2-Chloro-5-(trifluoromethyl)-4-iodopyridine

Name: 2-Chloro-5-(trifluoromethyl)-4-iodopyridine
Brand: ChemScene
Availability: InStock
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CAS No. 505084-55-9
Cat. No. CS-W013962
Purity≥98%
MDL No.MFCD01862099

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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+
Accessible (Haz class 3, 4, 5 or 8), International	$238.00+

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2-Chloro-5-(trifluoromethyl)-4-iodopyridine|CS-W013962

Structure of 505084-55-9

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General Information

CAS No. 505084-55-9
Cat. No. CS-W013962
Purity ≥98%
MDL No. MFCD01862099
Storage 4°C, protect from light
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₆H₂ClF₃IN
Molecular Weight 307.44
Synonym(s) pyridine, 2-chloro-4-iodo-5-(trifluoromethyl)-; 2-Chloro-5-(trifluoromethyl)-4-iodopyridine
SMILES ClC1=NC=C(C(=C1)I)C(F)(F)F

Description

2-Chloro-5-(trifluoromethyl)-4-iodopyridine features a uniquely activated pyridine core with orthogonal halogen handles: a chloro group at C2 and an iodide at C4, flanked by a strongly electron-withdrawing trifluoromethyl substituent at C5. This combination enables selective cross-coupling transformations under mild conditions, particularly in Pd-catalyzed reactions where the iodo moiety serves as a high-reactivity partner. The molecule exhibits excellent bench stability and solubility in common organic solvents, facilitating use in iterative synthesis workflows.

Application

2-Chloro-5-(trifluoromethyl)-4-iodopyridine serves as a versatile building block for palladium-catalyzed cross-coupling reactions, enabling efficient construction of biaryl and heterocyclic scaffolds. The ortho-chloro and para-iodo substituents offer complementary reactivity for sequential functionalization. Its stability under standard reaction conditions and tolerance to diverse functional groups facilitate reliable synthesis of complex molecular architectures relevant to medicinal chemistry and materials science.

Synthesis

Route1
- In-stock
  
  52334-81-3
- ~%
- In-stock
  
  505084-55-9
- In-stock
  
  505084-56-0
References
- VERTEX PHARMACEUTICALS INCORPORATED Patent: WO2008/94992 A2, 2008 ; Location in patent: Page/Page column 174 ; WO 2008/094992 A2
Route2
- In-stock
  
  52334-81-3
- ~65%
- In-stock
  
  505084-55-9
References
- Cottet, Fabrice; Marull, Marc; Lefebvre, Olivier; Schlosser, Manfred European Journal of Organic Chemistry, 2003 , # 8 p. 1559 - 1568

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 12.89
LogP 3.3584
H_Acceptors 1
H_Donors 0
Rotatable_Bonds 0

Other Classifications

Building Blocks Functional Group Fluoride

Building Blocks Functional Group Chloride

Building Blocks Skeleton Aromatic heterocycle compounds Pyridine compounds

Key Words

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2-Chloro-5-(trifluoromethyl)-4-iodopyridine

CAS No. 505084-55-9

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