Synthesis of 4-methylbenzenediazonium

Preparation of 4-methylbenzenediazonium

100 ml of concentrated hydrochloric acid (1.2 moles) and 50 ml of water are poured into a 500 ml flask. 43 grams (or 43 ml) of p-toluidine (0.4 mole) are added and well mixed in order to convert the p-toluidine into the p-toluidine hydrochloride. To complete the reaction, the mixture is heated until the obtained p-toluidine hydrochloride is fully dissolved. The solution is cooled with shaking in a salt-ice bath and the p-toluidine hydrochloride separates as fine crystals. By keeping the mixture at a temperature of 0-5° C and by vigorous shaking in the salt-ice bath the p-toluidine hydrochloride is treated with a solution of 28 grams of sodium nitrite in 80 ml of water with shaking. The p-toluidine hydrochloride dissolves as the more soluble 4-methylbenzenediazonium diazonium salt is formed, and at the end of the addition of the sodium nitrite the solution should contain a trace of nitrous acid. 4-methylbenzenediazonium is not stable and should be consumed.

Experiments in Organic Chemistry, L. F. Fieser, 215-216, 1941





InChI Key


Canonical SMILES


MeSH Synonyms

4-methylbenzenediazonium, 4-methylbenzenediazonium chloride, 4-methylbenzenediazonium sulfate (1:1) salt, 4-methylbenzenediazonium sulfate (2:1) salt, 4-methylbenzenediazonium tetrafluoroborate salt, 4-methylbenzenediazonium triiodide

Depositor-Supplied Synonyms

4-Methylbenzenediazonium, 57573-52-1, AC1Q4PUJ, Benzenediazonium,4-methyl-, AC1L28UW, Benzenediazonium, 4-methyl-, SCHEMBL261743, CTK5A7084, AR-1G3570, 459-44-9 (tetrafluoroborate salt), LS-190062, 32066-79-8 (sulfate (1:1) salt), 38258-26-3 (sulfate (2:1) salt)

Removed Synonyms

CID68020, 59338-84-0

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