8-Phenylxanthine

Base Information

• Chemical Name: 8-Phenylxanthine
• CAS No.: 2879-14-3
• Molecular Formula: C11H8N4O2
• Molecular Weight: 228.21
• Hs Code.: 2933990090
• UNII: 0S2BVG6C31
• ChEMBL ID: CHEMBL285191
• DSSTox Substance ID: DTXSID50485464
• Nikkaji Number: J80.586F
• Wikidata: Q27237156
• Mol file: 2879-14-3.mol

Synonyms:8-Phenylxanthine;2879-14-3;Xanthine, 8-phenyl-;1H-Purine-2,6-dione, 3,9-dihydro-8-phenyl-;0S2BVG6C31;1H-Purine-2,6-dione, 3,7-dihydro-8-phenyl-;UNII-0S2BVG6C31;CHEMBL285191;8-phenyl-3,7-dihydropurine-2,6-dione;8-Phenyl-3,7-dihydro-purine-2,6-dione;8-Phenyl-1H-purine-2,6(3H,7H)-dione;SCHEMBL378879;DTXSID50485464;BDBM50042214;PD183367;8-phenyl-3, 7-dihydropurine-2, 6-dione;Q27237156

Chemical Property of 8-Phenylxanthine

Chemical Property:

• PSA: 94.92000
• LogP: 1.43110
• XLogP3: 0.9
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 228.06472551
• Heavy Atom Count: 17
• Complexity: 340

Purity/Quality:

95% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)C2=NC3=C(N2)C(=O)NC(=O)N3
• Uses: 8-Phenylxanthine is used as a reactant in the preparation of xanthine derivatives as adenosine A1 receptor antagonists.

Technology Process of 8-Phenylxanthine

There total 11 articles about 8-Phenylxanthine 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: 56.1%

benzoyl chloride (98-88-4) + 5,6-diaminouracil (3240-72-0) → 8-phenyl-9H-purine-2,6-diol (2879-14-3)

Guidance literature:

benzoyl chloride; 5,6-diaminouracil; Heating;

With sodium hydroxide; Heating;

DOI:10.1002/1521-4184(200112)334:11<345::AID-ARDP345>3.0.CO;2-1

Reference yield: 50.0%

8-Phenyl-7-hydroxyxanthine (82160-94-9) → 6-amino-5-nitrosouracil (5442-24-0) + 8-Phenylxanthine (2879-14-3)

Guidance literature:

With phosphate buffer; water; for 3h;

DOI:10.1002/jhet.5570190139

Reference yield: 28.0%

benzaldehyde (100-52-7) + 5,6-diaminouracil sulfate (42965-55-9) → 8-Phenylxanthine (2879-14-3)

Guidance literature:

With barium(II) acetate; In nitrobenzene; for 1h; Heating;

DOI:10.1021/jm00074a015

upstream raw materials:

ethyl 5-amino-2-phenylimidazole-4-carboxylate

urea

8-Phenyl-7-hydroxyxanthine

benzaldehyde

Downstream raw materials:

2,6-dichloro-8-phenyl-9H-purine

Refernces

• 1、 Mueller, Christa E.,Shi, Dan,Manning, Malcolm,Daly, John W.. "Synthesis of Paraxanthine Analogs (1,7-Disubstituted Xanthines) and Other Xanthines Unsubstituted at the 3-Position: Structure-Activity Relationships at Adenosine Receptors". . p. 3341 - 3349. Retrieved 2007/10/02.
• 2、 Zvilichovsky,Garbi,Nemes. "Synthesis and properties of 7-hydroxy-8-phenylxanthine and its derivatives. Disproportionation to derivatives of 8-phenylxanthine and 6-amino-5-nitrosouracil". . p. 205 - 209. Retrieved 2007/10/02.