Tosyl azide is a reagent used in organic synthesis.[1]
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| Names | |
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| Preferred IUPAC name
4-Methylbenzene-1-sulfonyl azide | |
| Other names
p-Toluenesulfonyl azide; p-Tosyl azide; p-Toluenesulfonazide; TsN3
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| Identifiers | |
3D model (JSmol)
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| ChemSpider | |
| ECHA InfoCard | 100.012.164 |
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PubChem CID
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| UNII | |
CompTox Dashboard (EPA)
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| Properties[1] | |
| 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).
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Uses
editTosyl 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
editTosyl azide can be prepared by the reaction of tosyl chloride with sodium azide in aqueous acetone.[2]
Safety
editTosyl 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
editReferences
edit- ^ a b c d e Heydt, H.; Regitz, M.; Mapp, A. K.; Chen, B. (2008). "P-Toluenesulfonyl Azide". p -Toluenesulfonyl Azide. Encyclopedia of Reagents for Organic Synthesis. doi:10.1002/047084289X.rt141.pub2. ISBN 978-0-471-93623-7.
- ^ Curphey, T. J. (1981). "Preparation of p-Toluenesulfonyl Azide. A Cautionary Note". Organic Preparations and Procedures International. 13 (2): 112–115. doi:10.1080/00304948109356105.