Di-tert-butyl dicarbonate
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Main Uses
Amino protecting reagent (core application):
In organic synthesis, used to protect the amino groups of primary amines (-NH₂) and secondary amines (-NH-):
Mild reaction conditions (typically at room temperature, in organic solvents, with the addition of a weak base such as triethylamine to promote the reaction); the generated Boc protecting group (-NHBoc) is stable under neutral or alkaline conditions and can withstand various reactions (such as alkylation, acylation, redox reactions, etc.).
Simple deprotection: Under acidic conditions (e.g., trifluoroacetic acid, hydrochloric acid/dioxane), the Boc protecting group can be quantitatively removed to release the free amine. The byproducts are carbon dioxide and tert-butanol, which are volatile and easily removed without affecting the purity of the target product.
Widely used in peptide synthesis and the preparation of pharmaceutical intermediates (such as antibiotics, amino acid derivatives, alkaloids, etc.), and is one of the preferred reagents for protecting amino groups in "solid-phase synthesis".
Other organic synthesis applications:
Used for the temporary protection of alcohol hydroxyl and phenol hydroxyl groups (forming carbonates), but this application is less common as acetyl or silyl ether reagents are more commonly used for hydroxyl protection.
Acts as a carbonylation reagent, participating in the synthesis of heterocyclic compounds (such as oxazolidines, pyrrolidines) and introducing the Boc group to modulate molecular structure.
Pharmaceutical and chemical production:
In drug synthesis, used to prepare anti-AIDS drugs, antibiotics, antitumor drugs, etc., improving reaction selectivity by protecting sensitive amino groups.
Used to synthesize pesticide intermediates and dye molecules, optimizing reaction pathways to reduce byproducts.
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