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词条 Tosyl azide
释义

  1. Uses

  2. Preparation

  3. Safety

  4. See also

  5. References

{{Chembox
| ImageFile = tosyl azide.svg
| ImageSize =
| 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}}
| 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 =[1]
| 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
| Solubility =
|Section3={{Chembox Hazards
| MainHazards =
| FlashPt =
| AutoignitionPt =
}}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]

Safety

Tosyl Azide is one of the more stable azide compounds but is still regarded as a potential explosive and should be carefully stored.

See also

  • Diphenylphosphoryl azide
  • Trifluoromethanesulfonyl azide

References

1. ^{{ cite encyclopedia |author1=Heydt, H. |author2=Regitz, M. |author3=Mapp, A. K. |author4=Chen, B. | 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 = 978-0471936237|chapter = P-Toluenesulfonyl Azide}}
2. ^{{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 }}

2 : Azides|Reagents for organic chemistry

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