1-CHLORO-6-FLUOROISOQUINOLINE

1-CHLORO-6-FLUOROISOQUINOLINE Property

Boiling point:

295.6±20.0 °C(Predicted)

Density 

1.366±0.06 g/cm3(Predicted)

storage temp. 

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

pka

1.91±0.38(Predicted)

Appearance

White to off-white Solid

Safety

HS Code 

2933491090

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..…

1-CHLORO-6-FLUOROISOQUINOLINE Chemical Properties,Usage,Production

Synthesis

1) Synthesis of 1-chloro-6-fluoroisoquinoline 6-Fluoro-2H-isoquinolin-1-one (1.3 g, 7.97 mmol) (for preparation, see PCT/GB02/00514 and WO 02/062816) was suspended in acetonitrile (20 mL), followed by the addition of phosphorus trichloride (3.7 g, 23.9 mmol). Dioxane solution (2 mL) of 4N hydrochloric acid was added dropwise. The reaction mixture was heated overnight at 50 °C with stirring. Upon completion of the reaction, the mixture was poured into saturated sodium bicarbonate solution and extracted with ethyl acetate. The organic layers were combined and concentrated to give an orange solid product (1.1 g, 78% yield). Mass spectral analysis showed [M+H]+ = 181.8. 1H NMR (300 MHz, CDCl3) δ: 7.42 (m, 2H), 8.26 (m, 3H). 21A) Synthesis of 1-chloro-6-fluoroisoquinoline An acetonitrile (20 mL) solution of 6-fluoro-2H-isoquinolin-1-one (PCT/GB02/00514; WO 02/062816) (1.3 g, 7.97 mmol) and phosphorous triclosan (3.7 g, 23.9 mmol) was heated with a dioxane solution of 4N hydrochloric acid (2 mL) at 50 °C overnight. Upon completion of the reaction, the reaction mixture was diluted with sodium bicarbonate solution and extracted with ethyl acetate. The organic layer was concentrated to give an orange solid product (1.1 g, 78% yield). Mass spectral analysis showed [M+H]+ = 181.8. 1H NMR (400 MHz, CDCl3) δ: 7.42 (m, 2H), 8.26 (m, 3H).

References

[1] Patent: WO2005/28444, 2005, A1. Location in patent: Page/Page column 47-48; 69-70