The Role of Chloroacetonitrile in Chemical Synthesis and Industry

Chemical Name: Chloroacetonitrile
Molecular Formula: C2H2ClN
CAS Number: 107-14-2
Molecular Weight: 75.49 g/mol
Appearance: Colorless to pale yellow liquid
Boiling Point: 123°C
Density: 1.19 g/cm³
Solubility: Slightly soluble in water; miscible with most organic solvents

Table of Contents

Section	Details
1. General Information	Overview of Chloroacetonitrile, its chemical structure, and common uses
2. Chemical Properties	Key properties including molecular formula, weight, boiling point, density, and solubility
3. Applications	Major applications in organic synthesis, pharmaceuticals, and as a chemical intermediate
4. Synthetic Utility	Explanation of how Chloroacetonitrile is utilized in various chemical reactions
5. Handling and Safety	Guidelines for safe handling, storage, and potential hazards associated with Chloroacetonitrile
6. Safety Data	Detailed hazard classifications, pictograms, and precautionary measures
7. Peer-Reviewed Studies	Summarization of scientific research focusing on the compound’s applications and effectiveness in organic synthesis

1. General Information

Chloroacetonitrile is a versatile organochlorine compound that plays a significant role in organic synthesis. It is commonly used as a building block in the synthesis of pharmaceuticals, agrochemicals, and other specialty chemicals. Its reactivity stems from the presence of both a nitrile group and a chloro group, making it an effective intermediate in various chemical processes.

2. Chemical Properties

• Molecular Formula: C2H2ClN
• Molecular Weight: 75.49 g/mol
• CAS Number: 107-14-2
• Appearance: Colorless to pale yellow liquid
• Boiling Point: 123°C
• Density: 1.19 g/cm³
• Solubility: Slightly soluble in water; miscible with most organic solvents
• Reactivity: Chloroacetonitrile is a reactive compound due to the electron-withdrawing nature of the nitrile and chloro groups, making it highly useful in nucleophilic substitution and other organic reactions.

3. Applications

Chloroacetonitrile is widely used in:

• Organic Synthesis: It serves as a key intermediate in the production of various chemical compounds, particularly in the synthesis of pharmaceuticals and agrochemicals.
• Pharmaceutical Manufacturing: It is utilized in the synthesis of active pharmaceutical ingredients (APIs) due to its reactivity and ability to introduce a nitrile group into a molecule.
• Chemical Intermediate: It acts as a precursor to more complex molecules, including those used in the production of dyes, pesticides, and specialty chemicals.

The versatility of Chloroacetonitrile in organic synthesis makes it a valuable reagent in various chemical industries, where it is often employed in the development of complex molecular structures.

4. Synthetic Utility

Chloroacetonitrile is a crucial reagent in organic chemistry due to its dual functional groups. It is frequently used in:

• Nucleophilic Substitution Reactions: The chloro group can be readily displaced by a nucleophile, leading to the formation of a variety of substituted nitriles.
• Cyclization Reactions: It is used in the synthesis of heterocyclic compounds, where the nitrile group participates in cyclization processes.
• Cross-Coupling Reactions: Chloroacetonitrile can be employed in metal-catalyzed cross-coupling reactions, contributing to the formation of carbon-carbon bonds in complex molecules.

These reactions highlight the compound’s importance in the synthesis of a wide range of organic molecules, particularly those with pharmaceutical applications.

5. Handling and Safety

Handling Chloroacetonitrile requires caution due to its toxic and reactive nature. It should be stored in a cool, dry place, away from moisture and incompatible substances. Proper personal protective equipment (PPE), including gloves, goggles, and protective clothing, should be worn when handling the compound. Work in a well-ventilated area or fume hood is recommended to avoid inhalation of vapors.

6. Safety Data

Hazard Classifications

• Toxic: Harmful if inhaled, ingested, or absorbed through the skin.
• Irritant: May cause severe irritation to the eyes, skin, and respiratory system.

Pictograms:

• skull and crossboens (Toxic)

Hazard Statements:

• H301: Toxic if swallowed.
• H311: Toxic in contact with skin.
• H331: Toxic if inhaled.
• H319: Causes serious eye irritation.
• H335: May cause respiratory irritation.

Precautionary Statements:

• P280: Wear protective gloves, protective clothing, and eye protection.
• P261: Avoid breathing vapors or mist.
• P301+P310: If swallowed, immediately call a poison center or doctor.
• P305+P351+P338: If in eyes, rinse cautiously with water for several minutes. Remove contact lenses if present and easy to do. Continue rinsing.

7. Peer-Reviewed Studies

Chloroacetonitrile has been the subject of various studies, particularly in the context of organic synthesis and chemical reactivity. Research has explored:

• Pharmaceutical Applications: Its role as an intermediate in the synthesis of complex drug molecules.
• Environmental Impact: Studies on its degradation and persistence in the environment, particularly concerning its use in agrochemicals.
• Reactivity Studies: Investigations into its behavior in different chemical reactions, including nucleophilic substitution and cyclization processes.

These studies emphasize the compound’s versatility and importance in synthetic organic chemistry, particularly in industries focused on pharmaceuticals and agrochemicals.

Conclusion

Chloroacetonitrile is a valuable chemical reagent with a broad range of applications in organic synthesis. Its reactivity and dual functional groups make it an indispensable tool in the synthesis of complex molecules, particularly in pharmaceuticals. Proper handling and adherence to safety protocols are essential to ensure its effective and safe use in the laboratory.

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