2-[9,9-Dioctyl-7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)fluoren-2-yl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Name: 2-[9,9-Dioctyl-7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)fluoren-2-yl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
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CAS No. 196207-58-6
Cat. No. CS-0036746
Purity≥97%
MDL No.None

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2-[9,9-Dioctyl-7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)fluoren-2-yl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane|CS-0036746

Structure of 196207-58-6

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General Information

CAS No. 196207-58-6
Cat. No. CS-0036746
Purity ≥97%
MDL No. None
Storage Store at room temperature
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₄₁H₆₄B₂O₄
Molecular Weight 642.57
Synonym(s) 9H-Carbazole, 9-(1-octylnonyl)-2,7-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-
SMILES CCCCCCCCC1(CCCCCCCC)C2=C(C=CC(=C2)B3OC(C)(C)C(C)(C)O3)C4=C1C=C(C=C4)B5OC(C)(C)C(C)(C)O5

Description

This boronate ester features a fluorene core functionalized with a sterically shielded diborane moiety, enabling efficient Suzuki-Miyaura coupling under standard conditions. The bulky dioctyl substituents enhance solubility and stability, while the tetramethyl-1,3,2-dioxaborolane ring ensures high reactivity and moisture tolerance in synthetic workflows.

Application

2-[9,9-Dioctyl-7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)fluoren-2-yl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane serves as a robust boron-containing building block for Suzuki-Miyaura cross-coupling reactions. Its fluorene core provides structural rigidity and electronic stability, while the sterically protected boronate ester enables high functional group tolerance and bench-stable handling. This compound facilitates efficient construction of complex conjugated systems and extended π-frameworks in materials and pharmaceutical synthesis.

Synthesis

Route1
- 61676-62-8
- In-stock
  
  198964-46-4
- ~94%
- In-stock
  
  196207-58-6
References
- Pasini, Mariacecilia; Destri, Silvia; Porzio, William; Botta, Chiara; Giovanella, Umberto Journal of Materials Chemistry, 2003 , vol. 13, # 4 p. 807 - 813
Route2
- 61676-62-8
- 1059179-65-5
- ~%
- In-stock
  
  196207-58-6
References
- EP2520576 A1, ; Page/Page column 77-78 ;
Route3
- In-stock
  
  76347-13-2
- In-stock
  
  198964-46-4
- ~79%
- In-stock
  
  196207-58-6
References
- Yang, Renqiang; Tian, Renyu; Yan, Jingai; Zhang, Yong; Yang, Jian; Hou, Qiong; Yang, Wei; Zhang, Chi; Cao, Yong Macromolecules, 2005 , vol. 38, # 2 p. 244 - 253

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 36.92
LogP 10.0527
H_Acceptors 4
H_Donors 0
Rotatable_Bonds 16

Other Classifications

Material Science Material Composite Block Semiconducting Polymer Synthetic Building Block

Material Science Solar Cell Materials Donor Intermediate DI

Chemical Synthesis Organometallic Reagents Organoboron Boronic Acids and Derivatives

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2-[9,9-Dioctyl-7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)fluoren-2-yl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

CAS No. 196207-58-6

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