33284-17-2

Basic information

• Product Name: Ethanone, 2,2,2-trifluoro-1-(2-pyridinyl)- (9CI)
• Synonyms: Ethanone, 2,2,2-trifluoro-1-(2-pyridinyl)- (9CI);2-trifluoroacetypyridine;2,2,2-trifluoro-1-(pyridin-2-yl)ethanone;2-(Trifluoroacetyl)pyridine;2-(Trifluoroacetyl)pyridine (contains gem-diol);Ethanone, 2,2,2-trifluoro-1-(2-pyridinyl)-;2,2,2-trifluoro-1-(2-pyridinyl)Ethanone;2,2,2-trifluoro-1-(pyridin-2-yl)ethan-1-one
• CAS NO: 33284-17-2
• Molecular Formula: C₇H₄F₃NO
• Molecular Weight: 175.1079696
• Product Categories: ACETYLHALIDE
• Mol File: 33284-17-2.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 172.9 °C at 760 mmHg
• Flash Point: 58.4 °C
• Appearance: /
• Density: 1.341 g/cm³
• Vapor Pressure: 1.3mmHg at 25°C
• Refractive Index: 1.446
• Storage Temp.: 2-8°C
• PKA: 0.95±0.10(Predicted)
• CAS DataBase Reference: Ethanone, 2,2,2-trifluoro-1-(2-pyridinyl)- (9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: Ethanone, 2,2,2-trifluoro-1-(2-pyridinyl)- (9CI)(33284-17-2)
• EPA Substance Registry System: Ethanone, 2,2,2-trifluoro-1-(2-pyridinyl)- (9CI)(33284-17-2)

Safety Data

• Hazardous Substances Data: 33284-17-2(Hazardous Substances Data)

Usage

Uses

Used in Chemical Synthesis:
Ethanone, 2,2,2-trifluoro-1-(2-pyridinyl)(9CI) is used as a reagent in chemical synthesis for its unique trifluoromethyl ketone functionality. It contributes to the formation of various complex organic molecules, enhancing the diversity and properties of synthesized compounds.
Used in Pharmaceutical Production:
In the pharmaceutical industry, Ethanone, 2,2,2-trifluoro-1-(2-pyridinyl)(9CI) serves as an intermediate in the production of various pharmaceuticals. Its unique structure and reactivity enable the development of novel drug candidates with improved therapeutic properties and reduced side effects.
Used in Research and Development:
Ethanone, 2,2,2-trifluoro-1-(2-pyridinyl)(9CI) is utilized in research and development for exploring its potential applications and understanding its chemical properties. It aids in the discovery of new synthetic routes, reaction mechanisms, and the development of innovative pharmaceuticals and chemical products.
Used in Analytical Chemistry:
Ethanone, 2,2,2-trifluoro-1-(2-pyridinyl)(9CI) can be employed in analytical chemistry as a reference material or a standard for the development and validation of analytical methods. Its unique structure and properties make it suitable for assessing the performance of chromatographic, spectroscopic, and other analytical techniques.

InChI:InChI=1/C7H4F3NO/c8-7(9,10)6(12)5-3-1-2-4-11-5/h1-4H

Upstream product

• 107040-75-5 2,2,2-trifluoro-1-(pyridin-2-yl)ethan-1-ol 
• 1121-60-4 pyridine-2-carbaldehyde 

Downstream Products

• 1184723-77-0 3-phenyl-1-(trifluoromethyl)imidazo[1,5-a]pyridine 
• 80483-84-7 (R)-2,2,2-trifluoro-1-(pyridin-2-yl)ethanol 
• 80483-85-8 (S)-2,2,2-trifluoro-1-(pyridin-2-yl)ethanol 
• 1616797-52-4 3-trifluoromethyl-[1,2,3]triazolo[1,5-a]pyridine 
• 107040-75-5 2,2,2-trifluoro-1-(pyridin-2-yl)ethan-1-ol 

Relevant articles and documents

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.

Asymmetric Radical-Radical Cross-Coupling through Visible-Light-Activated Iridium Catalysis

Combining single electron transfer between a donor substrate and a catalyst-activated acceptor substrate with a stereocontrolled radical-radical recombination enables the visible-light-driven catalytic enantio- and diastereoselective synthesis of 1,2-amino alcohols from trifluoromethyl ketones and tertiary amines. With a chiral iridium complex acting as both a Lewis acid and a photoredox catalyst, enantioselectivities of up to 99% ee were achieved. A quantum yield of 1 supports the proposed catalytic cycle in which at least one photon is needed for each asymmetric C-C bond formation mediated by single electron transfer.

Organocatalytic Aerobic Oxidation of α-Fluoroalkyl Alcohols to Fluoroalkyl Ketones at Room Temperature

The organocatalytic aerobic oxidation of electron-deficient α-fluoroalkyl alcohols at room temperature is described. The resulting fluoroalkyl ketones are versatile synthetic intermediates for a variety of fluorine-containing molecules. This otherwise difficult transformation has now been accomplished by the reaction of α-fluoroalkyl alcohols with N-oxyl radicals, catalytically generated from 9-azabicyclo[3.3.1]nonan-3-one N-oxyl/nitrogen oxide (keto-ABNO/NOx) and oxygen in acetic acid (AcOH), affording the corresponding fluoroalkyl ketones in high yield. This operationally simple reaction can be performed under mild conditions, and was applied to a wide range of alcohols (20 examples), thus demonstrating a high functional group tolerance. Moreover, a modified one-pot protocol based on this method was able to convert an aldehyde to a trifluoromethyl ketone on a gram scale.

Oxidation of α-trifluoromethyl alcohols using a recyclable oxoammonium salt

A simple, mild method for the oxidation of α-trifluoromethyl alcohols to trifluoromethyl ketones (TFMKs) using the oxoammonium salt 4-acetylamino-2,2,6,6-tetramethylpiperidine-1-oxoammonium tetrafluoroborate (1) is described. Under basic conditions, oxidation proceeds rapidly and affords good to excellent yields of TFMKs, without concomitant formation of the hydrate. The byproduct of the oxidation, 4-acetylamino-2,2,6,6-tetramethyl-1- piperidinyloxy (1c), is easily recovered and can be conveniently reoxidized to regenerate the oxoammonium salt.