57412-59-6

Usage

Uses

Used in Organic Synthesis:
(E)-5-CARBOXYVINYL URACIL is used as a synthetic building block for the creation of various organic compounds. Its unique structure allows it to be a valuable component in the synthesis of complex molecules, contributing to the development of new materials and pharmaceuticals.
Used in Pharmaceutical Industry:
(E)-5-CARBOXYVINYL URACIL is used as an intermediate in the development of new drugs. Its chemical properties make it a promising candidate for the synthesis of novel therapeutic agents, potentially leading to the discovery of innovative treatments for various medical conditions.
Used in Chemical Research:
(E)-5-CARBOXYVINYL URACIL is also utilized in chemical research to study the properties and behavior of uracil derivatives. This knowledge can be applied to understand the fundamental aspects of organic chemistry and contribute to the advancement of the field.

Upstream product

• 1195-08-0 2,4-dioxo-1,2,3,4-tetrahydropyrimidine-5-carbaldehyde 
• 141-82-2 malonic acid 

Downstream Products

• 69304-49-0 (E)-5-(2-bromovinyl)uracil 
• 69304-48-9 (E)-5-(2-Iodovinyl)-2'-deoxyuridine 
• 69304-47-8 (E)-5-(2-bromovinyl)-2'-deoxyuridine 
• 73446-77-2 C₂₇H₂₅IN₂O₇ 
• 73456-10-7 E-5-(2-iodovinyl)-3',5'-di-O-p-toluoyl-2'-deoxyuridine 
• 73446-75-0 (E)-5-(2-bromovinyl)-1-<2-deoxy-3,5-di-O-(p-toluoyl)-α-D-erythro-pentofuranosyl>uracil 
• 73446-74-9 (E)-5-(2-bromovinyl)-2'-deoxy-3',5'-di-O-(p-toluoyl)uridine 

Relevant academic research and scientific papers

Synthesis of Some 5-Halogenovinyl Derivatives of Uracil and their Conversion into 2'-Deoxyribonucleosides

Treatment of 5-formyluracil with malonic acid in the presence of piperidine gave (E)-5-(2-carboxyvinyl)uracil which, upon reaction with the appropriate N-halogenosuccinimide, gave (E)-5-(2-bromovinyl)uracil, (E)-5-(2-chlorovinyl)uracil, and (E)-5-(2-iodovinyl)uracil.The last mentioned compound was also obtained by the action of iodine chloride on 5-vinyluracil. 5-(1-Chlorovinyl)uracil upon treatment with bromine gave 5-(2-bromo-1-chlorovinyl)uracil which reacted with sodium methoxide to give 5-bromoethynyluracyl. (E)-5-(2-Bromovinyl)uracil was converted into its trimethylsilyl derivative which was condensed with 2-deoxy-3,5-di-O-(p-toluoyl)-α-D-erythro-pentofuranosyl chloride to give the α- and β-anomers of the blocked deoxyribonucleoside.Removal of the p-toluoyl blocking groups with sodium methoxide afforded (E)-5-(2-bromovinyl)-1-(2-deoxy-α-D-erythro-pentofuranosyl)uracil and (E)-5-(2-bromovinyl)-2'-deoxyuridine.A similar series of reactions gave (E)-5-(2-iodovinyl)-2'-deoxyuridine and 5-(2-bromo-1-chlorovinyl)-2'-deoxyuridine. 5-(1-Chlorovinyl)uracil could be condensed similarly with the blocked sugar derivative to give the α- and β-anomers of the blocked deoxyribonucleoside.Attempted removal of the groups with sodium methoxide gave 2'-deoxy-5-ethynyluridine and mild treatment with methanolic ammonia gave the same product and some 2'-deoxy-5-ethynyl-5'-O-(p-toluoyl)uridine. 5-(1-Chlorovinyl)-2'-deoxyuridine was obtained by the addition of HCl to 2'-deoxy-5-ethynyluridine.Aspects of the elimination reactions of 5-(halogenovinyl)uracil derivatives are discussed.