1681-15-8

Basic information

• Product Name: 2-Chloropurine
• Synonyms: 2-CHLOROPURINE;1H-Purine, 2-chloro-;2-Chloro-7H-purine
• CAS NO: 1681-15-8
• Molecular Formula: C₅H₃ClN₄
• Molecular Weight: 154.56
• Product Categories: Purines
• Mol File: 1681-15-8.mol
• Article Data: 11

Chemical Properties

• Melting Point: 231-234 °C
• Boiling Point: 397.7 °C at 760 mmHg
• Flash Point: 226.5 °C
• Appearance: /
• Density: 1.653 g/cm³
• Vapor Pressure: 3.58E-06mmHg at 25°C
• Refractive Index: 1.739
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• PKA: 6.58±0.20(Predicted)
• CAS DataBase Reference: 2-Chloropurine(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Chloropurine(1681-15-8)
• EPA Substance Registry System: 2-Chloropurine(1681-15-8)

Safety Data

• Hazardous Substances Data: 1681-15-8(Hazardous Substances Data)

Usage

Description

2-Chloropurine is a purine analog chemical compound, characterized by a chlorine atom attached at the 2-position of the purine base. It has been recognized for its potential in pharmacological applications, particularly as an antiviral and antitumor agent. Additionally, it serves as a mutagen in research for inducing mutations in various cells and is considered for the synthesis of nucleotide analogs for pharmaceutical use, making it a multifaceted chemical with broad applications in both medicinal and research fields.

Uses

Used in Pharmaceutical Industry:
2-Chloropurine is used as an antiviral agent for its potential to combat viral infections, leveraging its chemical properties to interfere with viral replication mechanisms.
Used in Oncology Research:
In the field of oncology, 2-Chloropurine is used as an antitumor agent, where it may exhibit inhibitory effects on tumor growth, making it a candidate for cancer treatment development.
Used in Genetic Research:
2-Chloropurine is utilized as a mutagen in genetic research, where it is employed to induce mutations in bacterial and mammalian cells, facilitating studies on genetic variation and mutational effects.
Used in Chemical Synthesis:
2-Chloropurine is used as a precursor in the synthesis of nucleotide analogs, which are crucial for the development of new pharmaceuticals targeting specific biological processes and diseases.

InChI:InChI=1/C5H3ClN4/c6-5-7-1-3-4(10-5)9-2-8-3/h1-2H,(H,7,8,9,10)

Upstream product

• 5451-40-1 2,6 dichloropurine 
• 5404-88-6 1-(2-chloro-9H-purin-6-yl)hydrazine 
• 14631-08-4 2-chloro-4,5-diaminopyrimidine 
• 14036-53-4 dimethoxymethyl acetate 
• 122-51-0 orthoformic acid triethyl ester 
• 5451-40-1 2,6-dichloro-7H-purine 

Downstream Products

• 1516608-63-1 9-(methoxymethyl)-2-[(4-methoxyphenyl)thio]-9H-purine 
• 1516609-00-9 9-(methoxymethyl)-8-(4-methoxyphenyl)-2-[(4-methoxyphenyl)thio]-9H-purine 
• 1516608-93-7 ethyl 4-[2-chloro-9-(methoxymethyl)-9H-purin-8-yl]benzoate 
• 1389318-45-9 tert-butyl (2-chloro-9H-purin-9-yl)(cyclohexyl)methylcarbamate 
• 118807-48-0 2-chloro-9-phenyl-9H-purine 
• 455266-18-9 [1-(2-Phenyl-ethanesulfonyl)-piperidin-4-ylmethyl]-(9H-purin-2-yl)-amine 
• 28128-15-6 2-bromopurine 
• 28128-16-7 2-iodopurine 
• 1383381-71-2 diethyl 9-[(N-(2-(trityloxy)ethyl)-N-(2-phosphonoethyl))-2-aminoethyl]-6-chloropurine 
• 1351087-93-8 4-(dimethylamino)-N-methyl-3-(1H-purin-6-ylamino)benzenesulfonamide 
• 1351087-96-1 N-methyl-4-(methyloxy)-3-(1H-purin-6-ylamino)benzenesulfonamide 
• 929028-84-2 2-chloro-9-(2,4-dichloro-benzyl)-9H-purine 
• 929028-85-3 2-chloro-7-(2,4-dichloro-benzyl)-7H-purine 

Related news

On the mechanism of the two-way oxidation of 2-Chloropurine (cas 1681-15-8) by mammalian xanthine oxidase09/28/2019

2-Chloropurine is attacked by mammalian xanthine oxidase simultaneously at C-6 and C-8. The ratio of the two rates (=1) is insensitive to variations of pH or temperature. Experiments with 2-chloropurine as inhibitor indicate instantaneous association of this purine with the active center of the ...detailed

Relevant articles and documents

The synthesis of nebularine and its analogs via oxidative desulfuration in aqueous nitric acid

The synthesis of nebularine and its analogs has been achieved via oxidative desulfuration in H2O for the first time. With 50% HNO3as an oxidant and solvent, 18 products were obtained in good yields (70%–94%). The oxidative desulfuration system could tolerate different functional groups including fluoro, chloro, amino, alkyl, allyl, ribosyl, deoxyribosyl, and arabinofuranosyl groups.More importantly, the drug nebularine could be obtained successfully on a 20 g scale, which made this route more attractive for industrial applications.

Reduction of different electron-poor N-heteroarylhydrazines in strong basic conditions

The first application of the Wolff-Kishner reduction methodology to electron-poor heteroaromatic compounds is reported. Hydrazino-containing heterocycles with hydrazone-type tautomery have been reduced under basic conditions. This novel chemistry was successfully applied to mono-dehalogenate a number of electron-poor heterocycles in a regioselective manner. According to the experimental results, this reductive process is a base-catalyzed reaction that takes only place in the presence of air, probably through an oxygen-assisted mechanism. As consequence of the specific features of this kind of hydrazone/enehydrazine tautomers, the overall outcome of the process is the synthesis of a Shapirotype reduction product by simply using a milder version of the Huang-Minlon methodology.

Synthesis and properties of 2-guanidinopurines

2-Guanidinopurines were prepared as derivatives of 2,6-diamino-9-[2- (phosphonomethoxy)ethyl]-9H-purine (PMEDAP) (1), which shows an important antiviral activity. It completes earlier described synthesis of 6-guanidinopurine derivatives. The title compounds were obtained by the reaction of the corresponding 2-chloropurines with guanidine. 2- And 6-guanidinopurines were used as model compounds for determination of dissociation constants (pKa) of their ionogenic groups by capillary zone electrophoresis. The pKa values of ionogenic groups of the above compounds were compared with those of the corresponding aminopurines. The pKa of guanidino group at the purine moiety varies from 7.77 to 10.32. There is no protonation of N1-position in contrast to aminopurines. None of these compounds showed any antiviral activity.