4-(Chlorosulfonyl)-benzoic acid methyl ester

4-(Chlorosulfonyl)-benzoic acid methyl ester Property

Melting point:

72-73℃

Boiling point:

126 °C(Press: 0.05 Torr)

Density 

1.431

storage temp. 

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

form 

solid

color 

Faint to light orange

InChI

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

InChIKey

MOFQDKOKODUZPK-UHFFFAOYSA-N

SMILES

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

Safety

RIDADR 

3261

HazardClass 

IRRITANT

PackingGroup 

Ⅲ

HS Code 

2904990090

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Danger

Hazard statements

H314Causes severe skin burns and eye damage

Precautionary statements

P260Do not breathe dust/fume/gas/mist/vapours/spray.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P301+P330+P331IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.

P303+P361+P353IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.

4-(Chlorosulfonyl)-benzoic acid methyl ester Chemical Properties,Usage,Production

Uses

4-(Chlorosulfonyl)-benzoic acid methyl ester can be used as an organic synthesis raw material for the preparation of other heterocyclic compounds.

Synthesis

General procedure for the synthesis of methyl 4-(chlorosulfonyl)benzoate from methanol and 4-(chlorosulfonyl)benzoyl chloride: 4-chlorosulfonylbenzoic acid (5 g, 23 mmol) was dissolved in dichloroethane (10 mL), thionyl chloride (20 mL) was added, and the reaction mixture was heated to 80 °C, and the reaction was maintained at this temperature for 2 hours. Upon completion of the reaction, the reaction mixture was concentrated by rotary evaporator to give a brown solid. The resulting solid was cooled in an ice bath for 5 min, followed by the slow addition of pre-cooled methanol (40 mL) at 0 °C with stirring, a process that lasted for 5 min. The reaction mixture was gradually warmed up to room temperature and stirring was continued for 10 minutes. Finally, ice-cold water (40 mL) was added, at which time a white solid precipitated, and the solid product was collected by filtration and dried under vacuum to afford pure methyl 4-(chlorosulfonyl)benzoate (4.5 g, 84% yield). The product was characterized by NMR (400 MHz, DMSO-d6): δ, ppm: 3.84 (s, 3H), 7.70 (d, 2H, J = 8.4Hz), 7.93 (d, 2H, J = 8.4Hz).

References

[1] Patent: WO2005/66126, 2005, A1. Location in patent: Page/Page column 73-74
[2] Patent: US9247759, 2016, B2. Location in patent: Page/Page column 144; 145
[3] Recueil des Travaux Chimiques des Pays-Bas, 1957, vol. 76, p. 129,138,145