124612-15-3

Basic information

• Product Name: 5-(Trifluoromethyl)cyclohexane-1,3-dione
• Synonyms: 5-(Trifluoromethyl)cyclohexane-1,3-dione;1,3-Cyclohexanedione, 5-(trifluoromethyl)-
• CAS NO: 124612-15-3
• Molecular Formula: C₇H₇F₃O₂
• Molecular Weight: 180.1244896
• Mol File: 124612-15-3.mol
• Article Data: 3

Chemical Properties

• Melting Point: 140-142 °C(Solv: ethyl acetate (141-78-6); hexane (110-54-3))
• Boiling Point: 222.4±40.0 °C(Predicted)
• Appearance: /
• Density: 1.359±0.06 g/cm3(Predicted)
• PKA: 4.14±0.20(Predicted)
• CAS DataBase Reference: 5-(Trifluoromethyl)cyclohexane-1,3-dione(CAS DataBase Reference)
• NIST Chemistry Reference: 5-(Trifluoromethyl)cyclohexane-1,3-dione(124612-15-3)
• EPA Substance Registry System: 5-(Trifluoromethyl)cyclohexane-1,3-dione(124612-15-3)

Safety Data

• Hazardous Substances Data: 124612-15-3(Hazardous Substances Data)

Usage

General Description

5-(Trifluoromethyl)cyclohexane-1,3-dione is a chemical compound with the molecular formula C8H9F3O2. It is a cyclohexanedione derivative with a trifluoromethyl group attached to the carbon backbone. 5-(Trifluoromethyl)cyclohexane-1,3-dione is commonly used in organic synthesis as a building block for the preparation of various pharmaceuticals and agrochemicals. It is also utilized in the production of specialty chemicals and materials. The presence of the trifluoromethyl group in 5-(Trifluoromethyl)cyclohexane-1,3-dione makes it a valuable compound for applications in medicinal and chemical research.

Upstream product

• 25597-16-4 ethyl 4,4,4-trifluorocrotonate 
• 141-97-9 ethyl acetoacetate 

Downstream Products

• 1048703-55-4 3-amino-5-(trifluoromethyl)cyclohex-2-en-1-one 
• 1052719-57-9 7-bromo-9-(2-fluorophenyl)-3-(trifluoromethyl)-3,4-dihydroacridin-1(2H)-one 
• 1052719-58-0 7-nitro-9-phenyl-3-(trifluoromethyl)-3,4-dihydroacridin-1(2H)-one 
• 1210418-38-4 3-oxo-5-(trifluoromethyl)cyclohex-1-en-1-yl trifluoromethanesulfonate 
• 1625669-42-2 4-(2,5-dioxo-7-(trifluoromethyl)-1-(3-(trifluoromethyl)phenyl)-1,2,3,4,5,6,7,8-octahydroquinazolin-4-yl)benzonitrile 
• 1625672-15-2 1-((4-cyanophenyl)(2-ethoxy-6-oxo-4-(trifluoromethyl)cyclohex-1-enyl)methyl)-3-(3-(trifluoromethyl)phenyl)urea 
• 1625672-14-1 1-((4-cyanophenyl)(2-hydroxy-6-oxo-4-(trifluoromethyl)cyclohex-1-enyl)methyl)-3-(3-(trifluoromethyl)phenyl)urea 

Relevant articles and documents

Design and development of trifluoromethylated enaminone derivatives as potential anticonvulsants

Enaminone derivatives have been widely studied as potential anticonvulsant agents to treat epilepsy. Our research group is focused on evaluating the anticonvulsant activities of cyclic enaminones connected to a substituted aromatic ring via a sp2 hybridized linker. We herein report our lead optimization efforts and the subsequent synthesis of the target fluorinated N-benzamide enaminone analog N-(3-oxo-5-(trifluoromethyl) cyclohex-1-en-1-yl)-4-(trifluoromethyl) benzamide (compound 7) from fluorinated intermediates, and its bioevaluation in acute seizure rodent models. The synthesis of the fluorinated cycloalkyl intermediates, 5-(trifluoromethyl) cyclohexane-1,3-dione (compound 5) and 3-amino-5-(trifluoromethyl) cyclohex-2-en-1-one (compound 6) were derived from an improve method of a one-pot hydrolysis and acid catalyzed decarboxylation of 4-carbo-tert-butoxy-5-trifluoromethylcyclohexane-1,3-dione (compound 4). Compound 7 produced pharmacological response at a higher dose of 300 mg/kg with only 25% protection observed, when compared to our previous lead compound THA40 in the 6 Hz 44 mA animal model. In the maximal electroshock (MES) model, compound 7 showed moderate activity at 100 mg/kg with 25% after 2 h. At a higher dose of 300 mg/kg, 25% of the animals were protected both at 0.5 h and 2 h. Although compound 7 did not produce the expected results, it allowed for a new avenue to investigate during our lead optimization studies.

Synthesis of 5-(trifluoromethyl)cyclohexane-1,3-dione and 3-amino-5-(trifluoromethyl)cyclohex-2-en-1-one: new trifluoromethyl building block

A simple synthesis of 5-(trifluoromethyl)cyclohexane-1,3-dione and 3-amino-5-(trifluoromethyl)cyclohex-2-en-1-one from the sodium salt of methyl or ethyl-4-hydroxy-2-oxo-6-(trifluoromethyl)cyclohex-3-en-1-oate is demonstrated. The compounds represent high