4-Toluenesulfonyl chloride
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| Names | |
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| IUPAC name
4-methylbenzenesulfonyl chloride
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| Other names
Tosyl chloride, p-toluenesulfonyl chloride, p-TsCl, TsCl
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| Identifiers | |
98-59-9  |
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| ChemSpider | 7119 |
| Jmol 3D model | Interactive image |
| PubChem | 160808444 |
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| Properties | |
| C7H7ClO2S | |
| Molar mass | 190.65 g/mol |
| Appearance | White solid |
| Melting point | 65 to 69 °C (149 to 156 °F; 338 to 342 K) |
| Boiling point | 134 °C (273 °F; 407 K) at 10 mmHg |
| Hydrolysis | |
| Vapor pressure | {{{value}}} |
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Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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| Infobox references | |
4-Toluenesulfonyl chloride (p-toluenesulfonyl chloride, toluene-p-sulfonyl chloride) is an organic compound with the formula CH3C6H4SO2Cl. This white, malodorous solid is a reagent widely used in organic synthesis.[1] Abbreviated TsCl or TosCl, it is a derivative of toluene and contains a sulfonyl chloride (-SO2Cl) functional group.
Contents
Uses
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In characteristic manner, TsCl converts alcohols (abbreviated ROH) into the corresponding toluenesulfonate esters, or tosyl derivatives ("tosylates"):
- CH3C6H4SO2Cl + ROH → CH3C6H4SO2OR + HCl
Tosylates can be cleaved with lithium aluminium hydride:
- 4 CH3C6H4SO2OR + LiAlH4 → LiAl(O3SC6H4CH3)4 + 4 RH
Thus, tosylation followed by reduction allows for removal of a hydroxyl group.
Likewise, TsCl is used to prepare sulfonamides from amines:[2]
- CH3C6H4SO2Cl + R2NH → CH3C6H4SO2NR2 + HCl
The resulting sulfonamides are non-basic and, when derived from primary amines, are even acidic.
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. Unusual bases are also used; for example, catalytic amounts of trimethylammonium chloride in the presence of triethylamine is highly effective by virtue of the trimethylamine.[1]
Other reactions
Being a widely available reagent, TsCl has been heavily examined from the perspective of reactivity. It is used in dehydrations to make nitriles, isocyanides and diimides.[1] In an unusual reaction focusing on the sulfur center, zinc reduces TsCl to the sulfinate, CH3C6H4SO2Na.[3]
Manufacture
TsCl is inexpensively available for laboratory use. It is a by-product from the production of o-toluenesulfonyl chloride (a precursor for the synthesis of saccharin), via the chlorosulfonation of toluene:[4]
- CH3C6H5 + SO2Cl2 → CH3C6H4SO2Cl + HCl
References
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