2-Cyanopyridine-5-boronic acid pinacol ester

Name: 2-Cyanopyridine-5-boronic acid pinacol ester
Brand: ChemScene
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CAS No. 741709-63-7
Cat. No. CS-W003994
Purity≥95%
MDL No.MFCD06657825

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Type	HazMat Fee
Excepted Quantity	$0.00
FedEx Limited Quantities Ground	$0.00
Hazmat Ground shipping	$50.00+
Inaccessible (Haz class 6.1 or 9), Domestic	$68.00+
Accessible (Haz class 3, 4, 5 or 8), Domestic	$158.00+
Inaccessible (Haz class 6.1 or 9), International	$108.00+
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2-Cyanopyridine-5-boronic acid pinacol ester|CS-W003994

Structure of 741709-63-7

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General Information

CAS No. 741709-63-7
Cat. No. CS-W003994
Purity ≥95%
MDL No. MFCD06657825
Storage 4°C
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₁₂H₁₅BN₂O₂
Molecular Weight 230.07
Synonym(s) 6-Cyano-3-pyridylboronic Acid Pinacol Ester
SMILES N#Cc1ccc(cn1)B1OC(C(O1)(C)C)(C)C

Description

5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)picolinonitrile features a boronate ester group paired with a nitrile-substituted pyridine ring, enabling efficient Suzuki-Miyaura coupling under mild conditions. The tetramethylcyclohexadienyl moiety enhances stability and moisture tolerance, while the electron-deficient pyridine facilitates selective reaction with aryl halides. This structure supports modular synthesis of functionalized heteroaromatics in medicinal chemistry and materials science workflows.

Application

5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)picolinonitrile serves as a versatile boronate building block for palladium-catalyzed cross-coupling reactions. The picolinonitrile moiety provides a readily accessible handle for further functionalization, while the tetramethylboronate group ensures excellent stability, mild handling requirements, and compatibility with diverse reaction conditions. This compound facilitates efficient synthesis of substituted pyridine derivatives relevant to medicinal chemistry and materials science.

Synthesis

Route1
- In-stock
  
  97483-77-7
- In-stock
  
  73183-34-3
- ~85%
- In-stock
  
  741709-63-7
References
- Patrick, Donald A.; Ismail, Mohamed A.; Arafa, Reem K.; Wenzler, Tanja; Zhu, Xiaohua; Pandharkar, Trupti; Jones, Susan Kilgore; Werbovetz, Karl A.; Brun, Reto; Boykin, David W.; Tidwell, Richard R. Journal of Medicinal Chemistry, 2013 , vol. 56, # 13 p. 5473 - 5494
Route2
- In-stock
  
  31181-90-5
- ~%
- In-stock
  
  741709-63-7
References
- Bioorganic and Medicinal Chemistry Letters, , vol. 16, # 5 p. 1277 - 1281

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 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

Chemical Synthesis Organometallic Reagents Organoboron Boronic Acids and Derivatives

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2-Cyanopyridine-5-boronic acid pinacol ester

CAS No. 741709-63-7

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