Synthesis of benzenediazonium chloride (phenyldiazonium chloride)

Preparation of benzenediazonium chloride

15 ml (or 15.4 g) of aniline is dissolved in a mixture of 40 ml of concentrated hydrochloric acid and 40 ml of water. The solution is cooled to 5° C by immersing the flask in a mixture of ice and water. While stirring, the solution of 12 5 g of powdered sodium nitrite dissolved in 30 ml of water is dropwise added to the solution of aniline hydrochloride. During the diazotization heat is evolved, and the addition of sodium nitrite is interrupted, by allowing the temperature to fall again to 5° C. The temperature must not be allowed to rise above 10°, otherwise noticible decomposition of the benzenediazonium chloride to phenol will occur: on the other hand, the temperature should not be allowed to fall as low as 0° C, as at this temperature diazotization becomes very slow, and free nitrous acid may remain in the solution for a considerable time. The obtained benzene diazonium chloridesolution must be kept in ice-water until required.

Practical organic chemistry, by F. G. Mann, 86-88, 1960

IUPAC Name

benzenediazonium;chloride

InChI

InChI=1S/C6H5N2.ClH/c7-8-6-4-2-1-3-5-6;/h1-5H;1H/q+1;/p-1

InChI Key

CLRSZXHOSMKUIB-UHFFFAOYSA-M

Canonical SMILES

C1=CC=C(C=C1)[N+]#N.[Cl-]

MeSH Synonyms

benzenediazonium, benzenediazonium chloride, benzenediazonium hexafluorophosphate (-1), benzenediazonium ion, benzenediazonium nitrate, benzenediazonium sulfate (1:1), benzenediazonium sulfate (2:1), benzenediazonium tetrafluoroborate, benzenediazonium tetrafluoroborate (-1), benzenediazonium tri-iodide, phenyldiazonium compounds

Depositor-Supplied Synonyms

Benzenediazonium chloride, 100-34-5, Phenyldiazonium chloride, AC1L1UB3, AC1Q1S6X, SCHEMBL73874, BENZENE DIAZONIUM CHLORIDE, Benzene diazonium chloride (dry), CTK3J8820, Benzenediazonium,chloride (1:1), CLRSZXHOSMKUIB-UHFFFAOYSA-M, EINECS 202-842-6, Benzene diazonium chloride (dry) [Forbidden]

Removed Synonyms

2684-02-8 (Parent), CID60992

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