Ethanol, 2-methoxy-, 4-methylbenzenesulfonate
2-Methoxyethyl p-toluenesulfonate (CAS 17178-10-8), also named 2-methoxyethyl 4-methylbenzenesulfonate, p-toluenesulfonic acid 2-methoxyethyl ester or 2-methoxyethyl tosylate, is the tosylate ester of 2-methoxyethanol. It is a colourless to pale yellow liquid with a boiling point near 141 degrees Celsius at reduced pressure and a purity of 98 percent or higher by gas chromatography, and it is supplied at a density close to 1.2 grams per cubic centimetre. The molecule is a classical alkylating agent: the p-toluenesulfonate group is an excellent leaving group, so the 2-methoxyethyl unit is transferred readily to nucleophiles including amines, thiols, alkoxides, phenoxides and stabilised carbanions. It is stable when stored cool and dry but hydrolyses slowly in the presence of water; its practical value lies in delivering the methoxyethyl fragment efficiently under mild conditions.
1. Alkylating agent for pharmaceuticals: used to install the 2-methoxyethyl side chain in drug molecules, for example in the synthesis of antihistamines, analgesics, central nervous system agents and kinase inhibitors where the ether improves solubility and metabolic profile.
2. Synthetic chemistry reagent: provides a mild, high-yielding route to methoxyethyl ethers, tertiary amines and thioethers where direct alkylation of the nucleophile would be difficult, unselective or require harsher conditions such as phase-transfer catalysis with alkyl halides.
3. Impurity and reference standard: also serves as a reference material for controlling sulfonate ester genotoxic impurities such as 2-methoxyethyl mesylate in drug substances and intermediates during toxicological risk assessment and method validation.
4. Handling and storage: alkylating and irritating to skin and eyes; store in a sealed container, cool and dry, away from water, bases, amines and oxidising agents, use appropriate gloves and eye protection, avoid inhalation of vapours and treat waste as regulated chemical waste.
Product Name: Ethanol, 2-methoxy-, 4-methylbenzenesulfonate
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