79953-03-0

Basic information

• Product Name: 8-phenylguanosine
• CAS NO: 79953-03-0
• Molecular Formula: C₁₆H₁₇N₅O₅
• Molecular Weight: 359.3367
• Mol File: 79953-03-0.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 769.9°C at 760 mmHg
• Flash Point: 419.4°C
• Density: 1.85g/cm³
• Vapor Pressure: 6.21E-25mmHg at 25°C
• Refractive Index: 1.843
• CAS DataBase Reference: 8-phenylguanosine(CAS DataBase Reference)
• NIST Chemistry Reference: 8-phenylguanosine(79953-03-0)
• EPA Substance Registry System: 8-phenylguanosine(79953-03-0)

Safety Data

• Hazardous Substances Data: 79953-03-0(Hazardous Substances Data)

Upstream product

• 4016-63-1 8-bromoguanosine 
• 98-80-6 phenylboronic acid 
• 118-00-3 G 
• 591-50-4 iodobenzene 
• 4016-63-1 8-bromoguanosine 
• 369-57-3 benzenediazonium tetrafluoroborate 

Downstream Products

• 7780-10-1 8-phenylguanine 

Relevant articles and documents

Self-Assembly of Functionalized Lipophilic Guanosines into Cation-Free Stacked Guanine-Quartets

The hierarchical self-assembly of various lipophilic guanosines exposing either a phenyl or a ferrocenyl group in the C(8) position was investigated. In a solution, all the derivatives were found to self-assemble primarily into isolated guanine (G)-quartets. In spite of the apparent similar bulkiness of the two substituents, most of the derivatives form disordered structures in the solid state, whereas a specific 8-phenyl derivative self-assembles into an unprecedented, cation-free stacked G-quartet architecture.

Suzuki-Miyaura cross-coupling of unprotected halopurine nucleosides in water - Influence of catalyst and cosolvent

Reaction conditions for the Suzuki-Miyaura cross-coupling of unprotected halopurine nucleosides with arylboronic acids in aqueous media were investigated. A series of arylated purine nucleosides was prepared in water without an organic cosolvent, using either Pd(PPh3)4 or Pd(OAc)2/TPPTS as the catalyst. Copyright Taylor & Francis Group, LLC.

Efficient one-step Suzuki arylation of unprotected halonucleosides, using water-soluble palladium catalysts

Modification of nucleosides to give pharmaceutically active compounds, mutagenesis models, and oligonucleotide structural probes continues to be of great interest. The aqueous-phase modification of unprotected halonucleosides is reported herein. Using a catalyst derived from tris(3-sulfonatophenyl)phosphine (TPPTS) and palladium acetate, 8-bromo-2′-deoxyguanosine (8-BrdG) is coupled with arylboronic acids to give 8-aryl-2′-deoxyguanosine adducts (8-ArdG) in excellent yield in a 2: 1 water: acetonitrile solvent mixture. The TPPTS ligand was found to be superior to water-soluble alkylphosphines for this coupling reaction. The coupling chemistry has been extended to 8-bromo-2′-deoxyadenosine (8-BrdA) and 5-iodo-2′-deoxyuridine (5-IdU), as well as the ribonucleosides 8-bromoguanosine and 8-bromoadenosine. Good to excellent yields of arylated adducts are obtained in all cases. With use of tri(4,6-dimethyl-3-sulfonatophenyl)phosphine (TXPTS), the Suzuki coupling of 8-BrdA and 5-IdU can be accomplished in less than 1 h at room temperature. This methodology represents an efficient and general method for halonucleoside arylation that does not require prior protection of the nucleoside.