4-CYANOBENZENE-1-SULFONAMIDE Chemical Properties

Melting point:

166 °C

Boiling point:

400.7±47.0 °C(Predicted)

Density 

1.3827 (rough estimate)

refractive index 

1.6000 (estimate)

RTECS 

DB1582000

storage temp. 

Sealed in dry,Room Temperature

pka

9.57±0.10(Predicted)

form 

solid

color 

Off-white

Water Solubility 

1.111g/L(15 ºC)

CAS DataBase Reference

3119-02-6(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi,Xn

Risk Statements 

20/21/22-36/37/38

Safety Statements 

26-36/37/39-36/37

RIDADR 

3276

Hazard Note 

Harmful

HazardClass 

IRRITANT

HS Code 

29350090

4-CYANOBENZENE-1-SULFONAMIDE Usage And Synthesis

Uses

4-Cyanobenzene-1-sulfonamide is a carbonic anhydrase inhibitor.

Synthesis

General procedure for the synthesis of p-cyanobenzenesulfonamide from 4-cyanobenzenesulfonyl chloride: 4-cyanobenzenesulfonyl chloride (10 mmol) was dissolved in anhydrous tetrahydrofuran (40 mL). A 30% aqueous ammonium hydroxide solution (3 mL) was slowly added to the reaction mixture at 0 °C, followed by stirring the reaction for 1 h at room temperature. After completion of the reaction, the reaction mixture was extracted with ethyl acetate and the organic phase was dried with anhydrous sodium sulfate. After concentration under reduced pressure, the white solid product p-cyanobenzenesulfonamide (1.6 g, 88% yield) was obtained by grinding with ether. The structure of the product was confirmed by 1H NMR (400 MHz, DMSO-d6) and 13C NMR (100 MHz, DMSO-d6): 1H NMR δ 8.11 (2H, d, J = 8.58 Hz), 8.02 (2H, d, J = 8.62 Hz), 7.69 (2H, bs, NH2, exchange with D2O); 13C NMR δ 148.9, 134.2, 127.4, 118.8, 115.3.

References

[1] European Journal of Medicinal Chemistry, 2018, vol. 157, p. 1214 - 1222
[2] Zhurnal Obshchei Khimii, 1948, vol. 18, p. 110,112
[3] Chem.Abstr., 1948, p. 4976
[4] American Chemical Journal, 1896, vol. 18, p. 163,165
[5] Bioorganic and Medicinal Chemistry, 2017, vol. 25, # 16, p. 4397 - 4406

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