4-[3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]morpholine

Name: 4-[3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]morpholine
Brand: ChemScene
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CAS No. 852227-95-3
Cat. No. CS-W005450
Molecule weight289.18
Purity≥95%
MDL No.None

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Excepted Quantity	$0.00
FedEx Limited Quantities Ground	$0.00
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4-[3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]morpholine|CS-W005450

Structure of 852227-95-3

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General Information

CAS No. 852227-95-3
Cat. No. CS-W005450
Purity ≥95%
MDL No. None
Storage Store at room temperature
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₁₆H₂₄BNO₃
Molecular Weight 289.18
Synonym(s) morpholine, 4-[3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-
SMILES CC1(C)C(C)(C)OB(C2=CC(N3CCOCC3)=CC=C2)O1

Description

4-[3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]morpholine features a boronate ester group enabling efficient Suzuki-Miyaura coupling, paired with a morpholine moiety that enhances solubility and modulates electronic properties. This structure supports rapid diversification in medicinal chemistry and materials synthesis under standard conditions.

Application

4-[3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]morpholine serves as a versatile boronate building block for Suzuki-Miyaura cross-coupling reactions. The morpholine moiety provides solubility and polarity benefits, while the tetramethylboronate group enables reliable coupling under mild conditions. This compound facilitates efficient construction of biaryl scaffolds in medicinal chemistry and materials science, offering excellent bench stability and straightforward purification.

Synthesis

Route1
- In-stock
  
  5414-19-7
- In-stock
  
  210907-84-9
- ~%
- In-stock
  
  852227-95-3
References
- WO2012/167423 A1, ; Page/Page column 37 ; WO 2012/167423 A1
Route2
- In-stock
  
  73183-34-3
- In-stock
  
  197846-82-5
- ~34%
- In-stock
  
  852227-95-3
References
- Patel, Gautam; Karver, Caitlin E.; Behera, Ranjan; Guyett, Paul J.; Sullenberger, Catherine; Edwards, Peter; Roncal, Norma E.; Mensa-Wilmot, Kojo; Pollastri, Michael P. Journal of Medicinal Chemistry, 2013 , vol. 56, # 10 p. 3820 - 3832

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 30.93
LogP 1.8224
H_Acceptors 4
H_Donors 0
Rotatable_Bonds 2

Other Classifications

Building Blocks Skeleton Aliphatic heterocycle compounds Morpholine compounds

Building Blocks Skeleton Aromatic ring compounds Benzene compounds

Chemical Synthesis Organometallic Reagents Organoboron Boronic Acids and Derivatives

Key Words

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4-[3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]morpholine

CAS No. 852227-95-3

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