2,4,6-Trimethyl-N,N-bis(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)aniline

CAS Number 1282616-14-1

Boronates, Chemistry Building Blocks, Heterocyclic Building Blocks, Monomers

2,4,6-Trimethyl-N,N-bis(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)aniline MSDS

2,4,6-Trimethyl-N,N-bis(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)aniline CAS 1282616-14-1

2,4,6-Trimethyl-N,N-bis(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)aniline, Triphenylamine derivative

A convenient boronic ester for the synthesis of hole transport semiconducting small molecules and polymers in application of organic light-emitting devices and perovskite solar cells.

Overview
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2,4,6-Trimethyl-N,N-bis(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)aniline, CAS number 1282616-14-1, the boronic ester of triarylamine with a slightly more steric trimethylphenyl as one of the three aryl groups. The methyl groups also make the targeted molecules more soluble in the organic solvents. The double boronic ester functional groups enable the intermediate to construct more complex structures or polymers via C-C formation reactions. Structures bearing triarylamine fragments or backbones can be used as hole transport layer materials in perovskite solar cells.

2,4,6-Trimethyl-N,N-bis(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)aniline can be readily produced by reacting bis(pinacolato)diboron with N,N-Bis(4-bromophenyl)-2,4,6-trimethylaniline. 2,4,6-Trimethyl-N,N-bis(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)aniline is a useful boronic ester for Suzuki cross coupling reactions.

General Information

CAS Number	1282616-14-1
Chemical Formula	C₃₃H₄₃B₂NO₄
Molecular Weight	539.32 g/mol
Full Name	2,4,6-Trimethyl-N,N-bis(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)aniline
Synonyms	Benzenamine, 2,4,6-trimethyl-N,N-bis[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-
Classification / Family	Triphenylamine derivatives, Semiconductor synthesis intermediates, Hole transport layer, Perovskite solar cells

Chemical Structure

Product Details

Purity	>98% (¹H NMR)
Melting Point	N/A
Appearance	White to light yellow powder/crystals

MSDS Documentation

2,4,6-Trimethyl-N,N-bis(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)aniline MSDS Sheet

Literature and Reviews

Suzuki polycondensation for the synthesis of polytriarylamines: A method to improve hole-transport material performance in perovskite solar cells, M. Tepliakova et al., Tetrahedron Lett., 61 (38), 152317 (2020); DOI: 10.1016/j.tetlet.2020.152317.
Molecular Design with Silicon Core: Toward Commercially Available Hole Transport Materials for High-performance Planar p-i-n Perovskite Solar Cells, R. Xue et al., J. Mater. Chem. A, 6, 404-413 (2018); DOI: 10.1039/C7TA09716F.
Combination of Metal Oxide and Polytriarylamine: A Design Principle to Improve the Stability of Perovskite Solar Cells, M. Tepliakova et al., Energies, 14, 5115 (2021); DOI: 10.3390/en14165115.

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