Benzonitrile, 5-acetyl-2-fluoro- (9CI)

Benzonitrile, 5-acetyl-2-fluoro- (9CI) Property

Boiling point:

277.5±25.0 °C(Predicted)

Density 

1.21±0.1 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

Appearance

Light yellow to yellow Solid

Safety

HS Code 

2926907090

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

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

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

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).

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

P362Take off contaminated clothing and wash before reuse.

Benzonitrile, 5-acetyl-2-fluoro- (9CI) Chemical Properties,Usage,Production

Synthesis

Under argon protection, 449 mg (0.490 mmol) of tris(dibenzylideneacetone)dipalladium and 671 mg (1.078 mmol) of rac-1,1'-binaphthyl-2,2'-diylbis(diphenylphosphine) were dissolved in 180 mL of toluene with 1.90 g (24.5 mmol) of 3-bromo-6-fluorobenzonitrile. Subsequently 10.6 g (29.4 mmol) of (1-ethoxyvinyl)tributylstannane was added and the reaction mixture was stirred overnight under reflux conditions. Upon completion of the reaction, the mixture was concentrated and the residue was dissolved in 200 mL of tetrahydrofuran. 50 mL of aqueous 2N hydrochloric acid was added and stirred for 4 hours at room temperature. The reaction mixture was neutralized with saturated aqueous sodium bicarbonate and extracted with ethyl acetate. The organic phases were combined, dried with magnesium sulfate, filtered and concentrated under reduced pressure. The crude product was purified by fast column chromatography (eluent: cyclohexane/ethyl acetate, 10:1→3:1) to give 3.50 g (88% yield) of 2-fluoro-5-acetylbenzonitrile. The product was characterized as follows: 1H-NMR (400 MHz, DMSO-d6): δ = 8.55 (dd, 1H), 8.31 (ddd, 1H), 7.68 (t, 1H), 2.63 (s, 3H). gC-MS (Method 11): Rt = 4.34 min; MS (EIpos): m/z = 163 [M]+.

References

[1] Patent: US2013/45999, 2013, A1. Location in patent: Paragraph 0247; 0248; 0249; 0250