21860-03-7

Usage

Uses

Used in Chemical Synthesis:
2,5-Di-tert-butylaniline is used as a key intermediate in the preparation of new rigid bidentate nitrogen ligands. These ligands are essential in various chemical reactions and processes, particularly in the field of coordination chemistry and homogeneous catalysis.
Used in the Preparation of dtb-BIAN:
2,5-Di-tert-butylaniline is used as a starting material for the synthesis of 1,2-bis[(2,5-di-tert-butylphenyl)imino]acenaphthene (dtb-BIAN). 2,5-DI-TERT-BUTYLANILINE is a rigid bidentate nitrogen ligand that can be employed in various applications, such as in the development of new catalysts and coordination complexes.
Used in the Preparation of N-(2,5-di-tert-butylphenyl)perylene-3,4-dicarboximide:
2,5-Di-tert-butylaniline is also utilized in the synthesis of N-(2,5-di-tert-butylphenyl)perylene-3,4-dicarboximide, another rigid bidentate nitrogen ligand. This ligand can be used in the development of advanced materials, such as organic light-emitting diodes (OLEDs), photovoltaic cells, and other optoelectronic devices.

Purification Methods

The aniline recrystallises from EtOH in fine needles after steam distillation. It has a pKa2 5 of 3.58 (50% aqueous EtOH). The tosylate has m 164o (from AcOH). [Bell & Wilson J Chem Soc 2340 1956, Carpenter et al. J Org Chem 16 586 1951, Bartlett et al. J Am Chem Soc 76 2349 1954, Beilstein 12 IV 2891.]

InChI:InChI=1/C14H23N/c1-13(2,3)10-7-8-11(12(15)9-10)14(4,5)6/h7-9H,15H2,1-6H3

Upstream product

• 3463-35-2 2,5-di-tert-butylnitrobenzene 
• 87086-78-0 methyl 3,6-di-tert-butyl-1H-azepine-1-carboxylate 
• 1012-72-2 1,4-di-tert-butylbenzene 
• 253185-03-4 tert-butylbenzene 
• 71-43-2 benzene 

Downstream Products

• 5875-45-6 2,5-di-tert-butylphenol 
• 23278-20-8 N-(2,5-di-tert-butyl-phenyl)-acetamide 
• 22503-23-7 4-bromo-2,5-di-tert-butyl-aniline 
• 101425-68-7 2,5-di-tert-butyl-N,N-dimethyl-aniline 
• 6683-74-5 2-bromo-1,4-di-tert-butylbenzene 
• 14035-05-3 2,5-di(tert-butyl)-4-nitroaniline 
• 22503-18-0 3-Nitro-2,5-di-t-butylanilin 
• 18628-50-7 N-(2,5-Di-t-butylphenyl)-formimidsaeureethylester 
• 128869-06-7 N-(2,5-di-tert-butylphenyl) maleimide 
• 128844-23-5 N-(2,5-di-tert-butylphenyl)phthalimide 
• 130296-50-3 N²-(2,5-Di-tert-butylphenyl)-3,4:9,10-perylentetracarboxdiimid 
• 101315-17-7 N-(2,5-Di-tert-butylphenyl)benzodiindeno<1,2,3-cd:1',2',3'-lm>perylen-6,7-dicarboximid 
• 130296-51-4 N-(2,5-Di-tert-butylphenyl)-1,8-naphthalin-dicarboximid 
• 137769-13-2 2-(2',5'-di-tert-butylphenyl)-1H-benzisoindole-1,3(2H)-dione 

Relevant academic research and scientific papers

Intramolecular Pd-catalyzed reductive amination of enolizable sp3-C-H bonds

A palladium-catalyzed reductive cyclization of nitroarenes has been designed to construct sp3-C-NHAr bonds from sp3-C-H bonds by using an enolizable nucleophile to intercept a nitrosoarene intermediate. Exposure of ortho-substituted nitroarenes to 5 mol ?% of Pd(OAc)2 and 10 mol ?% of phenanthroline under 2 atm of CO constructs partially saturated 5-, 6-, or 7-membered N-heterocycles using α-pyridyl carboxylates, malonates, 1,3-dimethylbarbituric acid, 1,3-diones, or difurans as the nucleophile.

Rotational features of carbon-nitrogen bonds in N-aryl maleimides. Atroposelective reactions of o-tert-butylphenylmaleimides

Atroposelective addition and cycloaddition reactions of N-2- (tertbutylphenyl)- and N-2,5 (di-tert-butylphenyl)maleimide and a substituted derivative have been studied. Good to excellent stereoselectivities are generally observed, and high rotation barriers (about 29 kcal/mol) prevent the products from inter, converting. Crystal structures of the precursors and products support a straightforward model where reactants attack trans to the o-tert butyl group.

Synthesis and Characterization of 2H-, 3H- and 4H-Azepine: The First Observation of the Thermal Distribution Equilibrium of Azepines

Demethoxycarbonylation of methyl 2,5-di-tert-butyl-1H-azepine-1-carboxylate using 1,8-diazabicycloundec-7-ene gives exclusively two isomers of 3H-azepine derivatives, while methyl 3,6-di-tert-butyl-1H-azepine-1-carboxylate gives a mixture of 2H-, 3H- and 4H-azepine derivatives under the same conditions because of a 1,5-hydrogen shift in the resulting triene system.