Benzoic acid, 5-(chlorosulfonyl)-2-methyl- (9CI) Chemical Properties

Melting point:

152-154°

Boiling point:

398.7±35.0 °C(Predicted)

Density 

1.514±0.06 g/cm3(Predicted)

storage temp. 

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

pka

2.57±0.25(Predicted)

Appearance

White to off-white Solid

Safety Information

RIDADR 

UN3261

HazardClass 

IRRITANT

HS Code 

2916399090

Benzoic acid, 5-(chlorosulfonyl)-2-methyl- (9CI) Usage And Synthesis

Uses

5-(Chlorosulfonyl)-2-methylbenzoic acid

Synthesis

General procedure for the synthesis of 5-chlorosulfonyl-2-methylbenzoic acid from o-toluic acid: chlorosulfonic acid (50 mL, 752 mmol) was added to a 250 mL round-bottomed flask and cooled to 0 °C under nitrogen protection. O-toluic acid (10.0 g, 73.4 mmol) was added in small portions over 2 min and the reaction mixture turned brown. The reaction solution was slowly warmed to room temperature and then heated to 145°C for overnight reaction. After the reaction was completed, the mixture was cooled to room temperature and poured into ice water (~750 mL). The precipitate was collected by filtration, washed with water and dried in a vacuum oven at 80 °C for 7 h to give 15.53 g (90% yield) of an off-white solid product. The structure of the product was confirmed by 1H NMR (DMSO-d6): δ 2.53 (s, 3H), 7.26 (d, J = 7.9 Hz, 1H), 7.63 (d, J = 7.9 Hz, 1H), 8.07 (s, 1H), 13.60 (br s, 1H).

References

[1] Tetrahedron, 2013, vol. 69, # 12, p. 2640 - 2646
[2] Patent: WO2004/18414, 2004, A2. Location in patent: Page 133-134
[3] Patent: WO2007/91140, 2007, A1. Location in patent: Page/Page column 65
[4] Patent: US2237974, 1939,
[5] Journal of the American Chemical Society, 2013, vol. 135, # 15, p. 5656 - 5668

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