4-(dimethylamino)benzenesulphonic acid Chemical Properties

Melting point:

270.5°C

Density 

1.3156 (rough estimate)

refractive index 

1.5364 (estimate)

storage temp. 

Store at room temperature

pka

-1.15±0.50(Predicted)

Appearance

White to off-white Solid

InChI

InChI=1S/C8H11NO3S/c1-9(2)7-3-5-8(6-4-7)13(10,11)12/h3-6H,1-2H3,(H,10,11,12)

InChIKey

KZVBBVPCVQEVQK-UHFFFAOYSA-N

SMILES

C1(S(O)(=O)=O)=CC=C(N(C)C)C=C1

EPA Substance Registry System

Benzenesulfonic acid, 4-(dimethylamino)- (121-58-4)

4-(dimethylamino)benzenesulphonic acid Usage And Synthesis

Uses

N,N-Dimethylsulfanilic Acid, is a benzoic acid derivative acting as a weak yeast sirtuin inhibitors.

Synthesis

4-(Dimethylamino)benzenesulfonic acid was synthesized as follows: to a 250 mL three-necked round-bottomed flask, a solution of N,N-dimethylaniline (20 g, 165.29 mmol) in ether (40 mL) was added under ice bath conditions. Subsequently, a solution of sulfuric acid (16.1 g, 161.00 mmol) in ether (160 mL) was added slowly and dropwise. Upon completion of the reaction, the ether solvent was removed by rotary evaporator. The resulting mixture was reacted under stirring conditions at 170 °C under vacuum for 4 hours. Eventually, 10.5 g of 4-(dimethylamino)benzenesulfonic acid was obtained in 32% yield and the product was a white solid.

References

[1] Patent: US2010/256092, 2010, A1. Location in patent: Page/Page column 134
[2] European Journal of Medicinal Chemistry, 2001, vol. 36, # 10, p. 809 - 828
[3] Synthesis, 1982, # 4, p. 277 - 280
[4] Patent: US2008/318941, 2008, A1. Location in patent: Page/Page column 37
[5] Patent: US2008/200471, 2008, A1. Location in patent: Page/Page column 60