5-Azacytosine

Base Information

• Chemical Name: 5-Azacytosine
• CAS No.: 931-86-2
• Deprecated CAS: 4040-10-2
• Molecular Formula: C3H4N4O
• Molecular Weight: 112.091
• Hs Code.: 2933.59 DERIVATION
• European Community (EC) Number: 213-242-9
• NSC Number: 54006,51100
• UNII: C5UW4MS7VR
• DSSTox Substance ID: DTXSID80239275
• Nikkaji Number: J152.179I
• Wikidata: Q27139948
• Metabolomics Workbench ID: 65979
• ChEMBL ID: CHEMBL1230389
• Mol file: 931-86-2.mol

Synonyms:5-azacytosine

Chemical Property of 5-Azacytosine

Chemical Property:

• Appearance/Colour: crystalline solid
• Melting Point: >300 °C(lit.)
• Refractive Index: 1.801
• Boiling Point: 503.1 °C at 760 mmHg
• PKA: 7.61±0.10(Predicted)
• Flash Point: 258.1 °C
• PSA: 84.66000
• Density: 1.86 g/cm³
• LogP: -0.67170
• Storage Temp.: -20°C Freezer
• Solubility.: Aqueous Base (Slightly, Heated), DMSO (Slightly, Heated)
• XLogP3: -1.2
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 112.03851076
• Heavy Atom Count: 8
• Complexity: 170

Purity/Quality:

99% ^*data from raw suppliers

5-Azacytosine 98+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi,Xn
• Hazard Codes: Xi,Xn
• Statements: 20/21/22-36/37/38
• Safety Statements: 22-24/25-36-26

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=NC(=O)NC(=N1)N
• Uses: Used as the most effective cytosine mimics for the design of novel antiviral and anti-tumor drug candidates. 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. Reactant for:Enzymic synthesis of nucleoside analogs using immobilized 2′-deoxyribosyltransferase from Lactobacillus reuteriReactions with oxide radical ionPotential antitumor and antiproliferative agent against human leukemia cells

Technology Process of 5-Azacytosine

There total 13 articles about 5-Azacytosine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 90.0%

guanylurea formate (10043-39-7) + N,N-dimethyl-formamide dimethyl acetal (4637-24-5) → 5-azacytosine (931-86-2)

Guidance literature:

With sodium methylate; In methanol; at 40 - 50 ℃; for 4h; Large scale;

DOI:10.1021/op300192e

Reference yield: 85.0%

formic acid (64-18-6) + N-Cyanoguanidine (127099-85-8,780722-26-1,461-58-5) → 5-azacytosine (931-86-2)

Guidance literature:

formic acid; N-Cyanoguanidine; With toluene-4-sulfonic acid; at 110 ℃; Autoclave; Large scale;

With hydrogenchloride; In water; for 0.5h; Temperature; Reagent/catalyst; Reflux; Large scale;

Reference yield: 80.0%

propyl methanoate (110-74-7) + N-cyanoacetamidine (56563-07-6) → 5-azacytosine (931-86-2)

Guidance literature:

at 115 ℃; for 2h;

upstream raw materials:

formic acid

N-Cyanoguanidine

4-amino-2-chloro-1,3,5-triazine

5-aza-2'-deoxycytidine

Downstream raw materials:

5-methyl-4-[(5-methyl-3-oxo-2-phenyl-2,4-dihydro-3H-pyrazol-4-yl)methylene]-2-phenyl-2,4-dihydro-3H-pyrazol-3-one

1-(2,3,5-tri-O-benzoyl-β-L-ribofuranosyl)-5-azacytosine

1-(2-O-acetyl-3,5-di-O-benzoyl-β-L-xylofuranosyl)-5-azacytosine

N-butyl-[1,3,5]triazine-2,4-diamine

Refernces

• 1、 Hartenstein,R.,Fridovich,I.. "-". . p. 1653 - 1654. Retrieved 1967.
• 2、 -. "A 5 - azacytosine new synthesis method". Paragraph 0028; 0029; 0030; 0031; 0039; 0040; 0041-0047. . Retrieved 2019/01/08.
• 3、 -. "5-azacytosine preparation method". Paragraph 0025; 0026; 0027; 0028. . Retrieved 2016/11/21.