4-CHLORO-6-FLUOROQUINAZOLINE Chemical Properties

Boiling point:

284.9±20.0 °C(Predicted)

Density 

1.447±0.06 g/cm3(Predicted)

storage temp. 

Inert atmosphere,Store in freezer, under -20°C

pka

0.17±0.30(Predicted)

Appearance

Off-white to light yellow Solid

InChI

InChI=1S/C8H4ClFN2/c9-8-6-3-5(10)1-2-7(6)11-4-12-8/h1-4H

InChIKey

XIKGISGZFBCGDW-UHFFFAOYSA-N

SMILES

N1=C2C(C=C(F)C=C2)=C(Cl)N=C1

Safety Information

Hazard Codes 

Xn

Risk Statements 

22-37/38-41

Safety Statements 

26-39

HazardClass 

IRRITANT

HS Code 

2933992000

4-CHLORO-6-FLUOROQUINAZOLINE Usage And Synthesis

Synthesis

General procedure for the synthesis of 4-chloro-6-fluoroquinazoline from 6-fluoro-4-hydroxyquinazoline: a mixture of 6-fluoro-4-hydroxyquinazoline (1.64 g, 10 mmol) with phosphoryl chloride (7.5 mL, 50 mmol) and phosphorus pentachloride (6 g, 30 mmol) was heated and refluxed for 2 hours in a water bath. Upon completion of the reaction, the reaction mixture was cooled to room temperature and slowly poured into crushed ice to quench the reaction. The precipitated solid product was collected by filtration, washed well with water to remove residual acid and subsequently dried. The crude product was purified by column chromatography (eluent: hexane/ethyl acetate) to afford the target compound 4-chloro-6-fluoroquinazoline. Yield: 65%; Melting point: 140-142 °C; 1H-NMR (DMSO-d6, 300 MHz) δ 8.12 (s, 1H, ArH), 7.47 (dd, 1H, J = 7.9 Hz and 2.8 Hz, ArH), 7.53 (dd, 1H, J = 8.6 Hz and 5.1 Hz, ArH), 7.62 (s, 1H, ArH ); molecular formula: C8H4ClFN2 (molecular weight: 182); MS (ESI) m/z 183 [M + 1]+.

References

[1] Molecules, 2017, vol. 22, # 2,
[2] Patent: US5955464, 1999, A
[3] Organic Letters, 2010, vol. 12, # 3, p. 552 - 555
[4] Bioorganic and Medicinal Chemistry Letters, 2017, vol. 27, # 21, p. 4885 - 4888
[5] Bioorganic Chemistry, 2018, vol. 80, p. 433 - 443

4-CHLORO-6-FLUOROQUINAZOLINE(16499-61-9)Related Product Information

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