methyl 3-chlorosulfonylbenzoate Chemical Properties

Boiling point:

345.6±25.0 °C(Predicted)

Density 

1.431

storage temp. 

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

form 

powder

color 

light orange

InChI

InChI=1S/C8H7ClO4S/c1-13-8(10)6-3-2-4-7(5-6)14(9,11)12/h2-5H,1H3

InChIKey

SQIBNKUEUWGZBH-UHFFFAOYSA-N

SMILES

C(OC)(=O)C1=CC=CC(S(Cl)(=O)=O)=C1

EPA Substance Registry System

Benzoic acid, 3-(chlorosulfonyl)-, methyl ester (63555-50-0)

Safety Information

RIDADR 

3261

HazardClass 

IRRITANT

PackingGroup 

Ⅲ

HS Code 

2916399090

methyl 3-chlorosulfonylbenzoate Usage And Synthesis

Uses

Methyl 3-(chlorosulfonyl)benzoate

Synthesis

General procedure for the synthesis of methyl 3-(chlorosulfonyl)benzoate from methanol and 3-chlorosulfonylbenzoyl chloride: 3-(chlorosulfonyl)benzoic acid chloride (2.4 g) was dissolved in dichloromethane (20 mL) and cooled to 0 °C. Pyridine (791 mg) and methanol (320 mg) were added sequentially under stirring. The reaction mixture was stirred at room temperature for 2 hours. After completion of the reaction, the solvent was removed by evaporation under reduced pressure. The residue was filtered and washed with a solvent mixture of ethyl acetate and isopropyl ether. The filtrate was concentrated under reduced pressure and the resulting residue was purified by silica gel column chromatography with hexane-ethyl acetate (9:1→4:1) as eluent to afford the target compound methyl 3-(chlorosulfonyl)benzoate (2.17 g, 92% yield) as colorless oil. The structure of the product was confirmed by 1H-NMR (CDCl3): δ 3.99 (3H, s), 7.74 (1H, t, J=8.1 Hz), 8.21-8.24 (1H, m), 8.39-8.43 (1H, m), 8.69-8.70 (1H, m).

References

[1] Patent: EP1728793, 2006, A1. Location in patent: Page/Page column 127
[2] Patent: WO2006/36024, 2006, A1. Location in patent: Page/Page column 156
[3] Patent: EP2336107, 2015, B1. Location in patent: Paragraph 0296
[4] Recueil des Travaux Chimiques des Pays-Bas, 1921, vol. 40, p. 726
[5] Patent: WO2007/23186, 2007, A1. Location in patent: Page/Page column 49

methyl 3-chlorosulfonylbenzoate(63555-50-0)Related Product Information

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