2-Chloro-4-(trifluoromethyl)nicotinic acid

Name: 2-Chloro-4-(trifluoromethyl)nicotinic acid
Brand: ChemScene
Availability: InStock
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CAS No. 590371-81-6
Cat. No. CS-W013040
Purity≥98%
MDL No.MFCD08458125

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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-4-(trifluoromethyl)nicotinic acid|CS-W013040

Structure of 590371-81-6

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General Information

CAS No. 590371-81-6
Cat. No. CS-W013040
Purity ≥98%
MDL No. MFCD08458125
Storage 4°C
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₇H₃ClF₃NO₂
Molecular Weight 225.55
Synonym(s) 3-pyridinecarboxylic acid, 2-chloro-4-(trifluoromethyl)-
SMILES O=C(O)C1=C(Cl)N=CC=C1C(F)(F)F

Description

2-Chloro-4-(trifluoromethyl)nicotinic acid features a trifluoromethyl group at the 4-position and a chlorine substituent at the 2-position of the pyridine ring, imparting strong electron-withdrawing character. This configuration enhances reactivity in coupling processes and facilitates incorporation into bioactive scaffolds. The compound exhibits stability under standard bench conditions and is compatible with diverse synthetic transformations.

Application

2-Chloro-4-(trifluoromethyl)nicotinic acid serves as a versatile building block in medicinal chemistry and agrochemical synthesis, enabling efficient construction of bioactive heterocycles. Its electron-deficient pyridine core facilitates nucleophilic aromatic substitution and palladium-catalyzed coupling reactions. The trifluoromethyl group enhances metabolic stability and lipophilicity, while the chloro substituent provides a reliable handle for further functionalization. This compound exhibits excellent bench stability and is readily purified by recrystallization, making it well-suited for scalable synthetic workflows.

Synthesis

Route1
- 124-38-9
- In-stock
  
  81565-18-6
- ~84%
- In-stock
  
  590371-81-6
References
- Cottet, Fabrice; Schlosser, Manfred Tetrahedron, 2004 , vol. 60, # 51 p. 11869 - 11874

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+H312-H315-H319-H335
Precautionary Statements : P261-P264-P270-P271-P280-P302+P352-P304+P340-P330-P362-P405-P501

Quality Control

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Computational Chemistry Data

TPSA 50.19
LogP 2.452
H_Acceptors 2
H_Donors 1
Rotatable_Bonds 1

Other Classifications

Building Blocks Functional Group Chloride

Building Blocks Functional Group Carboxylic Acid

Building Blocks Skeleton Aromatic heterocycle compounds Pyridine compounds

Key Words

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2-Chloro-4-(trifluoromethyl)nicotinic acid

CAS No. 590371-81-6

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