1-Methyl-4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)piperazine

Name: 1-Methyl-4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)piperazine
Brand: ChemScene
Availability: InStock
Rating: 5 (1 reviews)

CAS No. 747413-21-4
Cat. No. CS-W012121
Purity≥97%
MDL No.MFCD06795650

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1-Methyl-4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)piperazine|CS-W012121

Structure of 747413-21-4

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General Information

CAS No. 747413-21-4
Cat. No. CS-W012121
Purity ≥97%
MDL No. MFCD06795650
Storage RT, protect from light
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₁₇H₂₇BN₂O₂
Molecular Weight 302.23
Synonym(s) 4-(4-METHYLPIPERAZIN-1-YL)PHENYLBORONIC ACID, PINACOL ESTER
SMILES CN1CCN(CC1)C1=CC=C(C=C1)B1OC(C)(C)C(C)(C)O1

Description

1-Methyl-4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)piperazine delivers a boronate ester handle for efficient Suzuki-Miyaura cross-coupling. The tetramethyl-substituted dioxaborolane moiety ensures high stability and moisture tolerance, enabling reliable use under standard conditions. This piperazine derivative integrates seamlessly into complex molecular architectures, particularly in pharmaceutical and materials science applications requiring robust functional group compatibility.

Application

1-Methyl-4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)piperazine serves as a versatile boronate building block in Suzuki-Miyaura cross-coupling reactions. The tetramethylboronate moiety enables reliable coupling with aryl halides under mild conditions, offering excellent functional group tolerance and bench stability. Its piperazine core provides structural diversity for medicinal chemistry applications, while the methylated nitrogen enhances solubility and metabolic stability. This reagent facilitates efficient construction of complex biaryl scaffolds common in pharmaceutical development.

Synthesis

Route1
- In-stock
  
  73183-34-3
- In-stock
  
  130307-08-3
- ~65%
- In-stock
  
  747413-21-4
References
- PROZYMEX A/S; PEDERSEN, John; LAURITZEN, Conni Patent: WO2012/130299 A1, 2012 ; Location in patent: Page/Page column 149 ; WO 2012/130299 A1
Route2
- In-stock
  
  76-09-5
- In-stock
  
  130307-08-3
- ~45%
- In-stock
  
  747413-21-4
References
- Andersen, Valdemar L.; Herth, Matthias M.; Lehel, Szabolcs; Knudsen, Gitte M.; Kristensen, Jesper L. Tetrahedron Letters, 2013 , vol. 54, # 3 p. 213 - 216
Route3
- 61676-62-8
- In-stock
  
  130307-08-3
- ~%
- In-stock
  
  747413-21-4
References
- WO2008/148867 A2, ; Page/Page column 49-50 ; WO 2008/148867 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-P305+P351+P338-P330-P362+P364-P403+P233-P405-P501

Quality Control

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Computational Chemistry Data

TPSA 24.94
LogP 1.7376
H_Acceptors 4
H_Donors 0
Rotatable_Bonds 2

Other Classifications

Building Blocks Skeleton Aliphatic heterocycle compounds Piperazine compounds

Building Blocks Skeleton Aromatic ring compounds Benzene compounds

Key Words

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1-Methyl-4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)piperazine

CAS No. 747413-21-4

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