1-(2-Methoxyethyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole

Name: 1-(2-Methoxyethyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole
Brand: ChemScene
Availability: InStock
Rating: 5 (1 reviews)

CAS No. 847818-71-7
Cat. No. CS-W006072
Purity≥97%
MDL No.MFCD12405649

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1-(2-Methoxyethyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole|CS-W006072

Structure of 847818-71-7

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General Information

CAS No. 847818-71-7
Cat. No. CS-W006072
Purity ≥97%
MDL No. MFCD12405649
Storage Store at room temperature
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₁₂H₂₁BN₂O₃
Molecular Weight 252.12
Synonym(s) 2-[1-(2-Methoxyethyl)-1H-pyrazol-4-yl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
SMILES COCC[N]1C=C(C=N1)B2OC(C(O2)(C)C)(C)C

Description

This pyrazole derivative features a methoxyethyl substituent and a boronate ester group, enabling efficient Suzuki-Miyaura coupling under standard conditions. The tetramethyl-1,3,2-dioxaborolane moiety ensures stability and compatibility with aqueous and protic solvents, while the electron-rich pyrazole core supports diverse functionalization in medicinal chemistry and materials synthesis.

Application

1-(2-Methoxyethyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole serves as a versatile boronate building block for Suzuki-Miyaura cross-coupling reactions. The pyrazole core provides metabolic stability and hydrogen-bonding capacity, while the 2-methoxyethyl side chain enhances solubility and modulates polarity. The tetramethyl-substituted dioxaborolane moiety ensures excellent bench stability, low toxicity, and high functional group tolerance, enabling efficient coupling under mild conditions. This reagent facilitates rapid assembly of complex heterocyclic scaffolds in medicinal chemistry and materials science applications.

Synthesis

Route1
- In-stock
  
  269410-08-4
- 6482-24-2
- ~69%
- In-stock
  
  847818-71-7
References
- WO2011/51342 A1, ; Page/Page column 95 ; WO 2011/051342 A1
Route2
- In-stock
  
  269410-08-4
- 627-42-9
- ~99%
- In-stock
  
  847818-71-7
References
- WO2014/15088 A1, ; Paragraph 00223 ;
Route3
- In-stock
  
  73183-34-3
- In-stock
  
  847818-49-9
- ~45%
- In-stock
  
  847818-71-7
References
- WO2008/88881 A1, ; Page/Page column 48 ; WO 2008/088881 A1

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

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Computational Chemistry Data

TPSA 45.51
LogP 0.8287
H_Acceptors 5
H_Donors 0
Rotatable_Bonds 4

Other Classifications

Building Blocks Functional Group Boronic Acid And Its Ester

Building Blocks Skeleton Aromatic heterocycle compounds Pyrazole compounds

Chemical Synthesis Organometallic Reagents Organoboron Boronic Acids and Derivatives

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1-(2-Methoxyethyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole

CAS No. 847818-71-7

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