2-Cyano-4-methylpyridine: Properties, Uses & FAQs

2-Cyano-4-methylpyridine is a versatile heterocyclic building block widely used in pharmaceutical synthesis, agrochemical research, and the preparation of ligands and functional materials.

IUPAC Name

4-methylpyridine-2-carbonitrile

Molecular Formula

C7H6N2

Molecular Weight

118.14 g/mol

CAS Number

1620-75-3

Key Functional Groups

Nitrile (–CN) and methyl (–CH3) substituents on a pyridine ring

Aladdin SKU

C132269

What Is 2-Cyano-4-methylpyridine?

2-Cyano-4-methylpyridine (CAS 1620-75-3, MW 118.14 g/mol) is an aromatic heterocyclic compound featuring a pyridine ring substituted with a nitrile group at the 2-position and a methyl group at the 4-position. Its IUPAC name is 4-methylpyridine-2-carbonitrile and it is also referred to as 2-cyanopicoline. The electron-withdrawing nitrile group significantly increases the electrophilicity of the ring, while the methyl group offers a handle for further functionalization such as benzylic oxidation or condensation reactions.

This compound is commercially available from Aladdin Scientific under SKU C132269 and is commonly supplied as a white to off-white crystalline solid.

Synthetic Applications and Reactivity

The nitrile group in 2-Cyano-4-methylpyridine participates in a broad range of transformations relevant to medicinal and synthetic chemistry:

• Hydrolysis: Acid- or base-catalyzed hydrolysis converts the nitrile to a carboxylic acid or amide, providing access to 4-methylpyridine-2-carboxylic acid derivatives.
• Cycloaddition and heterocycle formation: Reaction with hydroxylamine yields amidoximes, which are key intermediates in the synthesis of 1,2,4-oxadiazoles—an important motif in drug discovery.
• Reductive amination and coupling: The methyl group can be oxidized to an aldehyde or carboxylic acid for downstream coupling reactions.
• Coordination chemistry: The pyridyl nitrogen and nitrile group can act as donor atoms in metal-ligand complexes used in catalysis and materials science.

These versatile transformations make 2-Cyano-4-methylpyridine a valuable building block in both academic and industrial research settings.

Storage, Handling, and Safety

2-Cyano-4-methylpyridine should be stored in a cool, dry, well-ventilated location away from heat sources, strong oxidizers, and strong bases. The container should be kept tightly sealed to prevent moisture uptake and contact with air. Recommended storage temperature is typically room temperature (15–25 °C) unless otherwise specified on the Certificate of Analysis.

Standard laboratory precautions apply: wear appropriate personal protective equipment (PPE) including nitrile gloves, safety glasses, and a lab coat. Work in a fume hood when handling the compound in bulk or in open containers, as nitrile-containing compounds may release hydrogen cyanide under extreme conditions such as strong acid or base treatment at elevated temperatures. Consult the Safety Data Sheet (SDS) supplied with the product for full hazard classifications, first-aid measures, and disposal guidance.

Purity, Grades, and Quality Control

Aladdin Scientific's C132269 is offered for research use and is subject to quality control testing before release. Typical analytical methods used to confirm identity and purity include:

• Nuclear Magnetic Resonance (NMR) spectroscopy: Confirms the substitution pattern and absence of structural impurities.
• Gas Chromatography (GC) or High-Performance Liquid Chromatography (HPLC): Quantifies chemical purity.
• Melting point determination: Provides a rapid identity check against literature values.

The Certificate of Analysis (CoA) accompanies each lot and contains the measured purity, lot number, manufacturing date, and test results. Customers are encouraged to request the CoA at the time of ordering or upon receipt of the product. If your application demands a specific purity threshold not listed in the standard product specification, please contact Aladdin's technical support team to discuss available options.

Ordering and Related Products

2-Cyano-4-methylpyridine is available from Aladdin Scientific under SKU C132269. To place an order, visit the Aladdin Scientific website, search by SKU or product name, select the desired pack size, and add to cart. Bulk quantities and custom pack sizes may be available upon request—contact the sales team for pricing and lead time.

Researchers working with cyanopyridine-based scaffolds may also be interested in related pyridine carbonitriles and methylpyridine derivatives available in the Aladdin catalog. Contact technical support for recommendations tailored to your synthetic program.

Frequently asked questions

What is the CAS number for 2-Cyano-4-methylpyridine?

The CAS registry number for 2-Cyano-4-methylpyridine (4-methylpyridine-2-carbonitrile) is 1620-75-3. This number can be used to confirm identity when cross-referencing with supplier catalogs, safety databases, or literature sources.

What are the main applications of 2-Cyano-4-methylpyridine in research?

2-Cyano-4-methylpyridine serves primarily as a heterocyclic building block in pharmaceutical and agrochemical synthesis. Its nitrile group can be hydrolyzed, cyclized into oxadiazoles or imidazoles, or reduced to amines, while its methyl group is amenable to oxidation for further elaboration. It is also employed in coordination chemistry as a bidentate or mixed-donor ligand precursor.

How should 2-Cyano-4-methylpyridine be stored to maintain stability?

The compound should be stored in a tightly sealed container in a cool, dry, and well-ventilated area at room temperature (approximately 15–25 °C), away from moisture, strong oxidizers, acids, and bases. Always consult the product's Certificate of Analysis and Safety Data Sheet for lot-specific storage recommendations.

Is 2-Cyano-4-methylpyridine hazardous, and what PPE is recommended?

As a nitrile-containing aromatic compound, 2-Cyano-4-methylpyridine should be handled with caution. Recommended PPE includes nitrile gloves, safety goggles, and a lab coat. Handling should be performed in a fume hood, particularly when working with larger quantities or performing reactions that may generate hazardous decomposition products. Refer to the SDS for complete GHS hazard classifications and emergency procedures.

How do I obtain the Certificate of Analysis (CoA) for lot C132269?

The Certificate of Analysis for any Aladdin Scientific product can be requested through the product page on the Aladdin website by entering the lot number, or by contacting Aladdin's customer service team with the SKU (C132269) and lot number printed on the product label. The CoA details purity, analytical test results, and lot-specific information.

References

1. Clayden, J.; Greeves, N.; Warren, S. Organic Chemistry, 2nd ed.; Oxford University Press: Oxford, 2012. (General reference for nitrile reactivity and heterocyclic chemistry.)
2. Joule, J. A.; Mills, K. Heterocyclic Chemistry, 5th ed.; Wiley-Blackwell: Oxford, 2010. (Reference for pyridine chemistry and functionalization strategies.)
3. Aladdin Scientific. Product page: 2-Cyano-4-methylpyridine, SKU C132269. https://www.aladdin-e.com

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