4-CHLORO-6-FLUOROQUINAZOLINE

4-CHLORO-6-FLUOROQUINAZOLINE Property

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

Hazard Codes 

Xn

Risk Statements 

22-37/38-41

Safety Statements 

26-39

HazardClass 

IRRITANT

HS Code 

2933992000

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H302Harmful if swallowed

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P270Do not eat, drink or smoke when using this product.

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

P301+P312IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.

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

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

P321Specific treatment (see … on this label).

P330Rinse mouth.

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

P362Take off contaminated clothing and wash before reuse.

P501Dispose of contents/container to..…

4-CHLORO-6-FLUOROQUINAZOLINE Chemical Properties,Usage,Production

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