2-Chloro-5-cyano-3-picoline

Name: 2-Chloro-5-cyano-3-picoline
Brand: ChemScene
Availability: InStock
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CAS No. 66909-33-9
Cat. No. CS-W005726
Purity≥97%
MDL No.MFCD09261082

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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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Structure of 66909-33-9

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General Information

CAS No. 66909-33-9
Cat. No. CS-W005726
Purity ≥97%
MDL No. MFCD09261082
Storage Store at room temperature
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₇H₅ClN₂
Molecular Weight 152.58
Synonym(s) 6-Chloro-5-methylnicotinonitrile
SMILES CC1=CC(=CN=C1Cl)C#N

Description

2-Chloro-5-cyano-3-picoline features a trifunctional pyridine core with chlorine, cyano, and methyl groups positioned for orthogonal reactivity. This electron-deficient heterocycle enables selective coupling in transition-metal-catalyzed transformations. The nitrile moiety enhances solubility in polar solvents while maintaining stability under standard bench conditions.

Application

2-Chloro-5-cyano-3-picoline serves as a versatile building block in medicinal chemistry, enabling efficient construction of heterocyclic scaffolds via palladium-catalyzed cross-coupling reactions. The chloro group facilitates reliable functionalization under standard Suzuki, Stille, or Negishi conditions, while the nitrile moiety provides a handle for downstream transformations such as amide formation or reductive amination. Its bench-stable nature and compatibility with diverse reaction conditions make it well-suited for iterative synthesis campaigns in API development.

Synthesis

Route1
- In-stock
  
  59782-89-7
- 544-92-3
- ~81%
- In-stock
  
  66909-33-9
References
- Kagabu, Shinzo Synthetic Communications, 2006 , vol. 36, # 9 p. 1235 - 1245

Safety Information

Download SDS

GHS Pictogram :	GHS No : GHS06
Signal Word : Danger	UN#: 3439
Class : 6.1	Packing Group : Ⅲ
Hazard Statements : H301
Precautionary Statements : P264-P270-P330-P405-P501

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Computational Chemistry Data

TPSA 36.68
LogP 1.9151
H_Acceptors 2
H_Donors 0
Rotatable_Bonds 0

Other Classifications

Building Blocks Functional Group Cyanide/Nitrile

Building Blocks Skeleton Aromatic heterocycle compounds Pyridine compounds

Key Words

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2-Chloro-5-cyano-3-picoline

CAS No. 66909-33-9

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