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5-Azacytosine

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CAS:931-86-2
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5-Azacytosine Basic information
Product Name:5-Azacytosine
Synonyms:5-triazin-2(1h)-one,4-amino-3;2-Amino-4-hydroxy-1,3,5-triazine;2-AMINO-4-HYDROXY-S-TRIAZINE;4-AMINO-1,3,5-TRIAZIN-2-ONE;4-AMINO-1,3,5-TRIAZINE-2[1H]-ONE;4-AMINO-S-TRIAZIN-2(1H)-ONE;5-AZACYTOSINE;5-Azacytosine,98%
CAS:931-86-2
MF:C3H4N4O
MW:112.09
EINECS:213-242-9
Product Categories:Pyrimidine purine;Heterocyclic Compounds;Bases & Related Reagents;Inhibitors;Nucleotides;Amino Acids;All Inhibitors;Pyrimidines;bc0001;931-86-2
Mol File:931-86-2.mol
5-Azacytosine Structure
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
pka7.61±0.10(Predicted)
color White to Off-White
BRN 116378
InChIInChI=1S/C3H4N4O/c4-2-5-1-6-3(8)7-2/h1H,(H3,4,5,6,7,8)
InChIKeyMFEFTTYGMZOIKO-UHFFFAOYSA-N
SMILESN1C(N)=NC=NC1=O
CAS DataBase Reference931-86-2(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 Information
ProviderLanguage
5-Azacytosine English
SigmaAldrich English
ACROS English
5-Azacytosine Usage And Synthesis
Chemical PropertiesCrystalline Solid
UsesReactant 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
Uses5-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.
DefinitionChEBI: A monoamino-1,3,5-triazine that is cytosine in which the aromatic CH at position 5 is replaced by a nitrogen.
Synthesis
Formic acid

64-18-6

Guanidine, N''-cyano- (9CI)

127099-85-8

5-Azacytosine

931-86-2

(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 Preparation Products And Raw materials
Raw materialsFormic acid-->Guanidine, N''-cyano- (9CI)-->Hydrochloric acid
Tag: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

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