23192-64-5

Basic information

• Product Name: 5-amino-1-pentofuranosyl-1H-imidazole-4-carbonitrile
• CAS NO: 23192-64-5
• Molecular Formula: C₉H₁₂N₄O₄
• Molecular Weight: 240.216
• Mol File: 23192-64-5.mol
• Article Data: 8

Chemical Properties

• Boiling Point: 718.3°C at 760 mmHg
• Flash Point: 388.2°C
• Density: 1.87g/cm³
• Vapor Pressure: 1.18E-21mmHg at 25°C
• Refractive Index: 1.78
• CAS DataBase Reference: 5-amino-1-pentofuranosyl-1H-imidazole-4-carbonitrile(CAS DataBase Reference)
• NIST Chemistry Reference: 5-amino-1-pentofuranosyl-1H-imidazole-4-carbonitrile(23192-64-5)
• EPA Substance Registry System: 5-amino-1-pentofuranosyl-1H-imidazole-4-carbonitrile(23192-64-5)

Safety Data

• Hazardous Substances Data: 23192-64-5(Hazardous Substances Data)

Upstream product

• 23192-63-4 5-amino-1-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)imidazole-4-carbonitrile 
• 6974-32-9 1-O-acetyl-2,3,5-tri-O-benzoyl-β-D-ribofuranose 
• 5098-11-3 5-amino-1H-imidazole-4-carbonitrile 
• 110526-61-9 5-Amino-N'-methoxy-1-β-D-ribofuranosyl-1H-imidazole-4-carboxamidine 
• 94619-75-7 N-formyl-N'-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)diaminomaleonitrile 
• 94619-73-5 1-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)-4,5-dicyanoimidazole 
• 94619-71-3 N-(2',3',5'-tri-O-benzoyl-β-D-ribofuranosyl)diaminomaleonoitrile 
• 16205-60-0 2,3,5-tri-O-benzoyl-β-D-ribofuranosyl bromide 
• 23274-21-7 5-Amino-4-carbamoyl-1β-(2',3',5'-tri-O-acetyl-D-ribofuranosyl)imidazole 
• 2627-69-2 AICA riboside 
• 94619-77-9 methyl 4-cyano-1-(β-D-ribofuranosyl)imidazole-5-carboximidate 
• 129877-99-2 5-azido-1-β-D-ribofuranosyl-1H-imidazole-4-carbonitrile 

Downstream Products

• 53296-10-9 2-phenylaminoadenosine 
• 2627-69-2 AICA riboside 
• 19508-94-2 5-amino-1-(β-D-ribofuranosyl)imidazole-4-thiocarboxamide 
• 16526-56-0 2-methyladenosine 
• 125338-94-5 5-benzylideneamino-4-cyano-1-<2-O-triflyl-3,5-O-(tetraisopropyldisiloxane-1,3-diyl)-β-D-ribofuranosyl>imidazole 
• 125338-99-0 1-<2-azido-2-deoxy-3,5-O-(tetraisopropyldisiloxane-1,3-diyl)-β-D-arabinofuranosyl>-5-benzylideneamino-4-cyanoimidazole 
• 125338-98-9 1-<2-O-acetyl-3,5-O-(tetraisopropyldisiloxane-1,3-diyl)-β-D-arabinofuranosyl>-5-benzylideneamino-4-cyanoimidazole 
• 125338-92-3 5-benzylideneamino-4-cyano-1-<3,5-O-(tetraisopropyldisiloxane-1,3-diyl)-β-D-ribofuranosyl>imidazole 
• 125339-01-7 1-(2-azido-2-deoxy-β-D-arabinofuranosyl)-5-benzylideneamino-4-cyanoimidazole 
• 53296-16-5 6-methythio-2-phenylamino-9-(β-D-ribofuranosyl)purine 
• 79715-25-6 6-mercapto-2-phenylamino-9-(β-D-ribofuranosyl)purine 
• 125339-07-3 (2R,3S,4S,5R)-2-(6-Amino-2-phenyl-purin-9-yl)-5-hydroxymethyl-tetrahydro-furan-3,4-diol 
• 125339-08-4 (2R,3S,4S,5R)-2-(6-Amino-2-benzyl-purin-9-yl)-5-hydroxymethyl-tetrahydro-furan-3,4-diol 
• 125339-00-6 1-(2-O-acetyl-β-D-arabinofuranosyl)-5-benzylideneamino-4-cyanoimidazole 

Relevant articles and documents

High-throughput five minute microwave accelerated glycosylation approach to the synthesis of nucleoside libraries

The Vorbrueggen glycosylation reaction was adapted into a one-step 5 min/130 °C microwave assisted reaction. Triethanolamine in acetontrile containing 2% water was determined to be optimal for the neutralization of trimethylsilyl inflate allowing for direct MPLC purification of the reaction mixture. When coupled with a NH3/methanol deprotection reaction, a high-throughput method of nucleoside library synthesis was enabled. The method was demonstrated by examining the ribosylation of 48 nitrogen containing heteroaromatic bases that included 25 purines, four pyrazolopyrimidines, two 8-azapurines, one 2-azapurine, two imidazopyridines, two benzimidazoles, three imidazoles, three 1,2,4-triazoles, two pyrimidines, two 3-deazapyrimidines, one quinazolinedione, and one alloxazine. Of these, 32 yielded single regioisomer products, and six resulted in separable mixtures. Seven examples provided inseparable regioisomer mixtures of -two to three compounds (16 nucleosides), and three examples failed to yield isolable products. For the 45 single isomers isolated, the average two-step overall yield ± SD was 26 ± 16%, and the average purity ± SD was 95 ± 6%. A total of 58 different nucleosides were prepared of which 15 had not previously been accessed directly from glycosylation/deprotection of a readily available base.

A UNIQUE TRANSFORMATION OF 5-AMINO-N'-METHOXYIMIDAZOLE-4-CARBOXAMIDINES BY DIAZOTIZATION: SYNTHESIS OF THE 5-AZIDO ANALOGUE OF AICA RIBOSIDE

Diazotization of 1-substituted 5-amino-N'-methoxyimidazole-4-carboxamidines (I) was found to give the 5-azidoimidazole-4-carbonitriles II through the 1-methoxy-2-azaadenine intermediates IV.The product IIb from the riboside Ib was utilized for the synthesis of 5-azido-1-β-D-ribofuranosylimidazole-4-carboxamide (Vb), a novel AICA riboside analogue.

SYNTHESIS OF 2-FORMYLADENOSINE USING DIETHOXYACETONITRILE AS A SYNTHON

Diethoxyacetonitrile has been utilized for the effective synthesis of adenine derivatives as a synthon.Novel 2-formyladenine (2b) and 2-formyladenosine (5b) have been prepared in high yields starting from AICN (1) and AICNR (4b), respectively.