Pivalonitril: Properties, Handling & Lab Use Guidelines

Pivalonitril is a sterically hindered aliphatic nitrile reagent widely used in organic synthesis, coordination chemistry, and materials research due to its distinctive reactivity and moderate volatility.

Chemical Name

Pivalonitril (Trimethylacetonitrile)

Molecular Formula

C5H9N

Molecular Weight

83.13 g/mol

CAS Number

630-18-2

Appearance

Colorless liquid

Key Feature

Sterically hindered nitrile; bulky tert-butyl group adjacent to CN

SKU

P1539837

Physical and Chemical Properties

Pivalonitril, also known as trimethylacetonitrile or 2,2-dimethylpropanenitrile, is a colorless liquid aliphatic nitrile with the molecular formula C₅H₉N and a molecular weight of approximately 83.13 g/mol (CAS 630-18-2). Its structure features a cyano group (–C≡N) directly bonded to a tert-butyl moiety, rendering it one of the most sterically hindered simple nitriles commercially available.

The steric bulk of the tert-butyl group significantly modulates its reactivity compared to acetonitrile or propionitrile. Pivalonitril is moderately volatile and exhibits limited miscibility with water, while being fully miscible with most common organic solvents such as diethyl ether, dichloromethane, and tetrahydrofuran. Its boiling point and other precise physicochemical constants should be confirmed against the Certificate of Analysis supplied with each lot.

Safety and Handling Precautions

As with all nitrile-containing compounds, Pivalonitril should be treated as a toxic substance. Nitriles can potentially release cyanide species upon metabolic processing or in strongly acidic or basic aqueous conditions. Personnel must wear appropriate personal protective equipment (PPE), including chemically resistant gloves, safety goggles, and a laboratory coat, at all times when handling this reagent.

All manipulations should be conducted in a well-ventilated fume hood to minimize inhalation exposure. Avoid contact with strong oxidizing agents, strong acids, and strong bases. In the event of skin or eye contact, flush immediately with copious amounts of water for at least 15 minutes and seek medical attention. Consult the Safety Data Sheet (SDS) provided by Aladdin Scientific before use for comprehensive hazard, first-aid, and disposal information.

Waste disposal must comply with local, regional, and national regulations governing nitrile-containing chemical waste. Do not pour down the drain without proper treatment.

Storage Conditions and Stability

Pivalonitril should be stored in a tightly sealed container away from heat sources, open flames, and direct sunlight. Storage at cool temperatures (typically 2–8 °C or as specified on the product label) in a well-ventilated, flammable-chemical storage cabinet is recommended. Keep away from incompatible materials, particularly strong oxidizers and strong acids.

Under recommended storage conditions, Pivalonitril is expected to be stable. However, prolonged exposure to moisture or reactive impurities may lead to hydrolysis of the nitrile group to the corresponding amide or carboxylic acid. Always inspect the reagent for color changes, precipitation, or off-odors prior to use, and verify purity by the Certificate of Analysis (CoA). Refer to the product label for shelf-life information specific to each lot.

Research Applications

Pivalonitril is valued in synthetic organic chemistry primarily as a sterically hindered nitrile building block. Its bulky structure enables selective reactions where smaller nitriles would be too reactive, making it useful in the preparation of sterically demanding intermediates such as hindered amidines, tetrazoles, and heterocyclic compounds.

In coordination chemistry, Pivalonitril can act as a monodentate nitrogen-donor ligand for transition metals, where its steric profile helps stabilize or selectively direct metal coordination environments. It has also found utility as a solvent or co-solvent additive in electrochemical studies, including lithium-ion battery electrolyte research, where nitrile additives can influence solid electrolyte interphase (SEI) formation.

Researchers in pharmaceutical and agrochemical synthesis may employ Pivalonitril as a masked carbonyl equivalent or a precursor to functional groups accessible via nitrile chemistry, including carboxylic acids, amides, amines, and aldehydes upon appropriate reduction.

Quality and Procurement

Aladdin Scientific supplies Pivalonitril (SKU: P1539837) for research use. Each lot is accompanied by a Certificate of Analysis (CoA) documenting purity, appearance, and relevant physicochemical data measured by validated analytical methods. Researchers and procurement personnel are encouraged to review the CoA and SDS prior to ordering to confirm suitability for their specific application.

For bulk quantities, custom packing, or technical enquiries regarding specification and grade, please contact Aladdin Scientific customer support. Ensure that ordering, storage, and use comply with all applicable institutional and regulatory requirements for handling potentially toxic organic reagents.

Frequently asked questions

What makes Pivalonitril different from acetonitrile?

Pivalonitril possesses a bulky tert-butyl group adjacent to the nitrile function, making it far more sterically hindered than acetonitrile. This steric bulk reduces its reactivity in many nucleophilic or coordination reactions, enabling selective synthetic transformations not achievable with acetonitrile. It is also less polar and less water-miscible than acetonitrile.

Is Pivalonitril hazardous, and what PPE is required?

Yes, Pivalonitril is considered toxic and should be handled accordingly. Chemically resistant gloves, safety goggles, and a laboratory coat must be worn. All handling should take place in a fume hood. The full hazard profile is detailed in the Safety Data Sheet (SDS) available from Aladdin Scientific.

How should Pivalonitril be stored to maintain stability?

Pivalonitril should be stored in a tightly sealed container at cool temperatures (2–8 °C or as stated on the product label), away from heat, flames, moisture, strong acids, and oxidizers. Under these conditions the reagent is expected to remain stable for the duration of the stated shelf life. Always consult the CoA for lot-specific guidance.

Can Pivalonitril be used as a ligand in metal coordination chemistry?

Yes, Pivalonitril can coordinate to transition metals via its nitrogen lone pair, functioning as a monodentate N-donor ligand. Its steric bulk makes it particularly useful for generating coordinatively selective metal complexes or stabilizing reactive metal centers compared to less hindered nitrile ligands.

References

1. March, J. Advanced Organic Chemistry: Reactions, Mechanisms, and Structure. Wiley-Interscience. (General reference for nitrile chemistry.)
2. Aladdin Scientific. Product Certificate of Analysis, Pivalonitril, SKU P1539837. Aladdin Scientific internal documentation.
3. Aladdin Scientific. Safety Data Sheet, Pivalonitril (CAS 630-18-2). Aladdin Scientific.

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