tosyl azide
{{Short description|Chemical compound used in organic synthesis}}
{{Chembox
|ImageFile = tosyl azide.svg
|ImageFile1 = Tosyl Azide Ball and Stick.png
|ImageSize1 = 200px
|PIN = 4-Methylbenzene-1-sulfonyl azide
|OtherNames = p-Toluenesulfonyl azide; p-Tosyl azide; p-Toluenesulfonazide; TsN3
|Section1={{Chembox Identifiers
|CASNo = 941-55-9
|CASNo_Ref = {{cascite|correct|CAS}}
|UNII_Ref = {{fdacite|correct|FDA}}
|UNII = 97F7BLE97S
|PubChem = 13661
|ChemSpiderID = 13072
|EINECS = 213-381-5
|SMILES = O=S(=O)([N-][N+]#N)c1ccc(cc1)C
|InChI = 1S/C7H7N3O2S/c1-6-2-4-7(5-3-6)13(11,12)10-9-8/h2-5H,1H3
}}
|Section2={{Chembox Properties
|Properties_ref ={{ cite encyclopedia |author1=Heydt, H. |author2=Regitz, M. |author3=Mapp, A. K. |author4=Chen, B. |title=p -Toluenesulfonyl Azide | encyclopedia = Encyclopedia of Reagents for Organic Synthesis | year = 2008 | doi = 10.1002/047084289X.rt141.pub2 | chapter-url = http://onlinelibrary.wiley.com/o/eros/articles/rt141/frame.html |isbn = 978-0-471-93623-7|chapter = P-Toluenesulfonyl Azide}}
|C=7 | H=7 | N=3 | O=2 | S=1
|Appearance = Oily colorless liquid
|Density = 1.286 g/cm3
|MeltingPtC = 21 to 22
|BoilingPtC = 110 to 115
|BoilingPt_notes = at 0.001 mmHg
}}
}}
Tosyl azide is a reagent used in organic synthesis.
Uses
Tosyl azide is used for the introduction of azide and diazo functional groups. It is also used as a nitrene source and as a substrate for [3+2] cycloaddition reactions.
Preparation
Tosyl azide can be prepared by the reaction of tosyl chloride with sodium azide in aqueous acetone.{{cite journal | title = Preparation of p-Toluenesulfonyl Azide. A Cautionary Note | author = Curphey, T. J. | journal = Organic Preparations and Procedures International | year = 1981 | volume = 13 | issue = 2 | pages = 112–115 | doi = 10.1080/00304948109356105 }}