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

Name: 2-Methoxy-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-3-amine
Brand: ChemScene
Availability: InStock
Rating: 5 (1 reviews)

CAS No. 893440-50-1
Cat. No. CS-B1261
Purity≥97%
MDL No.MFCD12923427

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2-Methoxy-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-3-amine|CS-B1261

Structure of 893440-50-1

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General Information

CAS No. 893440-50-1
Cat. No. CS-B1261
Purity ≥97%
MDL No. MFCD12923427
Storage 4°C, protect from light
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₁₂H₁₉BN₂O₃
Molecular Weight 250.10
Synonym(s) None
SMILES NC1=CC(B2OC(C)(C)C(C)(C)O2)=CN=C1OC

Description

3-Amino-2-methoxy-5-(4,4,5,5-tetramethyl[1,3,2-dioxaborolan-2-yl)pyridine features a boronate ester handle paired with an electron-rich pyridine core, enabling efficient Suzuki-Miyaura coupling under mild conditions. The methoxy and amino substituents enhance solubility and reactivity, while the tetramethyl dioxaborolane moiety ensures stability during storage and handling. This compound integrates seamlessly into complex molecular architectures requiring precise C–C bond formation.

Application

3-Amino-2-methoxy-5-(4,4,5,5-tetramethyl[1,3,2-dioxaborolan-2-yl)pyridine serves as a versatile boronate building block for Suzuki-Miyaura cross-coupling reactions. The pinacol boronate group enables stable, air-tolerant handling and facilitates efficient coupling with aryl halides and triflates under mild conditions. The amino and methoxy substituents provide orthogonal reactivity and tune electronic properties, making this compound well-suited for the synthesis of functionalized heterocyclic scaffolds in medicinal chemistry and materials science applications.

Synthesis

Route1
- In-stock
  
  884495-39-0
- In-stock
  
  73183-34-3
- ~92%
- In-stock
  
  893440-50-1
References
- GLAXOSMITHKLINE LLC; BOTYANSZKI, Janos; DICKERSON, Scott Howard; LEIVERS, Martin Robert; LI, Xiaofei; MCFADYEN, Robert Blount; REDMAN, Aniko Maria; SHOTWELL, John Bradford; XUE, Jianjun Patent: WO2012/174312 A2, 2012 ; Location in patent: Page/Page column 287 ; WO 2012/174312 A2
Route2
- In-stock
  
  1083168-94-8
- ~93%
- In-stock
  
  893440-50-1
References
- Su, Weiguo; Zhang, Weihan; Yang, Haibin Patent: US2013/190307 A1, 2013 ; Location in patent: Paragraph 0151; 0152 ;
Route3
- 893440-45-4
- ~95%
- In-stock
  
  893440-50-1
References
- VERTEX PHARMACEUTICALS INCORPORATED Patent: WO2006/65946 A1, 2006 ; Location in patent: Page/Page column 72 ; WO 2006/065946 A1

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 66.6
LogP 0.9716
H_Acceptors 5
H_Donors 1
Rotatable_Bonds 2

Other Classifications

Building Blocks Functional Group Boronic Acid And Its Ester

Building Blocks Skeleton Aromatic heterocycle compounds Pyridine compounds

Chemical Synthesis Organometallic Reagents Organoboron Boronic Acids and Derivatives

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

CAS No. 893440-50-1

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