5-(4-Chlorophenyl)nicotinaldehyde - ≥98% , CAS No.887973-65-1

CAS: 887973-65-1 Cat. No.: C975102 Summenformel: C₁₂H₈ClNO Molekulargewicht: 217.650

GRADE & PURITY ≥98%

Storage

Room temperature

Specifications

Spezifikationen & Reinheit

≥98%

Storage

Room temperature

Reinheit

≥98%

Namen und Kennungen

Kanonisches Lächeln

C1=CC(=CC=C1C2=CN=CC(=C2)C=O)Cl

IUPAC Name

5-(4-chlorophenyl)pyridine-3-carbaldehyde

InChIKey

ZMKSDBAOUPRHQA-UHFFFAOYSA-N

INCHI

1S/C12H8ClNO/c13-12-3-1-10(2-4-12)11-5-9(8-15)6-14-7-11/h1-8H

Molekulargewicht

217.650

Taxonomic Classification

Taxonomy Tree

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

• Kingdom: Organic compounds
• Superclass: Organoheterocyclic compounds
• Klasse: Pyridines and derivatives
• Subclass: Phenylpyridines
• Intermediate Tree Nodes: Not available
• Direct Parent: Phenylpyridines
• Alternative Parents: Pyridine carboxaldehydes Chlorobenzenes Aryl-aldehydes Aryl chlorides Heteroaromatic compounds Azacyclic compounds Organonitrogen compounds Organochlorides Organic oxides Hydrocarbon derivatives
• Molecular Framework: Aromatic heteromonocyclic compounds
• Substituents: 3-phenylpyridine - 3-pyridine carboxaldehyde - Chlorobenzene - Halobenzene - Aryl-aldehyde - Aryl chloride - Aryl halide - Monocyclic benzene moiety - Benzenoid - Heteroaromatic compound - Azacycle - Organonitrogen compound - Organochloride - Organohalogen compound - Aldehyde - Hydrocarbon derivative - Organic oxide - Organic oxygen compound - Organic nitrogen compound - Organooxygen compound - Aromatic heteromonocyclic compound
• Beschreibung: 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

Chemische und physikalische Eigenschaften

• Molekulargewicht: 217.650 g/mol
• XLogP3: 2.600
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 217.029 Da
• Monoisotopic Mass: 217.029 Da
• Topological Polar Surface Area: 30.000 Ų
• Heavy Atom Count: 15
• Formal Charge: 0
• Complexity: 214.000
• 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 for bioassay formats (WB, IHC, IF, FC). This product is a chemical reagent for synthetic chemistry. For practical use, see Reaction & Applications and Reaction Conditions for literature‑based procedures.

Biological Roles

This is a synthetic heteroaryl aldehyde used as a chemical building block. It does not have established endogenous biological roles.

• General notes (literature/context):
  • Pyridine-containing motifs are common in bioactive molecules; this aldehyde enables rapid entry to 5‑aryl nicotinate/nicotinamide analog libraries via oxidation or reductive amination.
  • The aldehyde can form reversible imines with amines, a handle sometimes used in fragment-based screening; however, this product is supplied strictly for research and synthetic use.

No medical or clinical claims are made or implied. Use is restricted to laboratory research.

Buffer Applications

Not typically applicable. 5-(4‑Chlorophenyl)nicotinaldehyde is a hydrophobic, non-ionic (at neutral pH) building block, not a buffering agent. For aqueous work, employ miscible organic cosolvents or surfactants; see Solvent Selection for guidance.

Green Alternatives

Greener strategies focus on solvent and reagent choices for transformations of this aldehyde, as the substrate itself is a specialty building block.

• Solvent selection (comparative, literature/general):

  | Use case | Conventional | Greener alternative | Notes | |---|---|---|---| | Wittig/HWE olefination | THF, DCM | 2‑MeTHF, CPME | Similar polarity; better safety/renewable content (2‑MeTHF). | | Reductive amination | MeOH, DCM | EtOH, i‑PrOH, water‑lean EtOH/H2O | Lower toxicity; manage imine formation rate. | | Oxidation to acid | DCM, AcCN | EtOAc, MeCN, water biphasic | Choose catalytic TEMPO with green co‑oxidants (bleach/O2). | | Cross-coupling (post‑derivatization) | DMF, dioxane | MeCN, TAMI, Cyrene, propylene carbonate | Consider catalyst system compatibility and viscosity. |

• Reagent choices:

  • Prefer catalytic oxidations (TEMPO/bleach, O2) over stoichiometric chromium or permanganate.
  • Use aqueous ammonia or ammonium formate with catalytic Pd for reductive aminations (transfer hydrogenation) when feasible.

Trade‑offs: Greener solvents may alter rates/selectivity. Validate on small scale, and ensure workup/waste streams remain improved versus the baseline.

Pharmaceutical Uses

This product is not an excipient and has no pharmacopeial monograph listed in the Product Data. It may serve as a synthetic intermediate in discovery chemistry.

• Formulation role: None specified.
• Process chemistry context (general): provides a handle (–CHO) for late‑stage diversification to amines, alcohols, acids, or olefins when assembling heteroaryl frameworks.

No therapeutic or clinical claims are made; for research and process development only.

Physical Properties

Item-specific physicochemical specifications were not provided in the Product Data. Values below are general/literature-style guidance for this structural class and should not be treated as this item’s specification.

• Appearance (item-specific): Not specified for this item; refer to CoA/Spec Sheet.
• Molecular weight: ~217.65 g/mol (computed from C12H8ClNO; literature/computed)
• Molecular formula: C12H8ClNO (literature/computed)
• Boiling point, melting point, density, refractive index, UV cutoff, water/peroxide/metal limits: Not specified for this item; refer to CoA/Spec Sheet.
• Solubility (general expectations, literature):
  • Likely soluble in common organic solvents (e.g., dichloromethane, THF, acetonitrile, toluene, ethyl acetate)
  • Poorly soluble in water due to aromaticity and limited hydrogen-bond donor capacity
• Partitioning (qualitative, literature): Moderately lipophilic owing to biaryl core and a single heteroatom; aldehyde and ring nitrogen impart some polarity.

Notes:

• Actual numeric property values (mp, bp, density, etc.) vary with lot and measurement method. Consult the product’s CoA/Spec Sheet for authoritative specifications.

Quality and Grades

• Item-specific grade/purity: Not specified for this item; refer to CoA/Spec Sheet.
• Practical implications of grade (general guidance for heteroaryl aldehydes):
  • Research-grade materials typically control for identity (NMR/HRMS/HPLC) and purity suitable for synthetic use. Trace acid or peroxide levels are usually not specified unless sold as chromatography grade solvents.
  • For chromatography-sensitive applications (e.g., analytical reference work), request detailed impurity profiling (HPLC/GC, residual solvents, aldehyde oxidation products).
• Stabilizers/additives: Not specified for this item; refer to CoA/Spec Sheet. Many aldehydes are shipped neat without stabilizers; limiting air/light exposure reduces acid formation.
• Documentation: Aladdin provides CoA/Spec Sheets on request, including analytical methods and acceptance criteria relevant to batch release.
• Fit-for-purpose tips:
  • For robust C–C bond-forming reactions (Wittig, HWE, Knoevenagel), typical research-grade quality suffices.
  • For SAR libraries or material destined for scale-up, consider additional QC (water Karl Fischer, residual metals, and non-volatile content) depending on downstream steps.

Reaction and Applications

As a conjugated heteroaryl–aryl aldehyde, 5-(4‑chlorophenyl)nicotinaldehyde is a versatile building block for the construction of N‑heteroaryl scaffolds and extended π‑systems.

• Common transformations (literature/general):
  • Olefination: Wittig, Horner–Wadsworth–Emmons (HWE), Julia–Kocienski to access styryl‑pyridine derivatives (E/Z control via base/solvent).
  • Condensations: Knoevenagel with active methylenes; Schiff base formation with amines (imines), followed by reduction or metal-catalyzed coupling.
  • Reductions: Selective reduction to the benzylic alcohol (NaBH4 mild; DIBAL/BH3 variations) or to the corresponding methyl (via Wolff–Kishner/Clemmensen on alcohol/oxime intermediates).
  • Oxidations: To the corresponding carboxylic acid (e.g., with TEMPO/Oxone, MnO2, or Pinnick oxidation of oxime/hydrate intermediates).
  • Cyclizations/annulations: Access to aza-heteroacenes via aldol-like condensations with 1,3‑dicarbonyls.
• Utility of the 4‑chloro substituent (literature):
  • Serves as a handle for cross-coupling (Suzuki, Buchwald–Hartwig after amination, or direct C–Cl activation) enabling rapid diversification on the distal ring.
  • Facilitates nucleophilic aromatic substitution under appropriate conditions (electron demand dependent).
• Practical notes:
  • Maintain anhydrous/basic conditions for phosphonate or ylide chemistry; pre-dry aldehyde under high vacuum if necessary.
  • Monitor for over‑reaction (aldol self‑condensation is minimal but imine formation can proceed rapidly with primary amines).

Reaction Conditions

General literature guidance for typical transformations of heteroaryl aldehydes like 5-(4‑chlorophenyl)nicotinaldehyde (not product specifications):

• Wittig olefination:
  • Base: n‑BuLi or KOtBu to generate stabilized ylides
  • Solvent: THF or 2‑MeTHF; 0 to room temperature; 1–6 h
  • Outcome: E/Z dependent on ylide type; stabilized ylides favor E.
• HWE (Horner–Wadsworth–Emmons):
  • Reagents: dialkyl phosphonates, NaH/DBU
  • Solvent: THF/DMF or MeCN; 0–25 °C then warm to 40–60 °C; 2–12 h
  • Typically high E‑selectivity with electron‑withdrawing phosphonates.
• Reductive amination:
  • Pre-form imine in EtOH/i‑PrOH with molecular sieves or azeotropic removal of water; reduce with NaBH3CN or NaBH(OAc)3 at 0–25 °C; 2–16 h.
  • Catalytic hydrogenation (Pd/C, H2 1–3 bar) also effective.
• Reduction to alcohol:
  • NaBH4 in MeOH/THF at 0–25 °C; 0.5–2 h; quench carefully.
• Oxidation to acid:
  • TEMPO/NaClO (pH 9–10, biphasic) at 0–5 °C then rt; 1–3 h; or MnO2 in DCM at rt.

Typical isolated yields for well‑optimized procedures range 70–90% depending on substrate and conditions. Always validate on small scale to adjust for substrate electronics and metal coordination effects of the pyridine nitrogen.

Safety and Handling

• Regulatory/SDS status:
  • GHS signal word, hazard statements (H‑codes), pictograms, and classification: Not specified for this item; refer to the SDS for authoritative information.
• General chemical hazard profile (literature/general):
  • Aromatic aldehydes can be irritating to eyes/skin/respiratory tract; avoid inhalation and contact.
  • Aldehydes may undergo air oxidation to the corresponding carboxylic acids; minimize prolonged air exposure.
• PPE and engineering controls (good laboratory practice):
  • Use in a chemical fume hood.
  • Wear appropriate PPE: lab coat, safety glasses or face shield, and nitrile gloves; change gloves regularly.
• Incompatibilities (general):
  • Strong oxidizers (risk of over‑oxidation)
  • Strong bases under vigorous conditions (aldol/Cannizzaro-type side reactions, though heteroaryl aldehydes are less prone than aliphatic)
  • Strong reducing agents (will reduce the aldehyde to an alcohol)
• First aid (overview; defer to SDS):
  • Skin/eye contact: Rinse with water for at least 15 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 advice.
• Storage (aligns with Product Data):
  • Store at room temperature, tightly closed, in a dry, well‑ventilated place. Protect from light and moisture. Using an inert gas blanket can help limit oxidation (general best practice).

Solvent Selection

This compound is an aromatic heteroaryl aldehyde with moderate lipophilicity and limited hydrogen-bond basicity (ring N) plus a polar carbonyl.

• Polarity/miscibility (literature/general):
  • Readily soluble in chlorinated solvents (DCM, chloroform), moderately to well soluble in ethyl acetate, THF, toluene, and acetonitrile.
  • Poor aqueous solubility; use a cosolvent or emulsification for aqueous workups.
• Typical solvent choices by operation:
  • Carbonyl transformations (Wittig/HWE/Knoevenagel): THF, toluene, or MeCN.
  • Reductive amination: MeOH/EtOH with a co-solvent (THF/DCM) as needed.
  • Cross-coupling (if further derivatized): Polar aprotic solvents (DMF/DMAc/MeCN) or toluene with Pd catalysts.
• Comparison notes:
  • THF: good for organometallic and phosphonate chemistry; consider peroxide testing if stored long-term (solvent safety).
  • MeCN: clean workups, higher dielectric constant helps with ionic reagents.
  • Toluene: useful at elevated temperatures; enhances selectivity in some condensations by water removal via Dean–Stark with a cosolvent.
• Practical tips:
  • Degas solvents for base- or Pd-catalyzed reactions to improve reproducibility.
  • Dry solvents when enolates/phosphorus ylides are involved; aldehydes are moisture sensitive in basic media.

Storage and Reconstitution

• Storage (item-specific): Room temperature (per Product Data). Keep container tightly closed in a dry, well‑ventilated place. Protect from light and ambient moisture.
• Handling notes (general best practice for aldehydes):
  • Minimize headspace oxygen; consider storing under inert gas after opening to limit oxidation to carboxylic acid.
  • If solids/oils form upon storage, warm gently and sonicate or dissolve in a suitable dry organic solvent (e.g., DCM, THF, EtOAc) before use.
  • Inspect by TLC/HPLC or NMR if material has been stored long term to check for oxidation products.
• Shipped in: Not specified for this item; refer to CoA/Spec Sheet.
• Reconstitution: Not applicable unless provided as a solid that requires dissolution; choose dry, oxygen-low solvents compatible with the planned reaction.

Research Use Note: For research use only.

Structure and Identity

A heteroaromatic aldehyde bearing a 4‑chlorophenyl substituent on a nicotinaldehyde (pyridine‑3‑carbaldehyde) core; useful as a heteroaryl–aryl formyl building block.

• Item-specific identifiers (from Product Data):

  • CAS: 887973-65-1
  • SKU: C975102
  • Category: Life Science reagents (research use only)
  • InChIKey: Not specified for this item; refer to CoA/Spec Sheet.
  • SMILES: Not specified for this item; refer to CoA/Spec Sheet.

• Computed/literature identity details (for reference; not item specifications):

  • Preferred name: 5-(4‑Chlorophenyl)nicotinaldehyde (a.k.a. 5-(4-chlorophenyl)pyridine-3-carboxaldehyde)
  • Core features: pyridine ring (N at position 1), aldehyde at the 3‑position (–CHO), 4‑chlorophenyl substituent at the 5‑position of the pyridine ring
  • Stereochemistry: none (achiral)
  • Molecular formula (calculated): C12H8ClNO (literature/computed)
  • Molecular weight (calculated): ~217.65 g/mol (literature/computed)

• 2D structural description (verbal): A six‑membered pyridine ring bearing an aldehyde group meta to the ring nitrogen (3‑position), and a para‑chlorophenyl group bonded at the 5‑position; the two rings are conjugated via a biaryl C–C bond, and the aldehyde carbonyl is conjugated with the pyridine ring.

Synthetic Utility

Key functional features and their reactivity (literature/general):

• Aldehyde (electrophile):
  • Engages in nucleophilic additions (RMgX/RLi cautiously; stabilized carbanions preferred for selectivity).
  • Imine/enamine chemistry with amines; enables reductive amination to benzylic amines on a heteroaryl scaffold.
  • Carbonyl olefination (Wittig/HWE/Julia) to generate styryl‑pyridines with tunable E/Z selectivity.
• Pyridine ring nitrogen (Lewis basic site):
  • Can coordinate to transition metals, affecting catalyst speciation and regioselectivity in downstream steps.
  • Directs ortho‑metalation on the aryl partner in some systems.
• Para‑chloro on the phenyl ring:
  • Cross-coupling handle for diversification (Suzuki, Negishi, Stille, Kumada; or Buchwald–Hartwig after amination), expanding library space.

Retrosynthetic value: This aldehyde situates the formyl group meta to N on the pyridine, enabling divergent routes to nicotinic acid derivatives, nicotinamides, and extended conjugated systems relevant to materials and medicinal chemistry.

Target Specificity

Not applicable. This product is a small‑molecule building block and is not an antibody, enzyme, or biological ligand with defined target specificity. No item-specific target data are provided.