81565-18-6

Basic information

• Product Name: 2-Chloro-4-(trifluoromethyl)pyridine
• Synonyms: Pyridine,2-chloro-4-(trifluoromethyl)-;2-Chloro-4-(trifluor;2-Chloro-alpha,alpha,alpha-trifluoro-4-picoline;2-CHLORO-4-(TRIFLUOROMETHYL)PYRIDINE;BUTTPARK 27\01-81;2-Chloro-4-(trifluoromethyl)pyridine 98%;2-Chloro-4-(trifluoromethyl)pyridine98%
• CAS NO: 81565-18-6
• Molecular Formula: C₆H₃ClF₃N
• Molecular Weight: 181.54
• EINECS: 1308068-626-2
• Product Categories: Heterocyclic Building Blocks;Building Blocks;C5 to C6;C6 to C7;Chemical Synthesis;Halogenated Heterocycles;Heterocyclic Building Blocks;Fluorine series;Pyridine series;Halides;Pyridines;Pyridine;Pyridines derivates;C6Heterocyclic Building Blocks;Halogenated Heterocycles
• Mol File: 81565-18-6.mol

Chemical Properties

• Melting Point: -19°C
• Boiling Point: 146-147 °C(lit.)
• Flash Point: 127 °F
• Appearance: Light yellow liquid
• Density: 1.411 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.0688mmHg at 25°C
• Refractive Index: n20/D 1.4490(lit.)
• Storage Temp.: Room temperature.
• Solubility: Chloroform, Methanol (Sparingly)
• PKA: -1.34±0.10(Predicted)
• BRN: 4246276
• CAS DataBase Reference: 2-Chloro-4-(trifluoromethyl)pyridine(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Chloro-4-(trifluoromethyl)pyridine(81565-18-6)
• EPA Substance Registry System: 2-Chloro-4-(trifluoromethyl)pyridine(81565-18-6)

Safety Data

• Hazard Codes: Xi,T,F
• Statements: 10-36/37/38-25-11
• Safety Statements: 26-36-45-36/37/39-22-16
• RIDADR: UN 1993 3/PG 3
• WGK Germany: 3
• HazardClass: 3
• PackingGroup: III
• Hazardous Substances Data: 81565-18-6(Hazardous Substances Data)

Usage

Uses

Used in Chemical Synthesis:
2-Chloro-4-(trifluoromethyl)pyridine is used as a chemical intermediate for the synthesis of various compounds, including 4,4′-bis(trifluoromethyl)-2,2′-bipyridine, 4-(trifluoromethyl)pyridine, and 1,3-bis(4-(trifluoromethyl)pyridin-2-yl)benzene. Its unique structure and functional groups make it a valuable building block in the development of new pharmaceuticals, agrochemicals, and other specialty chemicals.

InChI:InChI=1/C11H11F3O2/c1-2-16-10(15)7-8-5-3-4-6-9(8)11(12,13)14/h3-6H,2,7H2,1H3

Upstream product

• 153034-86-7 2-chloro-4-iodopyridine 
• 81290-20-2 (trifluoromethyl)trimethylsilane 
• 695-34-1 2-Amino-4-methylpyridine 
• 58310-28-4 (Difluoromethyl)triphenylphosphonium bromide 
• 75-45-6 Chlorodifluoromethane 
• 73583-37-6 2-chloro-4-bromopyridine 
• 339539-96-7 3-hydroxy-3-trifluoromethyl-1,5-pentanedialdehyde 
• 36610-32-9 4-hydroxy-4-trifluoromethyl-1,6-heptadiene 
• 3796-24-5 4-trifluoromethylpyridine 
• 50650-59-4 4-(trifluoromethyl)-2-pyridone 
• 22253-59-4 1-oxido-4-(trifluoromethyl)pyridin-1-ium 

Downstream Products

• 175205-81-9 2-bromo-4-(trifluoromethyl)pyridine 
• 158063-66-2 4-(trifluoromethyl)nicotinic acid 
• 588702-62-9 4-(trifluoromethyl)-2-pyridinecarboxylic acid 
• 1416854-62-0 1,2-bis((4-(trifluoromethyl)pyridin-2-yl)ethynyl)benzene 
• 50650-59-4 4-(trifluoromethyl)-2-pyridone 
• 935265-46-6 2-(1-(tert-butyldimethylsilyloxy)-7-phenylheptyl)-5-(4-(trifluoromethyl)pyridin-2-yl)oxazole 
• 118708-88-6 1-(4-(trifluoromethyl)pyridin-2-yl)piperazine 
• 590371-81-6 2-chloro-4-(trifluoromethyl)pyridine-3-carboxylic acid 
• 106447-97-6 2-amino-4-(trifluoromethyl)pyridine 
• 142946-79-0 4,4′-bis-(trifluoromethyl)-2,2′-bipyridine 
• 89570-84-3 2-hydrazinyl-4-(trifluoromethyl)pyridine 

Relevant articles and documents

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PREPARATION OF SULFONAMIDE HERBICIDE PROCESS INTERMEDIATES

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Method for producing 2-chloro-4-trifluoromethylpyridine

The invention discloses a method for producing 2-chloro-4-trifluoromethylpyridine, and belongs to the technical field of fine chemical synthesis. The method comprises the following steps: taking 2-amino-4-methylpyridine as a raw material, and successively carrying out diazotization, chlorination and fluoridation on the 2-amino-4-methylpyridine to obtain 2-chloro-4-trifluoromethylpyridine. The diazotization comprises the following steps: taking the 2-amino-4-methylpyridine as the raw material, and carrying out diazotization on the 2-amino-4-methylpyridine, sodium nitrite and hydrogen chloride in a reactor to obtain 2-chloro-4-methylpyridine. The chlorination comprises the following steps: taking the 2-chloro-4-methylpyridine as the raw material, feeding chlorine and carrying out chlorination to obtain 2-chloro-4-(trichloromethyl) pyridine as a main product and hydrogen chloride as a side product. The fluoridation comprises the following steps: taking the 2-chloro-4-(trichloromethyl) pyridine as the raw material, and carrying out fluoridation on the 2-chloro-4-(trichloromethyl) pyridine and anhydrous hydrogen fluoride in an autoclave to obtain the 2-chloro-4-trifluoromethylpyridine as a main product. Industrial production of the 2-chloro-4-trifluoromethylpyridine is realized.

Trifluoromethylation of (hetero)aryl iodides and bromides with copper(i) chlorodifluoroacetate complexes

A new copper-mediated trifluoromethylation reaction using copper(i) chlorodifluoroacetate complexes as reagents is reported. The complex [L2Cu][O2CCF2Cl] (L = bpy, dmbpy, phen) reacted with (hetero)aryl iodides and bromides in the presence of CsF in DMF at 75 °C to afford the trifluoromethylarenes in good to excellent yields. High compatibility with various chemical functions or (hetero)cycles was also observed in the reaction. A reaction mechanism involving a difluorocarbene intermediate, along with a subsequent formation of a -CF3 anion was proposed.

DBU-Promoted Trifluoromethylation of Aryl Iodides with Difluoromethyltriphenylphosphonium Bromide

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1,8-Diazabicyclo[5.4.0]undec-7-ene (DBU)-promoted decomposition of difluorocarbene and the subsequent trifluoromethylation

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Copper-mediated perfluoroalkylation of heteroaryl bromides with (phen)CuRF

The attachment of perfluoroalkyl groups onto organic compounds has been a major synthetic goal over the past several decades. Previously, our group reported phenanthroline-ligated perfluoroalkyl copper reagents, (phen)CuR F, which react with aryl iodides and aryl boronates to form the corresponding benzotrifluorides. Herein the perfluoroalkylation of a series of heteroaryl bromides with (phen)CuCF3 and (phen)CuCF 2CF3 is reported. The mild reaction conditions allow the process to tolerate many common functional groups. Perfluoroethylation with (phen)CuCF2CF3 occurs in somewhat higher yields than trifluoromethylation with (phen)CuCF3, creating a method to generate fluoroalkyl heteroarenes that are less accessible from trifluoroacetic acid derivatives.

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Method For Producing Substituted Halopyridines

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Compounds with anti-cancer activity

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