Isocytosine

Base Information

• Chemical Name: Isocytosine
• CAS No.: 108-53-2
• Molecular Formula: C4H5N3O
• Molecular Weight: 111.103
• Hs Code.: 29335990
• European Community (EC) Number: 203-592-0
• NSC Number: 49118
• DSSTox Substance ID: DTXSID00148350
• Nikkaji Number: J2.864I
• Wikipedia: Isocytosine
• Wikidata: Q10859790
• Metabolomics Workbench ID: 52593
• ChEMBL ID: CHEMBL56260
• Mol file: 108-53-2.mol

Synonyms:isocytosine

Chemical Property of Isocytosine

Chemical Property:

• Appearance/Colour: white to off-white solid
• Vapor Pressure: 0.019mmHg at 25°C
• Melting Point: 275 °C
• Refractive Index: 1.688
• Boiling Point: 252.7 °C at 760 mmHg
• PKA: 9.59±0.40(Predicted)
• Flash Point: 106.7 °C
• PSA: 72.03000
• Density: 1.55 g/cm³
• LogP: 0.34560
• Storage Temp.: Room temperature.
• Solubility.: DMSO (Slightly)
• Water Solubility.: Soluble in DMF, DMSO, hot water, and AcOH.
• XLogP3: -1
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 111.043261792
• Heavy Atom Count: 8
• Complexity: 170

Purity/Quality:

99% ^*data from raw suppliers

Isocytosine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xn
• Statements: 22-36
• Safety Statements: 26

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=CN=C(NC1=O)N
• Uses: Isocytosine is a useful intermediate for chemical modifications of base and sugar moieties in natural nucleosides Isocytosine (2-aminouracil) is an isomer of cytosine used in physical chemical studies involving metal complex binding, hydrogen-bonding, and tautomerism and proton transfer effects in nucleobases.

Technology Process of Isocytosine

There total 40 articles about Isocytosine 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: 85.0%

2-aminopyrimidine (109-12-6) → isocytosine (108-53-2,145358-63-0,674-97-5,176772-97-7)

Guidance literature:

With Agrobacterium sp. DSM 6136; for 48h;

DOI:10.1016/S0040-4020(97)00301-3

Reference yield: 58.0%

pyrimidin-2-yl-carbamic acid benzyl ester (191487-39-5) → 2-aminopyrimidine (109-12-6) + isocytosine (108-53-2,145358-63-0,674-97-5,176772-97-7) + (6-Oxo-1,6-dihydro-pyrimidin-2-yl)-carbamic acid benzyl ester

Guidance literature:

With Rhodococcus erythropolis DSM 6138; In ethanol; for 16h;

DOI:10.1016/S0040-4020(97)00301-3

Reference yield: 49.0%

imidazolo<1,2-a>pyrimidine-5(1H)-one (55662-68-5) → isocytosine (108-53-2,145358-63-0,674-97-5,176772-97-7) + 6-bromoimidazolo<1,2-a>-pyrimidine-5(1H)-one (140685-72-9)

Guidance literature:

With N-Bromosuccinimide; In water; 1.) RT, 1 h, 2.) 80 deg C, 1 h;

DOI:10.1248/cpb.40.235

upstream raw materials:

4-methoxypyrimidin-2-amine

2-ethoxypyrimidin-4-one

2-amino-4-chloropyrimidine

malic acid

Downstream raw materials:

imidazolo<1,2-a>pyrimidine-5(1H)-one

9H-Pyrimido[1,2-a][1,3,5]triazine-2,4,8-trione

imidazolo<1,2-a>pyrimidine-7(8H)-one

2-amino-4-hydroxypyrimidine

Refernces

• 1、 Tibiletti, Francesco,Simonetti, Marco,Nicholas, Kenneth M.,Palmisano, Giovanni,Parravicini, Matteo,Imbesi, Federico,Tollari, Stefano,Penoni, Andrea. "One-pot synthesis of meridianins and meridianin analogues via indolization of nitrosoarenes". . p. 1280 - 1288. Retrieved 2010.
• 2、 Gotor, Vicente,Quiros, Margarita,Ramon, Liz,Frigola, Jordi,Fernandez, Rosa. "Fungal and bacterial regioselective hydroxylation of pyrimidine heterocycles". . p. 6421 - 6432. Retrieved 1997.
• 3、 Saladino, Raffaele,Botta, Giorgia,Delfino, Michela,Di Mauro, Ernesto. "Meteorites as catalysts for prebiotic chemistry". . p. 16916 - 16922. Retrieved 2014/01/06.