68869-56-7

Basic information

• Product Name: Phenol, 2,6-bis(1,1-dimethylethyl)-4-(triphenylmethyl)-
• CAS NO: 68869-56-7
• Molecular Formula: C33H36O
• Molecular Weight: 448.648
• Mol File: 68869-56-7.mol

Chemical Properties

• CAS DataBase Reference: Phenol, 2,6-bis(1,1-dimethylethyl)-4-(triphenylmethyl)-(CAS DataBase Reference)
• NIST Chemistry Reference: Phenol, 2,6-bis(1,1-dimethylethyl)-4-(triphenylmethyl)-(68869-56-7)
• EPA Substance Registry System: Phenol, 2,6-bis(1,1-dimethylethyl)-4-(triphenylmethyl)-(68869-56-7)

Safety Data

• Hazardous Substances Data: 68869-56-7(Hazardous Substances Data)

Upstream product

• 56640-71-2 2,6-di-tert-butyl-4-tritylphenoxyl radical 
• 14390-96-6 ammonia 
• 7664-41-7 ammonia 

Relevant articles and documents

Diversion of Catalytic C-N Bond Formation to Catalytic Oxidation of NH3 through Modification of the Hydrogen Atom Abstractor

We report that (TMP)Ru(NH3)2 (TMP = tetramesitylporphryin) is a molecular catalyst for oxidation of ammonia to dinitrogen. An aryloxy radical, tri-tert-butylphenoxyl (ArO·), abstracts H atoms from a bound ammonia ligand of (TMP)Ru(NH3)2, leading to the discovery of a new catalytic C-N coupling to the para position of ArO· to form 4-amino-2,4,6-tri-tert-butylcyclohexa-2,5-dien-1-one. Modification of the aryloxy radical to 2,6-di-tert-butyl-4-tritylphenoxyl radical, which contains a trityl group at the para position, prevents C-N coupling and diverts the reaction to catalytic oxidation of NH3 to give N2. We achieved 125 ± 5 turnovers at 22 °C for oxidation of NH3, the highest turnover number (TON) reported to date for a molecular catalyst.

Multiple N-H and C-H Hydrogen Atom Abstractions through Coordination-Induced Bond Weakening at Fe-Amine Complexes

We report the use of the reported Fe-phthalocyanine complex, PcFe (1; Pc = 1,4,8,11,15,18,22,25-octaethoxy-phthalocyanine), to generate PcFe-amine complexes 1-(NH3)2, 1-(MeNH2)2, and 1-(Me2NH)2. Treatment of 1 or 1-(NH3)2 to an excess of the stable aryloxide radical, 2,4,6-tritert-butylphenoxyl radical (tBuArO?), under NH3 resulted in catalytic H atom abstraction (HAA) and C-N coupling to generate the product 4-amino-2,4,6-tritert-butylcyclohexa-2,5-dien-1-one (2) and tBuArOH. Exposing 1-(NH3)2 to an excess of the trityl (CPh3) variant, 2,6-di-tert-butyl-4-tritylphenoxyl radical (TrArO?), under NH3 did not lead to catalytic ammonia oxidation as previously reported in a related Ru-porphyrin complex. However, pronounced coordination-induced bond weakening of both α N-H and β C-H in the alkylamine congeners, 1-(MeNH2)2 and 1-(Me2NH)2, led to multiple HAA events yielding the unsaturated cyanide complex, 1-(MeNH2)(CN), and imine complex, 1-(MeN═CH2)2, respectively. Subsequent C-N bond formation was also observed in the latter upon addition of a coordinating ligand. Detailed computational studies support an alternating mechanism involving sequential N-H and C-H HAA to generate these unsaturated products.