ISOPROPYL P-TOLUENESULFONATE Chemical Properties

Melting point:

20

Boiling point:

107-109 °C(Press: 0.4 Torr)

Density 

1.142 g/mL at 25 °C

refractive index 

n20/D1.503

Flash point:

110

storage temp. 

2-8°C

solubility 

Chloroform (Slightly), Methanol (Slightly)

form 

Oil

color 

Colourless

InChI

InChI=1S/C10H14O3S/c1-8(2)13-14(11,12)10-6-4-9(3)5-7-10/h4-8H,1-3H3

InChIKey

SDQCGKJCBWXRMK-UHFFFAOYSA-N

SMILES

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

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26

WGK Germany 

3

Hazard Note 

Irritant

HS Code 

29041000

ISOPROPYL P-TOLUENESULFONATE Usage And Synthesis

Uses

Isopropyl p-Tosylate is a sulfonic acid ester, a potentialy alkylating agent. Studies suggest Isopropyl p-Tosylate may exert genotoxic effects in bacterial and mammalian cell systems.

Synthesis

The general procedure for the synthesis of isopropyl p-toluenesulfonate from sodium p-toluenesulfinate and isopropanol is as follows: to a solvent mixture containing dichloromethane (0.5 mL) and ethanol (0.5 mL) at room temperature, iodobenzene diacetate (DIB, 0.24 mmol, 1.2 eq.), sodium p-toluenesulfinate (0.2 mmol, 1 eq.), and acetic acid ( 0.01 g, 0.05 mL) or tetrabutylammonium chloride (TBAC, 55.5 mg, 0.2 mmol, 2 equiv) to dissolve the sulfonate. The reaction mixture was reacted under vigorous stirring for 15 minutes and subsequently monitored by thin layer chromatography (TLC) using a solvent mixture of acetic acid/ethyl acetate/hexane. Upon completion of the reaction, the mixture was filtered through silica gel and washed with ethyl acetate. Ultimately, the residue was purified by silica gel column chromatography using a mixed solvent of ethyl acetate/hexane to give the target product isopropyl p-toluenesulfonate (products 4, 6 and 8).

References

[1] Beilstein Journal of Organic Chemistry, 2018, vol. 14, p. 1203 - 1207

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