5-Bromouracil Chemical Properties

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

InChIKey

LQLQRFGHAALLLE-UHFFFAOYSA-N

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

Hazard Codes 

Xn

Risk Statements 

22-46

Safety Statements 

36/37-53-45-24/25

WGK Germany 

3

RTECS 

YQ9060000

TSCA 

Yes

HS Code 

29335995

Hazardous Substances Data

51-20-7(Hazardous Substances Data)

MSDS

• Language:English Provider:5-Bromo-2,4(1H,3H)-pyrimidinedione
• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

5-Bromouracil Usage And Synthesis

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.

Uses

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

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.

5-Bromouracil(51-20-7)Related Product Information

• 5-Bromopyrimidine
• Uracil
• Bromine
• 5-Bromouridine
• Broxuridine
• 5-Bromo-2'-deoxy-5'-uridylic acid disodium salt
• 5-Bromouracil-6-carboxylic acid
• Bromacil
• 5-bromo-2',3'-dideoxyuridine
• 6-amino-5-bromouraci
• 1-amino-5-bromouracil
• 5-BROMO-1,3-DIMETHYLURACIL
• 5-BROMO-2'-DEOXYURIDINE 5'-TRIPHOSPHATE SODIUM SALT
• 6-Amino-1-benzyl-5-bromouracil
• 5-BROMOURIDINE 5'-TRIPHOSPHATE SODIUM SALT
• 3',5'-DI-O-ACETYL-5-BROMO-2'-DEOXY-D-URIDINE
• 5-BROMO-6-METHYLURACIL
• 1,3,6-TRIMETHYL-5-BROMOURACIL