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

Name: 1-(tetrahydro-2H-pyran-4-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole
Brand: ChemScene
Availability: InStock
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CAS No. 1040377-03-4
Cat. No. CS-W000813
Purity≥97%
MDL No.MFCD12033229

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1-(tetrahydro-2H-pyran-4-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole|CS-W000813

Structure of 1040377-03-4

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General Information

CAS No. 1040377-03-4
Cat. No. CS-W000813
Purity ≥97%
MDL No. MFCD12033229
Storage Store at room temperature
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₁₄H₂₃BN₂O₃
Molecular Weight 278.16
Synonym(s) 1-(Tetrahydro-pyran-4-yl)-1H-pyrazole-4-Boronic acid pinacol ester
SMILES CC1(C)OB(OC1(C)C)c1cnn(c1)C1CCOCC1

Description

This pyrazole boronate ester integrates a tetrahydropyran-4-yl group and a stable diborane moiety, enabling efficient cross-coupling under mild conditions. The protected hydroxyl functionality enhances solubility and stability in aqueous and polar organic media. Designed for direct use in Suzuki-Miyaura reactions, it delivers high yields with minimal side-product formation.

Application

1-(Tetrahydro-2H-pyran-4-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 tetrahydro-2H-pyran-4-yl group provides excellent solubility and protection of the alcohol functionality, while the pinacol boronate enables efficient coupling with aryl, heteroaryl, and vinyl halides under mild conditions. Its high functional group tolerance and ease of purification make it ideal for constructing complex scaffolds in medicinal chemistry and materials science applications.

Synthesis

Route1
- In-stock
  
  1040377-02-3
- In-stock
  
  73183-34-3
- ~69%
- In-stock
  
  1040377-03-4
References
- Zhang, Dengyou; Zhang, Xiaowei; Ai, Jing; Zhai, Yun; Liang, Zhongjie; Wang, Ying; Chen, Yi; Li, Chunpu; Zhao, Fei; Jiang, Hualiang; Geng, Meiyu; Luo, Cheng; Liu, Hong Bioorganic and Medicinal Chemistry, 2013 , vol. 21, # 21 p. 6804 - 6820
Route2
- In-stock
  
  1175274-93-7
- In-stock
  
  73183-34-3
- ~38%
- In-stock
  
  1040377-03-4
References
- VERTEX PHARMACEUTICALS INCORPORATED; LAUFFER, David; LI, Pan; MCGINTY, Kira; RONKIN, Steven; TANG, Qing; GRILLOT, Anne-Laure; WAAL, Nathan Patent: WO2010/48131 A1, 2010 ; Location in patent: Page/Page column 53 ; WO 2010/048131 A1
Route3
- In-stock
  
  269410-08-4
- In-stock
  
  134419-59-3
- ~78%
- In-stock
  
  1040377-03-4
References
- Incyte Corporation; Lu, Liang; He, Chunhong; Yao, Wenqing Patent: US2014/45814 A1, 2014 ; Location in patent: Paragraph 0247; 0248 ;

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 1.5338
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

Chemical Synthesis Organometallic Reagents Organoboron Boronic Acids and Derivatives

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

CAS No. 1040377-03-4

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