4-Toluenesulfonyl chloride (''p''-toluenesulfonyl chloride, toluene-''p''-sulfonyl chloride) is an

organic compound Some chemical authorities define an organic compound as a chemical compound that contains a carbon–hydrogen or carbon–carbon bond; others consider an organic compound to be any chemical compound that contains carbon. For example, carbon-co ...

with the formula CH₃C₆H₄SO₂Cl. This white, malodorous solid is a

reagent In chemistry, a reagent ( ) or analytical reagent is a substance or compound added to a system to cause a chemical reaction, or test if one occurs. The terms ''reactant'' and ''reagent'' are often used interchangeably, but reactant specifies a ...

widely used in

organic synthesis Organic synthesis is a branch of chemical synthesis concerned with the construction of organic compounds. Organic compounds are molecules consisting of combinations of covalently-linked hydrogen, carbon, oxygen, and nitrogen atoms. Within the gen ...

. Abbreviated TsCl or TosCl, it is a derivative of

toluene Toluene (), also known as toluol (), is a substituted aromatic hydrocarbon with the chemical formula , often abbreviated as , where Ph stands for the phenyl group. It is a colorless, water Water is an inorganic compound with the c ...

and contains a

sulfonyl In organosulfur chemistry, a sulfonyl group is either a functional group found primarily in sulfones, or a substituent obtained from a sulfonic acid by the removal of the hydroxyl group, similarly to acyl groups. Group Sulfonyl groups can be w ...

chloride (−SO₂Cl)

functional group In organic chemistry, a functional group is any substituent or moiety (chemistry), moiety in a molecule that causes the molecule's characteristic chemical reactions. The same functional group will undergo the same or similar chemical reactions r ...

Uses

As typical for

Sulfonyl halide In chemistry, a sulfonyl halide consists of a sulfonyl () group singly bonded to a halogen atom. They have the general formula , where X is a halogen. The stability of sulfonyl halides decreases in the order fluorides > chlorides > bromides > iod ...

s, TsCl converts

alcohol Alcohol may refer to: Common uses * Alcohol (chemistry), a class of compounds * Ethanol, one of several alcohols, commonly known as alcohol in everyday life ** Alcohol (drug), intoxicant found in alcoholic beverages ** Alcoholic beverage, an alco ...

s (abbreviated ROH) into the corresponding toluenesulfonate esters, or tosyl derivatives ("tosylates"): : CH₃C₆H₄SO₂Cl + ROH → CH₃C₆H₄SO₂OR +

HCl HCL may refer to: Science and medicine * Hairy cell leukemia, an uncommon and slowly progressing B cell leukemia * Harvard Cyclotron Laboratory, from 1961 to 2002, a proton accelerator used for research and development * Hollow-cathode lamp, a s ...

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 In organic chemistry, the sulfonamide functional group (also spelled sulphonamide) is an organosulfur group with the Chemical structure, structure . It consists of a sulfonyl group () connected to an amine group (). Relatively speaking this gro ...

from amines: :CH₃C₆H₄SO₂Cl + R₂NH → CH₃C₆H₄SO₂NR₂ + HCl The resulting

sulfonamide In organic chemistry, the sulfonamide functional group (also spelled sulphonamide) is an organosulfur group with the Chemical structure, structure . It consists of a sulfonyl group () connected to an amine group (). Relatively speaking this gro ...

s 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 Pyridine is a basic (chemistry), basic heterocyclic compound, heterocyclic organic compound with the chemical formula . It is structurally related to benzene, with one methine group replaced by a nitrogen atom . It is a highly flammable, weak ...

and

triethylamine Triethylamine is the chemical compound with the formula N(CH2CH3)3, commonly abbreviated Et3N. Like triethanolamine and the tetraethylammonium ion, it is often abbreviated TEA. It is a colourless volatile liquid with a strong fishy odor remini ...

. 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 Trimethylamine (TMA) is an organic compound with the formula N(CH3)3. It is a trimethylated derivative of ammonia. TMA is widely used in industry. At higher concentrations it has an ammonia-like odor, and can cause necrosis of mucous membranes ...

Other reactions

Being a widely available reagent, TsCl has been heavily examined from the perspective of reactivity. It is used in dehydrations to make

nitrile In organic chemistry, a nitrile is any organic compound that has a functional group. The name of the compound is composed of a base, which includes the carbon of the , suffixed with "nitrile", so for example is called " propionitrile" (or pr ...

isocyanide An isocyanide (also called isonitrile or carbylamine) is an organic compound with the functional group –. It is the isomer of the related nitrile (–C≡N), hence the prefix is ''isocyano''.IUPAC Goldboo''isocyanides''/ref> The organic fragme ...

s and

diimide Diimide, also called diazene or diimine, is a compound having the formula HN=NH. It exists as two geometric isomers, ''E'' (''trans'') and ''Z'' (''cis''). The term diazene is more common for organic derivatives of diimide. Thus, azobenzene is an ...

s. In an unusual reaction focusing on the sulfur center, zinc reduces TsCl to the sulfinate, CH₃C₆H₄SO₂Na.

Manufacture

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 Food additives are substances added to food to preserve flavor or enhance taste, appearance, or other sensory qualities. Some additives, such as vinegar ( pickling), salt ( salting), smoke ( smoking) and sugar ( crystallization), have been used f ...

and catalyst

saccharin Saccharin, also called saccharine, benzosulfimide, or E954, or used in saccharin sodium or saccharin calcium forms, is a non-nutritive artificial sweetener. Saccharin is a sultam that is about 500 times sweeter than sucrose, but has a bitter or ...

), via the chlorosulfonation of

: : CH₃C₆H₅ + SO₂Cl₂ → CH₃C₆H₄SO₂Cl + HCl

Hazards

Tosyl chloride is "a corrosive

lachrymator Tear gas, also known as a lachrymatory agent or lachrymator (), sometimes colloquially known as "mace" after the Mace (spray), early commercial self-defense spray, is a chemical weapon that stimulates the nerves of the lacrimal gland in the ey ...

References

{{DEFAULTSORT:Toluenesulfonyl chloride, 4- Reagents for organic chemistry Sulfonyl halides p-Tosyl compounds Foul-smelling chemicals Chlorides