6-AMINO-5-BROMOPYRIMIDIN-2(1H)-ONE Chemical Properties

Melting point:

240-243 °C (dec.) (lit.)

Density 

1.7513 (rough estimate)

refractive index 

1.6520 (estimate)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

solubility 

Soluble in formic acid (50 mg/ml).

form 

Solid

pka

7.34±0.10(Predicted)

color 

White to yellow

BRN 

127286

InChI

InChI=1S/C4H4BrN3O/c5-2-1-7-4(9)8-3(2)6/h1H,(H3,6,7,8,9)

InChIKey

QFVKLKDEXOWFSL-UHFFFAOYSA-N

SMILES

C1(=O)NC(N)=C(Br)C=N1

NIST Chemistry Reference

5-Bromocytosine(2240-25-7)

Safety Information

Hazard Codes 

Xn

Risk Statements 

22-37/38-41-43-48-20/21/22

Safety Statements 

24/25-22-36/37/39-26-45-7/8

WGK Germany 

3

F 

10-23

HS Code 

29335990

MSDS

• Language:English Provider:ACROS
• Language:English Provider:SigmaAldrich

6-AMINO-5-BROMOPYRIMIDIN-2(1H)-ONE Usage And Synthesis

Chemical Properties

LIGHT YELLOW AMORPHOUS POWDER

Uses

4-Amino-5-bromo-2-hydroxypyrimidine can be used in the synthesis of cross-link products under anaerobic and aerobic conditions.

Uses

5-Bromocytosine was used in the synthesis of five cross-link products- C[5-N6]A, C[5-2]A, C[5-8]A, A[2-5]C, and A[8-5]C, under both aerobic and anaerobic conditions.

General Description

5-Bromocytosine derivative (β isomer) is a potent anti-HIV agent.

Synthesis

General procedure for the synthesis of 4-amino-5-bromopyrimidin-2(1H)-one from 6-aminopyrimidin-2(1H)-one: 6-aminopyrimidin-2(1H)-one (55.6 g, 0.5 mol), N-bromosuccinimide (106.8 g, 0.6 mol) and DMF (150 mL) were added to a reaction flask, cooled to 15°C, and ultrasonicated for reaction under ultrasonic condition for 1 hour. The progress of the reaction was monitored by thin layer chromatography (TLC) and after confirming the complete reaction of the raw materials, it was filtered. The filter cake was washed with distilled water (20 mL×2) and dried to obtain 4-amino-5-bromopyrimidin-2(1H)-one (90.9 g, 95.6% yield).

Purification Methods

5-Bromocytosine is recrystallised from H2O or 50% aqueous EtOH. Alternatively, dissolve ca 3g in conc HCl (10mL) and evaporate to dryness. Dissolve the residual hydrochloride in the minimum volume of warm H2O and make faintly alkaline with aqueous NH3. Collect the crystals and dry them in a vacuum at 100o. [Hilbdert & Jensen J Am Chem Soc 56 134 1934, Beilstein 25 III/IV 3689.]

References

[1] Patent: CN103819412, 2016, B. Location in patent: Paragraph 0023-0025; 0031-0032; 0037; 0038
[2] Synthesis, 2005, # 7, p. 1103 - 1108
[3] Tetrahedron Letters, 1992, vol. 33, # 50, p. 7779 - 7782
[4] Chemistry Letters, 1987, p. 2311 - 2312
[5] Bulletin of the Chemical Society of Japan, 1989, vol. 62, # 11, p. 3750 - 3751

6-AMINO-5-BROMOPYRIMIDIN-2(1H)-ONE(2240-25-7)Related Product Information

• Cytosine
• 5-Fluorouracil
• Fluorocytosine
• 5-Azacytosine
• 5-Bromouracil
• 5-Chlorouracil
• N4-Acetylcytosine
• 5-METHYLCYTOSINE
• 5-METHYLCYTOSINE HYDROCHLORIDE
• 5-BROMOPYRIMIDIN-4-AMINE
• 5-Bromopyrimidine
• 5-Bromo-2-hydroxypyrimidine
• 5-Bromo-2'-deoxycytidine
• 6-AMINO-5-BROMOPYRIMIDIN-2(1H)-ONE
• 5-BROMOCYTIDINE
• 6-AMINO-5-BROMOPYRIMIDIN-4(3H)-ONE
• 5-BROMO-DC CEP
• 5-BROMO-2'-DEOXYCYTIDINE-5'-TRIPHOSPHATE LITHIUM SALT