N,N-Dimethyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-amine

Name: N,N-Dimethyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-amine
Brand: ChemScene
Availability: InStock
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CAS No. 1036991-24-8
Cat. No. CS-W005741
Purity≥95%
MDL No.MFCD11975406

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N,N-Dimethyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-amine|CS-W005741

Structure of 1036991-24-8

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General Information

CAS No. 1036991-24-8
Cat. No. CS-W005741
Purity ≥95%
MDL No. MFCD11975406
Storage 4°C, protect from light
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₁₃H₂₁BN₂O₂
Molecular Weight 248.13
Synonym(s) N,N-Dimethyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2-pyridinamine
SMILES CC1(C)C(C)(C)OB(C2=CN=C(N(C)C)C=C2)O1

Description

N,N-Dimethyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-amine features a boronate ester group flanked by a dimethylamino-pyridine scaffold, enabling robust cross-coupling under mild conditions. This bench-stable reagent integrates efficiently into Suzuki-Miyaura reactions, delivering high yields with minimal protodeboronation. Its moisture-tolerant nature simplifies handling in synthetic workflows.

Application

N,N-Dimethyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-amine serves as a robust boronate building block for Suzuki-Miyaura cross-coupling reactions. Its pyridyl amine functionality enables efficient coupling with aryl and heteroaryl halides under mild conditions, offering excellent functional group tolerance and bench stability. The sterically protected boronate moiety ensures high reactivity and resistance to protodeboronation, making it ideal for constructing complex heterocyclic scaffolds in medicinal chemistry and materials science applications.

Synthesis

Route1
- In-stock
  
  26163-07-5
- In-stock
  
  73183-34-3
- ~76%
- In-stock
  
  1036991-24-8
References
- Wang, Lianhui; Li, Jingya; Cui, Xiuling; Wu, Yusheng; Zhu, Zhiwu; Wu, Yangjie Advanced Synthesis and Catalysis, 2010 , vol. 352, # 11-12 p. 2002 - 2010

Safety Information

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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 34.59
LogP 1.4468
H_Acceptors 4
H_Donors 0
Rotatable_Bonds 2

Other Classifications

Building Blocks Functional Group Boronic Acid And Its Ester

Building Blocks Skeleton Aromatic heterocycle compounds Pyridine compounds

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N,N-Dimethyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-amine

CAS No. 1036991-24-8

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