4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrazole

Name: 4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrazole
Brand: ChemScene
Availability: InStock
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CAS No. 894807-98-8
Cat. No. CS-0013023
Purity≥95%
MDL No.MFCD20486100

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Excepted Quantity	$0.00
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4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrazole|CS-0013023

Structure of 894807-98-8

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General Information

CAS No. 894807-98-8
Cat. No. CS-0013023
Purity ≥95%
MDL No. MFCD20486100
Storage 4°C
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₁₅H₂₉BN₂O₃Si
Molecular Weight None
Synonym(s) trimethyl-[2-[[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrazol-1-yl]methoxy]ethyl]silane
SMILES CC1(C)C(C)(C)OB(O1)C2=CN(COCC[Si](C)(C)C)N=C2

Description

This pyrazole boronate ester integrates a stable tetramethylborolane handle with a trimethylsilyl-protected alcohol, enabling efficient Suzuki-Miyaura coupling under mild conditions. The silyl ether group ensures moisture tolerance and selective deprotection during downstream transformations.

Application

This boronate ester serves as a versatile building block in Suzuki-Miyaura cross-coupling reactions, enabling efficient C–C bond formation under mild conditions. The pyrazole core is stabilized by the (trimethylsilyl)ethoxymethyl protecting group, which ensures bench stability and facilitates orthogonal deprotection. Its compatibility with diverse functional groups and ease of purification make it ideal for constructing complex heterocyclic scaffolds in medicinal chemistry and materials science applications.

Synthesis

Route1
- In-stock
  
  269410-08-4
- 76513-69-4
- ~85%
- In-stock
  
  894807-98-8
References
- SCHERING CORPORATION; TSUI, Hon-Chung; PALIWAL, Sunil; KIM, Hyunjin, M.; KEREKES, Angela, D.; CAPLEN, Mary Ann; ESPOSITE, Sara, J.; MCKITTRICK, Brian, A.; FISCHMANN, Thierry Olivier; DOLL, Ronald, J.; RAINKA, Matthew Paul; LI, Ang Patent: WO2011/149874 A2, 2011 ; Location in patent: Page/Page column 81-82 ;
Route2
- 76513-69-4
- ~62%
- In-stock
  
  894807-98-8
References
- Alcon, Inc. Patent: US2006/142307 A1, 2006 ; Location in patent: Page/Page column 7 ; US 20060142307 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 2.4946
H_Acceptors 5
H_Donors 0
Rotatable_Bonds 6

Other Classifications

Building Blocks Functional Group Boronic Acid And Its Ester

Building Blocks Functional Group Organosilicon compounds

Building Blocks Skeleton Aromatic heterocycle compounds Pyrazole compounds

Key Words

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4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrazole

CAS No. 894807-98-8

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