3-(2,4-dioxo-1H-pyrimidin-5-yl)prop-2-enoic acid

Base Information

• Chemical Name: 3-(2,4-dioxo-1H-pyrimidin-5-yl)prop-2-enoic acid
• CAS No.: 57412-59-6
• Molecular Formula: C7H6N2O4
• Molecular Weight: 182.136
• European Community (EC) Number: 866-611-7
• Mol file: 57412-59-6.mol

Synonyms:57412-59-6;(E)-3-(2,4-Dioxo-1,2,3,4-tetrahydropyrimidin-5-yl)acrylic acid;AKOS030239986;SB56759;NCI60_001667;NCI60_001885;FT-0664374

Chemical Property of 3-(2,4-dioxo-1H-pyrimidin-5-yl)prop-2-enoic acid

Chemical Property:

• PSA: 103.02000
• LogP: -0.83900
• XLogP3: -1
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 2
• Exact Mass: 182.03275668
• Heavy Atom Count: 13
• Complexity: 329

Purity/Quality:

99%min ^*data from raw suppliers

(E)-5-(2-Carboxvinyl)uracil ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=C(C(=O)NC(=O)N1)C=CC(=O)O
• Uses: (E)-5-(2-Carboxvinyl)uracil (cas# 57412-59-6) is a compound useful in organic synthesis.

Technology Process of 3-(2,4-dioxo-1H-pyrimidin-5-yl)prop-2-enoic acid

There total 3 articles about 3-(2,4-dioxo-1H-pyrimidin-5-yl)prop-2-enoic acid which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 78.0%

2,4-dioxo-1,2,3,4-tetrahydropyrimidine-5-carbaldehyde (1195-08-0) + malonic acid (141-82-2) → (E)-5-(2-carboxyvinyl)uracil (57412-59-6)

Guidance literature:

With piperidine; pyridine; for 2h; Heating;

DOI:10.1039/P19810001665

Reference yield:

→ (E)-5-(2-carboxyvinyl)uracil (57412-59-6)

Guidance literature:

With alkaline solution;

DOI:10.1093/geront/40.4.492

Reference yield:

→ (E)-5-(2-carboxyvinyl)uracil (57412-59-6)

Guidance literature:

Uracil 12, Malonsaeure;

DOI:10.1021/jo00942a015

upstream raw materials:

2,4-dioxo-1,2,3,4-tetrahydropyrimidine-5-carbaldehyde

malonic acid

Downstream raw materials:

(E)-5-(2-Iodovinyl)-2'-deoxyuridine

(E)-5-(2-bromovinyl)-2'-deoxyuridine

C₂₇H₂₅IN₂O₇

E-5-(2-iodovinyl)-3',5'-di-O-p-toluoyl-2'-deoxyuridine

Refernces

• 1、 Barr, Philip J.,Jones, A. Stanley,Verhelst, Gabriel,Walker, Richard T.. "Synthesis of Some 5-Halogenovinyl Derivatives of Uracil and their Conversion into 2'-Deoxyribonucleosides". . p. 1665 - 1670. Retrieved 2007/10/02.