6500-37-4

Usage

Structure

A ketone derivative with a trifluoromethyl group attached to a naphthalene ring.

Usage

Commonly used as a reagent in organic synthesis, particularly in the production of pharmaceuticals and agrochemicals.

Biological and pharmacological properties

Has potential antimicrobial, antifungal, and anti-inflammatory effects.

Other applications

Has been investigated for use as a fluorescent dye and in the development of new materials for various applications.

InChI:InChI=1/C12H7F3O/c13-12(14,15)11(16)10-7-3-5-8-4-1-2-6-9(8)10/h1-7H

Upstream product

• 703-55-9 1-naphthylmagnesiumbromide 
• 76-05-1 trifluoroacetic acid 
• 91-20-3 naphthalene 
• 96254-05-6 2-(trifluoroacetyloxy)pyridine 
• 383-63-1 ethyl trifluoroacetate, 
• 90-11-9 1-Bromonaphthalene 
• 407-25-0 trifluoroacetic anhydride 
• 2459-24-7 methyl 1-naphthoate 
• 456-56-4 phenyl trifluoromethylsulfide 
• 500-73-2 phenyl trifluoroacetate 
• 13922-41-3 1-Naphthylboronic acid 
• 66-77-3 1-naphthaldehyde 
• 17556-44-4 2,2,2-trifluoro-1-(1-naphthyl)ethanol 
• 4780-79-4 1-naphthalene methanol 

Downstream Products

• 17556-44-4 2,2,2-trifluoro-1-(1-naphthyl)ethanol 
• 123492-58-0 C₁₉H₁₄F₃NO₃S 
• 112260-69-2 2-fluoro-1-(naphthalen-1-yl)ethanone 
• 715-80-0 2,2-difluoro-1-(naphthalen-1-yl)ethan-1-one 

Relevant academic research and scientific papers

Trifluoromethylation of Benzoic Acids: An Access to Aryl Trifluoromethyl Ketones

The trifluoromethylation of benzoic acids with TMSCF3 was achieved through nucleophilic substitution with the use of anhydrides as an in situ activating reagent. Under the reaction conditions, a wide range of carboxylic acids including the bioactive ones worked well, thus providing a facile and efficient method for preparing aryl trifluoromethyl ketones from the readily available starting materials.

Synthesis of trifluoromethyl ketones by nucleophilic trifluoromethylation of esters under a fluoroform/KHMDS/triglyme system

A straightforward method that enables the formation of biologically attractive trifluoromethyl ketones from readily available methyl esters using the potent greenhouse gas fluoroform (HCF3, HFC-23) was developed. The combination of fluoroform and KHMDS in triglyme at ?40 °C was effective for this transformation, with good yields as high as 92%. Substrate scope of the trifluoromethylation procedure was explored for aromatic, aliphatic, and conjugated methyl esters. This study presents a straightforward trifluoromethylation process of various methyl esters that convert well to the corresponding trifluoromethyl ketones. The tolerance of various pharmacophores under the reaction conditions was also explored.

Palladium-catalyzed fluoroacylation of (Hetero)arylboronic acid with fluorothioacetates at ambient temperature

A palladium-catalyzed fluoroacylation of (hetero)aryl boronic acid with the fluorothioacetates is described at ambient temperature. A variety of aryl, and heteroaryl boronic acids are compatible in the reaction, affording the corresponding fluoroalkyl ketones in moderate to good yields. Further late-stage di-, and trifluoroacylation of drug molecule clofibrate and estrone demonstrated the synthetic practicability of this protocol.2009 Elsevier Ltd. All rights reserved.

N-phenyl-N-p-toluenesulfonyl trifluoroacetamide (NTFTS) and application

The invention belongs to the technical field of medical chemical engineering intermediates and related chemistry, and relates to N-phenyl-N-p-toluenesulfonyl trifluoroacetamide (NTFTS) and application. The N-phenyl-N-p-toluenesulfonyl trifluoroacetamide is taken as a trifluoroacetylation reagent, reacts with an arylboronic acid derivative in an anhydrous organic solvent under the action of a metalcatalyst, a ligand and an alkali, and is efficiently and highly selectively converted into a trifluoroacetophenone compound. According to a synthesis method of the trifluoroacetophenone compound, involved in the invention, reaction steps are few; the NTFTS which is stable in use, easy to store, cheap and easy to get is taken as a trifluoroacetyl source; environmental friendliness is realized; reaction conditions are mild; operation is easy; a high-yield and high-selectivity target product is obtained and has relatively good industrial production value and practical application value. The trifluoroacetophenone compound synthesized by utilizing the method can be further subjected to a functionalization reaction, and can be widely applied to the synthetic fields of medicine, pesticide, bioactive molecules, functional material molecules and the like.

Catalytic Oxidation of Alcohols Using a 2,2,6,6-Tetramethylpiperidine-N-hydroxyammonium Cation

The oxidation of alcohols to aldehydes, ketones, and carboxylic acids is reported using 2,2,6,6-tetramethylpiperidine-4-acetamido-hydroxyammonium tetrafluoroborate as a catalyst in conjunction with sodium hypochlorite pentahydrate as a terminal oxidant. The reaction is generally complete within 30–120 min using an acetonitrile/water mix as the solvent, and no additives are required. Product yields are good to excellent and of particular note is that the methodology can be used to access aryl α-trifluoromethyl ketones.

Oxidation of α-trifluoromethyl and non-fluorinated alcohols: Via the merger of oxoammonium cations and photoredox catalysis

We present an alcohol oxidation strategy to access α-trifluoromethyl ketones (TFMKs) merging catalytic oxoammonium cation oxidation with visible-light photoredox catalysis. This work uses 4-acetamido-(2,2,6,6-tetramethyl-piperidin-1-yl)oxyl as an organic oxidant capable of generating TFMKs in good yields. The methodology serves as an improvement over previous reports of an analogous oxidation strategy requiring superstoichiometric quantities of oxidant. Both primary and secondary non-fluorinated alcohols can also be oxidised in good yields.

Convenient, functional group-tolerant, transition metal-free synthesis of aryl and heteroaryl trifluoromethyl ketones with the use of methyl trifluoroacetate

A new convenient, functional group-tolerant, transition metal-free route to aryl trifluoromethyl ketones under mild conditions is described. The reaction of not only aryl Grignard reagents carrying reducible electrophilic functional groups, such as ester and cyano groups, but also electron-deficient nitrogen-containing heteroaryl Grignard reagents with methyl trifluoroacetate gives the corresponding aryl or heteroaryl trifluoromethyl ketones in good yields. Biological assays revealed that new heteroaryl trifluoromethyl ketones carrying 2,4-dimethoxypyrimidine and 3,5-dimethylisoxazole rings show good anti-tumor activities.

MgCl2-catalyzed trifluoromethylation of carbonyl compounds using (trifluoromethyl)trimethylsilane as the trifluoromethylating agent

Using (trifluoromethyl)trimethylsilane (TMSCF3) as the trifluoromethylating agent, MgCl2-catalyzed trifluoromethylation of carbonyl compounds proceeded readily at room temperature. In the presence of 10 mol% of MgCl2, a variety of carbonyl substrates such as aliphatic/aromatic aldehydes, acyclic/cyclic ketones and esters could be trifluoromethylated in DMF, giving the corresponding trimethylsilyl ethers (ketals) in up to 93% isolated yields. Trifluoromethylketones could be readily obtained after hydrolysis of the trimethylsilyl ketals. The reactions could tolerate air and moisture, and the use of oxygen and moisture-free conditions was not required.

Palladium-catalyzed carbonylative coupling of aryl iodides with an organocopper reagent: A straightforward procedure for the synthesis of aryl trifluoromethyl ketones

A palladium-catalyzed carbonylative coupling of aryl iodides with a (trifluoromethyl)copper reagent has been developed. A wide range of substrates have been transformed into their corresponding trifluoromethyl ketones in good to excellent yields under mild conditions with high efficiency and excellent functional-group compatibility. Preliminary mechanistic investigations suggest that the transmetallation of an acylpalladium intermediate with the (trifluoromethyl)copper reagent seems to be involved in the catalytic cycle. Notably, this report represents one of the few studies on carbonylative coupling with organocopper reagents.

NHC-Copper(I) Halide-Catalyzed Direct Alkynylation of Trifluoromethyl Ketones on Water

An efficient and easily scalable NHC-copper(I) halide-catalyzed addition of terminal alkynes to 1,1,1-trifluoromethyl ketones, carried out on water for the first time, is reported. A series of addition reactions were performed with as little as 0.1-2.0?mo