60388-84-3

Basic information

• Product Name: N-(2,2-dimethylpropyl)-N,N'-diphenylhydrazine
• Synonyms: N-(2,2-dimethylpropyl)-N,N'-diphenylhydrazine
• CAS NO: 60388-84-3
• Molecular Weight: 240.348
• Mol File: 60388-84-3.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: N-(2,2-dimethylpropyl)-N,N'-diphenylhydrazine(CAS DataBase Reference)
• NIST Chemistry Reference: N-(2,2-dimethylpropyl)-N,N'-diphenylhydrazine(60388-84-3)
• EPA Substance Registry System: N-(2,2-dimethylpropyl)-N,N'-diphenylhydrazine(60388-84-3)

Safety Data

• Hazardous Substances Data: 60388-84-3(Hazardous Substances Data)

Upstream product

• 507-19-7 t-butyl bromide 
• 1227476-15-4 Azobenzene 
• 594-19-4 tert.-butyl lithium 
• 89379-02-2 tert-butylmercury iodide 

Relevant articles and documents

Reductive tert-butylation of anils by tert-butylmercury halides

tert-Butyl radicals add to the carbon atom of benzylideneanilines to form anilino radicals, which are protonated in the presence of PTSA or NH4+ in Me2SO. Reduction of the resulting aniline radical cations occurs readily by the ate complex, t-BuHgI2. In the absence of a proton donor, f-BuHgI will also transfer a hydrogen atom to the anilino radical to give the reductive alkylation product. Protonation can promote a free radical chain process involving electron transfer by substrate activation and/or by increasing the electron affinity of the intermediate radicals. Since the adduct radicals formed from benzylideneanilines are more easily protonated than the parent Schiff bases, PTSA but not NH4+ demonstrates substrate activation, although both proton donors promote the free radical reaction.

Single Electron Transfer as Rate-Determining Step in an Aliphatic Nucleophilic Substitution

The rate of transfer of an electron between electrochemically generated anion radicals and alkyl halides has been measured by cyclic voltammetry and the dependence of the rate on the redox potential of the electron donors found.From this dependence, the rate of electron transfer from an electron donor with reorganization energy about 10 kcal mol-1 to a given alkyl halide can be calculated if the reversible oxidation potential of the donor is known.The method has been applied to show that the rate of the aliphatic nucleophilic substitution of the enolate ion of 4-methoxycarbonyl-4-methyl-1,4-dihydropyridine on t-butyl bromide, neopentyl bromide and adamantyl bromide is the same as that expected for a SET reaction for a donor with the same oxidation potential as the enolate ion.Primary alkyl halides react somewhat faster than expected for a pure SET reaction.The dianion of dihydroperylene reacts with t-butyl chloride and s-butyl bromide at the same rate as would be expected for a SET reaction with a donor with the same oxidation potential as the dianion.The model for the aliphatic nucleophilic substitution is discussed.