8-BROMO-2,4-DICHLOROQUINAZOLINE

8-BROMO-2,4-DICHLOROQUINAZOLINE Property

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

HazardClass 

IRRITANT

HS Code 

2933599590

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P271Use only outdoors or in a well-ventilated area.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P304+P340IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P312Call a POISON CENTER or doctor/physician if you feel unwell.

P321Specific treatment (see … on this label).

P332+P313IF SKIN irritation occurs: Get medical advice/attention.

P337+P313IF eye irritation persists: Get medical advice/attention.

P362Take off contaminated clothing and wash before reuse.

P403+P233Store in a well-ventilated place. Keep container tightly closed.

P405Store locked up.

P501Dispose of contents/container to..…

8-BROMO-2,4-DICHLOROQUINAZOLINE Chemical Properties,Usage,Production

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