98236-17-0

Basic information

• Product Name: [1,1'-Biphenyl]-4-amine, 4'-(1,1-dimethylethyl)-N,N-dimethyl-
• CAS NO: 98236-17-0
• Molecular Formula: C18H23N
• Molecular Weight: 253.387
• Mol File: 98236-17-0.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: [1,1'-Biphenyl]-4-amine, 4'-(1,1-dimethylethyl)-N,N-dimethyl-(CAS DataBase Reference)
• NIST Chemistry Reference: [1,1'-Biphenyl]-4-amine, 4'-(1,1-dimethylethyl)-N,N-dimethyl-(98236-17-0)
• EPA Substance Registry System: [1,1'-Biphenyl]-4-amine, 4'-(1,1-dimethylethyl)-N,N-dimethyl-(98236-17-0)

Safety Data

• Hazardous Substances Data: 98236-17-0(Hazardous Substances Data)

Usage

General Description

[1,1'-Biphenyl]-4-amine, 4'-(1,1-dimethylethyl)-N,N-dimethyl- is a chemical compound with the molecular formula C20H25N. It is also known as N-t-butyl-4-[(4-methylphenyl)amino]biphenyl-4-amine. [1,1'-Biphenyl]-4-amine, 4'-(1,1-dimethylethyl)-N,N-dimethyl- is an amine with a biphenyl group and a t-butyl group attached to the amine nitrogen. It is often used as a building block in the synthesis of organic compounds and is also used in the production of various pharmaceuticals and agrochemicals. The presence of the t-butyl group in the compound makes it more stable and less reactive compared to other amine compounds. Additionally, it is used as a chemical intermediate in the manufacturing of dyes, pigments, and other organic compounds.

Upstream product

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Relevant articles and documents

Oxidative Addition of Aryl Halides to Transient Anionic ?-Aryl-Palladium(0) Intermediates - Application to Palladium-Catalyzed Reductive Coupling of Aryl Halides

The rates and mechanism of the reactions of a series of aryl-ligated, anionic palladium(0) complexes Ar-Pd0-(PPh3)2- with para-substituted iodobenzenes were investigated by means of transient electrochemistry.The reaction was found to be first order in each reactant and to proceed similary to oxidative addition of aryl halides to the halide-ligated species X-Pd0(PPh3)2-, although much faster and less sensitive to electronic factors.Owing to the short lifetime (t1/2 ca. 1-5 ms) of the product of this reaction, it could not be characterized in datail.However, based on kinetic results, this transient species is thought to be an anionic pentacoordinated bisarylpalladium(II) complex, which undergoes rapid loss of halide ligand to yield, most probably, a bisarylpalladium(II) neutral species.Based on the study of this reaction and on previously reported results, we propose a mechanism for the palladium-catalyzed homocoupling of aryl halides consisting of a catalytic cycle initiated by oxidative addition of an aryl halide to a zerovalent tris-ligated palladium center.Two-electron reduction of the pentacoordinated arylpalldium(II) anionic species thus formed gives a tris-ligated anionic arylpalladium(0) center, which undergoes oxidative addition with a second aryl halide molecule to eventually lead to a bisarylpalldium(II) neutral species.Reductive elimination of a bisaryl molecule from this center closes the catalytic cycle by regenerating the initial zerovalent palldium complex.The application of this sequence to the catalytic heterocoupling of aryl halides is discussed, and it is concluded, on the basis of Hammett correlations, that statistical yields should be observed, in agreement with the results obtained for preparative reactions in DMF. - Keywords: catalysis; C-C coupling; mechanistic studies; oxidative addition; palladium complexes