4-(CHLOROSULFONYL)BENZOIC ACID Chemical Properties

Melting point:

230 °C

Boiling point:

379.1±25.0 °C(Predicted)

Density 

1.5116 (estimate)

storage temp. 

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

solubility 

soluble in DMSO, Methanol

pka

3.09±0.10(Predicted)

form 

Powder

color 

Off-white to beige

Water Solubility 

Reacts with water.

Sensitive 

Moisture Sensitive

CAS DataBase Reference

10130-89-9(CAS DataBase Reference)

EPA Substance Registry System

Benzoic acid, 4-(chlorosulfonyl)- (10130-89-9)

Safety Information

Hazard Codes 

C

Risk Statements 

34-29-22

Safety Statements 

8-45-36/37/39-26

RIDADR 

3261

WGK Germany 

3

TSCA 

Yes

HazardClass 

8

PackingGroup 

II

HS Code 

29173990

MSDS

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

4-(CHLOROSULFONYL)BENZOIC ACID Usage And Synthesis

Chemical Properties

off-white to beige powder

Uses

4-(Chlorosulfonyl)benzoic acid was used in the preparation of polymer bound transfer hydrogenation catalyst and 4-(carboxymethyl-sulfamoyl)-benzoyladenosine. It was also used as a reagent in the sulfonation of γ-cyclodextrin.

Synthesis

The general procedure for the synthesis of 4-(chlorosulfonyl)benzoic acid from 4-methylphenylsulfonic acid was as follows: a solution of potassium permanganate (KMnO4, 1.6 g) in water (H2O, 13 mL) was added slowly and dropwise at 80 °C to a solution of 4-methylphenylsulfonic acid (1.7 g, 10 mmol) and potassium hydroxide (KOH, 0.68 g, 12 mmol) in water (H2O, a 15 mL) solution. Upon completion of the reaction, the mixture was poured into ethanol (EtOH, 20 mL), filtered and concentrated to give potassium 4-carboxybenzenesulfonate (1.2 g). This intermediate was used directly in the next reaction without further purification. At room temperature, chlorosulfonic acid (4 mL) was slowly added dropwise to a stirring solution of potassium 4-carboxybenzenesulfonate (1.2 g). The reaction mixture was continued to be stirred for 2 hours and then poured into crushed ice. The resulting solid product was collected by filtration and washed with water (H2O) to give 4-(chlorosulfonyl)benzoic acid (0.22 g) as a white solid in 20% yield. The melting point of the product was 230-232 °C (literature value: 228-232 °C); 1H-NMR (CDCl3, 400 MHz) data: δ 8.30 (d, J=8.0 Hz, 2H), 8.42 (d, J=8.0 Hz, 2H).

References

[1] Bioorganic and Medicinal Chemistry Letters, 2012, vol. 22, # 2, p. 958 - 962

4-(CHLOROSULFONYL)BENZOIC ACID(10130-89-9)Related Product Information

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