104503-83-5Relevant academic research and scientific papers
Synthesis of nitrophenyl and fluorophenyl azides and diazides by SNAr under phase-transfer or microwave irradiation: Fast and mild methodologies to prepare photoaffinity labeling, crosslinking, and click chemistry reagents
Leyva, Elisa,Aguilar, Johana,González-Balderas, Regina M.,Vega-Rodríguez, Sarai,Loredo-Carrillo, Silvia E.
, (2021)
Two fast and mild methodologies to prepare nitrophenyl and fluorophenyl azides are presented. These aryl azides are extensively used as crosslinking, photoaffinity labeling, and click chemistry reagents. Substituted aryl azides are prepared by performing a SNAr substitution on halogenated benzenes with a phase-transfer catalyst (PTC) such as tetraethylammonium tetrafluoroborate (TEATFB), the reaction proceeds in several hours under rather mild temperatures (25°C to 70°C). Furthermore, aryl azides are also prepared within minutes under microwave irradiation at slightly higher temperatures (50°C to 70°C). These procedures could be applied in the preparation of other aryl azides. In the case of substituted pentafluoro benzene (pF), the type of products obtained in each reaction depends on the amount of sodium azide and the strength and position of electron-withdrawing substituents (COH, COR, COOR, CN, NO2, or F). A discussion on the mechanisms and the products obtained in these SNAr reactions is presented.
Facile One-Pot Synthesis of 2,1,3-Benzoxadiazole N-Oxide (Benzofuroxan) Derivatives Under Phase-Transfer Catalysis
Ayyangar, N. R.,Madan Kumar, S.,Srinivasan, K. V.
, p. 616 - 618 (2007/10/02)
Several 2,1,3-benzoxadiazole N-oxide (benzofuroxan) derivatives are synthesized from the corresponding o-chloronitrobenzenes in a one-pot operation by stirring with sodium azide in dichloroethane in the presence of benzyl tributylammonium bromide as a pha
Pyrolysis of Aryl Azides. VII. Interpretation of Hammett Correlations of Rates of Pyrolysis of Substituted 2-Nitroazidobenzenes
Dyall, Leonard K.
, p. 89 - 101 (2007/10/02)
Rates and products of pyrolysis have been obtained for ten 2-nitroazidobenzenes with 4- or 5-substituents.Rate data at 100 deg C are correlated with Hammett constants of the 4- and 5-substituents, with respect to both the azido (A) and nitro (N) reaction
