2-(Anthracen-9-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Name: 2-(Anthracen-9-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
Brand: ChemScene
Availability: InStock
Rating: 5 (1 reviews)

CAS No. 709022-63-9
Cat. No. CS-0175540
Purity≥98%
MDL No.None

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2-(Anthracen-9-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane|CS-0175540

Structure of 709022-63-9

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General Information

CAS No. 709022-63-9
Cat. No. CS-0175540
Purity ≥98%
MDL No. None
Storage 4°C
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₂₀H₂₁BO₂
Molecular Weight 304.19
Synonym(s) 9-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)anthracene
SMILES CC1(C(C)(OB(O1)C2=C3C=CC=CC3=CC4=CC=CC=C42)C)C

Description

This boronate ester features a sterically protected boronate moiety linked to an anthracene unit, enabling efficient coupling in palladium-catalyzed cross-coupling reactions. The electron-rich anthracenyl group enhances reactivity and stability under standard conditions, facilitating the construction of complex conjugated architectures with high fidelity.

Application

2-(Anthracen-9-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane serves as a stable, bench-ready boronate building block for palladium-catalyzed cross-coupling reactions. Its anthracene moiety enables efficient incorporation into extended π-conjugated systems, facilitating the synthesis of functional materials and advanced heterocyclic scaffolds. The tetramethyl-substituted dioxaborolane offers excellent shelf stability, mild reaction conditions, and compatibility with diverse functional groups, making it ideal for iterative coupling strategies in organic synthesis.

Synthesis

Route1
- In-stock
  
  1564-64-3
- 61676-62-8
- ~71%
- In-stock
  
  709022-63-9
References
- Zhang, Hui; Yu, Tianzhi; Zhao, Yuling; Fan, Duowang; Xia, Yangjun; Zhang, Peng; Qiu, Yongqing; Chen, Lili Spectrochimica Acta - Part A: Molecular and Biomolecular Spectroscopy, 2010 , vol. 75, # 1 p. 325 - 329
Route2
- In-stock
  
  1564-64-3
- 25015-63-8
- ~76%
- In-stock
  
  709022-63-9
References
- Schmittel, Michael; Kishore Organic Letters, 2004 , vol. 6, # 12 p. 1923 - 1926
Route3
- In-stock
  
  1564-64-3
- In-stock
  
  73183-34-3
- ~92%
- In-stock
  
  709022-63-9
References
- Tang, Wenjun; Keshipeddy, Santosh; Zhang, Yongda; Wei, Xudong; Savoie, Jolaine; Patel, Nitinchandra D.; Yee, Nathan K.; Senanayake, Chris H. Organic Letters, 2011 , vol. 13, # 6 p. 1366 - 1369

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-P280-P302+P352

Quality Control

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Computational Chemistry Data

TPSA 18.46
LogP 4.2922
H_Acceptors 2
H_Donors 0
Rotatable_Bonds 1

Other Classifications

Building Blocks Functional Group Boronic Acid And Its Ester

Building Blocks Skeleton Aromatic ring compounds Anthracene compounds

Material Science Material Building Blocks Small Molecule Semiconductor Building Blocks Anthracenes, Anthraquinones

Chemical Synthesis Organometallic Reagents Organoboron Boronic Acids and Derivatives

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2-(Anthracen-9-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

CAS No. 709022-63-9

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