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Di-tert-butyl dicarbonate (CAS: 24424-99-5): A Versatile Chemical Compound

2023-10-30

Di-tert-butyl dicarbonate, often referred to as Boc anhydride, is a valuable chemical compound with the chemical formula C10H18O5. It has found widespread applications in various fields due to its unique properties and versatility.

 

 

Chemical Structure:

 

Di-tert-butyl dicarbonate features a chemical structure consisting of two tert-butyl (t-Bu) ester groups linked by a carbonyl group (C=O). The compound is a colorless to pale yellow liquid at room temperature.

 

Applications:

 

1. Protecting Group in Organic Synthesis: Di-tert-butyl dicarbonate is commonly used as a protecting group for amines in organic synthesis. It can block the amino group's reactivity, allowing selective reactions to occur at other functional groups. This is particularly useful in the synthesis of complex molecules.

 

2. Carbonylating Agent: It serves as a reagent for the introduction of carbonyl groups in various chemical reactions, enabling the formation of esters, amides, and other carbonyl-containing compounds.

 

3. Pharmaceuticals: Di-tert-butyl dicarbonate is widely used in the pharmaceutical industry for the synthesis of drugs and pharmaceutical intermediates. It helps protect sensitive functional groups during chemical reactions.

 

4. Peptide Synthesis: In the field of peptide chemistry, Boc anhydride is used for the protection and deprotection of amino acids, allowing the stepwise assembly of peptides.

 

5. Agrochemicals: It finds applications in the synthesis of agrochemicals and crop protection agents.

 

Key Features:

 

- Selective Protection: Di-tert-butyl dicarbonate offers selective protection of amino groups while leaving other functional groups unaffected.

 

- Stability: It is stable under most storage conditions and can be easily handled in a laboratory setting.

 

- Compatibility: It is compatible with a wide range of organic solvents and reagents, making it a versatile choice for various reactions.

 

Safety Considerations:

 

Di-tert-butyl dicarbonate should be handled with care, as it can be an irritant to the skin, eyes, and respiratory system. Proper safety precautions, including the use of protective equipment and adequate ventilation, should be observed when working with this compound.

 

In conclusion, di-tert-butyl dicarbonate is a valuable chemical reagent with diverse applications in organic synthesis, pharmaceuticals, and other industries. Its ability to selectively protect functional groups makes it an indispensable tool for chemists and researchers working on complex molecule synthesis and drug development.