Tosyl azide

Tosyl azide
Names
	IUPAC name 4-Methylbenzenesulfonyl azide
	Other names p-Toluenesulfonyl azide; p-Tosyl azide; p-Toluenesulfonazide
Identifiers
CAS Number	941-55-9 ;
3D model (JSmol)	Interactive image;
ChemSpider	13072;
ECHA InfoCard	100.012.164
EC Number	213-381-5;
PubChem CID	13661;
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
Chemical formula	C7H7N3O2S
Molar mass	197.21 g·mol−1
Appearance	Oily colorless liquid
Density	1.286 g/cm3
Boiling point	110–115 °C 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

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]

References

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

[EROS-1] "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.

[1]

[2]

Uses

Preparation

See also

References