3-PYRIDINECARBONITRILE

3-Pyridinecarbonitrile is a nitrogen-containing aromatic nitrile commonly known as 3-cyanopyridine or nicotinonitrile.
3-Pyridinecarbonitrile is a crystalline, water-soluble pyridine derivative used mainly as an industrial intermediate for nicotinamide, nicotinic acid, and other functional heterocyclic compounds.
3-Pyridinecarbonitrile contains both a pyridine-ring nitrogen and a reactive nitrile group, enabling hydrolysis, hydration, coordination, reduction, substitution, and heterocycle-forming reactions.

CAS Number: 100-54-9
EC Number: 202-863-0
Molecular Formula: C₆H₄N₂
Molecular Weight: 104.11 g/mol

SYNONYMS

Nicotinonitrile, Nicotinic Acid Nitrile, 3-Cyanopyridine, Pyridine-3-carbonitrile, 3-Pyridinecarbonitrile, Pyridine-3-nitrile, 3-Pyridinenitrile, 3-Pyridyl Carbonitrile, 3-Pyridylcarbonitrile, 3-Pyridyl Cyanide, Pyridine, 3-cyano-, 3-Cyanopyridin, 3-Cyanopyridine, β-Cyanopyridine, Beta-Cyanopyridine, Nicotinonitril, Nicotinenitrile, Nicotinic Nitrile, Nicotinic Acid Cyanide, Nicotinic Acid Nitrile, 3-Azabenzonitrile, meta-Azabenzonitrile, m-Azabenzonitrile, 3-Cyano-1-azabenzene, 1-Azabenzene-3-carbonitrile, 3-Cyanopyridine Nitrile, 3-Pyridinecarboxylic Acid Nitrile, 3-Pyridinecarbonitrile Intermediate, Vitamin B3 Intermediate, Nicotinamide Intermediate, Niacin Intermediate, Nicotinamide Precursor, Nicotinic Acid Precursor, Nitrile Hydratase Substrate, Nitrilase Substrate, Pyridine Nitrile, Heteroaromatic Nitrile, Nitrogen Heterocycle Nitrile, Fine-Chemical Intermediate, Pharmaceutical Intermediate, Nutritional-Chemical Intermediate, Organic-Synthesis Intermediate, Coordination-Chemistry Ligand, Analytical Reference 3-Pyridinecarbonitrile, High-Purity 3-Pyridinecarbonitrile, Technical-Grade 3-Pyridinecarbonitrile, Reagent-Grade 3-Pyridinecarbonitrile, Analytical-Grade 3-Pyridinecarbonitrile, 3-Pyridinecarbonitrile Analytical Standard, NSC 17558, PubChem CID 79, C₆H₄N₂, CAS 100-54-9, EC 202-863-0, GZPHSAQLYPIAIN-UHFFFAOYSA-N.

APPLICATIONS

3-Pyridinecarbonitrile serves as the principal industrial precursor for producing nicotinamide through controlled hydration of its nitrile group.
3-Pyridinecarbonitrile enables direct formation of the primary carboxamide group while preserving the pyridine-ring structure.
3-Pyridinecarbonitrile supports large-scale vitamin B3 manufacturing routes based on aqueous catalytic hydrolysis or hydration.
3-Pyridinecarbonitrile requires control of conversion and overhydrolysis because continued reaction can produce nicotinic acid or nicotinate salts.

3-Pyridinecarbonitrile functions as a substrate for nitrile-hydratase-catalyzed production of nicotinamide.
3-Pyridinecarbonitrile can be converted with high selectivity by suitable microbial cells or isolated enzyme systems.
3-Pyridinecarbonitrile supports biocatalytic processes operating under milder temperatures than many conventional chemical hydrolysis routes.
3-Pyridinecarbonitrile enables high-concentration nicotinamide production when substrate feeding, enzyme stability, temperature, and mass transfer are optimized.

3-Pyridinecarbonitrile serves as a precursor for nicotinic acid through complete hydrolysis of the nitrile functionality.
3-Pyridinecarbonitrile can be transformed chemically with aqueous acid or base under controlled temperature and pressure.
3-Pyridinecarbonitrile can also be converted enzymatically by nitrilases capable of producing nicotinic acid directly.
3-Pyridinecarbonitrile supports vitamin B3 production routes in which nicotinic acid is the desired final nutrient or chemical intermediate.

3-Pyridinecarbonitrile functions as a common intermediate linking 3-picoline manufacture with nicotinamide and nicotinic acid production.
3-Pyridinecarbonitrile is produced industrially by ammoxidation of 3-picoline with ammonia and an oxygen-containing gas over a suitable catalyst.
3-Pyridinecarbonitrile enables integrated processes in which pyridine-ring formation, ammoxidation, hydration, purification, and crystallization are combined.
3-Pyridinecarbonitrile supports high-throughput vitamin manufacturing because ammoxidation processes can achieve high conversion and selectivity.

3-Pyridinecarbonitrile serves as an upstream substrate in biotechnological routes to nicotinamide riboside.
3-Pyridinecarbonitrile is first converted enzymatically into nicotinamide before additional enzymatic reactions form the riboside product.
3-Pyridinecarbonitrile supports whole-cell processes designed to couple nitrile hydration with nucleoside-forming metabolism.
3-Pyridinecarbonitrile enables researchers to investigate integrated biosynthesis of nicotinamide-derived NAD⁺ precursors.

3-Pyridinecarbonitrile functions as a building block for pharmaceutical and medicinal-chemistry research.
3-Pyridinecarbonitrile provides a pyridine nitrogen capable of modifying molecular basicity, polarity, binding, and salt-forming behavior.
3-Pyridinecarbonitrile provides a nitrile group that can be retained as a pharmacophore or converted into an amide, acid, amine, amidine, or heterocycle.
3-Pyridinecarbonitrile supports preparation of structurally diverse pyridine derivatives for biological screening and synthetic-route development.

3-Pyridinecarbonitrile serves as an intermediate in the preparation of substituted nicotinamides and nicotinic-acid derivatives.
3-Pyridinecarbonitrile can undergo ring functionalization before or after controlled transformation of the nitrile group.
3-Pyridinecarbonitrile supports synthesis of compounds containing halogen, amino, hydroxy, alkyl, aryl, or additional cyano substituents.
3-Pyridinecarbonitrile enables chemists to vary pyridine-ring substitution while retaining access to carboxamide and carboxylic-acid products.

3-Pyridinecarbonitrile functions as a precursor for amidines, amidrazones, tetrazoles, oxadiazoles, triazoles, and other nitrogen-rich derivatives.
3-Pyridinecarbonitrile undergoes nucleophilic addition to the nitrile carbon under appropriately activated conditions.
3-Pyridinecarbonitrile supports cyclization reactions used to construct functional heterocyclic compounds.
3-Pyridinecarbonitrile enables incorporation of a 3-pyridyl group into heterocycles used in medicinal, coordination, and materials research.

3-Pyridinecarbonitrile serves as a substrate in reduction reactions that convert the nitrile group into a 3-pyridylmethylamine structure.
3-Pyridinecarbonitrile supports catalytic hydrogenation and hydride-reduction studies involving heteroaromatic nitriles.
3-Pyridinecarbonitrile enables preparation of primary amines that can undergo acylation, sulfonylation, alkylation, condensation, and salt formation.
3-Pyridinecarbonitrile requires selective reaction conditions to minimize hydrogenation or modification of the pyridine ring.

3-Pyridinecarbonitrile functions as a pyridine-containing ligand in coordination-chemistry research.
3-Pyridinecarbonitrile can coordinate suitable metal ions through its pyridine nitrogen.
3-Pyridinecarbonitrile can also participate in weaker nitrile–metal interactions depending on the metal, counterion, solvent, and crystal structure.
3-Pyridinecarbonitrile supports preparation of molecular complexes, coordination polymers, and supramolecular assemblies.

3-Pyridinecarbonitrile serves as an analytical reference material for vitamin B3 manufacturing processes.
3-Pyridinecarbonitrile supports determination of residual nitrile remaining after nicotinamide or nicotinic-acid production.
3-Pyridinecarbonitrile enables chromatographic measurement of conversion, selectivity, hydrolysis products, and process-related impurities.
3-Pyridinecarbonitrile requires traceable purity and controlled moisture when used for quantitative quality-control testing.

3-Pyridinecarbonitrile functions as a reference compound in infrared, ultraviolet, mass-spectrometric, and gas-chromatographic analysis.
3-Pyridinecarbonitrile provides established molecular, spectral, and retention information for identity confirmation.
3-Pyridinecarbonitrile supports differentiation from 2-pyridinecarbonitrile, 4-pyridinecarbonitrile, nicotinamide, and nicotinic acid.
3-Pyridinecarbonitrile enables analytical laboratories to monitor positional isomers and functional-group conversion through orthogonal methods.

3-Pyridinecarbonitrile serves as a model substrate for nitrile-hydratase, nitrilase, amidase, and aldoxime-dehydratase research.
3-Pyridinecarbonitrile supports enzyme-activity assays based on formation of nicotinamide, nicotinic acid, or liberated ammonia.
3-Pyridinecarbonitrile enables researchers to compare substrate tolerance, enzyme selectivity, catalytic stability, and whole-cell transport.
3-Pyridinecarbonitrile contributes to development of biotransformation systems for nitrile-containing fine chemicals.

3-Pyridinecarbonitrile functions as an educational and process-development reagent for demonstrating nitrile hydration and hydrolysis.
3-Pyridinecarbonitrile supports advanced instruction in ammoxidation, heteroaromatic chemistry, enzymatic catalysis, chromatography, and vitamin-intermediate manufacturing.

DESCRIPTION

3-Pyridinecarbonitrile is the registry-style name of the compound commonly known as 3-cyanopyridine or nicotinonitrile.
3-Pyridinecarbonitrile is identified by CAS Number 100-54-9 and EC Number 202-863-0.
3-Pyridinecarbonitrile has the molecular formula C₆H₄N₂.
3-Pyridinecarbonitrile has a molecular weight of approximately 104.11 g/mol.

Structurally, 3-Pyridinecarbonitrile contains a six-membered aromatic pyridine ring bearing a nitrile group at the 3-position.
The molecule contains one ring nitrogen atom and one nitrile nitrogen atom.
The pyridine nitrogen functions as a weak base and coordination site.
The nitrile carbon functions as an electrophilic center during hydration, hydrolysis, reduction, and addition reactions.

The preferred systematic name of 3-Pyridinecarbonitrile is pyridine-3-carbonitrile.
The position of the nitrile group distinguishes it from pyridine-2-carbonitrile and pyridine-4-carbonitrile.
The three positional isomers possess the same molecular formula and molecular weight but differ in symmetry, melting point, reactivity, and downstream products.
Chromatographic control of positional-isomer contamination is therefore important in high-purity material.

3-Pyridinecarbonitrile is a solid at normal ambient temperature.
A measured melting point near 50°C is reported in the EPA hazard-characterization data.
The material may therefore soften or melt in warm storage areas or heated process equipment.
Cooling of molten material can produce a compact crystalline mass rather than a free-flowing powder.

3-Pyridinecarbonitrile has a measured boiling point near 240°C.
The comparatively high boiling point permits purification under reduced pressure when thermal exposure is carefully controlled.
Prolonged heating can increase discoloration, impurity formation, or decomposition.
Vacuum processing may reduce the temperature required for distillation or stripping.

3-Pyridinecarbonitrile has a measured vapor pressure of approximately 0.296 mmHg at 25°C in the cited physical-property compilation.
This vapor pressure is moderate for a crystalline industrial intermediate.
Inhalation exposure may arise from dust at room temperature and from vapor when the material is heated or molten.
Closed transfer and local exhaust ventilation are appropriate during bulk charging, melting, distillation, and sampling.

3-Pyridinecarbonitrile is highly soluble in water compared with many neutral aromatic nitriles.
A measured water-solubility value of approximately 135 g/L at 20°C is reported.
Its pyridine nitrogen and low molecular weight contribute to substantial aqueous compatibility.
Solubility depends on temperature, pH, purity, and the presence of salts or other organic compounds.

3-Pyridinecarbonitrile is a weak pyridine base.
A measured conjugate-acid pKa near 1.39 is reported in the EPA physical-property summary.
The neutral form therefore predominates through much of the ordinary neutral and moderately acidic pH range.
Strong acid produces protonated pyridinium salts with increased ionic character.

3-Pyridinecarbonitrile has a measured log octanol–water partition coefficient near 0.36.
This low value is consistent with limited bioaccumulation potential and substantial preference for aqueous phases.
Environmental assessments predict high mobility in soil because of its water solubility and relatively weak hydrophobic partitioning.
Concentrated releases should nevertheless be prevented because mobility can facilitate movement into groundwater or wastewater systems.

3-Pyridinecarbonitrile has a low Henry’s-law constant.
Transfer from water into air is therefore less favorable than for highly volatile hydrophobic solvents.
Volatilization can still occur from warm solutions, aerated equipment, or large exposed liquid surfaces.
Wastewater treatment must consider both aqueous mobility and biological degradation.

Industrial 3-Pyridinecarbonitrile is commonly manufactured through ammoxidation of 3-picoline.
The reaction combines 3-picoline, ammonia, and an oxygen-containing gas over a heterogeneous oxidation catalyst.
Published processes describe gas-phase reaction temperatures broadly within approximately 280–400°C.
Suitable catalyst and feed conditions can provide very high conversion and 3-Pyridinecarbonitrile yields approaching 99% in optimized processes.

Ammoxidation formally converts the methyl substituent of 3-picoline into a nitrile group.
Water is produced as a reaction coproduct.
Catalyst systems commonly contain metal oxides capable of oxygen transfer, dehydrogenation, and ammonia activation.
Temperature, ammonia ratio, oxygen ratio, water content, residence time, and catalyst condition influence selectivity.

Incomplete ammoxidation can leave residual 3-picoline or generate oxygenated pyridine intermediates.
Excessive oxidation can lower nitrile yield and produce carbon oxides or other degradation products.
Ammonia concentration influences nitrile formation and suppression of undesired oxidation.
Product recovery can involve cooling, absorption, extraction, distillation, and crystallization under process-specific conditions.

3-Pyridinecarbonitrile is an organic nitrogen-containing solid capable of burning when exposed to sufficient heat and ignition.
Thermal decomposition or combustion can generate nitrogen oxides, carbon monoxide, carbon dioxide, smoke, and irritating organic fumes.
Fine airborne powder may increase fire and exposure hazards.
The current grade-specific Safety Data Sheet should determine firefighting media, classification, and emergency controls.

PROPERTIES

Chemical Name: 3-Pyridinecarbonitrile
Preferred IUPAC Name: Pyridine-3-carbonitrile
Common Name: 3-Cyanopyridine
Alternative Common Name: Nicotinonitrile
CAS Number: 100-54-9
EC Number: 202-863-0
PubChem CID: 79
NSC Number: 17558
Molecular Formula: C₆H₄N₂
Molecular Weight: 104.11 g/mol
Exact Molecular Weight: Approximately 104.0374 Da
InChIKey: GZPHSAQLYPIAIN-UHFFFAOYSA-N
Chemical Family: Pyridine nitriles
Chemical Classification: Heteroaromatic nitrile
Functional Groups: Pyridine nitrogen and nitrile group
Nitrile Position: 3-position relative to the pyridine nitrogen
Physical State at 20°C: Solid
Appearance: White to pale-yellow crystalline solid or powder
Melting Point: Approximately 50°C
Boiling Point: Approximately 240°C
Vapor Pressure at 25°C: Approximately 0.296 mmHg measured
Water Solubility at 20°C: Approximately 135 g/L measured
Estimated Water Solubility at 25°C: Approximately 27.9 g/L
Measured Conjugate-Acid pKa: Approximately 1.39
Measured Log Pow: Approximately 0.36
Henry’s Law Constant: Approximately 3.4 × 10⁻⁷ atm·m³/mol measured
Volatility: Moderate for a crystalline solid and increased by heating
Primary Industrial Function: Chemical intermediate
Primary Production Route: Ammoxidation of 3-picoline
Primary Downstream Product: Nicotinamide
Secondary Downstream Product: Nicotinic acid
Biocatalytic Function: Substrate for nitrile hydratase and nitrilase
Primary Hydration Product: Nicotinamide
Complete Hydrolysis Product: Nicotinic acid
Reduction Product: 3-Pyridylmethylamine
Coordination Function: Pyridine-nitrogen ligand
Analytical Function: Reference material and process-impurity standard
Acute Toxicity Summary: Low acute oral and dermal toxicity in the cited screening assessment
Repeated-Dose Oral NOAEL: 5 mg/kg body weight per day in the cited rat study
Repeated-Dose Oral LOAEL: 30 mg/kg body weight per day in the cited rat study
Repeated-Dose Target Organ: Liver
Additional Repeated-Dose Concern: Effects on spermatocytes and spermatids at higher doses
Bacterial Mutagenicity: Negative in cited assays
Environmental Mobility: Expected to be high in soil
Environmental Persistence: Expected to be low
Bioaccumulation Potential: Expected to be low
Biodegradation: Expected to be rapid to moderate
Combustibility: Combustible organic solid
Dust Exposure Potential: Possible during grinding, charging, conveying, and packaging
Chemical Stability: Stable under recommended controlled storage conditions
Incompatible Materials: Strong oxidizing agents, strong acids, strong bases, and reactive reducing agents
Hydrolysis Conditions: Promoted by acid, base, water, and elevated temperature
Hazardous Decomposition Products: Nitrogen oxides, carbon monoxide, carbon dioxide, smoke, and irritating organic fumes
Recommended Storage: Cool, dry, tightly closed, and well ventilated
Environmental Precaution: Prevent concentrated release to drains, soil, groundwater, and surface water
Quality-Control Parameters: Appearance, assay, melting range, water, color, residual 3-picoline, positional isomers, nicotinamide, and nicotinic acid
Current Data Requirement: Confirm purity, classification, occupational controls, transport status, packaging, and shelf life from current grade-specific documentation.

FIRST AID

Inhalation:
Move the affected person to fresh air.
Keep the person at rest in a position comfortable for breathing.
Avoid further exposure to 3-Pyridinecarbonitrile dust, vapor, smoke, or thermal-decomposition fumes.
Obtain medical attention if coughing, sore throat, headache, dizziness, nausea, breathing discomfort, or other symptoms develop or persist.
Provide oxygen or assisted breathing only through trained personnel using suitable protective equipment.

Skin Contact:
Remove contaminated clothing and footwear.
Brush away loose powder carefully without dispersing dust.
Wash the affected skin thoroughly with soap and plenty of water.
Continue rinsing if redness, irritation, itching, or discomfort occurs.
Obtain medical advice after extensive contact or if symptoms persist.
Wash contaminated clothing before reuse.

Eye Contact:
Rinse the eyes immediately with plenty of clean, gently flowing water.
Hold the eyelids open to ensure complete irrigation.
Remove contact lenses when present and easy to do, then continue rinsing.
Continue rinsing for at least 15 minutes.
Obtain prompt medical attention if pain, redness, tearing, blurred vision, or irritation persists.

Ingestion:
Rinse the mouth thoroughly with water.
Do not induce vomiting unless directed by qualified medical personnel or a poison center.
Never give anything by mouth to an unconscious, drowsy, or convulsing person.
Obtain medical advice following significant ingestion or if nausea, vomiting, abdominal discomfort, dizziness, or weakness develops.
Provide the current Safety Data Sheet and product label to medical personnel.

Note to Physicians:
No substance-specific antidote should be assumed.
Provide supportive care and treat according to the patient’s symptoms and clinical condition.
Assess respiratory, neurological, gastrointestinal, hepatic, renal, and reproductive-system concerns after substantial exposure.
Consider the possibility of delayed effects after significant ingestion, inhalation, or prolonged skin contact.
Use current poison-center guidance and the grade-specific Safety Data Sheet as the primary medical references.

HANDLING AND STORAGE

Handling:
Handle 3-Pyridinecarbonitrile in accordance with good industrial-hygiene and chemical-safety practices.
Review the current technical specification and Safety Data Sheet before opening, sampling, melting, transferring, or processing the material.
Avoid unnecessary contact with the skin, eyes, and clothing.
Do not breathe dust, vapor, aerosol, smoke, or thermal-decomposition fumes.
Use enclosed charging, weighing, transfer, reaction, filtration, and packaging systems wherever reasonably practicable.
Avoid pouring, grinding, sweeping, or pneumatic-transfer procedures that generate uncontrolled airborne powder.
Use clean, dry, and chemically compatible equipment for sampling, weighing, transfer, and reaction.
Heat the material gradually and indirectly when melting is required.
Avoid prolonged exposure to temperatures near the boiling or decomposition region.
Add acids, bases, oxidants, reducing agents, and hydrolysis catalysts gradually under controlled temperature and agitation.
Provide adequate cooling because nitrile hydration and hydrolysis can be exothermic.
Wash the hands, face, and exposed skin thoroughly after handling.
Do not eat, drink, or smoke in areas where 3-Pyridinecarbonitrile is processed.
Keep containers tightly closed whenever the material is not being sampled or transferred.

Ventilation:
Provide effective general ventilation in storage and processing areas.
Use local exhaust ventilation at weighing stations, bag-emptying points, melting vessels, reactors, dryers, mills, filters, and packaging equipment.
Capture airborne dust and heated vapor at the source.
Provide additional ventilation during melting, distillation, spraying, drying, or operation of open heated equipment.
Use dust-collection equipment suitable for combustible organic particulate material where required.
Prevent recirculation of contaminated air unless it has been adequately filtered.
Use suitable particulate respiratory protection when engineering controls cannot adequately limit dust exposure.
Use appropriate vapor or supplied-air protection during heated operations, emergencies, major spills, or unknown concentrations.
Select respiratory equipment through a documented occupational-exposure assessment.
Inspect and maintain ventilation, filters, dust collectors, and process enclosures regularly.

Storage:
Store 3-Pyridinecarbonitrile in tightly closed and correctly labeled containers.
Keep the material in a cool, dry, clean, secure, and well-ventilated location.
Protect 3-Pyridinecarbonitrile from excessive heat, direct sunlight, moisture, contamination, and physical damage.
Keep 3-Pyridinecarbonitrile separated from strong oxidizing agents, strong acids, strong bases, and reactive reducing agents.
Keep the material away from flames, sparks, hot surfaces, and uncontrolled ignition sources.
Maintain the storage temperature stated in the current grade-specific documentation.
Prevent repeated uncontrolled melting and recrystallization.

Spill and Leak Procedures:
Restrict access to the affected area and remove unnecessary personnel.
Eliminate ignition sources when this can be done safely.
Provide effective ventilation before beginning recovery operations.
Wear suitable gloves, protective clothing, eye protection, and particulate respiratory protection.
Avoid dry sweeping, compressed-air cleaning, or other methods that disperse powder.
Carefully collect dry material with a suitable industrial vacuum or another low-dust recovery method.
Sweep material gently into covered containers only when appropriate vacuum equipment is unavailable.

Handling Precautions:
Wear chemical-resistant protective gloves selected from documented compatibility and permeation information.
Use safety spectacles with side protection or tightly fitting chemical goggles.
Wear a face shield in addition to goggles where molten material, solution, or reaction-mixture splashing is reasonably foreseeable.
Use protective clothing and closed chemical-resistant footwear.
Use heat-resistant gloves and protective sleeves during handling of molten material.
Provide accessible eyewash and emergency-shower equipment near major handling locations.
Use suitable particulate respiratory protection during dusty operations.
Control temperature, pressure, catalyst addition, and heat removal during ammoxidation, hydration, hydrolysis, and reduction.
Prevent cross-contamination of 3-Pyridinecarbonitrile with finished nicotinamide, nicotinic acid, food, feed, pharmaceutical, or nutritional products.
Review the current technical specification, Safety Data Sheet, certificate of analysis, occupational requirements, environmental regulations, and transport rules before production, storage, cleaning, or disposal.