118655-99-5

Basic information

• Product Name: 2,3-dimethyl-2,3-bis(phenylazo)butane
• Synonyms: 2,3-dimethyl-2,3-bis(phenylazo)butane
• CAS NO: 118655-99-5
• Molecular Weight: 294.399
• Mol File: 118655-99-5.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: 2,3-dimethyl-2,3-bis(phenylazo)butane(CAS DataBase Reference)
• NIST Chemistry Reference: 2,3-dimethyl-2,3-bis(phenylazo)butane(118655-99-5)
• EPA Substance Registry System: 2,3-dimethyl-2,3-bis(phenylazo)butane(118655-99-5)

Safety Data

• Hazardous Substances Data: 118655-99-5(Hazardous Substances Data)

Downstream Products

• 103-02-6 acetone phenylhydrazone 

Relevant articles and documents

Synthesis, thermochemistry, and reactions of vicinal bis(azoalkanes). The chemistry of α- and β-azo radicals

Two vicinal bis(azo)alkanes, 8P and 8B, were prepared from acetone phenylhydrazone (APH) and acetone tert-butylhydrazone (ATBH), respectively. Thermolysis of 8P above 130°C in the presence of thiophenol affords APH in quantitative yield, showing that the central C-C bond of 8P cleaves in preference to the usual C-N homolysis of azoalkanes. The resulting radicals 9P recombine to the C-N dimer 16P about 40 times faster than to the more stable C-C dimer 8P. From the combustion heat of 8P, we deduce that its strain enthalpy Hs is 5.5 kcal/mol, while the resonance stabilization energy (RSE) of 9P is 15.3 kcal/mol. The tert-butyl analog 8B loses 2 mol of N2, showing that C-N homolysis greatly dominates over C-C homolysis. Nevertheless, we estimate that the latter process would occur with ΔG* (150°C) > 40.3 kcal/mol, which implies that the RSE of aliphatic hydrazonyl radical 9B is at least 6 kcal/mol below that of 9P and is little or no more than the RSE of the 1,1-dimethylallyl radical.