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

Name: 1-(tert-Butyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole
Brand: ChemScene
Availability: InStock
Rating: 5 (1 reviews)

CAS No. 1256359-15-5
Cat. No. CS-W005224
Purity≥95%
MDL No.MFCD16660302

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1-(tert-Butyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole|CS-W005224

Structure of 1256359-15-5

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General Information

CAS No. 1256359-15-5
Cat. No. CS-W005224
Purity ≥95%
MDL No. MFCD16660302
Storage Store at room temperature
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₁₃H₂₃BN₂O₂
Molecular Weight None
Synonym(s) 1-tert-Butyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole
SMILES CC1(C)C(C)(C)OB(C2=CN(C(C)(C)C)N=C2)O1

Description

This boronate-functionalized pyrazole integrates readily into Suzuki-Miyaura coupling reactions under standard conditions, offering high stability and compatibility with diverse reaction matrices. The tert-butyl group enhances solubility and steric protection, enabling efficient cross-coupling without significant decomposition.

Application

1-(tert-Butyl)-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 pyrazole core provides a rigid, polar heterocyclic scaffold with moderate basicity and hydrogen-bonding capacity, while the tetramethylboronate group enables efficient coupling under mild conditions. Its tert-butyl substituent enhances solubility and reduces aggregation, facilitating purification and handling in complex synthetic sequences.

Synthesis

Route1
- In-stock
  
  70951-85-8
- In-stock
  
  73183-34-3
- ~24%
- In-stock
  
  1256359-15-5
References
- F. HOFFMANN-LA ROCHE AG; GENENTECH, INC.; DO, Steven; HU, Huiyong; KOLESNIKOV, Aleksandr; TSUI, Vickie, H.; WANG, Xiaojing Patent: WO2014/1377 A1, 2014 ; Location in patent: Page/Page column 104; 105 ;
Route2
- In-stock
  
  70951-85-8
- 61676-62-8
- ~64%
- In-stock
  
  1256359-15-5
References
- GLAXO GROUP LIMITED; Atkinson, Francis Louis; Barker, Michael David; Douault, Clement; Garton, Neil Stuart; Liddle, John; Patel, Vipulkumar Kantibhai; Preston, Alexander George Steven; Wilson, David Matthew Patent: US2013/40984 A1, 2013 ; Location in patent: Paragraph 0484-0485 ;
Route3
- In-stock
  
  15754-60-6
- ~%
- In-stock
  
  1256359-15-5
References
- F. HOFFMANN-LA ROCHE AG; GENENTECH, INC.; DO, Steven; HU, Huiyong; KOLESNIKOV, Aleksandr; TSUI, Vickie, H.; WANG, Xiaojing Patent: WO2014/1377 A1, 2014 ;

Safety Information

Download SDS

GHS Pictogram :	GHS No : GHS07
Signal Word : Warning	UN#: N/A
Class : N/A	Packing Group : N/A
Hazard Statements : H315-H319-H335
Precautionary Statements : P260-P264-P271-P280-P302+P352-P304+P340-P305+P351+P338-P312-P332+P313-P337+P313-P362+P364-P403+P233-P405-P501

Quality Control

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Computational Chemistry Data

TPSA 36.28
LogP 1.9373
H_Acceptors 4
H_Donors 0
Rotatable_Bonds 1

Other Classifications

Building Blocks Skeleton Aromatic heterocycle compounds Pyrazole compounds

Key Words

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

CAS No. 1256359-15-5

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