5-Bromouracil

Base Information

• Chemical Name: 5-Bromouracil
• CAS No.: 51-20-7
• Deprecated CAS: 5909-23-9
• Molecular Formula: C4H3BrN2O2
• Molecular Weight: 190.984
• Hs Code.: 29335995
• European Community (EC) Number: 200-084-0
• NSC Number: 19940
• UN Number: 2811
• UNII: 4HK400G5UO
• DSSTox Substance ID: DTXSID2058758
• Nikkaji Number: J2.304C
• Wikipedia: 5-Bromouracil
• Wikidata: Q238477
• Metabolomics Workbench ID: 53768
• ChEMBL ID: CHEMBL144730
• Mol file: 51-20-7.mol

Synonyms:5 Bromouracil;5-Bromouracil;Bromouracil;Bromuracil

Chemical Property of 5-Bromouracil

Chemical Property:

• Appearance/Colour: White powder.
• Melting Point: >300 °C(lit.)
• Refractive Index: 1.59
• Boiling Point: 384oC
• PKA: 6.77±0.10(Predicted)
• PSA: 65.72000
• Density: 1.965 g/cm³
• LogP: -0.17430
• Storage Temp.: -20°C Freezer
• Solubility.: <1g/l
• Water Solubility.: SOLUBLE IN COLD WATER
• XLogP3: -0.2
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 189.93779
• Heavy Atom Count: 9
• Complexity: 199
• Transport DOT Label: Poison

Purity/Quality:

99% ^*data from raw suppliers

5-Bromouracil ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 22-46
• Safety Statements: 36/37-53-45-24/25

MSDS Files:

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Biological Agents -> Nucleic Acids and Derivatives
• Canonical SMILES: C1=C(C(=O)NC(=O)N1)Br
• Uses: A major chemical mutagen. Incorporates into DNA, altering base-pair sequencing by replacing thymine

Technology Process of 5-Bromouracil

There total 38 articles about 5-Bromouracil 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: 99.9%

uracil (66-22-8,144104-68-7,18324-22-6,27072-01-1,2920-92-5,51953-19-6) → 5-bromouracil (51-20-7)

Guidance literature:

With 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione; acetic anhydride; acetic acid; at 50 ℃; for 1.5h; Temperature; Reagent/catalyst;

Reference yield: 84.0%

5-bromo-2,4-bis(4-methoxybenzyloxy)pyrimidine (664988-37-8) → 5-bromouracil (51-20-7)

Guidance literature:

With trifluoroacetic acid; In dichloromethane; at 20 ℃; for 0.25h;

DOI:10.1039/b306341k

Reference yield: 84.0%

5,5'-mercuribis(uracil) (97759-31-4) → 5-bromouracil (51-20-7)

Guidance literature:

With bromine; potassium bromide; In water; at 80 ℃; for 0.5h;

DOI:10.1007/BF00479920

upstream raw materials:

5,5-dibromo-6-hydroxy-5,6-dihydrouracil

5-bromo-2,6-dioxo-1,2,3,6-tetrahydropyrimidine-4-carboxylic acid

uracil

5-bromo-2,4-dimethoxypyrimidine

Downstream raw materials:

5-morpholinopyrimidine-2,4(1H,3H)-dione

5-[(4-methylphenyl)amino]uracil

5-(phenylamino)pyrimidine-2,4(1H,3H)-dione

5-[(3-methylphenyl)amino]uracil

Refernces

• 1、 Hüttermann,Müller. "Free radicals in irradiated single crystals of 5-halo-uracil derivatives: 5-bromouracil, 5-bromodeoxyuridine and 5-iododeoxyuridine.". . p. 297 - 313. Retrieved 1969.
• 2、 Moore,Anderson. "-". . p. 590,591. Retrieved 1959.
• 3、 Moir, Michael,Lane, Samuel,Montgomery, Andrew P.,Hibbs, David,Connor, Mark,Kassiou, Michael. "The discovery of a potent and selective pyrazolo-[2,3-e]-[1,2,4]-triazine cannabinoid type 2 receptor agonist". . . Retrieved 2020/12/21.
• 4、 Kaspar, Felix,Giessmann, Robert T.,Neubauer, Peter,Wagner, Anke,Gimpel, Matthias. "Thermodynamic Reaction Control of Nucleoside Phosphorolysis". supporting information. p. 867 - 876. Retrieved 2020/01/24.