5-cyano-2-fluorobenzene-1-sulfonyl chloride

5-cyano-2-fluorobenzene-1-sulfonyl chloride Property

storage temp. 

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

Appearance

Light yellow to yellow Solid

Safety

HS Code 

2904990090

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H315Causes skin irritation

H319Causes serious eye 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.

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.

5-cyano-2-fluorobenzene-1-sulfonyl chloride Chemical Properties,Usage,Production

Synthesis

General procedure for the synthesis of 2-fluoro-5-cyanobenzenesulfonyl chloride from 3-amino-4-fluorobenzonitrile: An aqueous solution (2 mL) of NaNO2 (380 mg, 5.51 mmol) was slowly added to a suspension of 3-amino-4-fluorobenzonitrile (500 mg, 3.67 mmol) in concentrated HCl (5 mL) at 0 °C. The reaction mixture was kept stirred at 0 °C for 30 min. Meanwhile, SO2-saturated AcOH solution (5 mL) was prepared, followed by the addition of CuCl2-2H2O (188 mg, 1.10 mmol) and continued to pass SO2 gas for 5 min. This AcOH mixture was cooled to 5 °C and then the diazonium salt solution prepared as previously described was added over 5 min. The reaction mixture was continued to be stirred at 0°C for 1 hour, followed by warming up to room temperature and stirring for another 1 hour. After completion of the reaction, the mixture was diluted with water and extracted twice with CH2Cl2. The organic phases were combined, washed twice with water, dried over Na2SO4 and concentrated under reduced pressure to remove the solvent. Purification by column chromatography (eluent: hexane/EtOAc, 19:1 to 9:1 gradient elution) afforded 2-fluoro-5-cyanobenzenesulfonyl chloride as a yellow oil (569 mg, 71% yield).1H NMR (400 MHz, CDCl3) δ 8.31 (dd, J = 6.2, 2.1 Hz, 1H), 8.04 (dd, J = 8.7, 4.3, 2.1 Hz), 8.04 (ddd, J = 8.7, 4.3, 2.1 Hz). 4.3, 2.1 Hz, 1H), 7.51 (t, J = 8.7 Hz, 1H).LCMS (APCI-) m/z 200 ([M-Cl+O]-, 100%).

References

[1] Bioorganic and Medicinal Chemistry Letters, 2017, vol. 27, # 2, p. 187 - 190
[2] European Journal of Medicinal Chemistry, 2013, vol. 65, p. 32 - 40