5-IODOCYTOSINE Chemical Properties

Density 

2.65±0.1 g/cm3(Predicted)

storage temp. 

Keep in dark place,Inert atmosphere,Store in freezer, under -20°C

solubility 

formic acid: 50mg/mL

pka

7.58±0.10(Predicted)

form 

powder

Appearance

Off-white to light yellow Solid

biological source

synthetic (organic)

Safety Information

Hazard Codes 

Xn

Risk Statements 

22

Safety Statements 

24/25

WGK Germany 

3

RTECS 

HA6125000

F 

8-10-23

HS Code 

29335990

Toxicity

mouse,LDLo,intraperitoneal,50mg/kg (50mg/kg),Biochemical Pharmacology. Vol. 13, Pg. 1249, 1964.

MSDS

• Language:English Provider:SigmaAldrich

5-IODOCYTOSINE Usage And Synthesis

Chemical Properties

Off-white solid

Uses

6-Amino-5-iodopyrimidin-2(1H)-one is an iodinated nucleobase for peptide modified nucleic acids.

Synthesis

A mixture of N-iodosuccinimide (18.562 g, 82.5 mmol) and 6-aminopyrimidin-2(1H)-one (8.333 g, 75 mmol) was dissolved in DMF (50 mL) under argon protection. The reaction vessel was covered with aluminum foil and sonicated for 30 min to fully dissolve the solids at the bottom. Subsequently, the reaction mixture was stirred at room temperature for 12 hours. Upon completion of the reaction, the mixture was poured into water (150 mL) to quench the reaction. The resulting precipitate was collected by filtration, washed with water and dried in the presence of phosphorus pentoxide (P2O5) to afford 4-amino-5-iodopyrimidin-2(1H)-one as a light tan solid (17.703 g, 99% yield). The product could be used in the subsequent reaction without further purification.

References

[1] Patent: US7741294, 2010, B1. Location in patent: Page/Page column 17
[2] European Journal of Organic Chemistry, 2015, vol. 2015, # 32, p. 7160 - 7175
[3] Journal of Medicinal Chemistry, 1983, vol. 26, # 2, p. 152 - 156
[4] Tetrahedron, 2012, vol. 68, # 26, p. 5145 - 5151
[5] Journal of Heterocyclic Chemistry, 2015, vol. 52, # 5, p. 1382 - 1389

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