22679-53-4

Basic information

• Product Name: Methanone, [2-(1,1-dimethylethyl)phenyl]phenyl-
• Synonyms: 2-tert.-butylbenzophenone;o-tert-butylbenzophenone;2-tert-Butyl-benzophenon
• CAS NO: 22679-53-4
• Molecular Formula: C17H18O
• Molecular Weight: 238.329
• Mol File: 22679-53-4.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: Methanone, [2-(1,1-dimethylethyl)phenyl]phenyl-(CAS DataBase Reference)
• NIST Chemistry Reference: Methanone, [2-(1,1-dimethylethyl)phenyl]phenyl-(22679-53-4)
• EPA Substance Registry System: Methanone, [2-(1,1-dimethylethyl)phenyl]phenyl-(22679-53-4)

Safety Data

• Hazardous Substances Data: 22679-53-4(Hazardous Substances Data)

Upstream product

• 507-19-7 t-butyl bromide 
• 37774-78-0 2-cyanobenzophenone 
• 119-61-9 benzophenone 
• 16636-96-7 di-tert-butylzinc 
• 253185-03-4 tert-butylbenzene 
• 98-88-4 benzoyl chloride 
• 1077-58-3 2-tert-butylbenzoic acid 
• 591-51-5 phenyllithium 
• 594-19-4 tert.-butyl lithium 

Downstream Products

• 49822-83-5 (2-tert-butyl-phenyl)-phenyl-(1-vinyl-1H-imidazol-2-yl)-methanol 
• 49822-92-6 (2-tert-butyl-phenyl)-(1-methoxymethyl-1H-imidazol-2-yl)-phenyl-methanol 

Relevant articles and documents

Donor-activated alkali metal dipyridylamides: Co-complexation reactions with zinc alkyls and reactivity studies with benzophenone

Previously it was reported that activation of tBu2Zn by [(TMEDA)Na(μ-dpa)]2led to tert-butylation of benzophenone at the challenging para-position, where the sodium amide functions as a metalloligand towards tBu2Zn manifested in crystalline [{(TMEDA)Na(dpa)}2ZntBu2] (TMEDA is N,N,N′,N′-tetramethylethylenediamine, dpa is 2,2′-dipyridylamide). Here we find altering the Lewis donor or alkali metal within the metalloligand dictates the reaction outcome, exhibiting a strong influence on alkylation yields and reaction selectivity. Varying the former led to the synthesis of three novel complexes, [(PMDETA)Na(dpa)]2, [(TMDAE)Na(dpa)]2, and [(H6-TREN)Na(dpa)], characterised through combined structural, spectroscopic and theoretical studies [where PMDETA is N,N,N′,N′′,N′′-pentamethyldiethylenetriamine, TMDAE is N,N,N′,N′-tetramethyldiaminoethylether and H6-TREN is N′,N′-bis(2-aminoethyl)ethane-1,2-diamine]. Each new sodium amide can function as a metalloligand to generate a co-complex with tBu2Zn. Reacting these new co-complexes with benzophenone proved solvent dependent with yields in THF much lower than those in hexane. Most interestingly, sub-stoichiometric amounts of the metalloligands [(TMEDA)Na(dpa)]2and [(PMEDTA)Na(dpa)]2with 1 : 1, tBu2Zn-benzophenone mixtures produced good yields of the challenging 1,6-tert-butyl addition product in hexane (52% and 53% respectively). Although exchanging Na for Li gave similar reaction yields, the regioselectivity was significantly compromised; whereas the K system was completely unreactive. Replacing tBu2Zn with (Me3SiCH2)2Zn shut down the alkylation of benzophenone; in contrast, tBuLi generates only the reduction product, benzhydrol. Zincation of the parent amine dpa(H) generated the crystalline product [Zn(dpa)2], as structurally elucidated through X-ray crystallography and theoretical calculations. Although the reaction mechanism for the alkylation of benzophenone remains unclear, incorporation of the radical scavenger TEMPO (2,2,6,6-tetramethylpiperidine-N-oxyl radical) into the reaction system completely inhibits benzophenone alkylation.

Ring tert-butylation of benzophenones and benzaldehyde with tert-butyllithium and thionyl chloride

One-flask ring tert-butylation of benzophenones and benzaldehyde with tert-butyllithium and thionyl chloride is reported. The scope of the reaction and the suggested mechanism are discussed.

REVERSAL OF THE BENZOPHENONE REACTIVITY UPON η2 -COMPLEXATION TO BIS( η5 -CYCLOPENTADIENYL)ZIRCONIUM

Reversal of the carbonyl activity of benzophenone, serving as electron donor in single-electron transfer processes and acting as a proton acceptor through the 'carbonyl'carbon atom, is observed upon η2 -complexation to zirconocene.