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Chemical compound From Wikipedia, the free encyclopedia
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.[2] Abbreviated TsCl or TosCl, it is a derivative of toluene and contains a sulfonyl chloride (−SO2Cl) functional group.
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Names | |
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Preferred IUPAC name
4-Methylbenzene-1-sulfonyl chloride | |
Other names
Tosyl chloride, p-toluenesulfonyl chloride, p-TsCl, TsCl | |
Identifiers | |
3D model (JSmol) |
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ChemSpider | |
ECHA InfoCard | 100.002.441 |
PubChem CID |
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UNII | |
CompTox Dashboard (EPA) |
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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 |
Reacts with water | |
Hazards[1] | |
Occupational safety and health (OHS/OSH): | |
Main hazards |
Releases HCl on contact with water |
NFPA 704 (fire diamond) | |
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).
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In characteristic manner, TsCl converts alcohols (abbreviated ROH) into the corresponding toluenesulfonate esters, or tosyl derivatives ("tosylates"):
Tosylates can be cleaved with lithium aluminium hydride:
Thus, tosylation followed by reduction allows for removal of a hydroxyl group.
Likewise, TsCl is used to prepare sulfonamides from amines:[3]
The resulting sulfonamides are non-basic and, when derived from primary amines, are even acidic.
TsCl reacts with hydrazine to give p-toluenesulfonyl hydrazide.
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.[2]
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.[2] In an unusual reaction focusing on the sulfur center, zinc reduces TsCl to the sulfinate, CH3C6H4SO2Na.[4]
This reagent is inexpensively available for laboratory use. It is a by-product from the production of ortho-toluenesulfonyl chloride (a precursor for the synthesis of the common food additive and catalyst saccharin), via the chlorosulfonation of toluene:[5]
Tosyl chloride is "a corrosive lachrymator."[2]
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