3-BROMOBENZENESULFONAMIDE Chemical Properties

Melting point:

151-156 °C(lit.)

Boiling point:

375.8±44.0 °C(Predicted)

Density 

1.754±0.06 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

form 

powder to crystal

pka

9.81±0.60(Predicted)

color 

White to Light yellow

CAS DataBase Reference

89599-01-9(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

37/39-26

WGK Germany 

3

HazardClass 

IRRITANT

HS Code 

29350090

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

3-BROMOBENZENESULFONAMIDE Usage And Synthesis

Uses

3-Bromobenzenesulfonamide is an amine derivative that can be used as a pharmaceutical intermediate.

Application

3-Bromobenzenesulfonamide can be used as a pharmaceutical synthesis intermediate. It can be prepared by reacting 3-bromobenzenesulfonyl chloride with ammonia, or by preparing it in one step from the diazonium salt of m-bromobenzene tetrafluoride.

Chemical Properties

white powder

Synthesis

Under ice bath conditions, 3-bromobenzenesulfonyl chloride (4.073 g, 15.94 mmol) was dissolved in dichloromethane (67 mL) and 25% ammonia solution (3.7 mL, 57.15 mmol) was slowly added. The reaction mixture was stirred at ice bath temperature for 0.5 hr, then brought to room temperature and continued stirring for 6 hr. Upon completion of the reaction, the precipitated solid was collected by filtration, washed with water and dried under vacuum in the presence of phosphorus pentoxide to afford 3-bromobenzenesulfonamide (3.270 g, 87% yield) in white crystalline form. NMR hydrogen spectrum (DMSO-d6) δ: 7.97 (t, J = 1.9 Hz, 1H), 7.84-7.80 (m, 2H), 7.54 (t, J = 7.9 Hz, 1H), 7.50 (bs, 2H). Liquid chromatography-mass spectrometry (ESI) m/z: 235.98 [M-H]-.

References

[1] Patent: WO2016/129983, 2016, A1. Location in patent: Page/Page column 18; 19
[2] Justus Liebigs Annalen der Chemie, 1875, vol. 177, p. 82
[3] ACS Medicinal Chemistry Letters, 2011, vol. 2, # 8, p. 603 - 607
[4] Bioorganic and Medicinal Chemistry Letters, 2014, vol. 24, # 9, p. 2222 - 2225

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