14013-11-7

Basic information

• Product Name: 9-Benzylinosine
• Synonyms: 1,9-Dihydro-9-(phenylmethyl)-6H-purin-6-one;9-Benzyl-1,9-dihydro-6H-purine-6-one;9-Benzyl-9H-purin-6(1H)-one;9-Benzyl-9H-purin-6-ol;9-Benzylhypoxanthine;9-Benzylinosine;6H-Purin-6-one, 1,9-dihydro-9-(phenylmethyl)-;6H-Purin-6-one, 1,9-dihydro-9-(phenylmethyl)- (9CI)
• CAS NO: 14013-11-7
• Molecular Formula: C₁₂H₁₀N₄O
• Molecular Weight: 226.24
• Mol File: 14013-11-7.mol
• Article Data: 10

Chemical Properties

• Boiling Point: 492°Cat760mmHg
• Flash Point: 251.4°C
• Appearance: /
• Density: 1.39g/cm³
• Vapor Pressure: 7.98E-10mmHg at 25°C
• Refractive Index: 1.719
• CAS DataBase Reference: 9-Benzylinosine(CAS DataBase Reference)
• NIST Chemistry Reference: 9-Benzylinosine(14013-11-7)
• EPA Substance Registry System: 9-Benzylinosine(14013-11-7)

Safety Data

• Hazardous Substances Data: 14013-11-7(Hazardous Substances Data)

Usage

General Description

9-Benzylinosine is a compound that belongs to the class of chemicals known as nucleosides, which are the building blocks of DNA and RNA. It is a modified form of the natural nucleoside inosine, with a benzyl group attached to the 9th carbon atom of the purine ring. This modification gives 9-benzylinosine unique properties and potential applications in various fields including medicine, biochemistry, and pharmaceuticals. It has been studied for its potential as an anti-cancer agent, as well as for its role in nucleic acid modification and gene regulation. Further research on 9-benzylinosine may lead to the development of new drugs and therapeutic strategies for various diseases.

InChI:InChI=1/C12H10N4O/c17-12-10-11(13-7-14-12)16(8-15-10)6-9-4-2-1-3-5-9/h1-5,7-8H,6H2,(H,13,14,17)

Upstream product

• 4261-14-7 9-benzyl-9H-purin-6-ylamine 
• 110-86-1 pyridine 
• 100-46-9 benzylamine 
• 1422048-55-2 C₂₂H₂₆N₄O 
• 1928-76-3 9-benzyl-6-chloro-9H-purine 
• 73-24-5 7H-purin-6-ylamine 
• 100-44-7 benzyl chloride 
• 68462-61-3 ethyl 5‐amino‐1‐benzyl‐1H‐imidazole‐4‐carboxylate 
• 101073-76-1 5-amino-1-benzylimidazole-4-carbohydrazide 
• 83135-13-1 9-benzyl-6-iodo-9H-purine 
• 3287-99-8 benzylamine hydrochloride 
• 68-94-0 hypoxanthine 
• 122-51-0 orthoformic acid triethyl ester 
• 3815-69-8 5-amino-1-(phenylmethyl)-1H-imidazole-4-carboxamide 

Downstream Products

• 4022-95-1 7-benzyl-7H-[1,2,4]triazolo[4,3-g]purine 
• 10553-44-3 7-benzyl-1,2,3,4-tetrazolo[5,1-i]purine 
• 1928-76-3 9-benzyl-6-chloro-9H-purine 
• 6268-73-1 9-benzyl-6-hydrazino-9H-purine 
• 7026-49-5 1-benzyl-5-aminoimidazole-4-carboxylic acid benzylamide 
• 110287-91-7 1-acetonyl-9-benzylhypoxanthine 
• 95633-81-1 1-phenacyl-9-benzylhypoxanthine 

Relevant articles and documents

N1-substituted hypoxanthine derivatives from the reaction of 6-halopurines with Michael acceptors under the conditions of Heck reaction

The reaction of 6-iodo-, 9-benzyl-6-chloropurine and 7-benzyl-6-chloropurine with butyl acrylate, acrylonitrile, methyl vinyl ketone or methyl methacrylate under conditions of the Heck reaction in the presence of TlOAc or AgOAc afforded N1-alky

Synthetic studies on compounds related to aminoimidazolecarboxamide: Synthesis of angularly fused purine derivatives and a solid phase ring transformation (ANRORC) to imidazo [1,5-a] pyrazine

l-Benzyl-5-aminoimidazole-4-carboxamide la has been used as a convenient precursor for the synthesis of new triazolo [3,4-i] purines 6 and the corresponding tetrazolo analogue 7. A mesoionic isomer 8 seems to exist along with 7. Interesting heteroaryl-purine motifs have also been prepared via suitably substituted 9-benzyIpurines. Imidazo |I,5-a| pyrazine derivative has been prepared in a solid phase exploitation of suitable imidazolium salt via ANRORC.

Synthesis of N-aryl uracils and hypoxanthines and their biological properties

1-Benzyluracils 2a,b were treated with iodobenzene in the presence of cuprous oxide in 2,4,6-trimethylpyridine at 180°C to give the N1-phenyl derivatives 3a and 3b in 47% and 55%, respectively. Similar reaction of 2a with 2-bromopyridine at 120°C gave the 3-(2-pyridinyl)uracil 4a in 42% yield. However, unusual product 5 as well as 3-(2-pyridinyl) derivative 4b were obtained in the case of 2b. The structure of 5 was identified as 1- (2,6-difluorobenzyl)-3-[(2,4-dimethyl-2-pyridinyl)methyl]uracil from spectroscopic data. Reaction of the hypoxanthines 7a, b with 2-bromopyridine gave the 1-(2-pyridinyl)hypoxanthines 8a, b in low yields. But N-phenylation of 7a,b were unsuccessful.