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HomeProduct name list5-Bromouracil

5-Bromouracil

Synonym(s):5-Bromo-2,4-dihydroxypyrimidine

  • CAS NO.:51-20-7
  • Empirical Formula: C4H3BrN2O2
  • Molecular Weight: 190.98
  • MDL number: MFCD00006017
  • EINECS: 200-084-0
  • SAFETY DATA SHEET (SDS)
  • Update Date: 2024-10-31 18:15:48
5-Bromouracil Structural

What is 5-Bromouracil?

Description

5-bromouracil (5-BU) is a uracil derivative, and its 5' position of the pyrimidine ring is halogenated. If 5-BU is incorporated into DNA in place of thymine, the tautomeric shift will occur, and the 5-BU will base pair with guanine. After the replication, an A-T to G-C transition occurs. Furthermore, the presence of 5-BU within DNA increases the sensitivity of the molecule to UV light. 5-BU is structurally similar to thymine. Therefore, it is considered a thymine analog and base-pairs normally with adenine. It is rarely present in its enol form, where its base pairs with guanine. 5-Bromouracil treats neoplasms in the form of its nucleoside, 5-bromo-2-deoxy-uridine[1-2].

Chemical properties

Prisms from H 2 O.

The Uses of 5-Bromouracil

A major chemical mutagen. Incorporates into DNA, altering base-pair sequencing by replacing thymine

What are the applications of Application

5-Bromouracil is a major chemical mutagen

Definition

ChEBI: A pyrimidine having keto groups at the 2- and 4-positions and a bromo group at the 5-position.

General Description

White powder.

Air & Water Reactions

Insoluble in water.

Reactivity Profile

A halogenated amide. Organic amides/imides react with azo and diazo compounds to generate toxic gases. Flammable gases are formed by the reaction of organic amides/imides with strong reducing agents. Amides are very weak bases (weaker than water). Imides are less basic yet and in fact react with strong bases to form salts. That is, they can react as acids. Mixing amides with dehydrating agents such as P2O5 or SOCl2 generates the corresponding nitrile. The combustion of these compounds generates mixed oxides of nitrogen (NOx).

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.

References

[1] Bhagavan, N. and C. Ha. “Chapter 21 – Structure and Properties of DNA.” (2015): 381-400.
[2] Shen, Chang-Hui. “Nucleic Acid-Based Cellular Activities.” Diagnostic Molecular Biology 25 1 (2019): 27-57.

Properties of 5-Bromouracil

Melting point: >300 °C (lit.)
Density  1.8710 (rough estimate)
refractive index  1.6200 (estimate)
storage temp.  Keep in dark place,Sealed in dry,Room Temperature
solubility  <1g/l
form  Solid
pka 6.77±0.10(Predicted)
color  White
Water Solubility  SOLUBLE IN COLD WATER
Merck  14,1445
BRN  127176
CAS DataBase Reference 51-20-7(CAS DataBase Reference)
NIST Chemistry Reference 5-Bromouracil(51-20-7)
EPA Substance Registry System 5-Bromouracil (51-20-7)

Safety information for 5-Bromouracil

Signal word Warning
Pictogram(s)
ghs
Health Hazard
GHS08
GHS Hazard Statements H341:Germ cell mutagenicity
Precautionary Statement Codes P201:Obtain special instructions before use.
P202:Do not handle until all safety precautions have been read and understood.
P280:Wear protective gloves/protective clothing/eye protection/face protection.
P308+P313:IF exposed or concerned: Get medical advice/attention.
P405:Store locked up.

Computed Descriptors for 5-Bromouracil

InChIKey LQLQRFGHAALLLE-UHFFFAOYSA-N

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