5-Bromouracil
[CAS# 51-20-7]

Identification

• Classification: Pharmaceutical intermediate >> Heterocyclic compound intermediate >> Pyrimidine compound >> Urinary (urea) pyrimidine
• Name: 5-Bromouracil
• Synonyms: 5-Bromo-2,4(1H,3H)-pyrimidinedione; 5-Bromopyrimidine-2,4-diol
• Molecular Formula: C₄H₃BrN₂O₂
• Molecular Weight: 190.98
• CAS Registry Number: 51-20-7
• EC Number: 200-084-0
• SMILES: C1=C(C(=O)NC(=O)N1)Br

Properties

• Melting point: 310 ºC
• Water solubility: SOLUBLE IN COLD WATER

Safety Data

• Hazard Symbols: GHS07 Warning
• Hazard Statements: H302
• Precautionary Statements: P264-P270-P301+P317-P330-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Acute toxicity	Acute Tox.	4	H302

Discovory and Applicatios

5-Bromouracil (C4H3BrN2O2) is a halogenated pyrimidine derivative that is commonly used in research and pharmaceutical applications. It is a synthetic analogue of uracil, one of the four nucleotide bases found in RNA. The compound is characterized by the substitution of a bromine atom at the 5-position of the uracil ring, which significantly alters its chemical behavior and biological activity. Its discovery and applications have played a key role in advancing various fields of chemistry and biology, particularly in molecular biology, medicinal chemistry, and cancer research.

The discovery of 5-bromouracil dates back to the mid-20th century, as part of ongoing research to study the effects of halogenated pyrimidines on nucleic acids. This discovery was driven by the growing understanding of the importance of nucleotide analogues in influencing the synthesis and replication of nucleic acids. Researchers identified 5-bromouracil as a compound that could interfere with DNA and RNA processes by substituting for uracil, thus leading to a broad range of biological and biochemical effects. Over time, 5-bromouracil has proven to be a useful tool in scientific studies, especially for its ability to incorporate into DNA and RNA and induce mutations.

In molecular biology, 5-bromouracil is often used as a mutagen in experiments involving the study of DNA replication and repair. Its similarity to uracil allows it to be incorporated into the growing strand of DNA during replication, where it pairs with adenine instead of thymine. This mispairing leads to base substitutions during DNA replication, making 5-bromouracil a valuable tool in mutagenesis studies. These mutations can be studied to gain insights into the mechanisms of genetic variation, mutagenesis, and the effects of DNA damage.

5-Bromouracil is also employed in research to study the properties and behavior of nucleic acids. As a thymine analogue, it is used to explore the structural and functional roles of the base pairs in DNA. Researchers can investigate how the presence of 5-bromouracil affects the stability of the double helix, the replication process, and the fidelity of DNA synthesis. Its incorporation into RNA is similarly studied for understanding RNA structure and function, especially in the context of RNA transcription and translation.

In the pharmaceutical industry, 5-bromouracil and its derivatives are being explored for their potential therapeutic applications. The compound has shown promise as an anticancer agent due to its ability to induce DNA damage and inhibit cancer cell proliferation. Some studies have also suggested that 5-bromouracil may have antiviral properties, particularly against RNA viruses, although more research is required to fully understand its therapeutic potential. Its use in cancer research is particularly noteworthy, as it can be incorporated into the DNA of rapidly dividing cancer cells, leading to mutagenic effects that can slow or halt cell growth.

In addition to its biological applications, 5-bromouracil is utilized in the synthesis of other chemical compounds, including nucleoside analogues and pharmaceutical intermediates. Its bromine substitution provides a useful handle for further chemical modifications, which can enhance its biological activity or modify its pharmacological properties. These modified compounds are being investigated for a wide range of applications, including as antiviral agents, anticancer drugs, and immunosuppressive agents.

In summary, 5-bromouracil is a halogenated pyrimidine derivative with a wide range of applications in molecular biology, cancer research, and drug development. Its ability to mimic uracil in DNA and RNA allows it to be used as a mutagen, enabling studies on genetic mutations and nucleic acid behavior. Additionally, its potential as an anticancer and antiviral agent positions it as a compound of interest in medicinal chemistry. Ongoing research into the properties of 5-bromouracil continues to expand its potential applications in both basic science and drug development.

References

2007. Mitochondrial Thymidine Kinase and the Enzymatic Network Regulating Thymidine Triphosphate Pools in Cultured Human Cells. The Journal of biological chemistry, 282(47).
DOI: 10.1074/jbc.m705923200

2005. Electron ionization induced mass spectral study of 2-alkylthio- and 4-alkykthio-5-bromouracils. Rapid communications in mass spectrometry : RCM, 19(8).
DOI: 10.1002/rcm.1898

2003. Phagocytes Produce 5-Chlorouracil and 5-Bromouracil, Two Mutagenic Products of Myeloperoxidase, in Human Inflammatory Tissue. The Journal of biological chemistry, 278(26).
DOI: 10.1074/jbc.m303928200