8-BROMO-2-CHLOROQUINAZOLINE Chemical Properties

Boiling point:

309.7±24.0 °C(Predicted)

Density 

1.762

storage temp. 

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

pka

-1.09±0.30(Predicted)

Appearance

Yellow to orange Solid

Safety Information

Risk Statements 

41

Safety Statements 

26-39

RIDADR 

UN2811

HazardClass 

IRRITANT

HS Code 

2933998090

8-BROMO-2-CHLOROQUINAZOLINE Usage And Synthesis

Synthesis

General procedure for the synthesis of 8-bromo-2-chloroquinazoline from 4-amino-8-bromo-2-chloroquinazoline: 8-bromo-2-chloroquinazolin-4-amine (12.93 g, 50 mmol) was dissolved in THF (500 mL) under stirring conditions, and isoamyl nitrite (23.43 g, 200 mmol) was added slowly dropwise over a dropwise period of 3 hours. Subsequently, the reaction mixture was continued to be stirred at 60 °C for 40 min. Upon completion of the reaction, the progress of the reaction was monitored by TLC (unfolding agent: PE:EA = 1:1). When the reaction was complete, the mixture was cooled to room temperature and the solvent was removed by distillation under reduced pressure. The residue was dissolved in DCM (300 mL) and the organic layer was washed sequentially with brine (100 mL) and water (100 mL). The organic layer was dried over anhydrous Na2SO4 and purified by column chromatography (eluent: DCM:PE = 1:1) to afford the target compound 8-bromo-2-chloroquinazoline as a yellow solid (8.21 g, 67% yield).1H NMR (DMSO-d6, 400 MHz): δ 9.66 (s, 1H), 8.45 (dd, J = 0.8, 7.6 Hz, 1H), 8.26 (dd, J = 0.8, 8.0 Hz, 1H), 7.73 (dd, J = 7.6, 8.0 Hz, 1H).

References

[1] Patent: WO2007/125405, 2007, A2. Location in patent: Page/Page column 25; 81-82
[2] Patent: EP3287463, 2018, A1. Location in patent: Paragraph 0191; 0195
[3] Patent: WO2015/27222, 2015, A2. Location in patent: Paragraph 0216
[4] Patent: US2018/208604, 2018, A1. Location in patent: Paragraph 0484-0485

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