2-(9,9-Dimethyl-9H-fluoren-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

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

CAS No. 569343-09-5
Cat. No. CS-0041017
Purity≥97%
MDL No.MFCD08704229

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2-(9,9-Dimethyl-9H-fluoren-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane|CS-0041017

Structure of 569343-09-5

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General Information

CAS No. 569343-09-5
Cat. No. CS-0041017
Purity ≥97%
MDL No. MFCD08704229
Storage Store at room temperature
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₂₁H₂₅BO₂
Molecular Weight None
Synonym(s) 9,9-Dimethylfluorene-2-boronic Acid Pinacol Ester
SMILES CC1(C)C(C)(C)OB(C2=CC(C(C)(C)C3=C4C=CC=C3)=C4C=C2)O1

Description

This boronate ester features a sterically shielded fluorenyl moiety that enhances stability and facilitates efficient cross-coupling reactions. The dimethylfluorene group provides robustness under standard conditions, while the tetramethyl-substituted dioxaborolane ring ensures high reactivity in Suzuki-Miyaura transformations.

Application

2-(9,9-Dimethyl-9H-fluoren-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane serves as a stable, bench-ready boron building block for Suzuki-Miyaura cross-coupling reactions. Its fluorenyl moiety provides excellent electronic and steric control, enabling efficient coupling with aryl and heteroaryl halides under mild conditions. The tetramethyl-substituted dioxaborolane enhances shelf stability and minimizes protodeboronation, while the sterically hindered fluorenyl group facilitates clean functionalization and straightforward purification in complex synthesis workflows.

Synthesis

Route1
- 61676-62-8
- In-stock
  
  28320-31-2
- ~78%
- In-stock
  
  569343-09-5
References
- Grisorio, Roberto; Suranna, Gian Paolo; Mastrorilli, Piero; Mazzeo, Marco; Colella, Silvia; Carallo, Sonia; Gigli, Giuseppe Dalton Transactions, 2013 , vol. 42, # 24 p. 8939 - 8950
Route2
- In-stock
  
  28320-31-2
- In-stock
  
  73183-34-3
- ~78%
- In-stock
  
  569343-09-5
References
- ALPHA CHEM CO., LTD.; NAM, Hyun Goog; LIM, Dae Won; KIM, Jae Yong; PARK, Sang Mi; JANG, Seung Hee; LEE, Sang Youn; HAM, Ju Seok; CHO, Kyu Oh; KIM, Hyun Don Patent: WO2013/180376 A1, 2013 ; Location in patent: Paragraph 138; 139; 140 ;
Route3
- 61676-62-8
- In-stock
  
  144981-85-1
- ~64%
- In-stock
  
  569343-09-5
References
- Liang, Bo; Wang, Lei; Zhu, Xuhui; Shi, Huahong; Peng, Junbiao; Cao, Yong Journal of Organometallic Chemistry, 2009 , vol. 694, # 19 p. 3172 - 3178

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

Quality Control

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Computational Chemistry Data

TPSA 18.46
LogP 4.2921
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 Benzene compounds

Material Science Material Building Blocks Small Molecule Semiconductor Building Blocks Fluorenes, Fluorenones

Chemical Synthesis Organometallic Reagents Organoboron Boronic Acids and Derivatives

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2-(9,9-Dimethyl-9H-fluoren-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

CAS No. 569343-09-5

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