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

Name: 1-(tetrahydro-2H-pyran-2-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole
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CAS No. 1003846-21-6
Cat. No. CS-W000826
Purity≥97%
MDL No.MFCD16556148

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1-(tetrahydro-2H-pyran-2-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole|CS-W000826

Structure of 1003846-21-6

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General Information

CAS No. 1003846-21-6
Cat. No. CS-W000826
Purity ≥97%
MDL No. MFCD16556148
Storage Store at room temperature
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₁₄H₂₃BN₂O₃
Molecular Weight 278.16
Synonym(s) 1-Tetrahydropyran-2-yl-4-(4,4,5,5-tetraMethyl-1,3,2-dioxaborolan-2-yl)pyrazole
SMILES CC1(C)OB(OC1(C)C)c1cnn(c1)C1CCCCO1

Description

This pyrazole boronate ester integrates a tetrahydropyranyl protecting group and a stable dioxaborolane moiety, enabling orthogonal functionalization in complex synthesis. The bench-stable, moisture-tolerant structure facilitates reliable cross-coupling under standard conditions.

Application

1-(Tetrahydro-2H-pyran-2-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole serves as a stable, bench-ready boronate building block for Suzuki-Miyaura cross-coupling reactions. The tetrahydropranyl (THP) ether protects the pyrazole nitrogen, enabling orthogonal handling in complex syntheses. The pinacol boronate group facilitates reliable coupling with aryl and heteroaryl halides under mild conditions, offering high functional group tolerance and ease of purification—ideal for constructing biaryl scaffolds in medicinal chemistry and materials science.

Synthesis

Route1
- 110-87-2
- In-stock
  
  269410-08-4
- ~92%
- In-stock
  
  1003846-21-6
References
- WO2014/1973 A1, ; Page/Page column 60; 61; 62 ;

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 1.8814
H_Acceptors 5
H_Donors 0
Rotatable_Bonds 2

Other Classifications

Building Blocks Skeleton Aliphatic heterocycle compounds Tetrahydropyran compounds

Building Blocks Skeleton Aromatic heterocycle compounds Pyrazole compounds

Key Words

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

CAS No. 1003846-21-6

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