; building block for small-molecule libraries. Not an excipient.
• Regulatory/compendial status
  • No pharmacopeial monograph is known for this specific compound. If used in regulated settings, establish appropriate specifications (identity, assay, impurities, residual solvents, metals) per ICH guidelines.
• Formulation notes
  • Due to low aqueous solubility, it is not intended for direct formulation. Any handling for screening would typically be as DMSO stock solutions, with attention to final vehicle percentages in assays.

No therapeutic claims are made; for research use only (per Product Data).

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.
• Literature/general reference values (non-spec; for planning only)
  • Physical state: Typically a low-melting solid or high-boiling liquid for analogous 2-aryl-4-methylpyridines; exact MP/BP for this CAS should be confirmed from primary literature or CoA.
  • Expected solubility profile: Low aqueous solubility; good solubility in common organic solvents (e.g., dichloromethane, chloroform, toluene, THF, acetonitrile) due to aromaticity and modest polarity of the pyridine nitrogen (literature/general).
  • LogP/logD: Heteroaryl biaryls of this size commonly show moderate hydrophobicity; check measured value for this exact compound if critical to your work (literature/general).
  • pKa: Pyridine N basicity (conjugate acid pKa typically ~5.1 for unsubstituted pyridine); aryl substituents can shift basicity slightly (literature/general). Verify experimentally if pKa-sensitive.
  • Density, refractive index, UV cutoff: Not specified for this item; refer to CoA/Spec Sheet.
• Practical notes
  • The pyridine nitrogen can engage in metal coordination and hydrogen-bond acceptance, which can influence chromatographic behavior (e.g., tailing on silica; consider basic modifiers).
  • Verify exact thermophysical constants from the item’s CoA prior to scale-up or process design.

Quality and Grades

• Item-specific grade/purity
  • Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.
• Guidance on grades (general)
  • Research grade: Suitable for most synthetic and discovery workflows. Verify trace impurity profile (e.g., residual halides, metals, solvents) if your application is sensitive.
  • High-purity/assay-stated materials: Provide tighter assay limits and impurity controls; may be preferred for catalysis development, photophysics, or materials applications.
  • Stabilizers/inhibitors: Not typically required for this scaffold. If present (not specified for this item), they may affect analytical baselines; consult the CoA.
• Documentation and lot control
  • For this item, use the CoA to confirm assay, water content, and chromatographic purity before critical experiments.
  • If employing this compound as a ligand or coupling partner, low UV baseline impurities can be important for kinetic studies; consider HPLC-grade solvents and pre-rinsed glassware.
• What is specific to this listing
  • Storage: Room temperature (from Product Data).
  • Shipped In: Not specified for this item; refer to CoA/Spec Sheet.

Reaction and Applications

• As a functionalized heteroaryl building block
  • Para-aryl chloride enables cross-coupling diversification: Suzuki–Miyaura (to install aryl/alkenyl/heteroaryl), Buchwald–Hartwig amination (to install anilines), Negishi/Kumada/Stille (to install various carbon fragments). Aryl chlorides generally require more active ligand systems (e.g., XPhos, SPhos, BrettPhos) and elevated temperatures.
  • N-Coordination: The pyridine nitrogen coordinates to transition metals (Pd, Ir, Pt, Ru), enabling cyclometalation (e.g., C–H activation at the ortho-position of the phenyl ring) to build phosphorescent or catalytic complexes. The 4-methyl substituent modulates sterics/electronics.
• Strategies enabled by the scaffold
  • Directed ortho-metalation (DoM) adjacent to the pyridine N on the pyridine ring can be feasible with strong bases (e.g., s-BuLi/TMEDA) to introduce substituents; strict cryogenic control recommended (literature/general).
  • Benzylic manipulations at the 4-methyl group: Oxidation to the corresponding aldehyde/acid or halogenation can provide handles for further elaboration.
  • SNAr at the aryl chloride is generally disfavored (para position on non-activated ring), but possible under harsh conditions with strong nucleophiles or via metal-catalyzed pathways.
• Representative use cases (literature/general)
  • Late-stage diversification libraries in medicinal chemistry using the aryl chloride handle.
  • Assembly of cyclometalated Ir(III)/Pt(II) complexes based on substituted 2-phenylpyridine-type ligands.
  • Cross-coupling to introduce electron-donating/withdrawing groups para to the biaryl junction to tune photophysical or binding properties.
• Practical notes
  • Control of homocoupling and dehalogenation by catalyst/ligand choice, base, and rigorous exclusion of water/air.

Reaction Conditions

General literature guidance for transformations at the para-aryl chloride of 2-(4-chlorophenyl)-4-methylpyridine (not product specifications):

• Suzuki–Miyaura coupling (Ar–Cl → Ar–Ar/Ar–vinyl)
  • Catalyst: Pd2(dba)3 (0.5–1 mol%) + XPhos/SPhos (1–2 mol%) or Pd-PEPPSI precatalysts.
  • Base: K3PO4 or Cs2CO3 (2–3 equiv).
  • Solvent: 1,4-dioxane/H2O, toluene/H2O, or EtOH/H2O.
  • Temperature/time: 80–110 °C, 2–16 h.
  • Notes: Degas solvents; water cosolvent improves boronate transmetalation.
• Buchwald–Hartwig amination (Ar–Cl → Ar–NR2)
  • Catalyst/ligand: Pd2(dba)3 or Pd(OAc)2 (1–2 mol%) with BrettPhos/RuPhos or XPhos (2–4 mol%).
  • Base: NaOtBu, KOtBu, or K3PO4.
  • Solvent: Toluene, dioxane, or t-AmylOH.
  • Temperature: 90–120 °C.
• Sonogashira (coupling to alkynes)
  • PdCl2(PPh3)2 (1–2 mol%) + CuI (1–5 mol%).
  • Base: Et3N or i-Pr2NH.
  • Solvent: THF, DMF, or amine solvent.
  • Temperature: RT–80 °C; exclude moisture/air to minimize Glaser homocoupling.
• Directed ortho-metalation at pyridine ring (if desired)
  • Base: s-BuLi/TMEDA, −78 to −40 °C, then electrophile quench.
  • Notes: Strict anhydrous/cryogenic technique; quench carefully.

These are representative conditions from the literature for aryl chlorides and 2-phenylpyridine-type substrates; optimize for your substrate and scale.

Safety and Handling

• Item-specific hazard data
  • GHS Classification: Not specified for this item; refer to SDS.
  • Signal Word: Not specified for this item; refer to SDS.
  • H-Statements / P-Statements: Not specified for this item; refer to SDS.
  • Pictograms: Not specified for this item; refer to SDS.
• General safety guidance for aryl chlorides and pyridines (literature/general)
  • Likely hazards: May cause irritation to skin, eyes, or respiratory tract. Avoid inhalation of dust/vapors and contact with skin/eyes. Handle in a fume hood.
  • PPE: Lab coat, nitrile gloves, safety glasses; consider splash goggles for larger-scale transfers. Use a fume hood.
  • Incompatibilities: Strong oxidizers (risk of exotherm); strong acids may protonate pyridine nitrogen; strong bases can induce side reactions at benzylic or aryl chloride positions under forcing conditions.
  • Spill/accidental release: Absorb with inert material (e.g., vermiculite), place in chemical waste. Prevent discharge to drains.
  • First aid (overview; defer to SDS): Move to fresh air if inhaled; rinse skin with water upon contact; flush eyes with water for several minutes; seek medical attention if symptoms persist.
• Waste disposal
  • Collect organic waste containing chlorinated aromatics separately per institutional and local regulations. Incineration with energy recovery is typical for halogenated organics.
• Note: Always consult the product-specific SDS for authoritative hazard classification and response measures.

Solvent Selection

• Solubility/miscibility (general expectation)
  • Organic solubility: Good in chlorinated solvents (DCM, CHCl3), aromatics (toluene), ethers (THF, 2-MeTHF), and polar aprotics (DMF, DMAc, DMSO, MeCN).
  • Aqueous solubility: Low; salts can be formed under acidic conditions by protonating the pyridine nitrogen (enhancing water solubility for workup).
• Polarity and behavior
  • Moderately polar aromatic heterocycle; behaves as a Lewis base (pyridine N). Can cause tailing on silica; 0.1–1% Et3N or NH3 in eluent often improves chromatography.
• When to choose it vs alternatives
  • As a building block: Use when an aryl chloride handle on the para position is desired for subsequent cross-coupling, SNAr (with strong nucleophiles under forcing conditions), or metalation strategies.
  • Compare to non-chloro analogs (e.g., 2-phenyl-4-methylpyridine): Choose the chloro derivative when late-stage diversification is planned; choose the non-chloro analog for inert scaffolding.
• Small comparison (general)
  • Aryl chloride vs aryl bromide: Chlorides are cheaper and more stable but less reactive; require optimized catalysts (e.g., Buchwald ligands) for Pd-catalyzed couplings. Bromides couple more readily but are less atom-economical and can be less stable.
• Practical tips
  • Degas solvents for cross-coupling. Dry solvents for base-sensitive steps (e.g., metalations). Consider mixed toluene/EtOH/H2O or dioxane/H2O for Suzuki chemistry on the aryl chloride.

Storage and Reconstitution

• Storage (item-specific from Product Data)
  • Store at room temperature. Protect from moisture and strong oxidizers. Keep container tightly closed.
• Handling and stability (general)
  • Under dry, ambient conditions, aryl–pyridine scaffolds are typically stable for extended periods. Minimize exposure to light and air if performing sensitive metal-catalyzed transformations subsequently.
• Solution preparation (general guidance)
  • Prepare stock solutions in dry organic solvents (e.g., DMSO, MeCN, THF, toluene, or DCM) as required by your application. For biological screening, DMSO stocks are common; filter if particulates are present.
  • No reconstitution buffer is specified for this item; if forming a pyridinium salt to aid solubility, choose a non-nucleophilic acid compatible with downstream steps.
• Shipping
  • Shipped In: Not specified for this item; refer to CoA/Spec Sheet.
• Shelf life
  • Not specified for this item; refer to CoA/Spec Sheet. Periodically verify purity by NMR/HPLC if stored for long durations or after repeated openings.

Structure and Identity

Brief overview: 2-(4-Chlorophenyl)-4-methylpyridine is a chlorinated biaryl-heteroaryl building block featuring a pyridine ring bearing a para-methyl group and a para-chlorophenyl substituent at the 2-position.

• Item-specific (from Product Data)
  • CAS: 23182-19-6
  • InChIKey: Not specified for this item; refer to CoA/Spec Sheet. (Product Data lists a truncated value.)
  • SMILES: Not specified for this item; refer to CoA/Spec Sheet.
• Computed/literature identity (for reference; not a product specification)
  • Typical molecular formula: C12H10ClN (literature/computed from name)
  • Typical molecular weight: ~203.67 g/mol (literature/computed)
• Structural features (descriptive)
  • Rings: One six-membered pyridine (heteroaromatic) and one six-membered benzene ring (para-chloro substituted) linked in a biaryl arrangement at pyridine C2.
  • Substituents: Methyl at pyridine C4; chloro at the para position of the phenyl ring.
  • Functional groups: Aromatic C–Cl (aryl chloride), pyridine nitrogen (Lewis basic site), methyl substituent (benzylic C–H on the pyridine ring’s para-carbon).
  • Stereochemistry: None (achiral, planar aromatic system).
  • 2D description in words: A pyridine ring with nitrogen at position 1; a methyl group at position 4; a phenyl ring para-chlorinated attached at position 2 of the pyridine (biaryl connection).

Synthetic Utility

• Functional handles
  • Aryl chloride (para to biaryl junction): Platform for Pd-catalyzed cross-couplings (Suzuki–Miyaura, Buchwald–Hartwig, Sonogashira, Negishi, Stille). Chloride requires optimized ligands and temperatures versus bromide/iodide analogs but is cost-effective and robust.
  • Pyridine nitrogen: Lewis-basic site for coordination chemistry; can direct metalation/functionalization on the pyridine ring (DoM). Can be quaternized to tune solubility or serve as a phase-transfer element.
  • 4-Methyl on pyridine: Benzylic oxidations (to aldehyde/acid), radical bromination (NBS) to enable substitution, or cross-dehydrogenative coupling under oxidative conditions.
• Retrosynthetic value
  • Serves as a convergent node: biaryl linkage (2-phenylpyridine core) formed via C–H activation or Suzuki coupling, followed by site-selective para-chlorination or vice versa.
  • The chloro group offers a programmable site for diversification late in a sequence without perturbing the pyridine’s coordination properties.
• Purification/analysis tips
  • Basic analyte: Add 0.1–1% Et3N to eluents to reduce silica tailing. For LC, acidic or basic modifiers can sharpen peaks depending on stationary phase. Monitor for dehalogenation impurities in couplings.

Target Specificity

Not applicable. This product is a small-molecule building block, not a biological macromolecule or antibody. No target, epitope, clone, isotype, or species reactivity applies.