3-SULFAMOYL-BENZOIC ACID Chemical Properties

Melting point:

251-252℃

Boiling point:

476.1±47.0 °C(Predicted)

Density 

1.536±0.06 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

pka

pK1:3.54 (25°C)

Appearance

White to off-white Solid

Safety Information

Hazard Codes 

Xi

Risk Statements 

36

Safety Statements 

26-24/25-22

HazardClass 

IRRITANT

HS Code 

29350090

3-SULFAMOYL-BENZOIC ACID Usage And Synthesis

Chemical Properties

White solid

Synthesis

General procedure for the synthesis of 3-sulfobenzoic acid from 3-chlorosulfonylbenzoic acid: 25 g of 3-(chlorosulfonyl)benzoic acid (commercially available, Aldrich) was added in batches to 250 mL of 25% ammonium hydroxide solution under ice bath conditions. The reaction mixture was stirred at room temperature for 15 hours. Upon completion of the reaction, the solvent was concentrated by distillation under reduced pressure to about 50 mL. Subsequently, the mixture was acidified with concentrated hydrochloric acid to pH < 2. The precipitated white solid was collected by filtration and dried with a vacuum desiccator to afford 22 g (96% yield) of 3-sulfobenzoic acid. The product was characterized as follows: 1H NMR (DMSO-d6) δ 13.44 (br s, 1H), 8.38 (s, 1H), 8.14 (d, J = 7.5 Hz, 1H), 8.04 (d, J = 7.9 Hz, 1H), 7.72 (t, J = 7.9 Hz, 1H), 7.49 (s, 2H); HPLC (max plot) 97%; Rt 0.68 min; LC/MS (ES-): 199.8.

References

[1] Patent: WO2007/23186, 2007, A1. Location in patent: Page/Page column 45
[2] European Journal of Medicinal Chemistry, 2014, vol. 89, p. 503 - 523
[3] Journal of the American Chemical Society, 2011, vol. 133, # 40, p. 16235 - 16242
[4] ChemMedChem, 2015, vol. 10, # 9, p. 1548 - 1558
[5] Patent: US2013/35364, 2013, A1. Location in patent: Paragraph 0233-0235

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