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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 universitet, Teknisk-naturvetenskapliga fakulteten, Kemiska institutionen.
Umeå universitet, Teknisk-naturvetenskapliga fakulteten, Kemiska institutionen.
2017 (engelsk)Inngår i: Tetrahedron Letters, ISSN 0040-4039, E-ISSN 1359-8562, Vol. 58, nr 34, s. 3350-3352Artikkel i tidsskrift (Fagfellevurdert) 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.

sted, utgiver, år, opplag, sider
Elsevier, 2017. Vol. 58, nr 34, s. 3350-3352
Emneord [en]
Diazirine, Preparative synthesis, Photolysis, Stability
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Identifikatorer
URN: urn:nbn:se:umu:diva-139141DOI: 10.1016/j.tetlet.2017.07.031ISI: 000407657600005Scopus ID: 2-s2.0-85025638864OAI: oai:DiVA.org:umu-139141DiVA, id: diva2:1146643
Tilgjengelig fra: 2017-10-03 Laget: 2017-10-03 Sist oppdatert: 2023-03-24bibliografisk kontrollert

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