55169-03-4

Basic information

• Product Name: 1-butyl-4-(1-methylethyl)benzene
• Synonyms: 1-butyl-4-(1-methylethyl)benzene
• CAS NO: 55169-03-4
• Molecular Weight: 176.302
• Mol File: 55169-03-4.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: 1-butyl-4-(1-methylethyl)benzene(CAS DataBase Reference)
• NIST Chemistry Reference: 1-butyl-4-(1-methylethyl)benzene(55169-03-4)
• EPA Substance Registry System: 1-butyl-4-(1-methylethyl)benzene(55169-03-4)

Safety Data

• Hazardous Substances Data: 55169-03-4(Hazardous Substances Data)

Upstream product

• 100532-13-6 1-(4-isopropyl-phenyl)-butan-1-ol 
• 185416-14-2 4-(1-butyl)phenylmagnesium bromide 
• 41492-05-1 p-bromobutylbenzene 
• 15499-27-1 4-n-butylchlorobenzene 
• 1888-75-1 isopropyllithium 
• 78575-06-1 1-(4-isopropyl-phenyl)-butan-1-one 
• 920-39-8 isopropylmagnesium bromide 
• 14534-83-9 4-butyl-tri-N-methyl-anilinium; iodide 

Relevant articles and documents

Nickel-induced Conversion of Carbon-Nitrogen into Carbon-Carbon Bonds. One step Transformations of Aryl, Quaternary Ammonium Salts into Alkylarenes and Biaryls

Aryltrimethylammonium iodides are shown to undergo reaction with Grignard reagents under phosphinate-ligated, low-valent nickel catalysis with the formation of alkylarenes and biaryls.

Facile Hydrogenolysis of C(sp3)–C(sp3) σ Bonds

The modification of benzylic quaternary, tertiary, and secondary carbon centers through palladium-catalyzed hydrogenolysis of C(sp3)–C(sp3) σ bonds is presented. When benzyl Meldrum's acid derivatives bearing quaternary benzylic centers are treated under mild hydrogenolysis conditions – palladium on carbon and atmospheric pressure of hydrogen – aromatics substituted with tertiary benzylic centers and Meldrum's acid are obtained with good to excellent yield. Analogously, substrates containing tertiary or secondary benzylic centers yield aromatics substituted with secondary benzylic centers or toluene derivatives, respectively. Furthermore, this strategy is used for the high yielding synthesis of diarylmethanes. The scope of the reductive dealkylation reaction is explored and the limitations with respect to steric and electronic factors are determined. A mechanistic analysis of the reaction is described that consisted of deuterium labelling experiments and hydrogenolysis of enantioenriched derivatives. The investigation shows that the C(sp3)–C(sp3) σ bond-cleaving events occur through a hybrid SN1/SN2 mechanism, in which the palladium center displaces a carbon-based leaving group, namely Meldrum's acid, with inversion of configuration, followed by reductive elimination of palladium to furnish a C?H bond. (Figure presented.).