6-Chloro-2-fluoropurine

Base Information

• Chemical Name: 6-Chloro-2-fluoropurine
• CAS No.: 1651-29-2
• Molecular Formula: C5H2ClFN4
• Molecular Weight: 172.549
• Hs Code.: 29335990
• European Community (EC) Number: 634-083-5
• NSC Number: 37363
• UNII: 726CLW3V39
• DSSTox Substance ID: DTXSID80415330
• Nikkaji Number: J1.499.256A
• Wikidata: Q72451318
• Metabolomics Workbench ID: 148033
• Mol file: 1651-29-2.mol

Synonyms:6-CHLORO-2-FLUOROPURINE;1651-29-2;6-Chloro-2-fluoro-9H-purine;6-chloro-2-fluoro-7H-purine;2-Fluoro-6-chloropurine;MFCD02183557;9H-Purine, 6-chloro-2-fluoro-;726CLW3V39;6-chloranyl-2-fluoranyl-7H-purine;NSC-37363;C5H2ClFN4;1jdj;2-fluoro,6-chloro-purine;2-fluoro-6-chloro-purine;6-chloro-2-fluoro-purine;CFP;SCHEMBL356177;SCHEMBL357172;UNII-726CLW3V39;2-Fluoro-6-chloro-7H-purine;6-Chloro-2-fluoropurine, 97%;DTXSID80415330;UNRIYCIDCQDGQE-UHFFFAOYSA-N;AM779;BCP30954;NSC37363;BBL100449;MFCD08461765;NSC 37363;STL554243;6-chloro-2-fluoropurine, AldrichCPR;AKOS005063531;AKOS005254438;CS-W002924;DB03520;PS-6852;AC-23432;PD039170;SY018648;C2221;FT-0633733;EN300-761520;A810622;W-205943;Z1741959673

Chemical Property of 6-Chloro-2-fluoropurine

Chemical Property:

• Appearance/Colour: almost white crystalline powder
• Vapor Pressure: 0.101mmHg at 25°C
• Melting Point: 162-163 °C
• Refractive Index: 1.304
• Boiling Point: 553.2 °C at 760 mmHg
• PKA: 4.88±0.20(Predicted)
• Flash Point: 288.4 °C
• PSA: 54.46000
• Density: 1.766 g/cm³
• LogP: 1.14540
• Storage Temp.: 2-8°C
• XLogP3: 1.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 0
• Exact Mass: 171.9952019
• Heavy Atom Count: 11
• Complexity: 157

Purity/Quality:

99% ^*data from raw suppliers

6-Chloro-2-fluoropurine >97.0%(HPLC)(T) ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi,Xn
• Hazard Codes: Xi,Xn
• Statements: 36/37/38-41-37/38-22-37/39-26
• Safety Statements: 26-36/37/39-39

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=NC2=C(N1)C(=NC(=N2)F)Cl
• Description: 6-Chloro-2-fluoropurine is a heterocyclic building block. It has been used in the synthesis of purine nucleosides that inhibit cyclin-dependent kinases (CDKs) in vitro. 6-Chloro-2-fluoropurine has also been used in the synthesis of purine nucleosides that are active against HIV-1 and hepatitis B virus (HBV) in vitro.
• Uses: 6-Chloro-2-fluoropurine is used as a reagent in the synthesis of several organic compounds including that of 2''-Fluoro-3''-Hydroxymethyl-5''-deoxythreosyl phosphonic acid nucleoside analogues which may potentially act as antiviral agents. It is also used in the synthesis of 2'',5'',5''-trifluoro-3''-hydroxy-apiosyl nucleoside phosphonic acid analogues which may possess potent anti-HCMV properties.

Technology Process of 6-Chloro-2-fluoropurine

There total 7 articles about 6-Chloro-2-fluoropurine 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: 91.0%

2-amino-6-chloropurine (10310-21-1) → 6-chloro-2-fluoro-7H-purine (1651-29-2)

Guidance literature:

2-amino-6-chloropurine; With tetrafluoroboric acid; copper (I) fluoride; In water; at 20 ℃; for 0.5h;

With sodium nitrite; In water; at -10 ℃;

DOI:10.5012/jkcs.2010.54.4.429

Reference yield: 89.0%

2-Amino-6-chloropurin (10310-21-1) → 6-chloro-2-fluoropurine (1651-29-2)

Guidance literature:

With tetrafluoroboric acid; sodium nitrite; at -10 - 0 ℃; for 0.5h;

DOI:10.1021/jo00040a031

Reference yield: 83.0%

C10H10ClN5O3 → 6-chloro-2-fluoro-7H-purine (1651-29-2)

Guidance literature:

With ammonium fluoride; In N,N-dimethyl-formamide; at 20 ℃; for 10h;

upstream raw materials:

2-Amino-6-chloropurin

2-amino-6-chloropurine

6-chloro-9-(tetrahydro-2H-pyran-2-yl)-9H-purine

Downstream raw materials:

2-fluoro-N-(4-nitrobenzyl)-9H-purin-6-amine

olomoucine

2-fluoro-6-phenylsulfenylpurine

9-[(1RS,4S)-5-O-benzoyl-2,3-dideoxy-3,3-difluoro-L-ribofuranosyl]-6-chloro-2-fluoropurine

Refernces

• 1、 Calzaferri, Francesco,Narros-Fernández, Paloma,De Pascual, Ricardo,De Diego, Antonio M.G.,Nicke, Annette,Egea, Javier,García, Antonio G.,De Los Ríos, Cristóbal. "Synthesis and Pharmacological Evaluation of Novel Non-nucleotide Purine Derivatives as P2X7 Antagonists for the Treatment of Neuroinflammation". . p. 2272 - 2290. Retrieved 2021/03/01.
• 2、 Coxon, Christopher R.,Anscombe, Elizabeth,Harnor, Suzannah J.,Martin, Mathew P.,Carbain, Benoit,Golding, Bernard T.,Hardcastle, Ian R.,Harlow, Lisa K.,Korolchuk, Svitlana,Matheson, Christopher J.,Newell, David R.,Noble, Martin E. M.,Sivaprakasam, Mangaleswaran,Tudhope, Susan J.,Turner, David M.,Wang, Lan Z.,Wedge, Stephen R.,Wong, Christopher,Griffin, Roger J.,Endicott, Jane A.,Cano, Céline. "Cyclin-Dependent Kinase (CDK) Inhibitors: Structure-Activity Relationships and Insights into the CDK-2 Selectivity of 6-Substituted 2-Arylaminopurines". . p. 1746 - 1767. Retrieved 2017/03/17.