Abstract

This article provides an in-depth exploration of the compound 1,1'-Carbonyldiimidazole (CAS 530-62-1), commonly known as CDI. It serves as an ultimate guide, covering its chemical properties, synthesis methods, applications in organic synthesis, safety considerations, and environmental impact. By delving into these aspects, the article aims to unlock the secrets of this versatile compound, offering valuable insights for researchers and chemists in various fields.

Introduction to 1,1'-Carbonyldiimidazole (CDI)

1,1'-Carbonyldiimidazole, with the chemical formula C₆H₄N₂O, is a versatile organic compound widely used in organic synthesis. It is a colorless crystalline solid that is highly reactive and plays a crucial role in the formation of carbon-carbon bonds. CDI is commonly used as a coupling agent in the synthesis of various organic compounds, including heterocycles, amino acids, and pharmaceuticals.

Chemical Properties of 1,1'-Carbonyldiimidazole

1. **Structure and Molecular Formula**: CDI consists of two imidazole rings connected by a carbonyl group. This unique structure allows it to act as a nucleophile and electrophile, facilitating various chemical reactions.
2. **Solubility**: CDI is soluble in organic solvents such as dimethylformamide (DMF), dimethyl sulfoxide (DMSO), and tetrahydrofuran (THF). However, it is sparingly soluble in water.
3. **Reactivity**: CDI is highly reactive and can undergo various reactions, including condensation, cyclization, and substitution. Its reactivity is influenced by the reaction conditions, such as temperature, pH, and the presence of catalysts.

Synthesis of 1,1'-Carbonyldiimidazole

1. **Synthesis from 2,4-Dichloro-5-nitropyrimidine**: One of the most common methods for synthesizing CDI involves the reaction of 2,4-dichloro-5-nitropyrimidine with formaldehyde in the presence of a base, such as sodium hydroxide.
2. **Synthesis from 2,4-Dichloro-5-aminopyrimidine**: Another method involves the reaction of 2,4-dichloro-5-aminopyrimidine with chloral hydrate in the presence of a base.
3. **Synthesis from 2,4-Dichloro-5-mercapto-pyrimidine**: This method utilizes the reaction of 2,4-dichloro-5-mercapto-pyrimidine with chloral hydrate and sodium hydroxide.

Applications in Organic Synthesis

1. **Coupling Reactions**: CDI is widely used as a coupling agent in the synthesis of various organic compounds, including heterocycles, amino acids, and pharmaceuticals.
2. **Synthesis of Amines**: CDI can be used to synthesize amines by reacting with alkyl halides or alkyl amines in the presence of a base.
3. **Synthesis of Heterocycles**: CDI is employed in the synthesis of heterocycles, such as pyrimidines, pyrazoles, and imidazoles.

Safety Considerations

1. **Handling**: CDI should be handled with care, as it is a hazardous substance. It should be stored in a cool, dry place, away from direct sunlight and incompatible materials.
2. **Exposure**: In case of exposure, immediate medical attention should be sought. CDI can cause irritation to the skin, eyes, and respiratory system.
3. **Disposal**: CDI should be disposed of according to local regulations and guidelines to minimize environmental impact.

Environmental Impact

1. **Toxicity**: CDI is toxic to aquatic organisms and can cause long-term adverse effects in the aquatic environment.
2. **Persistence**: CDI is persistent in the environment, which means it can remain in the ecosystem for an extended period.
3. **Regulation**: The use of CDI is regulated in many countries due to its potential environmental impact.

Conclusion

In conclusion, 1,1'-Carbonyldiimidazole (CAS 530-62-1) is a versatile compound with numerous applications in organic synthesis. This ultimate guide has provided an in-depth exploration of its chemical properties, synthesis methods, applications, safety considerations, and environmental impact. By understanding these aspects, researchers and chemists can make informed decisions regarding the use of CDI in their work.

Keywords: 1,1'-Carbonyldiimidazole, CAS 530-62-1, organic synthesis, coupling agent, safety, environmental impact