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

Name: 5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrazole
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CAS No. 903550-12-9
Cat. No. CS-0091812
Purity≥95%
MDL No.MFCD09037502

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5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrazole|CS-0091812

Structure of 903550-12-9

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General Information

CAS No. 903550-12-9
Cat. No. CS-0091812
Purity ≥95%
MDL No. MFCD09037502
Storage -20°C, sealed storage, away from moisture
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₁₅H₂₉BN₂O₃Si
Molecular Weight None
Synonym(s) 1-(2-Trimethylsilylethoxy)methyl-1H-pyrazole-5-boronic acid pinacol ester
SMILES C[Si](CCOCN1N=CC=C1B2OC(C)(C)C(C)(C)O2)(C)C

Description

This pyrazole boronate ester integrates a stable tetramethylboronate group with a silyl-protected aldehyde handle, enabling orthogonal functionalization in late-stage diversification. The trimethylsilyl ether moiety provides enhanced stability and selective deprotection under mild conditions.

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 provides a stable heterocyclic scaffold with moderate bioavailability relevance, while the 1-(trimethylsilyl)ethoxymethyl group offers orthogonal protection and facile deprotection. Bench-stable and compatible with diverse functional groups, **5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrazole** facilitates streamlined synthesis of complex pyrazole derivatives for medicinal chemistry and materials applications.

Synthesis

Route1
- In-stock
  
  76-09-5
- In-stock
  
  133560-57-3
- ~74%
- In-stock
  
  903550-12-9
References
- Gerard, Anne-Laure; Bouillon, Alexandre; Mahatsekake, Clement; Collot, Valerie; Rault, Sylvain Tetrahedron Letters, 2006 , vol. 47, # 27 p. 4665 - 4669
Route2
- 76513-69-4
- ~%
- In-stock
  
  903550-12-9
References
- Gerard, Anne-Laure; Bouillon, Alexandre; Mahatsekake, Clement; Collot, Valerie; Rault, Sylvain Tetrahedron Letters, 2006 , vol. 47, # 27 p. 4665 - 4669

Safety Information

Download SDS

GHS Pictogram :	GHS No : GHS07
Signal Word : Warning	UN#: N/A
Class : N/A	Packing Group : N/A
Hazard Statements : H317-H319
Precautionary Statements : P264-P280-P305+P351+P338-P337+P313

Quality Control

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

CAS No. 903550-12-9

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