6-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)quinoline

Name: 6-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)quinoline
Brand: ChemScene
Availability: InStock
Rating: 5 (1 reviews)

CAS No. 406463-06-7
Cat. No. CS-W000927
Molecule weight255.12
Purity≥95%
MDL No.MFCD06411327

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6-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)quinoline|CS-W000927

Structure of 406463-06-7

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General Information

CAS No. 406463-06-7
Cat. No. CS-W000927
Purity ≥95%
MDL No. MFCD06411327
Storage Store at room temperature
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₁₅H₁₈BNO₂
Molecular Weight 255.12
Synonym(s) Quinoline-6-boronic Acid Pinacol Ester
SMILES CC(C(C)(O1)C)(OB1C2=CC=C3C(C=CC=N3)=C2)C

Description

6-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)quinoline is a bench-stable boronate ester featuring a quinoline scaffold with enhanced reactivity in palladium-catalyzed cross-coupling. The tetramethyl-substituted dioxaborolane moiety enables efficient coupling under mild conditions, while the electron-deficient quinoline ring facilitates selective functionalization. This compound integrates readily into complex molecular architectures via Suzuki-Miyaura reactions.

Application

6-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)quinoline serves as a versatile boronate building block for Suzuki-Miyaura cross-coupling reactions. The tetramethylboronate group exhibits excellent stability under ambient conditions and tolerates a broad range of functional groups, enabling efficient C–C bond formation with aryl and heteroaryl halides. Its compatibility with standard reaction protocols makes it a practical choice for constructing complex quinoline-based scaffolds in medicinal chemistry and materials science applications.

Synthesis

Route1
- In-stock
  
  612-57-7
- In-stock
  
  73183-34-3
- ~53%
- In-stock
  
  406463-06-7
References
- Fuerstner, Alois; Seidel, Guenter Organic Letters, 2002 , vol. 4, # 4 p. 541 - 543
Route2
- 1092513-18-2
- In-stock
  
  73183-34-3
- ~87%
- In-stock
  
  406463-06-7
References
- Chow, Wing Kin; So, Chau Ming; Lau, Chak Po; Kwong, Fuk Yee Chemistry - A European Journal, 2011 , vol. 17, # 25 p. 6913 - 6917
Route3
- In-stock
  
  13327-31-6
- In-stock
  
  73183-34-3
- ~74%
- In-stock
  
  406463-06-7
References
- Nagashima, Yuki; Takita, Ryo; Yoshida, Kengo; Hirano, Keiichi; Uchiyama, Masanobu Journal of the American Chemical Society, 2013 , vol. 135, # 50 p. 18730 - 18733

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-H335
Precautionary Statements : P261-P264-P271-P280-P302+P352-P304+P340-P362-P405-P501

Quality Control

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Computational Chemistry Data

TPSA 31.35
LogP 2.534
H_Acceptors 3
H_Donors 0
Rotatable_Bonds 1

Other Classifications

Building Blocks Skeleton Aromatic heterocycle compounds quinoline compounds

Chemical Synthesis Organometallic Reagents Organoboron Boronic Acids and Derivatives

Key Words

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6-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)quinoline

CAS No. 406463-06-7

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