103604-49-5

Usage

Structure

Naphthalene derivative with a nitrile group, a methoxy group, and a trifluoromethyl group

Applications

Organic synthesis, medicinal chemistry, pharmaceuticals, and agrochemicals development

Electron-withdrawing

Strong electron-withdrawing properties due to the presence of the nitrile and trifluoromethyl groups

Lipophilic

Exhibits lipophilic properties, making it useful in the synthesis of complex organic molecules

Unique physical and chemical properties

The presence of the trifluoromethyl group imparts unique properties to the compound

Importance

Serves as an important building block for the synthesis of complex organic molecules due to its strong electron-withdrawing and lipophilic properties

Fields of application

Chemistry, biology, and materials science

Upstream product

• 103604-48-4 5-iodo-6-methoxy-1-cyanonaphthalene 
• 563-83-7 ISOPROPYLAMIDE 
• 2923-18-4 sodium 2,2,2-trifluoroacetate 

Relevant academic research and scientific papers

Process for recovering cuprous iodide catalyst used in synthesis of (trifluoromethyl)napthalenes

In a process for preparing a (trifluoromethyl)napthalene by reacting a halonapthalene with a trifluoroacetate in the presence of cuprous iodide and a dipolar aprotic solvent and separating out the inorganic ingredients of the final reaction mixture in the recovery of the product, the cuprous iodide is recovered by washing the separated inorganic ingredients with an alcohol and a carboxylic acid and then with water to purify the cuprous iodide.

Recovery process

A (trifluoromethyl)naphthalene which has been prepared by reacting a halonaphthalene with a trifluoroacetate salt in the presence of cuprous iodide and a dipolar aprotic solvent is recovered by (1) replacing the dipolar aprotic solvent in the final reaction mixture with an alkane containing 6-12 carbons, (2) heating the resultant slurry to a temperature sufficient to dissolve the organic ingredients, (3) allowing the inorganic ingredients of the slurry to settle, (4) decanting the organic layer, and (5) cooling to precipitate the (trifluoromethyl)naphthalene.

Substituted naphthoic acid process

6-Alkoxy-5-trifluoromethyl-1-naphthoic acids are prepared by (1) cyanating a 6-alkoxytetralone so as to form a 6-alkoxy-1-cyano-3,4-dihydronaphthalene, (2) converting the 6-alkoxy-1-cyano-3,4-dihydronaphthalene to a naphthoic acid precursor selected from a 6-alkoxy-1-cyanonaphthalene and a hydrocarbyl 6-alkoxy-1-naphthoate, (3) halogenating the naphthoic acid precursor to the corresponding 5-halo derivative, (4) trifluoromethylating the 5-halo derivative to replace the 5-halo substituent with a 5-trifluoromethyl group, and (5) hydrolyzing the resultant product to a 6-alkoxy-5-trifluoromethyl-1-naphthoic acid. In a preferred embodiment of the invention, the process is conducted so as to prepare 6-methoxy-5-trifluoromethyl-1-naphthoic acid, which, like the other products, is known to be useful as a pharmaceutical intermediate.