Chloroacetonitrile: Properties, Uses & Safe Handling

Chloroacetonitrile is a highly reactive haloacetonitrile building block widely employed in organic synthesis, distinguished by its strong lachrymatory properties and significant acute toxicity that demand rigorous laboratory safety measures.

CAS Number

107-14-2

Molecular Formula

C₂H₂ClN

Molecular Weight

75.50 g/mol

Physical State

Colorless to pale yellow liquid

Primary Hazard

Toxic by inhalation, ingestion, and skin contact; strong lachrymatory agent

Key Application

Organic synthesis intermediate and alkylating agent

SKU

C107567

Chemical Properties and Structure

Chloroacetonitrile (CAS 107-14-2) is a simple α-halonitrile with the molecular formula C₂H₂ClN and a molecular weight of approximately 75.50 g/mol. Its structure consists of a methylene group bearing both a chlorine atom and a nitrile group, making it a bifunctional molecule with two distinct reactive sites.

The nitrile group confers electrophilic character at the carbon center, while the chlorine atom serves as an excellent leaving group in nucleophilic substitution reactions. This combination renders chloroacetonitrile a versatile and reactive intermediate. The compound is a colorless to pale yellow liquid at room temperature with a pungent, irritating odor. It is miscible with common organic solvents such as ethanol, diethyl ether, and acetone, and exhibits limited miscibility with water.

The presence of the electron-withdrawing nitrile group significantly activates the adjacent C–Cl bond toward S_N2 displacement, making chloroacetonitrile considerably more reactive than simple alkyl chlorides of comparable size.

Synthetic Applications

Chloroacetonitrile is a valued building block in pharmaceutical, agrochemical, and fine-chemical synthesis. Its dual functionality as both an alkylating agent and a masked acetic acid equivalent—after hydrolysis of the nitrile—makes it highly adaptable across numerous synthetic routes.

Key applications include:

• N-Alkylation reactions: Chloroacetonitrile reacts readily with amines, imidazoles, pyrazoles, and related nitrogen nucleophiles to introduce the cyanomethyl (–CH₂CN) group, a useful handle for further transformation.
• O-Alkylation: Phenols, alcohols, and thiolates undergo efficient O- or S-alkylation, providing cyanomethyl ethers and thioethers that serve as intermediates in heterocycle synthesis.
• Synthesis of glycine derivatives: The cyanomethyl group can be hydrolyzed or reduced to furnish glycine-type frameworks relevant to amino acid chemistry.
• Heterocyclic synthesis: Chloroacetonitrile is employed in the preparation of thiazoles, imidazoles, pyrimidines, and other nitrogen-containing rings through cyclization strategies involving its reactive methylene.

Researchers should note that the high reactivity of chloroacetonitrile necessitates careful control of reaction stoichiometry and temperature to avoid over-alkylation or decomposition.

Safety, Hazards and Regulatory Considerations

Chloroacetonitrile is classified as an acutely toxic and severely irritating substance. It is toxic by inhalation, ingestion, and skin absorption, and acts as a potent lachrymatory (tear-inducing) agent even at low exposure concentrations. Researchers and laboratory managers must treat this compound with the highest level of caution.

Personal Protective Equipment (PPE): Work with chloroacetonitrile must be performed using a full-face respirator equipped with appropriate organic-vapor cartridges, chemical-resistant protective clothing (such as a lab coat and chemical splash suit), impermeable chemical-resistant gloves, and closed-toe shoes. Safety goggles alone are insufficient given its lachrymatory potency.

Engineering Controls: All handling must be conducted inside a well-functioning chemical fume hood. Secondary containment is recommended when storing or transferring the reagent.

Storage: Store in a cool, well-ventilated area away from heat sources, oxidizers, and strong bases. Keep containers tightly sealed when not in use.

Disposal: Dispose of chloroacetonitrile and contaminated materials in accordance with local, national, and institutional regulations for hazardous chemical waste. Do not pour down the drain.

Emergency Procedures: In case of skin or eye contact, flush immediately with large amounts of water for at least 15 minutes and seek medical attention. In case of inhalation, move the affected person to fresh air immediately and obtain medical assistance. Consult the Safety Data Sheet (SDS) for comprehensive emergency guidance.

Ordering Information and Specifications

Aladdin Scientific offers chloroacetonitrile under SKU C107567. When placing an order, researchers and procurement officers should confirm the required purity grade, package size, and any applicable regulatory documentation (e.g., SDS, certificate of analysis) with the Aladdin Scientific sales team.

Given that chloroacetonitrile is a regulated hazardous chemical in many jurisdictions, customers are advised to verify import/export restrictions and carrier requirements before ordering. Aladdin Scientific's logistics team can assist with documentation and shipping compliance for domestic and international orders.

For bulk quantities, custom purity specifications, or special packaging requirements, please contact Aladdin Scientific customer service directly. Volume pricing may be available for qualifying research institutions and industrial clients.

Frequently asked questions

What are the primary uses of chloroacetonitrile in organic synthesis?

Chloroacetonitrile serves as an alkylating agent for nitrogen, oxygen, and sulfur nucleophiles, introducing the cyanomethyl group that can be further elaborated by hydrolysis or reduction. It is commonly used in heterocycle synthesis and as a building block for pharmaceutical and agrochemical intermediates.

What personal protective equipment is required when handling chloroacetonitrile?

A full-face respirator with organic-vapor cartridges, chemical-resistant protective clothing, impermeable gloves, and closed-toe shoes are mandatory. All work should be performed in a chemical fume hood. Standard safety goggles alone are not sufficient protection due to the compound's strong lachrymatory effect.

How should chloroacetonitrile be stored safely in a laboratory?

Chloroacetonitrile should be stored in a cool, well-ventilated area in tightly sealed containers, away from heat sources, oxidizers, and strong bases. Secondary containment is recommended to prevent accidental spills. Always consult the current Safety Data Sheet for storage requirements specific to your jurisdiction.

Is chloroacetonitrile available in different purity grades from Aladdin Scientific?

Aladdin Scientific offers chloroacetonitrile under SKU C107567. For specific purity grades, package sizes, or certificates of analysis, please contact Aladdin Scientific's sales or customer service team directly to confirm current availability and specifications.

References

1. March, J. Advanced Organic Chemistry: Reactions, Mechanisms, and Structure, 4th ed.; Wiley: New York, 1992.
2. Chloroacetonitrile Safety Data Sheet. Aladdin Scientific, SKU C107567.
3. National Institute for Occupational Safety and Health (NIOSH). Pocket Guide to Chemical Hazards: Chloroacetonitrile.

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