Pivalonitrile: Properties, Uses & Handling FAQs

Pivalonitrile is a sterically hindered aliphatic nitrile compound widely used as a building block and solvent additive in organic synthesis, battery electrolyte research, and coordination chemistry.

IUPAC Name

2,2-Dimethylpropanenitrile

Common Synonyms

Trimethylacetonitrile; tert-butyl cyanide; pivalonit rile

Molecular Formula

C5H9N

Molecular Weight

83.13 g/mol

CAS Number

630-18-2

Appearance

Colorless liquid

Functional Group

Nitrile (C≡N)

What Is Pivalonitrile and What Are Its Key Chemical Properties?

Pivalonitrile (CAS 630-18-2), also known as trimethylacetonitrile or 2,2-dimethylpropanenitrile, is a short-chain aliphatic nitrile with the molecular formula C₅H₉N and a molecular weight of 83.13 g/mol. It features a nitrile group (C≡N) attached to a quaternary carbon bearing three methyl substituents, making it one of the simplest sterically hindered nitriles.

The compound is a colorless liquid at room temperature with a characteristic nitrile odor. Its steric bulk relative to acetonitrile or propionitrile reduces nucleophilicity at the nitrogen lone pair and slows hydrolysis rates, which can be advantageous in reactions requiring a controlled coordination environment. The nitrile nitrogen remains available for metal coordination and hydrogen-bond acceptance despite the steric shielding of the adjacent carbon center.

Key physicochemical parameters (verify against current certificate of analysis): boiling point approximately 105–106 °C, density approximately 0.76 g/mL, refractive index approximately 1.377, and flash point approximately 14 °C (closed cup), classifying it as a flammable liquid.

What Are the Main Applications of Pivalonitrile in Research?

Pivalonitrile serves multiple roles across different research disciplines:

• Organic synthesis building block: The nitrile group can be hydrolyzed to pivalic acid, reduced to the corresponding amine (tert-butylamine), or converted to amidines, tetrazoles, and other nitrogen-containing heterocycles, making pivalonitrile a versatile precursor.
• Ligand in coordination chemistry: The nitrile nitrogen coordinates to transition metals. The steric bulk of the tert-butyl group modulates ligand lability and electronics, enabling fine-tuning of metal complex properties for catalysis and materials research.
• Electrolyte additive in battery research: Nitrile-functionalized molecules have been explored as electrolyte additives or co-solvents in lithium-ion battery systems due to their ability to coordinate to electrode surfaces and stabilize interfaces. Pivalonitrile's low viscosity and moderate polarity make it a candidate for such investigations.
• Solvent and co-solvent: In specialized synthetic contexts, pivalonitrile can function as a relatively inert polar aprotic co-solvent.

Researchers should consult primary literature for specific reaction conditions; application data stated here are general and require verification against experimental publications.

How Should Pivalonitrile Be Handled and Stored Safely?

Pivalonitrile is a flammable liquid and a toxic nitrile compound. Safe handling requires adherence to the following precautions:

• Personal protective equipment (PPE): Wear chemical-resistant gloves (e.g., nitrile or neoprene), safety goggles, and a laboratory coat. Work in a well-ventilated fume hood to avoid inhalation of vapors.
• Fire safety: With a flash point of approximately 14 °C, pivalonitrile vapors can form ignitable mixtures with air at room temperature. Keep away from open flames, sparks, and hot surfaces. Use appropriate Class B fire-extinguishing agents.
• Toxicity: Like all aliphatic nitriles, pivalonitrile may release cyanide ion upon metabolic oxidation. Avoid skin contact, eye contact, and inhalation. In case of exposure, follow institutional emergency response protocols and consult the Safety Data Sheet (SDS) immediately.
• Storage: Store in a tightly sealed container in a cool (typically 2–8 °C or per SDS recommendation), dry, well-ventilated area away from oxidizers and ignition sources.
• Waste disposal: Dispose of as hazardous chemical waste in accordance with local environmental regulations.

Always consult the current Aladdin Scientific SDS for P160477 before use, as it contains the most authoritative and up-to-date safety information.

Purchasing and Quality Information for Aladdin Scientific P160477

Aladdin Scientific offers pivalonitrile under SKU P160477. When placing an order or evaluating suitability for your application, consider the following:

• Purity and grade: Check the current product listing or certificate of analysis (CoA) on the Aladdin Scientific website for the stated purity grade. For sensitive synthetic applications, high-purity (≥98% or ≥99%) material is recommended.
• Available pack sizes: Multiple pack sizes are typically available to suit both exploratory screening and larger-scale synthesis. Contact Aladdin Scientific customer service for bulk or custom quantity inquiries.
• Ordering: Orders can be placed directly through the Aladdin Scientific online store. Academic and institutional purchase orders are accepted. For pricing and availability, visit the product page for P160477.
• Shipping: As a flammable liquid, pivalonitrile is subject to hazardous-goods shipping regulations. Aladdin Scientific complies with applicable IATA/IMDG/DOT regulations. Estimated delivery times and shipping restrictions vary by destination; confirm at checkout.
• Returns and refunds: Refer to Aladdin Scientific's standard return and refund policy. Products must generally be in original, unopened condition. Contact customer service for guidance on quality-related claims.

Frequently asked questions

What is pivalonitrile used for in organic synthesis?

Pivalonitrile is used as a versatile synthetic building block. Its nitrile group can be transformed into carboxylic acids (via hydrolysis), primary amines (via reduction), amidines, and nitrogen-containing heterocycles such as tetrazoles. The steric bulk of the tert-butyl group also makes it a useful probe for studying steric effects in reactions and a ligand precursor in coordination chemistry.

Is pivalonitrile the same as trimethylacetonitrile?

Yes. Pivalonitrile, trimethylacetonitrile, tert-butyl cyanide, and 2,2-dimethylpropanenitrile are all names for the same compound with CAS number 630-18-2 and molecular formula C5H9N. When searching literature or databases, any of these synonyms may be used.

What safety precautions are required when working with pivalonitrile?

Pivalonitrile is both flammable (flash point ~14 °C) and toxic. Always handle it in a certified fume hood wearing nitrile or neoprene gloves, safety goggles, and a lab coat. Keep it away from all ignition sources. As with other aliphatic nitriles, metabolic conversion to cyanide is a toxicity concern; follow your institution's chemical hygiene plan and consult the current SDS for P160477 before use.

How should pivalonitrile be stored to maintain its quality?

Store pivalonitrile in a tightly sealed container in a cool, dry, well-ventilated location, away from oxidizing agents and ignition sources. Refrigerated storage (2–8 °C) is commonly recommended for long-term stability. Always verify storage conditions on the current Aladdin Scientific CoA or SDS for SKU P160477.

Can pivalonitrile be used as an electrolyte additive in battery research?

Nitrile compounds, including sterically hindered ones like pivalonitrile, have been investigated as electrolyte additives and co-solvents in lithium-ion battery systems because nitrile groups can coordinate to electrode surfaces and help stabilize the solid-electrolyte interphase (SEI). However, specific performance data for pivalonitrile should be sourced from peer-reviewed electrochemistry literature, as results depend heavily on the battery chemistry and cell configuration.

References

1. Lide, D. R. (Ed.). CRC Handbook of Chemistry and Physics. CRC Press. (Physical constants for 2,2-dimethylpropanenitrile.)
2. Aladdin Scientific. Product page and Safety Data Sheet for Pivalonitrile, SKU P160477. Aladdin Scientific Co., Ltd.
3. March, J. Advanced Organic Chemistry: Reactions, Mechanisms, and Structure. Wiley-Interscience. (Nitrile chemistry and transformations.)

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