Tosyl azide

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

Tosyl azide

Names
Preferred IUPAC name 4-Methylbenzene-1-sulfonyl azide
Other names p-Toluenesulfonyl azide; p-Tosyl azide; p-Toluenesulfonazide; TsN3
Identifiers
CAS Number	941-55-9 Y
3D model (JSmol)	Interactive image
ChemSpider	13072
ECHA InfoCard	100.012.164
EC Number	213-381-5
PubChem CID	13661
UNII	97F7BLE97S Y
CompTox Dashboard (EPA)	DTXSID4061333
InChI InChI=1S/C7H7N3O2S/c1-6-2-4-7(5-3-6)13(11,12)10-9-8/h2-5H,1H3
SMILES O=S(=O)([N-][N+]#N)c1ccc(cc1)C
Properties[1]
Chemical formula	C7H7N3O2S
Molar mass	197.21 g·mol−1
Appearance	Oily colorless liquid
Density	1.286 g/cm3
Melting point	21 to 22 °C (70 to 72 °F; 294 to 295 K)
Boiling point	110 to 115 °C (230 to 239 °F; 383 to 388 K) at 0.001 mmHg
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

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]

Safety

Tosyl azide is one of the most stable azide compounds but is still regarded as a potential explosive and should be carefully stored, while particular caution is vital for all reactions in which it is heated at or above 100 °C. The initial temperature of the explosive decomposition is about 120 °C.^[1]

See also

• Fluorosulfonyl azide
• Diphenylphosphoryl azide
• Trifluoromethanesulfonyl azide