Isoguanine

Base Information

• Chemical Name: Isoguanine
• CAS No.: 149297-79-0
• Molecular Formula: C₅H₅N₅O
• Molecular Weight: 151.128
• European Community (EC) Number: 222-157-6
• NSC Number: 241501
• UNII: E335PK4428
• DSSTox Substance ID: DTXSID00187406
• Nikkaji Number: J12.865A
• Wikipedia: Isoguanine
• Wikidata: Q6085780
• Metabolomics Workbench ID: 37236
• ChEMBL ID: CHEMBL506639
• Mol file: 149297-79-0.mol

Synonyms:2-hydroxyadenine;2-OH-Ade;2-oxyadenine;isoguanine

Chemical Property of Isoguanine

Chemical Property:

• PKA: 9.50±0.40(Predicted)
• Density: 2.19±0.1 g/cm3(Predicted)
• XLogP3: -1.7
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 151.04940980
• Heavy Atom Count: 11
• Complexity: 313

Purity/Quality:

> 95% ^*data from raw suppliers

6-Amino-3,9-dihydro-2H-purin-2-one ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: C1=NC2=NC(=O)NC(=C2N1)N

Technology Process of Isoguanine

There total 4 articles about Isoguanine 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: 81.0%

5-(N1-benzoylthiocarbamoyl)aminoimidazole-4-carbonitrile → Isoguanine (3373-53-3,149297-79-0)

Guidance literature:

With ammonia; In ammonium hydroxide; ethanol; for 48h;

DOI:10.1016/S0040-4039(00)96067-2

Reference yield:

adenine (66224-66-6,66224-67-7,66224-68-8,66224-69-9,134434-48-3,134434-49-4,134454-76-5,134461-75-9) → Isoguanine (3373-53-3,149297-79-0)

Guidance literature:

With sodium hydroxide; phenyl chloroformate; In tetrahydrofuran; water; for 1h; Ambient temperature;

DOI:10.1016/S0040-4039(01)92925-9

Reference yield:

5-(N1-benzoylthiocarbamoyl)aminoimidazole-4-carboxamide (10333-86-5) → Isoguanine (3373-53-3,149297-79-0)

Guidance literature:

Multi-step reaction with 2 steps

1: dicyclohexylcarbodiimide / dimethylformamide / 24 h / Ambient temperature

2: 81 percent / NH₃ / ethanol; aq. NH₃ / 48 h

With ammonia; dicyclohexyl-carbodiimide; In ammonium hydroxide; ethanol; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4039(00)96067-2

upstream raw materials:

adenine

5-(N¹-benzoylthiocarbamoyl)aminoimidazole-4-carboxamide