886370-42-9

Basic information

• Product Name: 2,2,2-TRIFLUORO-1-(6-METHOXY-NAPHTHALEN-2-YL)-ETHANONE
• Synonyms: 6-METHOXY-2-TRIFLUOROACETYLNAPHTHALENE;2,2,2-TRIFLUORO-1-(6-METHOXY-NAPHTHALEN-2-YL)-ETHANONE;2-(6-METHOXYNAPHTHYL) TRIFLUOROMETHYL KETONE
• CAS NO: 886370-42-9
• Molecular Formula: C₁₃H₉F₃O₂
• Molecular Weight: 254.2
• Mol File: 886370-42-9.mol
• Article Data: 6

Chemical Properties

• Melting Point: 64-66 °C
• Boiling Point: 325.5°C at 760 mmHg
• Flash Point: 145.7°C
• Appearance: /
• Density: 1.3g/cm³
• Vapor Pressure: 0.00023mmHg at 25°C
• Refractive Index: 1.539
• CAS DataBase Reference: 2,2,2-TRIFLUORO-1-(6-METHOXY-NAPHTHALEN-2-YL)-ETHANONE(CAS DataBase Reference)
• NIST Chemistry Reference: 2,2,2-TRIFLUORO-1-(6-METHOXY-NAPHTHALEN-2-YL)-ETHANONE(886370-42-9)
• EPA Substance Registry System: 2,2,2-TRIFLUORO-1-(6-METHOXY-NAPHTHALEN-2-YL)-ETHANONE(886370-42-9)

Safety Data

• Hazardous Substances Data: 886370-42-9(Hazardous Substances Data)

Usage

General Description

2,2,2-Trifluoro-1-(6-methoxy-naphthalen-2-yl)-ethanone is a chemical compound with the molecular formula C14H11F3O2. It is a fluorinated ketone that contains a naphthalene ring with a methoxy group attached. 2,2,2-TRIFLUORO-1-(6-METHOXY-NAPHTHALEN-2-YL)-ETHANONE is used in the synthesis of pharmaceuticals, agrochemicals, and other organic compounds. It is also used as a building block in the production of specialty chemicals. 2,2,2-Trifluoro-1-(6-methoxy-naphthalen-2-yl)-ethanone has potential applications in the fields of medicine, agriculture, and materials science. Due to its unique structure and properties, it is a valuable and versatile chemical building block.

InChI:InChI=1/C13H9F3O2/c1-18-11-5-4-8-6-10(3-2-9(8)7-11)12(17)13(14,15)16/h2-7H,1H3

Upstream product

• 5111-65-9 2-Bromo-6-methoxynaphthalene 
• 104863-67-4 N-methoxy-N-methyltrifluoroacetamide 
• 3453-33-6 6-methoxynaphthalene-2-carbaldehyde 
• 383-63-1 ethyl trifluoroacetate, 
• 267410-94-6 6-Methoxy-2-naphthoic-N-methoxy-N-methyl amide 
• 81290-20-2 (trifluoromethyl)trimethylsilane 
• 2471-70-7 2-methoxy-6-naphthoic acid 

Downstream Products

• 1393448-89-9 methyl 1-(1-(6-(trans-4-tert-butylcyclohexyloxy)naphthalen-2-yl)-2,2,2-trifluoroethyl)piperidine-4-carboxylate 
• 1393448-90-2 1-(1-(6-(trans-4-tert-butylcyclohexyloxy)naphthalen-2-yl)-2,2,2-trifluoroethyl)piperidine-4-carboxylic acid 

Relevant articles and documents

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.

Access to Aryl and Heteroaryl Trifluoromethyl Ketones from Aryl Bromides and Fluorosulfates with Stoichiometric CO

We report a sequential one-pot preparation of aromatic trifluoromethyl ketones starting from readily accessible aryl bromides and fluorosulfates, the latter easily prepared from the corresponding phenols. The methodology utilizes low pressure carbon monoxide generated ex situ from COgen to generate Weinreb amides as reactive intermediates that undergo monotrifluoromethylation affording the corresponding aromatic trifluoromethyl ketones (TFMKs) in good yields. The stoichiometric use of CO enables the possibility for accessing 13C-isotopically labeled TFMK by switching to the use of 13COgen.

Palladium-Catalyzed Trimethylenemethane Cycloaddition of Olefins Activated by the δ-Electron-Withdrawing Trifluoromethyl Group

α-Trifluoromethyl-styrenes, trifluoromethyl-enynes, and dienes undergo palladium-catalyzed trimethylenemethane cycloadditions under mild reaction conditions. The trifluoromethyl group serves as a unique δ-electron-withdrawing group for the activation of the olefin toward the cycloaddition. This method allows for the formation of exomethylene cyclopentanes bearing a quaternary center substituted by the trifluoromethyl group, compounds of interest for the pharmaceutical, agrochemical, and materials industries. In the diene series, the cycloaddition operates in a [3 + 4] and/or [3 + 2] manner to give rise to seven- and/or five-membered rings. This transformation greatly improves the scope of the TMM cycloaddition technology and provides invaluable insights into the reaction mechanism.