6-Chloro-2-fluoropurine Chemical Properties

Melting point:

162-163°C

Boiling point:

221.8±50.0 °C(Predicted)

Density 

1.98±0.1 g/cm3(Predicted)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

solubility 

DMF: 30 mg/ml,DMSO: 30 mg/ml,Ethanol: 30 mg/ml

pka

4.88±0.20(Predicted)

form 

powder to crystal

color 

White to Light yellow to Green

InChI

InChI=1S/C5H2ClFN4/c6-3-2-4(9-1-8-2)11-5(7)10-3/h1H,(H,8,9,10,11)

InChIKey

UNRIYCIDCQDGQE-UHFFFAOYSA-N

SMILES

N1C2C(=NC(F)=NC=2Cl)NC=1

CAS DataBase Reference

1651-29-2(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi,Xn

Risk Statements 

36/37/38-41-37/38-22-37/39-26

Safety Statements 

26-36/37/39-39

WGK Germany 

3

HS Code 

29335990

6-Chloro-2-fluoropurine Usage And Synthesis

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.

Chemical Properties

Beige solid

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.

Synthesis

General procedure for the synthesis of 6-chloro-2-fluoro-9H-purine from 2-amino-6-chloropurine: 0.3 M NaNO2 aqueous solution (200 mL, 60 mmol) was slowly added dropwise to a vigorously stirred suspension of 2-amino-6-chloro-9H-purine (6.0 g, 35.4 mmol) at -15 °C. Subsequently, 120 mL of 48% HBF4 aqueous solution (0.92 mol) was added over 75 min. The reaction mixture was stirred at room temperature and kept in a light yellow reaction solution state for 20 min. After cooling again to -15 °C, it was neutralized with 50% NaOH aqueous solution to pH=6.0. The water was removed by vacuum and the orange solid obtained was purified by silica gel column chromatography (eluent ratio 90:10 dichloromethane to methanol, Rf value 0.50). 6-Chloro-2-fluoro-9H-purine was finally obtained as a white solid (3.0 g, 49.1% yield).

References

[1] Journal of Organic Chemistry, 1992, vol. 57, # 14, p. 3887 - 3894
[2] Journal of Medicinal Chemistry, 2017, vol. 60, # 5, p. 1746 - 1767
[3] Tetrahedron Letters, 1997, vol. 38, # 7, p. 1161 - 1164
[4] Patent: US2002/68721, 2002, A1
[5] Patent: WO2004/16612, 2004, A2. Location in patent: Page 54

6-Chloro-2-fluoropurine(1651-29-2)Related Product Information

• 6-Chloropurine
• Cyhalothrin
• Purine
• Flucloxacillin sodium
• Fluroxypyr
• Flucloxacillin
• λ-Cyhalothrin
• Fluorine
• Difluorochloromethane
• 2-Fluoropurine
• 2-FLUOROPYRIMIDINE
• 6-Chloro-2-fluoropurine