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

Name: 4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole
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CAS No. 1255309-13-7
Cat. No. CS-0099203
Purity≥97%
MDL No.None

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4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole|CS-0099203

Structure of 1255309-13-7

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General Information

CAS No. 1255309-13-7
Cat. No. CS-0099203
Purity ≥97%
MDL No. None
Storage Store at room temperature
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₁₈H₂₀BNO₂
Molecular Weight 293.17
Synonym(s) 4-(9H-Carbazol-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
SMILES CC1(C)C(C)(C)OB(C2=CC=CC(N3)=C2C4=C3C=CC=C4)O1

Description

4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole is a bench-stable boronate ester featuring a planar carbazole core with enhanced solubility and compatibility in cross-coupling reactions. The tetramethylcyclopentadienone moiety enables efficient palladium-catalyzed coupling under standard conditions, delivering conjugated heteroaryl architectures with high functional group tolerance.

Application

4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole serves as a versatile boronate building block in palladium-catalyzed cross-coupling reactions. Its carbazole core provides structural rigidity and electron-rich character, enabling efficient coupling with aryl, heteroaryl, and vinyl halides. The pinacol boronate group offers excellent stability, ease of handling, and compatibility with diverse reaction conditions, making it ideal for constructing complex scaffolds in medicinal chemistry and materials science applications.

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 : H315-H319
Precautionary Statements : P264-P280-P302+P352-P362

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

CAS No. 1255309-13-7

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