Tosylates

Tosylate ( three oxygen atoms)

p -Toluolsulfonsäureester (tosylate) to the blue labeled tosylate group bound to an organic radical R. The tosylate group containing 3 oxygen atoms.

Sodium salt of p -toluenesulfonic acid with the blue- marked tosylate anion ( tosylate group ). The tosylate anion contains 3 oxygen atoms.

Tosylates are esters or salts of p -toluenesulfonic acid .

INN nomenclature

In the medical and pharmaceutical sector, the internationally recognized short form for the anion of p-toluenesulfonic acid (p-toluenesulfonate) is "tosilate" according to the INN rules. Such short forms are created for molecular components if their systematic designation is too long. The “modified INN” (INNm) is created by combining a short form with the INN of the active component of the drug. Examples of such modified INN are for example ittramine tosilate or suplatast tosilate , the actual active ingredients are the bases of the counterions.

Likelihood of confusion

Tosyl group ( two oxygen atoms)

The tosyl group marked blue contains only 2 oxygen atoms. In the formula, R stands, for example, for Cl (tosyl chloride), NH 2 , NH-alkyl or N (alkyl) 2 (tosylamides), OH ( p -toluenesulfonic acid) and O-alkyl or O-aryl ( p -toluenesulfonic acid ester ).

The tosylate group always contains three oxygen atoms that are directly bonded to the sulfur atom. The tosylate group should not be confused with the tosyl group ; according to IUPAC rule C-641.7, the latter only contains two oxygen atoms bound to an organyl oxy residue (OR) or, for example, a chlorine atom in tosyl chloride .

Manufacturing

Tosylates can be produced by deprotonating an alcohol and then reacting with p -toluenesulphonic acid chloride, whereby one equivalent of hydrogen chloride , which is bound as a hydrochloride by a base , is formed:

use

Due to their property as a leaving group, tosylates are used in preparative organic chemistry . By converting alcohols into tosylates, the poor leaving group HO ^{- is converted} into a good leaving group, which enables substitution reactions at this position on the carbon structure. The anion of p -toluenesulfonic acid emerges as a leaving group . Even more reactive than the esters of p -toluenesulfonic acid (tosylates) are the corresponding triflates , which react up to 10,000 times faster and in which the 4-methylphenyl residue of the tosylate is replaced by a trifluoromethyl residue (hence the name triflate).

Drugs that an amino group be included sometimes as salts of p used toluenesulfonic acid, so as tosylates.

Individual evidence

1. ↑ International Nonproprietary Names (INN) for pharmaceutical substances - Names for radicals, groups & others , WHO 2012.
2. ↑ ^{a b} Author collective, Organikum , 21st edition, p. 217, Wiley-VCH, Weinheim, 2001, ISBN 3-527-29985-8 .