389104-62-5

Basic information

• Product Name: 3,5-bis(1-methylethyl)biphenyl-4-amine
• Synonyms: [1,1'-biphenyl]-4-amine, 3,5-bis(1-methylethyl)-; 3,5-Diisopropyl-4-biphenylamine; 3,5-Diisopropylbiphenyl-4-amine
• CAS NO: 389104-62-5
• Molecular Formula: C₁₈H₂₃N
• Molecular Weight: 253.3819
• Mol File: 389104-62-5.mol
• Article Data: 9

Chemical Properties

• Boiling Point: 371°C at 760 mmHg
• Flash Point: 180.7°C
• Density: 0.985g/cm³
• Vapor Pressure: 1.06E-05mmHg at 25°C
• Refractive Index: 1.562
• CAS DataBase Reference: 3,5-bis(1-methylethyl)biphenyl-4-amine(CAS DataBase Reference)
• NIST Chemistry Reference: 3,5-bis(1-methylethyl)biphenyl-4-amine(389104-62-5)
• EPA Substance Registry System: 3,5-bis(1-methylethyl)biphenyl-4-amine(389104-62-5)

Safety Data

• Hazardous Substances Data: 389104-62-5(Hazardous Substances Data)

Upstream product

• 80058-84-0 4-bromo-2,6-diisopropylaniline 
• 98-80-6 phenylboronic acid 
• 24544-04-5 2,6-diisopropylbenzenamine 

Relevant articles and documents

Further enhancement of the clickability of doubly sterically-hindered aryl azides by: Para -amino substitution

Introduction of an amino group at the para position of doubly sterically-hindered aryl azides significantly enhances the reactivity with cyclooctynes. The distortability of the azido group is synergistically enhanced by the para-electron-donating group and two bulky ortho substituents, which increases the HOMO energy level and provoke the steric inhibition of resonance, respectively.

Chain-Walking Polymerization of Linear Internal Octenes Catalyzed by α-Diimine Nickel Complexes

The chain-walking polymerization of linear internal alkenes (i.e., trans-2-, 3-, and 4-octenes) using α-diimine nickel catalysts activated with modified methylaluminoxane (MMAO) was studied in comparison with the corresponding terminal alkene polymerization. The rates of polymerization were found to decrease in the following order: 1-octene > 4-octene ≥ 2-octene ≥ 3-octene. The obtained branched poly(2-octene)s and poly(4-octene)s with high molecular weight and Mw/Mn less than 2 were amorphous polymers with low glass transition temperature (Tg) of approximately -66 °C. At 0 °C, 4-octene polymerized in a living/controlled manner. The NMR analyses of the polymers showed that the chain-walking polymerization of 4-octene gave periodically branched polymers with the constant branching density, while that of 2-octene gave the polymer possessing fewer branches than the expected value due to monomer-isomerization. The (n+2),(n+3)- and (n+3),(n+2)-insertions of the internal (n+2)-alkene [CH3(CH2)nCH=CH(CH2)mCH3] followed by chain-walking were confirmed by the 13C NMR analysis of the produced polymers.

Elusive Terminal Copper Arylnitrene Intermediates

We report herein three new modes of reactivity between arylazides N3Ar with a bulky copper(I) β-diketiminate. Addition of N3ArX3 (ArX3=2,4,6-X3C6H2; X=Cl or Me) to [iPr2NN]Cu(NCMe) results in triazenido complexes from azide attack on the β-diketiminato backbone. Reaction of [iPr2NN]Cu(NCMe) with bulkier azides N3Ar leads to terminal nitrenes [iPr2NN]Cu]=NAr that dimerize via formation of a C?C bond at the arylnitrene p-position to give the dicopper(II) diketimide 4 (Ar=2,6-iPr2C6H3) or undergo nitrile insertion to give diazametallocyclobutene 8 (Ar=4-Ph-2,6-iPr2C6H2). Importantly, reactivity studies reveal both 4 and 8 to be “masked” forms of the terminal nitrenes [iPr2NN]Cu=NAr that undergo nitrene group transfer to PMe3, tBuNC, and even into a benzylic sp3 C?H bond of ethylbenzene.