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

Name: 9-Phenyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole
Brand: ChemScene
Availability: InStock
Rating: 5 (1 reviews)

CAS No. 1126522-69-7
Cat. No. CS-W000857
Purity≥96%
MDL No.MFCD16621140

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9-Phenyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole|CS-W000857

Structure of 1126522-69-7

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General Information

CAS No. 1126522-69-7
Cat. No. CS-W000857
Purity ≥96%
MDL No. MFCD16621140
Storage Store at room temperature
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₂₄H₂₄BNO₂
Molecular Weight 369.26
Synonym(s) 9-Phenylcarbazole-3-boronic Acid Pinacol Ester
SMILES CC(C(C)(O1)C)(OB1C2=CC(C3=CC=CC=C3N4C5=CC=CC=C5)=C4C=C2)C

Description

9-Phenyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole is a bench-stable boronate ester featuring a carbazole core with a phenyl substituent at the 9-position and a tetramethyl-substituted dioxaborolane group at the 3-position. This structure enables efficient coupling in Suzuki-Miyaura reactions, facilitating the construction of complex biaryl architectures under mild conditions. The sterically protected boron moiety enhances stability during storage and handling, while maintaining high reactivity in cross-coupling processes. Ideal for synthesizing conjugated materials and functionalized heterocycles in pharmaceutical and materials science applications.

Application

9-Phenyl-3-(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 rigid, electron-rich scaffold with established utility in optoelectronic materials and pharmaceutical intermediates. The pinacol boronate group enables high stability, excellent functional group tolerance, and straightforward purification, facilitating efficient C–C bond formation under mild reaction conditions.

Synthesis

Route1
- In-stock
  
  1153-85-1
- 61676-62-8
- ~82%
- In-stock
  
  1126522-69-7
References
- WO2012/23947 A1, ; Page/Page column 141-142 ;
Route2
- In-stock
  
  1153-85-1
- In-stock
  
  73183-34-3
- ~39%
- In-stock
  
  1126522-69-7
References
- US2013/26909 A1, ; Page/Page column ;
Route3
- In-stock
  
  1150-62-5
- ~%
- In-stock
  
  1126522-69-7
References
- US2011/260138 A1, ;

Safety Information

Download SDS

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 23.39
LogP 5.0829
H_Acceptors 3
H_Donors 0
Rotatable_Bonds 2

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

CAS No. 1126522-69-7

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