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3-Pyridinecarbonitrile is a nitrogen-containing aromatic nitrile used as an industrial intermediate and heterocyclic building block.
3-Pyridinecarbonitrile combines a pyridine nitrogen with a reactive carbonitrile group at the 3-position.
3-Pyridinecarbonitrile is particularly important in the production of nicotinamide, nicotinic acid, pharmaceutical intermediates, agrochemical intermediates and specialty pyridine derivatives.
CHEMICAL IDENTITY AND COMMON NAMES
3-Pyridinecarbonitrile consists of a six-membered pyridine ring bearing a carbonitrile group at the 3-position.
The two nitrogen atoms provide distinct reactivity through the basic pyridine nitrogen and the chemically convertible nitrile group.
3-Pyridinecarbonitrile is the nitrile precursor of nicotinamide and nicotinic acid.
3-Pyridinecarbonitrile is not nicotinamide and must not be used directly as vitamin B3 in foods, supplements, feed, pharmaceuticals or cosmetics.
Common Name: 3-Cyanopyridine
Chemical Family: Pyridine nitriles
Functional Groups: Aromatic nitrile and pyridine nitrogen
Synonyms: 3-Cyanopyridine, Pyridine-3-carbonitrile, Nicotinonitrile, Nicotinic acid nitrile, 3-Pyridinenitrile, 3-Pyridylcarbonitrile, 3-Pyridyl cyanide, 3-Azabenzonitrile, beta-Cyanopyridine, β-Cyanopyridine, Pyridine, 3-cyano-, 3-Pyridinecarboxylic acid nitrile, 3-Pyridinecarboxylic acid, nitrile, Nicotinamide Impurity B, 3-Cyanpyridin, Nicotinsäurenitril, Nicotinsaeurenitril, Nicotinonitril, 3-Pyridincarbonitril, 3-Cyjanopirydyna, Nitryl kwasu nikotynowego, 3-CP and NSC 17558
TECHNICAL IDENTIFICATION
CAS Number: 100-54-9
EC Number: 202-863-0
Molecular Formula: C6H4N2
Molecular Weight: 104.11 g/mol
IUPAC Name: Pyridine-3-carbonitrile
Exact Mass: 104.0374
UNII: X64V0K6260
InChIKey: GZPHSAQLYPIAIN-UHFFFAOYSA-N
Canonical SMILES: N#Cc1cccnc1
MDL Number: MFCD00006372
PHYSICAL AND CHEMICAL PROPERTIES
Appearance: White to pale yellow crystalline powder, crystals, chunks or crystalline mass
Physical State: Low-melting solid at 20 °C
Odour: Pungent or pyridine-like
Melting Point: Approximately 48–52 °C
Boiling Point: Approximately 201–208 °C
Density: Approximately 1.159 g/cm³
Flash Point: Approximately 84–88 °C
Water Solubility: Approximately 135–140 g/L at 20 °C
Organic Solubility: Soluble in alcohol, ether, benzene and other compatible polar organic solvents
pKa: Approximately 1.4 for the conjugate acid
LogP: Approximately 0.36
Vapour Pressure: Approximately 0.395 hPa at 25 °C
Moisture Sensitivity: Hygroscopic
Air Sensitivity: Protect from prolonged exposure to air
Flammability: Combustible organic solid
Nitrile Infrared Absorption: Strong absorption in the region around 2230 cm⁻¹
Thermal Decomposition: Carbon oxides, nitrogen oxides and hazardous nitrogen-containing fumes may form during fire or severe heating
The relatively low melting point of 3-Pyridinecarbonitrile allows solid material to soften or melt in hot warehouses and process areas.
Controlled storage temperature helps preserve the preferred crystalline form and minimizes caking.
The appreciable water solubility of 3-Pyridinecarbonitrile facilitates aqueous hydration and hydrolysis processes.
Compatibility with several organic solvents also supports extraction, purification and synthetic conversion operations.
FUNCTIONAL CHARACTERISTICS
The carbonitrile group of 3-Pyridinecarbonitrile can undergo selective hydration to form nicotinamide.
More extensive chemical or enzymatic hydrolysis converts the carbonitrile group into nicotinic acid or a nicotinate salt.
Controlled reduction can convert 3-Pyridinecarbonitrile into pyridine-3-carboxaldehyde or 3-aminomethylpyridine derivatives.
Addition reactions with organometallic reagents can produce pyridyl ketones after hydrolytic work-up.
The pyridine nitrogen of 3-Pyridinecarbonitrile can coordinate with metal ions and participate in acid-base interactions.
The electron-withdrawing nitrile group modifies the basicity and electronic behaviour of the pyridine ring.
3-Pyridinecarbonitrile can participate in cycloaddition, condensation, reduction, oxidation and nucleophilic-addition reactions.
This broad reactivity makes 3-Pyridinecarbonitrile useful for constructing amidines, tetrazoles, imidazolines, thiazolines and other nitrogen-containing heterocycles.
PRODUCTION AND COMMERCIAL FORM
Industrial production of 3-Pyridinecarbonitrile primarily uses the catalytic vapour-phase ammoxidation of 3-picoline.
The reaction combines 3-picoline, ammonia and oxygen over a mixed-metal oxide catalyst at elevated temperature.
Vanadium-containing catalysts are widely suited to the selective conversion of the methyl group into a carbonitrile group.
Catalyst composition, feed ratio, temperature, residence time and water content influence conversion, selectivity and by-product formation.
The reactor effluent is cooled and transferred to an absorption or recovery system.
Extraction, distillation, crystallization and drying can then provide purified 3-Pyridinecarbonitrile in the required commercial form.
Manufacturing control focuses on residual 3-picoline, pyridine, positional cyanopyridine isomers, high-boiling residues, water and colour.
Efficient purification is especially important when 3-Pyridinecarbonitrile is intended for vitamin or pharmaceutical intermediate production.
Commercial 3-Pyridinecarbonitrile is supplied as crystals, crystalline powder, chunks or a low-melting crystalline mass.
Industrial processing can also handle 3-Pyridinecarbonitrile in molten form when temperature-controlled equipment is available.
APPLICATIONS AND INDUSTRIES
Nicotinamide production
3-Pyridinecarbonitrile serves as the principal nitrile intermediate for manufacturing nicotinamide.
Selective nitrile hydration converts 3-Pyridinecarbonitrile into the corresponding carboxamide without changing the pyridine ring.
Biocatalytic production uses nitrile-hydratase activity to obtain high selectivity for nicotinamide.
Controlled substrate feeding helps manage reaction rate, heat generation and enzyme inhibition in concentrated processes.
Chemical hydration can also convert 3-Pyridinecarbonitrile into nicotinamide.
Reaction conditions require careful control to restrict further hydrolysis and minimize nicotinic-acid formation.
Nicotinic acid production
Complete hydrolysis of 3-Pyridinecarbonitrile provides nicotinic acid or an intermediate nicotinate salt.
Acidification of a purified nicotinate solution subsequently produces the free carboxylic acid.
Enzymatic nitrilase processes can convert 3-Pyridinecarbonitrile directly into nicotinic acid under comparatively mild conditions.
The selected route influences conversion rate, salt formation, wastewater load and downstream purification requirements.
Vitamin B3 manufacturing
3-Pyridinecarbonitrile supports the industrial production chain for the two principal vitamin B3 forms, nicotinamide and nicotinic acid.
The required final vitamin form determines whether selective hydration or complete hydrolysis is employed.
High-purity 3-Pyridinecarbonitrile helps control residual nitrile, positional isomers and colour in the final vitamin product.
Vitamin-intermediate grades therefore require tighter impurity management than general synthesis grades.
Pharmaceutical intermediates
3-Pyridinecarbonitrile functions as a building block for pharmaceutical compounds containing a 3-substituted pyridine structure.
The carbonitrile group provides a controlled entry point to amides, acids, aldehydes, amines, ketones and heterocyclic derivatives.
Partial reduction of 3-Pyridinecarbonitrile can produce pyridine-3-carboxaldehyde for further medicinal-chemistry synthesis.
Complete hydrogenation can provide 3-aminomethylpyridine derivatives used in more complex pharmaceutical intermediates.
Oxidation of the pyridine nitrogen can form 3-Pyridinecarbonitrile N-oxide.
Subsequent functionalization or hydrolysis provides access to additional oxygenated pyridine intermediates.
Agrochemical intermediates
3-Pyridinecarbonitrile is used in manufacturing pyridine-containing crop-protection intermediates and active-ingredient building blocks.
Its transformations support the introduction of amide, acid, aldehyde, aminomethyl and substituted heterocyclic functionality.
Pyridine-3-carboxaldehyde derived from 3-Pyridinecarbonitrile is an important intermediate in selected insecticide production routes.
Other agrochemical processes use 3-Pyridinecarbonitrile as a starting material for functionalized nicotinyl and cyanopyridyl structures.
Specialty heterocyclic synthesis
3-Pyridinecarbonitrile participates in reactions with diamines, amino alcohols and amino thiols to form nitrogen- or sulfur-containing ring systems.
These transformations provide pyridyl-substituted imidazolines, oxazolines and thiazolines for research and specialty synthesis.
Reaction with azide reagents can convert the nitrile group into a tetrazole ring.
The resulting pyridyl tetrazoles are useful in coordination chemistry, medicinal chemistry and advanced intermediate development.
Organometallic addition to 3-Pyridinecarbonitrile provides a route to substituted pyridyl ketones.
Reaction design must account for coordination between the pyridine nitrogen and the organometallic reagent.
Coordination chemistry and materials research
3-Pyridinecarbonitrile can act as a nitrogen-donor ligand through the pyridine nitrogen.
The nitrile group modifies ligand electronics and can provide an additional interaction site in selected coordination structures.
Metal complexes and coordination polymers containing 3-Pyridinecarbonitrile are investigated for structural, magnetic and materials-science applications.
Ligand concentration, solvent, counterion and metal coordination geometry determine the resulting molecular or polymeric architecture.
Analytical and impurity standards
3-Pyridinecarbonitrile is used as an impurity reference material during the analysis of nicotinamide.
This application is commonly associated with the designation Nicotinamide Impurity B.
Reference-standard grades require a highly characterized identity, purity and impurity profile.
Analytical documentation can include chromatographic purity, water content, spectroscopy and assigned-content information.
GRADE SELECTION AND PRODUCT SUITABILITY
Industrial intermediate grades of 3-Pyridinecarbonitrile are selected for vitamin, pharmaceutical, agrochemical and specialty-chemical production.
The required assay and impurity profile depend on the sensitivity of the downstream conversion and purification sequence.
Vitamin-intermediate grades emphasize high assay, low residual 3-picoline, controlled cyanopyridine isomers and minimal high-boiling residue.
Low water content and controlled colour support consistent biocatalytic or chemical conversion.
Pharmaceutical-intermediate grades require enhanced traceability and tighter control of related pyridine compounds, residual solvents and elemental impurities.
Additional documentation can support regulated starting-material qualification and change-control procedures.
Agrochemical-intermediate grades focus on reaction performance, assay, isomer distribution, water content and process consistency.
Impurities that consume reagents, poison catalysts or carry into the active ingredient require particular control.
Reagent and synthesis grades are commonly supplied at a minimum purity of approximately 98.0% by gas chromatography.
These grades support laboratory synthesis, reaction development, screening and analytical method work.
Reference-standard grades require comprehensive characterization and accurately assigned purity.
Small sealed packs protect analytical material from moisture, contamination and repeated exposure to air.
FORMULATION AND PROCESS CONSIDERATIONS
3-Pyridinecarbonitrile melts slightly above normal ambient temperatures.
Heated environments can therefore cause softening, agglomeration or conversion of free-flowing crystals into a solidified mass.
Molten transfer requires temperature-controlled vessels, lines and valves.
Excessive heating is avoided because higher temperature increases vapour generation, oxidation and decomposition risk.
Aqueous conversion processes use the water solubility of 3-Pyridinecarbonitrile to prepare reaction feeds.
Substrate concentration, temperature and dosing rate are balanced against catalyst activity and product crystallization.
Biocatalytic hydration can employ gradual or fed-batch addition of 3-Pyridinecarbonitrile.
This approach maintains a manageable dissolved-substrate concentration and reduces inhibition of the biocatalyst.
Chemical hydrolysis requires controlled acid or alkali concentration, temperature and residence time.
Partial hydrolysis targets nicotinamide, while complete hydrolysis favours nicotinic acid or a nicotinate salt.
Anhydrous organometallic reactions require dry equipment, dry solvent and an inert atmosphere.
The pyridine nitrogen can coordinate with catalysts or organometallic reagents and thereby influence stoichiometry and reaction rate.
Purification can use vacuum distillation, extraction, crystallization or combinations of these operations.
The low melting point requires attention during filtration, centrifugation, drying and packaging.
QUALITY, SPECIFICATIONS AND DOCUMENTATION
Routine identification of 3-Pyridinecarbonitrile can use infrared spectroscopy, nuclear magnetic resonance spectroscopy or chromatographic retention.
The strong nitrile absorption provides a useful structural confirmation during infrared analysis.
Assay is commonly determined by gas chromatography or high-performance liquid chromatography.
Water content can be measured separately because moisture affects assay, handling and downstream reaction concentration.
A detailed impurity profile can include 3-picoline, pyridine, 2-Pyridinecarbonitrile, 4-Pyridinecarbonitrile, nicotinamide, nicotinic acid and high-boiling residues.
Colour, melting range, residue after evaporation and elemental impurities can be added according to the selected application.
Procurement documentation can include a certificate of analysis, safety data sheet, technical data sheet, manufacturing-origin declaration and packaging information.
Regulated downstream applications can also require traceability, residual-solvent, elemental-impurity and change-control documentation.
SAFETY AND REGULATORY CONSIDERATIONS
3-Pyridinecarbonitrile is harmful if swallowed.
3-Pyridinecarbonitrile can irritate the skin and respiratory tract and can cause serious eye irritation or damage.
Airborne dust and vapour must be controlled during melting, transfer, sampling and packaging.
Suitable gloves, protective clothing, chemical goggles and local exhaust ventilation provide essential workplace protection.
3-Pyridinecarbonitrile is a combustible material with a flash point in the range of approximately 84–88 °C.
Heat, sparks, open flames, static discharge and uncontrolled dust accumulation must be prevented.
The nitrile group does not make 3-Pyridinecarbonitrile interchangeable with inorganic cyanide salts.
Fire or severe decomposition can nevertheless generate highly hazardous nitrogen-containing fumes.
3-Pyridinecarbonitrile can be harmful to aquatic life with long-lasting effects.
Process drainage, contaminated wash water and bulk spills must be contained and managed as chemical waste.
3-Pyridinecarbonitrile is not regulated as dangerous goods for standard road, sea or air transport.
Packages must remain securely closed and protected from heat, moisture and physical damage during transportation.
FIRST AID
Inhalation: Move the exposed person to fresh air and keep the person at rest.
Obtain immediate medical attention if breathing difficulty, dizziness or persistent respiratory irritation occurs.
Skin Contact: Remove contaminated clothing and wash the affected skin thoroughly with soap and water.
Obtain medical attention if redness, pain or irritation continues.
Eye Contact: Rinse cautiously with clean water for at least 15 minutes while holding the eyelids open.
Remove contact lenses when easy to do and obtain prompt medical attention.
Ingestion: Rinse the mouth and do not induce vomiting.
Contact a poison centre or physician immediately because 3-Pyridinecarbonitrile is harmful if swallowed.
Note to Physicians: Provide symptomatic and supportive treatment.
Monitor significant exposures for respiratory, neurological, gastrointestinal, hepatic and renal effects.
HANDLING AND STORAGE
Handling: Handle 3-Pyridinecarbonitrile in a closed or well-ventilated system.
Prevent dust formation, vapour exposure and direct contact with the skin or eyes.
Ventilation: Provide local exhaust ventilation at transfer, melting, charging and sampling points.
Use suitable respiratory protection when engineering controls cannot maintain safe airborne concentrations.
Storage: Store 3-Pyridinecarbonitrile in tightly closed packaging in a cool, dry and dark area.
Protect 3-Pyridinecarbonitrile from moisture, air, excessive heat and direct sunlight.
Incompatibilities: Keep 3-Pyridinecarbonitrile away from strong oxidizing agents, strong reducing agents, strong acids and strong bases.
Prevent contact with uncontrolled sources of heat and chemically reactive materials.
Packaging: Use tightly sealed lined drums, compatible rigid containers or moisture-resistant industrial packaging.
Small high-purity quantities are commonly packed in sealed bottles or cans under a protective atmosphere.
PACKAGING AND PROCUREMENT CONSIDERATIONS
Commercial packaging for 3-Pyridinecarbonitrile includes sealed bottles, lined drums and larger industrial containers.
Packaging selection depends on quantity, purity, physical form, storage temperature and downstream quality requirements.
Purchasing specifications should define assay, water content, melting range, colour, residual 3-picoline, positional isomers and high-boiling residues.
The inquiry should also state the intended conversion, annual volume, preferred pack size, destination and documentation requirements.
Temperature conditions during transport and warehousing should preserve the desired solid form.
Warm conditions above the melting range can produce caking or a solidified mass after cooling without changing the molecular identity.
ATAMAN KIMYA SUPPLY AND CONTACT
Ataman Kimya supports the supply of 3-Pyridinecarbonitrile for vitamin, pharmaceutical, agrochemical, laboratory and specialty-chemical applications.
Ataman Kimya can coordinate grade selection, specification alignment, documentation, packaging and delivery planning.
Email: info@atamankimya.com
Phone: +90 216 577 10 10
