Methyl 1-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole-5-carboxylate

Name: Methyl 1-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole-5-carboxylate
Brand: ChemScene
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CAS No. 929899-20-7
Cat. No. CS-0369215
Purity≥97%
MDL No.MFCD16995823

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Methyl 1-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole-5-carboxylate|CS-0369215

Structure of 929899-20-7

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General Information

CAS No. 929899-20-7
Cat. No. CS-0369215
Purity ≥97%
MDL No. MFCD16995823
Storage -20°C
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₁₂H₁₉BN₂O₄
Molecular Weight 266.10
Synonym(s) Methyl 1-Methyl-3-(4,4,5,5-tetraMethyl-1,3,2-dioxaborolan-2-yl)-pyrazole-5-carboxylate
SMILES O=C(C1=CC(B2OC(C)(C)C(C)(C)O2)=NN1C)OC

Description

Methyl 1-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole-5-carboxylate features a boronate ester group enabling efficient Suzuki-Miyaura coupling. The tetramethyl-substituted dioxaborolane enhances stability and solubility in organic media. This pyrazole derivative integrates readily into complex heterocyclic scaffolds under standard conditions.

Application

Methyl 1-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole-5-carboxylate serves as a stable, bench-ready boron building block for Suzuki-Miyaura cross-coupling reactions. The tetramethylboronate moiety enables efficient palladium-catalyzed coupling with aryl, heteroaryl, and vinyl halides, while the pyrazole core provides a versatile scaffold for medicinal chemistry applications. Functional group tolerance and ease of purification support robust integration into complex molecule synthesis workflows.

Synthesis

Route1
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  929899-20-7
References
- PFIZER PRODUCTS INC. Patent: WO2007/34278 A2, 2007 ; Location in patent: Page/Page column 56-57 ; WO 2007/034278 A2

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-P330-P362+P364-P405-P501

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Computational Chemistry Data

TPSA 62.58
LogP 0.5059
H_Acceptors 6
H_Donors 0
Rotatable_Bonds 2

Other Classifications

Building Blocks Functional Group Ester

Building Blocks Skeleton Aromatic heterocycle compounds Pyrazole compounds

Key Words

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Methyl 1-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole-5-carboxylate

CAS No. 929899-20-7

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