Tosyl azide

Tosyl azide
IUPAC name 4-Methylbenzenesulfonyl azide
Other names p-Toluenesulfonyl azide; p-Tosyl azide; p-Toluenesulfonazide
Identifiers
CAS number	941-55-9 Y
PubChem	13661
ChemSpider	13072
EC number	213-381-5
Jmol-3D images	Image 1
SMILES O=S(=O)([N-][N+]#N)c1ccc(cc1)C
InChI InChI=InChI=1S/C7H7N3O2S/c1-6-2-4-7(5-3-6)13(11,12)10-9-8/h2-5H,1H3
Properties[1]
Molecular formula	C7H7N3O2S
Molar mass	197.21 g mol−1
Appearance	Oily colorless liquid
Density	1.286 g/cm3
Melting point	21-22 °C, 294-295 K, 70-72 °F
Boiling point	110–115 °C at 0.001 mmHg
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

Tosyl azide is a reagent used in organic synthesis.^[1]

Uses

Tosyl azide is used for the introduction of azide and diazo functional groups.^[1] It is also used as a nitrene source and as a substrate for [3+2] cycloaddition reactions.^[1]

Preparation

Tosyl azide can be prepared by the reaction of tosyl chloride with sodium azide in aqueous acetone.^[2]

See also

• Trifluoromethanesulfonyl azide

References

1. ^ ^{a b c d} "p-Toluenesulfonyl Azide". Heydt, Heinrich; Regitz, Manfred. Encyclopedia of Reagents for Organic Synthesis (2001)
2. ^ Curphey, Thomas J. (1981). "Preparation of p-toluenesulfonyl azide. A cautionary note". Organic Preparations and Procedures International ( 13 (2): 112–115.