N,N-Diphenyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline

Name: N,N-Diphenyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline
Brand: ChemScene
Availability: InStock
Rating: 5 (1 reviews)

CAS No. 267221-88-5
Cat. No. CS-0130477
Purity≥97%
MDL No.MFCD13195770

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N,N-Diphenyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline|CS-0130477

Structure of 267221-88-5

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General Information

CAS No. 267221-88-5
Cat. No. CS-0130477
Purity ≥97%
MDL No. MFCD13195770
Storage 4°C
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₂₄H₂₆BNO₂
Molecular Weight 371.28
Synonym(s) Triphenylamine-4-boronic Acid Pinacol Ester
SMILES CC1(C(C)(OB(O1)C2=CC=C(N(C3=CC=CC=C3)C4=CC=CC=C4)C=C2)C)C

Description

N,N-Diphenyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline delivers a stable, bench-ready boronate handle for cross-coupling reactions. The tetramethyl-1,3,2-dioxaborolane moiety enables efficient Suzuki-Miyaura coupling under mild conditions. This electron-rich arylboronate features excellent functional group tolerance and moisture stability, facilitating seamless integration into complex molecular architectures.

Application

N,N-Diphenyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline serves as a robust boron-containing building block for Suzuki-Miyaura cross-coupling reactions. The diborane moiety enables efficient coupling with aryl and heteroaryl halides under mild conditions, while the N,N-diphenylamino group provides steric and electronic stabilization. This compound exhibits excellent bench stability, ease of purification, and broad functional group tolerance, making it a reliable reagent for constructing biaryl scaffolds in medicinal chemistry and materials science applications.

Synthesis

Route1
- In-stock
  
  36809-26-4
- In-stock
  
  73183-34-3
- ~90%
- In-stock
  
  267221-88-5
References
- Samsung Display Co., Ltd. Patent: EP2535331 A1, 2012 ; Location in patent: Page/Page column 29 ;
Route2
- In-stock
  
  73183-34-3
- ~96%
- In-stock
  
  267221-88-5
References
- Semiconductor Energy Laboratory Co., Ltd. Patent: US2012/165523 A1, 2012 ; Location in patent: Page/Page column 27 ;
Route3
- 61676-62-8
- In-stock
  
  36809-26-4
- ~93%
- In-stock
  
  267221-88-5
References
- Lee, Junghoon; Kim, Jonggi; Kim, Gyoungsik; Yang, Changduk Tetrahedron, 2010 , vol. 66, # 48 p. 9440 - 9444

Safety Information

Download SDS

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-P305+P351+P338-P332+P313-P337+P313-P362+P364

Quality Control

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Computational Chemistry Data

TPSA 21.7
LogP 5.4556
H_Acceptors 3
H_Donors 0
Rotatable_Bonds 4

Other Classifications

Material Science Solar Cell Materials Donor Intermediate DI

Building Blocks Functional Group Boronic Acid And Its Ester

Building Blocks Skeleton Aromatic ring compounds Benzene compounds

Material Science Material Building Blocks Small Molecule Semiconductor Building Blocks Tertiary Arylamines

Chemical Synthesis Organometallic Reagents Organoboron Boronic Acids and Derivatives

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N,N-Diphenyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline

CAS No. 267221-88-5

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