(E)-5-(2-Bromovinyl)uracil

Base Information

• Chemical Name: (E)-5-(2-Bromovinyl)uracil
• CAS No.: 69304-49-0
• Molecular Formula: C6H5BrN2O2
• Molecular Weight: 217.022
• DSSTox Substance ID: DTXSID801310909
• Nikkaji Number: J535.342D,J275.186K
• ChEMBL ID: CHEMBL68200
• Mol file: 69304-49-0.mol

Synonyms:5-(2-bromovinyl)uracil;5-bromovinyluracil

Chemical Property of (E)-5-(2-Bromovinyl)uracil

Chemical Property:

• Melting Point: 189-194 °C (dec.)(lit.)
• Refractive Index: 1.685
• PKA: 7.54±0.10(Predicted)
• PSA: 65.72000
• Density: 1.881 g/cm³
• LogP: 0.42880
• Storage Temp.: -20?C Freezer, Under Inert Atmosphere
• Solubility.: DMSO (Slightly), Methanol (Slightly, Heated)
• XLogP3: 0.1
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 215.95344
• Heavy Atom Count: 11
• Complexity: 257

Purity/Quality:

≥99.0% ^*data from raw suppliers

(E)-5-(2-Bromovinyl)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=CBr
• Isomeric SMILES: C1=C(C(=O)NC(=O)N1)/C=C/Br

Technology Process of (E)-5-(2-Bromovinyl)uracil

There total 6 articles about (E)-5-(2-Bromovinyl)uracil 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: 84.0%

5-vinyluracil (37107-81-6) → (E)-5-(2-bromovinyl)uracil (69304-49-0)

Guidance literature:

In N-methyl-acetamide; water;

Reference yield: 81.0%

(E)-5-(2-carboxyvinyl)uracil (57412-59-6) → (E)-5-(2-bromovinyl)uracil (69304-49-0)

Guidance literature:

With N-Bromosuccinimide; potassium acetate; In water; at 90 ℃;

DOI:10.1039/P19810001665

Reference yield: 65.0%

E-5-(2-bromovinyl)-2,4-dimethoxypyrimidine (134700-28-0) → (E)-5-(2-bromovinyl)uracil (69304-49-0)

Guidance literature:

With sodium iodide; In acetic acid;

upstream raw materials:

(E)-5-(2-carboxyvinyl)uracil

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

E-5-(2-bromovinyl)-2,4-dimethoxypyrimidine

5-vinyluracil

Downstream raw materials:

furo[2,3-d]pyrimidin-2(3H)-one

3-benzoyl-5-(2-bromovinyl)uracil

(E)-5-(2-bromovinyl)-3',5'-di-O-p-toluoyl-2'-deoxy-4'-thiothymidine

α-(E)-5-(2-bromovinyl)-3',5'-di-O-p-toluoyl-2'-deoxy-4'-thiothymidine

Refernces

• 1、 Eger,Jalalian,Schmidt. "Steric fixation of bromovinyluracil: Synthesis of furo[2,3-d]pyrimidine nucleosides". . p. 211 - 218. Retrieved 2007/10/02.
• 2、 -. "Preparation of thionucleosides". . . Retrieved 2008/06/13.