5-Azacytosine Chemical Properties

Melting point:

>300 °C (lit.)

Boiling point:

209.98°C (rough estimate)

Density 

1.86

refractive index 

1.8010 (estimate)

storage temp. 

Keep in dark place,Inert atmosphere,2-8°C

solubility 

Aqueous Base (Slightly, Heated), DMSO (Slightly, Heated)

form 

Solid

pka

7.61±0.10(Predicted)

color 

White to Off-White

BRN 

116378

InChI

InChI=1S/C3H4N4O/c4-2-5-1-6-3(8)7-2/h1H,(H3,4,5,6,7,8)

InChIKey

MFEFTTYGMZOIKO-UHFFFAOYSA-N

SMILES

N1C(N)=NC=NC1=O

CAS DataBase Reference

931-86-2(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi,Xn

Risk Statements 

20/21/22-36/37/38

Safety Statements 

22-24/25-36-26

WGK Germany 

3

RTECS 

XZ2854300

HS Code 

29336990

MSDS

• Language:English Provider:5-Azacytosine
• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS

5-Azacytosine Usage And Synthesis

Chemical Properties

Crystalline Solid

Uses

Reactant for:

• Enzymic synthesis of nucleoside analogs using immobilized 2′-deoxyribosyltransferase from Lactobacillus reuteri
• Reactions with oxide radical ion

• Potential antitumor and antiproliferative agent against human leukemia cells

Uses

5-Azacytosine can inhibits the growth of Escherichia coli and used as the most effective cytosine mimics for the design of novel antiviral and anti-tumor drug candidates.

Definition

ChEBI: A monoamino-1,3,5-triazine that is cytosine in which the aromatic CH at position 5 is replaced by a nitrogen.

Synthesis

(1) Add 1.5Kg of anhydrous formic acid (99.5% purity), 2.5kg of dicyandiamide and 0.005Kg of p-toluenesulfonic acid catalyst to a 10L autoclave. Under the condition of sealing and stirring, the reaction system was slowly warmed up to 110°C and the reaction pressure was maintained. After the reaction was completed, the temperature was slowly cooled down to room temperature to obtain a white solid product. (2) The resulting white solid was transferred to a 50L glass reactor and 10L of dilute hydrochloric acid solution with a mass concentration of 5% was added. Heating was refluxed for 30 minutes until the solution was clarified. Subsequently, the mixture was filtered through a cartridge into a crystallizer. A 30% ammonia solution was added to the crystallizer and the pH was adjusted to 6. White crystals were precipitated. After centrifugation and drying in a hot air oven, 2.8-5 kg of 6-amino-1,3,5-triazin-2(1H)-one (85% yield as dicyandiamide) was finally obtained.

References

[1] Patent: CN105837524, 2016, A. Location in patent: Paragraph 0042; 0043; 0044; 0045; 0046; 0047; 0048-0079
[2] Chemische Berichte, 1954, vol. 87, p. 19,23
[3] Archiv der Pharmazie (Weinheim, Germany), 1955, vol. 288, p. 139
[4] Patent: CN104402836, 2016, B. Location in patent: Paragraph 0025; 0026; 0027; 0028

5-Azacytosine(931-86-2)Related Product Information

• 4-Aminoacetophenone
• ANILAZINE
• 5-METHYLCYTOSINE
• Toltrazuril
• beta-Methyl vinyl phosphate (MAP)
• CHLOROPHOSPHONAZO III
• 3-Aminoacetophenone
• ALTRENOGEST
• Cytosine
• Metribuzin
• Fluorocytosine
• Betaine
• 2-Aminoacetophenone
• Glycine
• 1,3,5-Triazine
• Buprofezin
• 5-Azacytidine / 5-Azacytosine
• 5-Aza-2'-deoxycytidine