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3-Chloro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)picolinonitrile

  • CAS No. 1220219-63-5

  • Cat. No. CS-0177439
  • Purity≥97%
  • MDL No.None

*For research and further manufacturing use only, not for direct human use.

3-Chloro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)picolinonitrile|CS-0177439

Structure of 1220219-63-5

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General Information

  • CAS No. 1220219-63-5
  • Cat. No. CS-0177439
  • Purity ≥97%
  • MDL No. None
  • Storage 4°C
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₂H₁₄BClN₂O₂
  • Molecular Weight 264.52
  • Synonym(s) None
  • SMILES N#CC1=NC=C(B2OC(C)(C)C(C)(C)O2)C=C1Cl

Description

This boronate-functionalized picolinonitrile integrates seamlessly into cross-coupling reactions, offering enhanced stability and selective reactivity. The electron-deficient pyridine ring pairs with a moisture-tolerant boronate moiety, enabling efficient C–C bond formation under standard conditions.

Application

3-Chloro-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 core provides a rigid, electron-deficient heterocyclic scaffold with orthogonal functional handles. The boronate moiety enables reliable Suzuki-Miyaura coupling under mild conditions, while the chloropyridine site permits subsequent functionalization via nucleophilic substitution or metal-catalyzed transformations. Bench-stable and readily purified by flash chromatography, it facilitates efficient construction of complex heteroaromatic systems in medicinal chemistry and materials science applications.

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-H312-H332
Precautionary Statements : P261-P264-P270-P271-P280-P302+P352-P304+P340-P330-P362+P364-P501

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Computational Chemistry Data

  • TPSA   55.14
  • LogP   1.90588
  • H_Acceptors   4
  • H_Donors   0
  • Rotatable_Bonds   1

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