Synthesis of p-toluenesulfonyl azide

Preparation of p-toluenesulfonyl azide

p-Toluenesulfonyl azide was prepared by adding with swirling 70 g. of sodium azide in 200 ml of water to 170 g. of freshly distilled p-toluenesulfonyl chloride in 1000 ml of 95% ethanol. After standing one hour the mixture was poured into 4 liter of water. The separated oily p-toluenesulfonyl azide was washed thrice with water and dried over sodium sulfate. p-Toluenesulfonyl azide could be used for the synthesis purpose without further purification.

T. Curtius and G. Kraemer, J. Prakt. Chem., [2] 125, 303 (1930).

W. von E. Doering and C. H. DePuy, J. Am. Chem. Soc., 75, 5955 (1953).

Org. Synth. 1968, 48, 36





InChI Key


Canonical SMILES


Depositor-Supplied Synonyms

Tosyl azide, p-Toluenesulfonyl azide, 941-55-9, p-Toluenesulfonazide, 4-methylbenzenesulfonyl azide, p-toluenesulfonylazide, tosylazide, 4-methylbenzene-1-sulfonyl azide, p-Toluenesulfonic acid azide, p-Tolylsulfonyl azide, Benzenesulfonyl azide, 4-methyl-, p-Methylphenylsulfonyl azide, N-diazo-4-methylbenzenesulfonamide, NDLIRBZKZSDGSO-UHFFFAOYSA-N, Tosyl nitride, p-Toluenesulfonyl azide or 4-Methylbenzenesulfonyl azide, Azido-p-toluenesulfonic acid, p-Tosyl azide, Tosyl azide solution, p-toluene-sulfonylazide, p-toluenesulphonyl azide, para-toluenesulfonylazide, 4-toluenesulphonyl azide, p-toluene-sulfonyl azide, AC1NSE1M, toluene-p-sulphonyl azide, para-toluene-sulfonylazide, 4-toluene sulphonyl azide, para toluene sulfonyl azide, para-toluene sulfonyl azide, AC1Q2LI5, p-Toluenesulfonazide solution, UNII-97F7BLE97S, SCHEMBL137120, 4-methyl-benzenesulfonyl azide, 4-TOLUENESULFONYL AZIDE, 97F7BLE97S, AC1L227L, diazonio(p-tolylsulfonyl)azanide, p-Toluenesulfonyl azide solution, CTK8E6383, P-TOLUENE SULPHONYL AZIDE, MolPort-002-492-608, 67842-69-7, ACT00384, EBD33436, ZINC4984589, NSC138649, ZINC04984589, 4-Methylbenzenesulfonyl azide solution, AKOS009237058, AB04417, MCULE-8753634248, NSC-138649, RP04112, RTC-063947, (NE)-N-diazo-4-methylbenzenesulfonamide, AN-48115, BC213440, OR032166, SC-19523, AB1007736, DB-008676, KB-309021, TC-063947, FT-0082318, FT-0650629, EN300-73297, A-8444, 113523-EP2281820A2, 113523-EP2298754A1, 113563-EP2281820A2, 113563-EP2298754A1, p-Toluenesulfonyl azide; 4-Methylbenzenesulfonyl azide, 3B3-064369, 4-Methylbenzenesulfonyl azide solution; Tosyl azide solution

Removed Synonyms

CID13661, ZINC06731680, CID5359526

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