6-Chloro-5-methylnicotinaldehyde: Handling & Lab Use Guide

6-Chloro-5-methylnicotinaldehyde is a halogenated pyridine-carboxaldehyde building block widely employed in medicinal chemistry and heterocyclic synthesis as a versatile electrophilic intermediate.

CAS Number

Not specified in source material — see product datasheet

Molecular Formula

C7H6ClNO

Molecular Weight

155.58 g/mol

Functional Groups

Aldehyde (–CHO), chloro (–Cl), methyl (–CH3) on pyridine ring

Recommended Storage

Cool, dry, well-ventilated area; away from light and moisture

SKU

C167962

Chemical Identity and Structure

6-Chloro-5-methylnicotinaldehyde is a substituted pyridine-3-carboxaldehyde bearing a chloro substituent at the 6-position and a methyl group at the 5-position of the pyridine ring. Its molecular formula is C₇H₆ClNO with a molecular weight of approximately 155.58 g/mol.

The compound combines three reactive or directing features in a single scaffold: (1) an electrophilic aldehyde carbonyl susceptible to nucleophilic addition, condensation, and reductive amination; (2) a halogen at C-6 amenable to palladium-catalyzed cross-coupling (Suzuki, Negishi, Buchwald–Hartwig) or nucleophilic aromatic substitution; and (3) a methyl group at C-5 that can be further functionalized via benzylic oxidation or halogenation if needed. This multi-functional character makes the compound a high-value synthetic building block in heterocyclic chemistry.

Laboratory Handling and Safety Guidelines

Personal Protective Equipment (PPE): Handle 6-Chloro-5-methylnicotinaldehyde wearing nitrile gloves, a laboratory coat, and safety glasses. Where dust or aerosol generation is possible, use a half-face respirator rated for organic vapours. All manipulations should be conducted inside a chemical fume hood.

Skin and Eye Contact: In the event of skin contact, wash the affected area thoroughly with soap and water for at least 15 minutes. For eye contact, irrigate immediately with copious water and seek medical attention. Aldehydes in general can cause irritation to mucous membranes; avoid inhalation of vapours.

Spill Management: Contain solid or solution spills with an inert absorbent (e.g., vermiculite or dry sand). Collect material into a labelled waste container compatible with halogenated organic solvents and dispose of in accordance with local regulations. Do not flush to drain.

First Aid — Ingestion: Do not induce vomiting. Seek immediate medical advice and present the product Safety Data Sheet (SDS) to attending personnel.

Note: A specific SDS for C167962 should be consulted for full hazard classification data. Flag for review.

Storage and Stability Recommendations

Storage Conditions: Store in a tightly sealed container in a cool (2–8 °C recommended as a general precaution for aldehyde-containing heterocycles), dry, and well-ventilated location, protected from light. Exposure to moisture can promote hydrate formation or aldol-type condensation side reactions, reducing compound purity over time.

Container Integrity: Upon receipt, inspect the container for damage. After each use, purge the headspace with inert gas (nitrogen or argon) before resealing to minimise oxidative degradation of the aldehyde functionality.

Shelf Life: Specific shelf-life data for C167962 are not provided in the current source material; consult the product Certificate of Analysis (CoA) for lot-specific expiry and re-test dates.

Incompatibilities: Avoid contact with strong oxidising agents, strong bases, and reactive nucleophiles during storage. Halogenated building blocks may be reactive towards Lewis-acidic metals; store away from metal salts where possible.

Applications in Synthesis and Medicinal Chemistry

6-Chloro-5-methylnicotinaldehyde serves as a versatile intermediate in the preparation of biologically active molecules and novel heterocyclic frameworks. The aldehyde group enables a broad range of downstream transformations:

• Reductive amination: Reaction with primary or secondary amines in the presence of sodium cyanoborohydride or sodium triacetoxyborohydride yields aminomethyl-pyridine derivatives relevant to CNS and kinase-inhibitor programmes.
• Condensation reactions: Knoevenagel, Wittig, or Horner–Wadsworth–Emmons reactions expand the carbon skeleton for the preparation of vinyl-pyridine pharmacophores.
• Nucleophilic aromatic substitution (SNAr) at C-6: The electron-withdrawing aldehyde activates the ring toward displacement of chloride by O-, N-, or S-nucleophiles, enabling rapid diversity synthesis.
• Palladium-catalysed coupling: The aryl chloride participates in Suzuki–Miyaura, Negishi, and Buchwald–Hartwig reactions when appropriate ligand/base systems are employed, extending conjugation or introducing amine functionality.

Because the pyridine nitrogen and aldehyde together act as a bidentate metal-coordinating motif, this scaffold is also explored in coordination chemistry and the design of metal-organic frameworks (MOFs).

Quality, Purity and Ordering Information

Product SKU: C167962

Purity: Specific purity grade and analytical data (e.g., HPLC, NMR) for this lot are reported on the Certificate of Analysis supplied with each shipment. Contact Aladdin Scientific technical support if a CoA is required prior to ordering.

Available Quantities: Please refer to the current Aladdin Scientific product page for available pack sizes and pricing. Bulk quantities may be available on request.

Ordering: Order online using SKU C167962 or contact your regional Aladdin Scientific representative. For questions on customs documentation, hazardous goods shipping classification, or export licences for this material, contact our logistics team before placing an international order.

Returns and Quality Concerns: Aladdin Scientific accepts returns for products that do not meet specification. Please retain original packaging and CoA, and contact customer service within the stated returns window. Full details are available in our Returns and Refunds policy.

Frequently asked questions

What solvents are recommended for dissolving 6-Chloro-5-methylnicotinaldehyde?

Polar aprotic solvents such as DMSO, DMF, and acetonitrile are generally suitable for dissolving heteroaryl aldehyde building blocks of this type. Dichloromethane and ethyl acetate can also be used for extraction and chromatography purposes. Aqueous solubility is expected to be low; specific solubility data should be verified against the product CoA or determined experimentally.

Can 6-Chloro-5-methylnicotinaldehyde be used directly in Suzuki–Miyaura cross-coupling reactions?

Yes, the aryl chloride functionality at the 6-position is compatible with palladium-catalysed Suzuki–Miyaura coupling under standard conditions (e.g., Pd(PPh3)4 or Pd(dppf)Cl2 as catalyst, aqueous carbonate base, dioxane or toluene as solvent). The aldehyde group is generally stable under these conditions, though strong base and prolonged heating should be minimised to avoid side reactions. Optimisation of catalyst loading and base is recommended.

How should I confirm the identity and purity of the received material before use?

Upon receipt, compare the lot-specific Certificate of Analysis (CoA) against your specification requirements. Identity can be confirmed by 1H NMR (characteristic aldehyde proton singlet ~δ 10.0 ppm; aromatic protons in the δ 8–9 ppm region) and by LC–MS or GC–MS for molecular weight verification. HPLC purity chromatograms are typically provided on the CoA. If discrepancies are found, contact Aladdin Scientific quality assurance before use.

Is 6-Chloro-5-methylnicotinaldehyde classified as a hazardous material for shipping?

Hazardous shipping classification depends on the specific regulatory framework (IATA, IMDG, DOT) and the quantity being shipped. As an aldehyde-containing chlorinated organic compound, it may be subject to hazardous goods regulations. Please consult the product SDS and contact Aladdin Scientific logistics for guidance specific to your shipment destination and mode of transport.

References

1. March, J. Advanced Organic Chemistry: Reactions, Mechanisms, and Structure, 4th ed.; Wiley-Interscience: New York, 1992. (General aldehyde reactivity and SNAr reactions.)
2. Miyaura, N.; Suzuki, A. Palladium-Catalyzed Cross-Coupling Reactions of Organoboron Compounds. Chem. Rev. 1995, 95, 2457–2483. doi:10.1021/cr00039a007
3. Aladdin Scientific. Product Certificate of Analysis for C167962 (6-Chloro-5-methylnicotinaldehyde). Available from Aladdin Scientific upon request.

Products are supplied for research and development use only. Not for use in humans, animals, diagnosis, or therapy.