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An improved synthesis of 3-[1-(trifluoromethy1)-3H-1,2-diazirin-3-yl] aniline: a key intermediate in the synthesis of photoaffinity probes
Umeå University, Faculty of Science and Technology, Department of Chemistry.
Umeå University, Faculty of Science and Technology, Department of Chemistry.
2017 (English)In: Tetrahedron Letters, ISSN 0040-4039, E-ISSN 1359-8562, Vol. 58, no 34, 3350-3352 p.Article in journal (Refereed) Published
Abstract [en]

An improved synthesis of 3-[3-(trifluoromethyl)-3H-1,2-diazirin-3-yflaniline, achieving an overall yield of 38% over seven steps is reported. Only three chromatographic separations were needed and the preparation of similar to 0.7 g of the target compound was demonstrated. The stability of the diazirine in solution at room temperature while exposed to ambient light was studied. No significant degradation of the compound was observed over the course of five weeks in a 130 mM sample and only minor degradation was observed in weaker samples (10, 5, and 2.5 mM), as demonstrated by H-1 and F-19 NMR.

Place, publisher, year, edition, pages
Elsevier, 2017. Vol. 58, no 34, 3350-3352 p.
Keyword [en]
Diazirine, Preparative synthesis, Photolysis, Stability
National Category
Organic Chemistry
Identifiers
URN: urn:nbn:se:umu:diva-139141DOI: 10.1016/j.tetlet.2017.07.031ISI: 000407657600005OAI: oai:DiVA.org:umu-139141DiVA: diva2:1146643
Available from: 2017-10-03 Created: 2017-10-03 Last updated: 2017-10-03Bibliographically approved

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