4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-2-pyridinecarbonitrile

Name: 4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-2-pyridinecarbonitrile
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CAS No. 741709-62-6
Cat. No. CS-W019792
Purity≥98%
MDL No.MFCD09607734

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4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-2-pyridinecarbonitrile|CS-W019792

Structure of 741709-62-6

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General Information

CAS No. 741709-62-6
Cat. No. CS-W019792
Purity ≥98%
MDL No. MFCD09607734
Storage -20°C
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₁₂H₁₅BN₂O₂
Molecular Weight 230.07
Synonym(s) 4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)picolinonitrile
SMILES N#CC1=NC=CC(B2OC(C)(C)C(C)(C)O2)=C1

Description

4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-2-pyridinecarbonitrile features a boronate ester group coupled to a pyridine ring bearing a nitrile at the ortho position. This combination enables efficient Suzuki-Miyaura coupling under mild conditions, with enhanced stability and moisture tolerance. The electron-deficient pyridine moiety facilitates selective reaction kinetics in cross-coupling processes.

Application

4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-2-pyridinecarbonitrile serves as a versatile boronate building block in Suzuki-Miyaura cross-coupling reactions. The pyridinecarbonitrile moiety provides enhanced electronic tuning and ortho-directing capability, while the pinacol boronate ester ensures excellent bench stability, ease of handling, and compatibility with a broad range of transition metal catalysts. This reagent facilitates efficient construction of complex heterocyclic scaffolds and functionalized aryl biaryls under mild reaction conditions.

Synthesis

Route1
- In-stock
  
  19235-89-3
- In-stock
  
  73183-34-3
- ~75%
- In-stock
  
  741709-62-6
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

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

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Computational Chemistry Data

TPSA 55.14
LogP 1.25248
H_Acceptors 4
H_Donors 0
Rotatable_Bonds 1

Other Classifications

Building Blocks Functional Group Cyanide/Nitrile

Building Blocks Skeleton Aromatic heterocycle compounds Pyridine compounds

Key Words

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4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-2-pyridinecarbonitrile

CAS No. 741709-62-6

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