2-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole

Name: 2-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole
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CAS No. 1242412-60-7
Cat. No. CS-0091571
Purity≥97%
MDL No.MFCD07784368

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2-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole|CS-0091571

Structure of 1242412-60-7

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General Information

CAS No. 1242412-60-7
Cat. No. CS-0091571
Purity ≥97%
MDL No. MFCD07784368
Storage 4°C, protect from light
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₁₈H₂₀BNO₂
Molecular Weight 293.17
Synonym(s) 2-(9H-Carbazol-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
SMILES CC1(C)C(C)(C)OB(C2=CC(NC3=C4C=CC=C3)=C4C=C2)O1

Description

2-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole features a boronate ester group tethered to a carbazole scaffold, enabling efficient Suzuki-Miyaura coupling under standard conditions. The tetramethyl-substituted dioxaborolane enhances stability and reactivity, while the electron-rich carbazole core facilitates conjugation in optoelectronic applications. This compound serves as a key building block for functionalized arylated systems in materials science and pharmaceutical synthesis.

Application

2-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole serves as a versatile boronate building block for Suzuki-Miyaura cross-coupling reactions. The carbazole core provides a stable, electron-rich heterocyclic scaffold with established utility in organic electronics and medicinal chemistry. The tetramethylboronate group enables efficient coupling under mild conditions, offering excellent functional group tolerance and bench stability, facilitating rapid access to biaryl architectures in multistep synthesis.

Safety Information

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GHS Pictogram :	GHS No : GHS07
Signal Word : Warning	UN#: N/A
Class : N/A	Packing Group : N/A
Hazard Statements : H302-H315-H319-H335
Precautionary Statements : P261-P264-P270-P271-P280-P302+P352-P304+P340-P305+P351+P338-P330-P362+P364-P403+P233-P405-P501

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Computational Chemistry Data

TPSA 34.25
LogP 3.6203
H_Acceptors 2
H_Donors 1
Rotatable_Bonds 1

Other Classifications

Building Blocks Skeleton Aromatic heterocycle compounds Carbazole compounds

Chemical Synthesis Organometallic Reagents Organoboron Boronic Acids and Derivatives

Key Words

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2-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole

CAS No. 1242412-60-7

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