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

Name: 1-phenyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole
Brand: ChemScene
Availability: InStock
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CAS No. 1002334-12-4
Cat. No. CS-W000782
Purity≥97%
MDL No.MFCD12400941

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1-phenyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole|CS-W000782

Structure of 1002334-12-4

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General Information

CAS No. 1002334-12-4
Cat. No. CS-W000782
Purity ≥97%
MDL No. MFCD12400941
Storage Store at room temperature
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₁₅H₁₉BN₂O₂
Molecular Weight 270.14
Synonym(s) 1-phenyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrazole
SMILES CC1(C)OB(OC1(C)C)c1cnn(c1)-c1ccccc1

Description

1-Phenyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole features a boronate ester group that enables efficient Suzuki-Miyaura cross-coupling reactions. The pyrazole core provides structural rigidity and electronic stability, while the tetramethyl-substituted dioxaborolane enhances moisture tolerance and shelf life. This compound integrates readily into complex molecular architectures under standard conditions.

Application

1-Phenyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole serves as a versatile boron-containing building block for Suzuki-Miyaura cross-coupling reactions. The pyrazole core provides metabolic stability and hydrogen-bonding capacity, while the pinacol boronate ester enables efficient, mild coupling with aryl and heteroaryl halides. Bench-stable and compatible with diverse functional groups, it facilitates rapid access to biaryl-pyrazole scaffolds prevalent in medicinal chemistry and agrochemical research.

Synthesis

Route1
- 508191-77-3
- In-stock
  
  347389-74-6
- ~46%
- In-stock
  
  1002334-13-5
- In-stock
  
  1002334-12-4
References
- Journal of the American Chemical Society, , vol. 131, p. 7762 - 7769
Route2
- In-stock
  
  15115-52-3
- In-stock
  
  73183-34-3
- ~50%
- In-stock
  
  1002334-12-4
References
- PROGENICS PHARMACEUTICALS, INC. Patent: WO2009/155527 A2, 2009 ; Location in patent: Page/Page column 134 ; WO 2009/155527 A2

Safety Information

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GHS Pictogram : N/A	GHS No : N/A
Signal Word : N/A	UN#: N/A
Class : N/A	Packing Group : N/A
Hazard Statements : N/A
Precautionary Statements : N/A

Quality Control

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Computational Chemistry Data

TPSA 36.28
LogP 2.1715
H_Acceptors 4
H_Donors 0
Rotatable_Bonds 2

Other Classifications

Building Blocks Skeleton Aromatic heterocycle compounds Pyrazole compounds

Building Blocks Skeleton Aromatic ring compounds Benzene compounds

Key Words

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

CAS No. 1002334-12-4

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