Thermal analysis of arenediazonium tetrafluoroborate salts: Stability and hazardous evaluation

Author(s)

Scarpa de Souza, Edson Leonardo ; Duarte Chorro, Tomaz Henrique ; Duarte Correia, Carlos Roque

• Document type: Journal article
• Source: PROCESS SAFETY AND ENVIRONMENTAL PROTECTION; v. 177, p. 13-pg., 2023-09-01.

Abstract

Arenediazonium salts represent an important class of aromatic organic compounds widely used as building blocks in academia and industry. Due to the high energy associated with the diazonium group, many of these salts are reported as thermally unstable and/or unsafe to work with. However, most of the tetrafluoroborate arenediazonium salts are fairly stable to handle at room temperature both in solution and when dry. Nevertheless, some of these salts, especially those containing heteroatoms in the aromatic moiety, are problematic for their synthesis, and some are indeed highly unstable. To bring some light on this controversial subject, the thermal stability and potential hazards of the 58 most common arenediazonium tetrafluoroborate salts used by us over the last two decades were evaluated under careful conditions. These results are expected to guide conscious decisions on the use and handling of arenediazonium tetrafluoroborates in organic synthesis. (AU)

• FAPESP's process: 13/07600-3 - CIBFar - Center for Innovation in Biodiversity and Drug Discovery
• Grantee: Glaucius Oliva
• Support Opportunities: Research Grants - Research, Innovation and Dissemination Centers - RIDC
• FAPESP's process: 14/25770-6 - New frontiers in cross-coupling reactions promoted by palladium: combining enantioselective catalysis, C-H activations, new materials and in flux reactions aiming at high efficiency and sustainability in synthetic processes
• Grantee: Carlos Roque Duarte Correia
• Support Opportunities: Research Projects - Thematic Grants
• FAPESP's process: 19/25657-9 - Radical arilations of endocyclic encarbamates by fotoredox: development of the new method, derivatization, and synthetic applications
• Grantee: Edson Leonardo Scarpa de Souza
• Support Opportunities: Scholarships in Brazil - Doctorate
• FAPESP's process: 21/14298-8 - Enantioselective desymmetrization via Heck-Matsuda reactions: development of new methodologies and applications
• Grantee: Tomaz Henrique Duarte Chorro
• Support Opportunities: Scholarships in Brazil - Doctorate (Direct)