VALERONITRILE

Valeronitrile is a linear five-carbon aliphatic nitrile used primarily as a specialty organic synthesis intermediate and research reagent.
Its terminal nitrile group supports controlled conversion into pentanoic acid, pentanamide, pentylamine, ketones, and other functional derivatives.
Its moderate polarity, low freezing point, limited water solubility, and approximately 140 °C boiling point also support specialised solvent, biocatalytic, analytical, and electrochemical applications.

CHEMICAL IDENTITY AND COMMON NAMES

Valeronitrile is the common name for pentanenitrile, a straight-chain saturated nitrile containing four alkyl carbons and one nitrile carbon.
The historical name butyl cyanide describes the n-butyl group bonded covalently to the carbon of the nitrile functionality and does not indicate an ionic cyanide salt.

The unbranched structure distinguishes Valeronitrile from branched C5 nitriles such as 3-methylbutanenitrile and 2,2-dimethylpropanenitrile.
Valeronitrile must also be distinguished from pentenenitriles, which contain a carbon–carbon double bond and have different reactivity, specifications, and applications.

Synonyms and Common Names: Pentanenitrile, n-Pentanenitrile, Pentanonitrile, n-Pentanonitrile, Pentanitrile, Pentane nitrile, Pentano-1-nitrile, Pentanoic acid nitrile, Valeric acid nitrile, n-Valeronitrile, Butyl cyanide, n-Butyl cyanide, 1-Butyl cyanide, Butylcyanide, n-Butylcyanide, 1-Butylcyanide, 1-Cyanobutane, Cyanobutane, Butane, 1-cyano-, Nitrile C5, BuCN, n-BuCN, VN, Valeronitril, Valéronitrile

TECHNICAL IDENTIFICATION

CAS Number: 110-59-8
EC / EINECS Number: 203-781-8
IUPAC Name: Pentanenitrile
Molecular Formula: C5H9N
Linear Formula: CH3(CH2)3CN
Molar Mass: 83.13 g/mol
SMILES: CCCCC#N
InChIKey: RFFFKMOABOFIDF-UHFFFAOYSA-N
Chemical Class: Saturated aliphatic mononitrile
Carbon Structure: Linear C5 chain with a terminal nitrile group

PHYSICAL AND CHEMICAL PROPERTIES

Appearance: Clear, colourless to pale yellow liquid
Physical State at 20 °C: Liquid
Melting / Freezing Point: Approximately -96.2 °C
Normal Boiling Point: 139–141 °C at 101.3 kPa
Flash Point: Approximately 40 °C
Autoignition Temperature: Approximately 520 °C
Density: Approximately 0.795 g/mL at 25 °C
Specific Gravity: Approximately 0.8008 at 20 °C
Refractive Index: n20/D 1.396–1.399
Vapour Pressure: Approximately 0.7 kPa at 20 °C
Vapour Density: Approximately 3.46 relative to air
Water Solubility: Approximately 1–5 g/L at 22.5 °C
Solubility in Alcohol: Soluble
Octanol / Water Partition Coefficient: log P approximately 0.94–1.12
Relative Permittivity: Approximately 20.03 at 20 °C
Dipole Moment: Approximately 4.12 D
Critical Temperature: 337.15 °C
Critical Pressure: 35.80 bar
Standard Enthalpy of Vaporisation: Approximately 44.0 kJ/mol

FUNCTIONAL CHARACTERISTICS

The carbon–nitrogen triple bond gives Valeronitrile a substantial molecular dipole and makes the nitrile nitrogen an effective electron-pair donor and hydrogen-bond acceptor.
The molecule is polar aprotic and does not provide a hydrogen-bond-donating proton.

Hydrolysis converts the nitrile group first into pentanamide and then into pentanoic acid.
Catalytic hydrogenation or chemical reduction converts the same functionality into a primary amine, providing access to n-pentylamine.

Organometallic addition to the nitrile carbon followed by hydrolysis provides a route to ketones carrying a linear n-butyl group.
These transformations make Valeronitrile a compact C5 building block for multistep synthesis and route development.

The combination of moderate dielectric constant and a strongly polar nitrile group supports the solvation of polar reactants and selected salts.
Limited water solubility can assist phase separation during aqueous work-up, although dissolved Valeronitrile must still be considered in solvent recovery and wastewater control.

Its boiling point is substantially higher than that of lower aliphatic nitriles, reducing evaporation during controlled processing and allowing a broader liquid-phase temperature window.
The flash point remains low enough to require full flammable-liquid controls throughout transfer, reaction, sampling, and recovery.

PRODUCTION AND COMMERCIAL FORM

Valeronitrile can be prepared through nucleophilic substitution of a primary n-butyl halide with an alkali-metal cyanide in a suitable polar aprotic medium.
This route introduces the nitrile carbon as the fifth carbon of the straight-chain product.

Alternative preparative routes include dehydration of pentanamide and conversion of pentanal through its oxime followed by dehydration.
The selected process determines the relevant residual organic compounds, inorganic residues, water content, and purification requirements.

Purification commonly includes phase separation, washing, drying, and fractional distillation.
Control of lower-boiling starting materials, closely related nitriles, residual halides, water, colour, and non-volatile residue is important for high-purity material.

Valeronitrile is supplied as a neat liquid.
Commercially encountered assay levels include approximately 98% synthesis grade and 99–99.5% high-purity reagent material, commonly measured by gas chromatography.

APPLICATIONS AND INDUSTRIES

ORGANIC AND FINE CHEMICAL SYNTHESIS

Valeronitrile functions as a straight-chain C5 building block in laboratory, pilot-scale, and specialty chemical synthesis.
Its compact structure is useful when a process requires a terminal nitrile or a precursor to a carboxylic acid, amide, amine, or ketone.

Hydrolysis provides pentanoic acid through pentanamide as the intermediate transformation product.
Where downstream production targets pentanoic acid or pentanoate derivatives, Valeronitrile serves as the upstream reactive intermediate, while the resulting acid or ester provides the final application properties.

Reduction and catalytic hydrogenation provide access to n-pentylamine.
The resulting amine can participate in alkylation, acylation, salt formation, surfactant chemistry, and further fine-chemical synthesis.

Reaction with suitable organometallic reagents followed by hydrolysis enables carbon–carbon bond formation and ketone preparation.
This chemistry supports route development for specialty intermediates requiring an n-butyl-substituted carbonyl structure.

PHARMACEUTICAL AND SPECIALTY PROCESS DEVELOPMENT

Valeronitrile is applicable to pharmaceutical and specialty-chemical route development when the target structure requires a linear C5 nitrile or one of its downstream functional derivatives.
Its value in these processes arises from defined carbon-chain length and predictable nitrile transformations rather than from direct use in finished formulations.

High assay, controlled water content, and a characterised impurity profile are particularly important when Valeronitrile enters a multistep synthesis.
Residual ionic material and closely boiling organic impurities can influence catalyst life, conversion, selectivity, purification load, and final impurity control.

BIOCATALYSIS AND ENZYME RESEARCH

Valeronitrile serves as a substrate and activity inducer in nitrilase research.
Selected microbial and fungal nitrilases hydrolyse Valeronitrile to pentanoic acid, making it useful for enzyme screening, activity measurement, induction studies, and biocatalytic process development.

Controlled Valeronitrile dosing helps researchers study substrate conversion, enzyme selectivity, cellular tolerance, and acid formation.
This application is specialised and depends on the selected organism, enzyme preparation, substrate concentration, pH, temperature, and mass-transfer conditions.

SPECIALTY SOLVENT APPLICATIONS

Valeronitrile functions as a polar aprotic solvent in selected synthesis and physical-chemistry applications.
Its dielectric behaviour and nitrile donor site support interactions with polar solutes, while the alkyl chain provides greater organic character and lower water affinity than lower homologous nitriles.

The approximately 140 °C boiling point permits operations at temperatures above the normal boiling point of acetonitrile without immediate pressurisation.
It also supports recovery by controlled distillation when the process composition provides adequate volatility differences.

ELECTROCHEMICAL AND ENERGY-STORAGE RESEARCH

Valeronitrile is investigated as a nonaqueous solvent or co-solvent in advanced electrolyte systems.
The nitrile nitrogen can coordinate lithium ions, while the low freezing point helps preserve a liquid medium under low-temperature research conditions.

Valeronitrile has been evaluated in lithium-salt solutions, mononitrile–dinitrile electrolyte systems, and lithium-ion battery formulations.
Its influence on salt solubility, ionic association, viscosity, conductivity, electrode-interface behaviour, and electrochemical stability depends on the complete electrolyte composition.

Mixtures containing Valeronitrile have also been examined as liquid electrolyte media in dye-sensitised solar-cell research.
These applications require high chemical purity, low moisture, controlled ionic contamination, and electrochemical testing within the intended cell chemistry.

ANALYTICAL AND RESEARCH USE

High-purity Valeronitrile can serve as an identity or retention reference during gas-chromatographic method development.
Its infrared, nuclear magnetic resonance, and mass-spectral characteristics also support compound identification, purity assessment, reaction monitoring, and impurity investigations.

GRADE SELECTION AND PRODUCT SUITABILITY

Synthesis-grade Valeronitrile is suitable for routine organic transformations where gas-chromatographic assay, identity, appearance, and predictable reaction performance are the principal requirements.
Material with an assay of at least 98% is commonly selected for preparative chemistry and nitrilase studies.

Higher-purity grades are appropriate for impurity-sensitive multistep synthesis, analytical method development, physical-property measurements, and catalyst-dependent reactions.
A complete chromatographic purity profile is more informative than assay alone when closely related volatile organics could affect downstream separation.

Electrochemical research requires Valeronitrile with particularly low water content and controlled ionic contamination.
Defined limits for residual halides, metals, free ionic residue, acidity, and non-volatile material support reproducible conductivity, interfacial behaviour, and cell performance.

Biocatalytic work benefits from consistent assay and low concentrations of residual processing chemicals that could inhibit microorganisms or enzymes.
Controlled substrate quality improves comparison between induction, screening, and conversion experiments.

Production-scale buyers commonly evaluate assay, water, colour, density, refractive index, distillation profile, organic impurity distribution, non-volatile residue, and packaging configuration.
The selected specification should reflect the transformation, catalyst system, separation method, and final-product impurity requirements.

FORMULATION AND PROCESS CONSIDERATIONS

Valeronitrile should be charged through closed or effectively ventilated equipment because its vapour is flammable and denser than air.
Grounding, bonding, non-sparking tools, static control, and explosion-protected electrical equipment are required wherever vapour release can occur.

Acidic or alkaline hydrolysis generates heat and proceeds through pentanamide toward pentanoic acid or its salt.
Controlled reagent addition, temperature management, mixing, and phase control support predictable conversion and limit localised overheating.

Hydrogenation requires attention to catalyst type, hydrogen pressure, temperature, residence time, and ammonia concentration.
These variables affect conversion to n-pentylamine and the formation of secondary or tertiary amine by-products.

When Valeronitrile is used as a solvent, its boiling point supports elevated-temperature reactions and subsequent distillation recovery.
The vapour space, condenser, receiver, vacuum system, and vent treatment must retain flammable-liquid containment throughout heating and recovery.

Electrolyte preparation benefits from dry equipment, low-humidity or inert-atmosphere handling, compatible filtration, and clean transfer systems.
Water, particulates, metals, and ionic residues can change lithium-ion solvation, conductivity, electrochemical stability, and electrode-interface behaviour.

Biocatalytic processes require controlled substrate feeding because nitrilase induction, conversion rate, and biological tolerance respond to Valeronitrile concentration.
Efficient mixing and pH control also support consistent conversion as pentanoic acid or its salt accumulates.

QUALITY, SPECIFICATIONS AND DOCUMENTATION

Gas chromatography is the principal quantitative method for Valeronitrile assay and volatile-organic impurity profiling.
Infrared spectroscopy, nuclear magnetic resonance, or gas chromatography–mass spectrometry can confirm molecular identity and support investigation of unknown peaks.

Density and refractive index provide rapid checks of liquid identity and composition.
Karl Fischer analysis is useful when water content affects hydrolysis-sensitive reactions, catalysts, analytical measurements, or electrochemical formulations.

Colour, appearance, distillation range, non-volatile residue, acidity, residual halide, and trace metals may be included when required by the intended application.
Electrochemical and catalyst-sensitive projects benefit from tighter control of water and ionic impurities than routine synthesis work.

The Certificate of Analysis should identify the production lot and report the agreed specification results.
The Safety Data Sheet supports hazard communication, transport planning, storage design, protective-equipment selection, and emergency procedures.
The Technical Data Sheet can provide product characteristics, available grade information, packaging options, and application-relevant handling details.

SAFETY AND REGULATORY CONSIDERATIONS

Valeronitrile is a flammable liquid and vapour with significant acute oral toxicity.
Contact can irritate the skin and eyes, while inhalation or skin absorption can also produce harmful exposure.

Symptoms of excessive exposure may include headache, dizziness, weakness, nausea, vomiting, respiratory difficulty, and central nervous system effects.
Aliphatic nitriles can undergo metabolic conversion that releases cyanide, making prompt medical assessment important after substantial exposure.

Vapours are heavier than air and can accumulate in low or poorly ventilated areas.
Vapour can travel to an ignition source and flash back, while heated closed containers can rupture from pressure.

Fire or severe thermal decomposition can generate carbon monoxide, carbon dioxide, nitrogen oxides, hydrogen cyanide, and other toxic fumes.
Firefighters require full protective equipment and positive-pressure self-contained breathing apparatus.

Suitable extinguishing media include alcohol-resistant foam, dry chemical, carbon dioxide, and water spray.
Water spray is appropriate for cooling exposed closed containers but should not be applied as a forceful stream that spreads burning liquid.

Spills require immediate ignition-source removal, area ventilation, restricted access, and suitable chemical protective equipment.
Liquid should be contained with an inert absorbent and collected in tightly closed, compatible containers for hazardous-waste disposal.

Valeronitrile must not enter drains, surface water, soil, or uncontrolled waste streams.
Transport requires dangerous-goods classification, compliant packaging, marking, documentation, and segregation appropriate to a flammable toxic nitrile.

FIRST AID

Inhalation: Move the exposed person immediately to fresh air and keep the person at rest in a position comfortable for breathing.
Inhalation: Obtain urgent medical attention and provide oxygen or assisted respiration only through trained personnel and suitable protective equipment.
Skin Contact: Remove contaminated clothing and shoes immediately, then wash the affected skin thoroughly with soap and plenty of water for at least 15 minutes.
Skin Contact: Obtain medical attention and wash contaminated clothing before reuse.
Eye Contact: Rinse cautiously with clean water for at least 15 minutes while holding the eyelids open.
Eye Contact: Remove contact lenses when easy to do, continue rinsing, and obtain immediate medical attention.
Ingestion: Rinse the mouth without inducing vomiting and contact a poison centre or emergency physician immediately.
Ingestion: Never give anything by mouth to an unconscious person.
Note to Physicians: Treat exposure as possible systemic aliphatic nitrile poisoning and monitor respiratory, neurological, cardiovascular, acid–base, and lactate status.
Note to Physicians: Metabolic cyanide release can contribute to toxicity, and immediate specialist toxicology consultation should guide supportive care and antidotal treatment.

HANDLING AND STORAGE

Handling: Use Valeronitrile only in closed processing equipment or with effective local exhaust ventilation.
Ignition Control: Keep away from heat, hot surfaces, sparks, open flames, static discharge, and all other ignition sources.
Transfer: Ground and bond containers and receiving equipment, and use non-sparking tools with explosion-protected pumps, ventilation, lighting, and electrical installations.
Personal Protection: Wear impermeable chemical-resistant gloves, protective clothing, chemical splash goggles, and face protection appropriate to the transfer or processing operation.
Respiratory Protection: Use respiratory protection selected for organic vapours when engineering controls cannot maintain safe airborne conditions.
Hygiene: Do not eat, drink, or smoke in handling areas, and wash hands and exposed skin thoroughly after use.
Storage: Keep the container tightly closed in a cool, dry, shaded, locked, and well-ventilated flammable-liquids storage area.
Storage Temperature: Cool storage below approximately 15 °C supports controlled vapour pressure and product condition.
Cold Storage: Use only refrigeration equipment designed for flammable liquids when refrigerated storage is selected.
Incompatibilities: Segregate from strong acids, strong bases, strong oxidising agents, peroxides, and strong reducing agents.
Fire Protection: Maintain suitable extinguishing equipment, spill-control materials, eyewash facilities, and an emergency safety shower near the handling area.
Packaging: Use clean, dry, chemically compatible containers with vapour-tight closures and suitable secondary containment.

PACKAGING AND PROCUREMENT CONSIDERATIONS

Valeronitrile packaging must preserve purity while controlling vapour release, ignition risk, leakage, and transport exposure.
Compatible containers require secure closures, appropriate headspace management, compliant dangerous-goods construction, and protection from heat and physical damage.

Procurement information should identify Valeronitrile by name and CAS Number 110-59-8 and state the required assay, water limit, application, pack size, annual quantity, and documentation.
Electrochemical, catalytic, analytical, and pharmaceutical-process applications should also define relevant trace-impurity, ionic-residue, colour, and non-volatile-residue requirements.

Ataman Kimya supports Valeronitrile enquiries for synthesis, biocatalysis, analytical work, specialised solvent use, and advanced electrochemical research with attention to grade, specification, documentation, packaging, and supply planning.
For Valeronitrile grade selection, specification review, Certificate of Analysis, Safety Data Sheet, packaging, or supply requirements, contact Ataman Kimya by telephone at +90 216 577 10 10 or by email at info@atamankimya.com.