8-BROMO-2,4-DICHLOROQUINAZOLINE Chemical Properties

Boiling point:

330.2±24.0 °C(Predicted)

Density 

1.851

storage temp. 

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

pka

-1.75±0.30(Predicted)

Appearance

Off-white to light yellow Solid

Safety Information

HazardClass 

IRRITANT

HS Code 

2933599590

8-BROMO-2,4-DICHLOROQUINAZOLINE Usage And Synthesis

Application

8-Bromo-2,4-Dichloroquinazoline is a quinazoline derivative, which is mainly used as an intermediate in pharmaceutical and chemical synthesis.

Synthesis

8-Bromoquinazoline-2,4(1H,3H)-dione (12.1 g, 50 mmol, 1 eq.) was used as starting material, which was dissolved in phosphorous trichloride (POCl3, 130 mL), followed by the addition of N,N-dimethylformamide (DMF, 0.5 mL) as catalyst. The reaction mixture was stirred at 130 °C for 12 h. After completion of the reaction, the reaction was cooled to room temperature. The reaction mixture was concentrated by rotary evaporator. The concentrated residue was dissolved in ethyl acetate (EA, 100 mL) and quenched by slowly pouring into ice water under vigorous stirring. The organic phase was separated, washed with saturated saline, dried over anhydrous sodium sulfate (Na2SO4), filtered and concentrated again. Finally, the target product 8-bromo-2,4-dichloroquinazoline was purified by column chromatography (eluent: petroleum ether/ethyl acetate = 10:1, v/v) as a yellow solid (9.1 g, 60% yield).

References

[1] Organic Letters, 2011, vol. 13, # 4, p. 676 - 679
[2] ACS Medicinal Chemistry Letters, 2018, vol. 9, # 9, p. 941 - 946
[3] Patent: WO2015/27222, 2015, A2. Location in patent: Paragraph 0214
[4] Patent: WO2016/133935, 2016, A1. Location in patent: Paragraph 0287

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