51-20-7 Usage
Description
5-Bromouracil is a pyrimidine derivative characterized by the presence of keto groups at the 2and 4-positions and a bromo group at the 5-position. It is a white powder that exhibits chemical properties, forming prisms from water (H2O). As a major chemical mutagen, it incorporates into DNA and alters base-pair sequencing by replacing thymine.
Uses
Used in Genetic Research:
5-Bromouracil is used as a mutagen for inducing genetic mutations in various organisms. Its incorporation into DNA alters the base-pair sequencing, which can lead to the development of new traits or characteristics in the organism.
Used in Cancer Research:
In cancer research, 5-Bromouracil is used as a tool to study the mechanisms of DNA repair and the role of thymine in DNA structure. Its mutagenic properties can help researchers understand how cancer cells develop and how they can be targeted for treatment.
Used in Pharmaceutical Industry:
5-Bromouracil is used as an intermediate in the synthesis of various pharmaceutical compounds. Its unique chemical structure allows for the development of new drugs with potential applications in treating various diseases, including cancer.
Used in Chemical Synthesis:
As a chemical mutagen, 5-Bromouracil is used in the synthesis of other chemical compounds with potential applications in various industries, such as agriculture, materials science, and environmental science.
Used in Diagnostics:
5-Bromouracil can be used in the development of diagnostic tools and tests for detecting specific genetic mutations or alterations in DNA sequences, which can be crucial in the early detection and treatment of various diseases, including cancer.
Air & Water Reactions
Insoluble in water.
Hazard
Moderately toxic, alters DNA by replacing
thymine.
Health Hazard
ACUTE/CHRONIC HAZARDS: When heated to decomposition 5-Bromouracil emits very toxic fumes of bromide ion and NOx.
Fire Hazard
Flash point data for 5-Bromouracil are not available, but 5-Bromouracil is probably combustible.
Safety Profile
Moderately toxic by
intraperitoneal route. Experimental
reproductive effects. Mutation data
reported. When heated to decomposition it
emits very toxic fumes of Brand NOx.
Check Digit Verification of cas no
The CAS Registry Mumber 51-20-7 includes 5 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 2 digits, 5 and 1 respectively; the second part has 2 digits, 2 and 0 respectively.
Calculate Digit Verification of CAS Registry Number 51-20:
(4*5)+(3*1)+(2*2)+(1*0)=27
27 % 10 = 7
So 51-20-7 is a valid CAS Registry Number.
InChI:InChI=1/C4H3BrN2O2/c5-2-1-6-4(9)7-3(2)8/h1H,(H2,6,7,8,9)
51-20-7Relevant articles and documents
Ettorre, Renato,Gonzalez Sanchez, Angeles
, p. 221 - 226 (1990)
Carbonic anhydrase inhibitory properties of some uracil derivatives
Alper Türko?lu, Emir,?entürk, Murat,Supuran, Claudiu T.,Ekinci, Deniz
, p. 74 - 77 (2017)
Inhibitors of carbonic anhydrase (CA) have been carried out in many therapeutic applications, especially antiglaucoma activity. In this study, we investigated some uracil derivatives (4–12) to inhibit human CA I (hCA I) and II (hCA II) isoenzymes. The KI values of the compounds 4–12 are in the range of 0.085–428 μM for hCA I and of 0.1715–645 μM against hCA II, respectively. It is concluded from the kinetic investigations, all compounds used in the study act as competitive inhibitors with substrate, 4-NPA. Uracil derivatives are emerging agents for the inhibiton of carbonic anhydrase which could be used in biomedicine.
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Riederer et al.
, p. 313 (1978)
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The synthesis and antituberculosis activity of 5-alkynyl uracil derivatives
Platonova, Yana B.,Tomilova, Larisa G.,Volov, Alexander N.
, (2020/06/26)
A series of new 5-alkynyl-substituted uracil and uridine derivatives were synthesised via palladium-catalysed Sonogashira cross-coupling reaction of 5-bromo-pyrimidine base with terminal acetylenes with good yields in DMF at room temperature. All obtained compounds were tested for antimycobacterial activity against Mycobacetrium bovis and Mycobacterium tuberculosis (H37Ra) at concentrations of 1–100 μg/ml using MABA test. Obtained results revealed that most of tested uracil derivatives exhibited high antimycobacterial activity (MIC50 = 1.1–19.2 μg/ml) in comparison with therapeutic agents such as rifampicin, isoniazid and D-cycloserine, excluding compounds having alkyl substituent at triple alkyne bond.
A 5 - bromo uracil preparation method
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Paragraph 0033-0040, (2019/10/04)
The invention discloses a preparation method for 5-bromouracil. By taking uracil as an initial raw material, sodium bromide and sodium hypochlorite as a green bromating agent, and water as a solvent, a mild brominating reaction is carried out under an acidic condition to obtain a high purity target product. The preparation method disclosed by the invention is green and environmental-friendly in synthetic process, convenient in post-treatment and suitable for large-scaled industrial production.