4-Toluenesulfonyl chloride

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4-Toluenesulfonyl chloride
Names
IUPAC name
4-Methylbenzene-1-sulfonyl chloride
Other names
4-Methylbenzenesulfonyl chloride
4-Toluenesulfonyl chloride
p-Toluenesulfonyl chloride
TosCl
Tosyl chloride
p-TsCl
Toluene-p-sulfonyl chloride
TsCl
Properties
C7H7ClO2S
CH3C6H4SO2Cl
Molar mass 190.65 g/mol
Appearance White solid
Density 1.3 g/cm3
Melting point 69–71 °C (156–160 °F; 342–344 K)
Boiling point 220 °C (428 °F; 493 K) (decomposes)
146 °C (295 °F; 419 K) (at 15 mmHg)
Reacts
Solubility Reacts with alcohols, amines
Soluble in benzene, chloroform, diethyl ether, THF, toluene
Vapor pressure 0.0012 mmHg
Hazards
Safety data sheet Sigma-Aldrich
Flash point 128 °C (262 °F; 401 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Tosyl chloride or 4-Toluenesulfonyl chloride is an organic compound with the formula CH3C6H4SO2Cl. It is often abbreviated TsCl or TosCl.

Properties

Chemical

Tosyl chloride converts alcohols into the corresponding toluenesulfonate esters or tosylates:

CH3C6H4SO2Cl + ROH → CH3C6H4SO2OR + HCl

Likewise, TsCl is used to prepare sulfonamides from amines:

CH3C6H4SO2Cl + R2NH → CH3C6H4SO2NR2 + HCl

The preparation of tosyl esters and amides are conducted in the presence of a base, which absorbs hydrogen chloride. The selection of the base is often crucial to the efficiency of tosylation. Typical bases include pyridine and triethylamine.

Physical

Tosyl chloride is a colorless solid, which reacts with water and alcohols, but dissolves in ethers.

Availability

Can be bought from chemical suppliers.

Preparation

Tosyl chloride can be synthesized via the chlorosulfonation of toluene, using sulfuryl chloride:[1]

CH3C6H5 + SO2Cl2 → CH3C6H4SO2Cl + HCl

Alternatively, it can be obtained in two steps, by reaction of conc. sulfuric acid with toluene to form toluenesulfonic acid, which is then chlorinated with phosphorus pentachloride to tosyl chloride.[2]

Projects

  • Make sulfonamides
  • Protecting group for amines
  • Compound collecting

Handling

Safety

Tosyl chloride readily reacts with water to form HCl, which is corrosive. Proper protection must be worn when handling this compound.

Storage

Should be kept in dry airtight containers, preferably under inert gas if possible.

Disposal

Should be neutralized with a diluted NaOH solution then destroyed with an oxidizing solution, such as Fenton's reagent.

References

  1. https://onlinelibrary.wiley.com/doi/10.1002/14356007.a03_507
  2. https://prepchem.com/synthesis-of-4-toluenesulfonyl-chloride

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