2,4-DICHLORO-6-FLUOROQUINAZOLINE Chemical Properties

Boiling point:

277.3±22.0 °C(Predicted)

Density 

1.571±0.06 g/cm3(Predicted)

storage temp. 

under inert gas (nitrogen or Argon) at 2-8°C

pka

-1.09±0.30(Predicted)

Appearance

White to yellow Solid

Safety Information

HazardClass 

IRRITANT

HS Code 

2933599590

2,4-DICHLORO-6-FLUOROQUINAZOLINE Usage And Synthesis

Synthesis

(Step 2) Synthesis of 2,4-dichloro-6-fluoroquinazoline: Phosphorus pentachloride (12.5 g, 60.0 mmol) was added to phosphorus trichloride (46.0 mL, 502.5 mmol), followed by the slow addition of 6-fluoroquinazoline-2,4(1H,3H)-dione (3.6 g, 20.0 mmol) under stirring. The reaction mixture was heated to reflux and stirred for 9 hours. After completion of the reaction, the mixture was cooled and the solvent was removed under vacuum. An ice-water mixture (400 mL) was added to the residue and stirring was continued for 0.5 hours. The mixture was extracted with dichloromethane (DCM, 250 mL x 3). The DCM layers were combined, dried with anhydrous sodium sulfate, filtered, and the filtrate was concentrated under vacuum. The residue was purified by silica gel column chromatography (eluent: petroleum ether/ethyl acetate, v/v=30/1) to afford the title compound 2,4-dichloro-6-fluoroquinazoline as a white solid (3.735 g, 86.0% yield). m/z MS (ESI, cationic): 216.9 [M + H]+; 1H NMR (CDCl3, 400 MHz) δ ( ppm): 8.03 (dd, J=9.2 Hz, 4.9 Hz, 1H), 7.86 (dd, J=8.1 Hz, 2.7 Hz, 1H), 7.79-7.73 (m, 1H).

References

[1] Patent: WO2017/12502, 2017, A1. Location in patent: Page/Page column 52
[2] Patent: WO2017/88759, 2017, A1. Location in patent: Paragraph 00214
[3] Patent: CN105949203, 2016, A. Location in patent: Paragraph 0179; 0185; 0186
[4] Bioorganic and Medicinal Chemistry, 2015, vol. 23, # 24, p. 7717 - 7727
[5] Journal of Medicinal Chemistry, 2008, vol. 51, # 24, p. 7855 - 7865

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