2,2,2-Trifluoroacetophenone

Base Information

• Chemical Name: 2,2,2-Trifluoroacetophenone
• CAS No.: 434-45-7
• Molecular Formula: C8H5F3O
• Molecular Weight: 174.122
• Hs Code.: 29147090
• European Community (EC) Number: 207-103-1
• NSC Number: 42752
• UNII: 6T7L1UPY09
• DSSTox Substance ID: DTXSID6059992
• Nikkaji Number: J150.547E
• Wikidata: Q27265490
• Pharos Ligand ID: U42XBU2CGG4K
• ChEMBL ID: CHEMBL293277
• Mol file: 434-45-7.mol

Synonyms:phenyl trifluoromethyl ketone;phenyltrifluoromethylketone

Chemical Property of 2,2,2-Trifluoroacetophenone

Chemical Property:

• Appearance/Colour: clear colorless to yellow liquid
• Vapor Pressure: 1.72mmHg at 25°C
• Melting Point: -40 °C
• Refractive Index: n20/D 1.458(lit.)
• Boiling Point: 165.499 °C at 760 mmHg
• Flash Point: 41.667 °C
• PSA: 17.07000
• Density: 1.268 g/cm³
• LogP: 2.43160
• Storage Temp.: Flammables area
• Solubility.: Chloroform, Ethyl Acetate
• Water Solubility.: PRACTICALLY INSOLUBLE
• XLogP3: 2.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 1
• Exact Mass: 174.02924926
• Heavy Atom Count: 12
• Complexity: 168

Purity/Quality:

99% ^*data from raw suppliers

2,2,2-Trifluoroacetophenone ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi, F
• Hazard Codes: Xi,F
• Statements: 10-36/37/38
• Safety Statements: 26-36-37/39-16

MSDS Files:

Useful:

• Chemical Classes: Toxic Gases & Vapors -> Tear Gas Agents
• Canonical SMILES: C1=CC=C(C=C1)C(=O)C(F)(F)F
• Uses: 2,2,2-Trifluoroacetophenone is a fluorinated acetophenone with inhibitory activity of acetylcholinesterase. 2,2,2-Trifluoroacetophenone was shown to have neuroprotective activity by inhibiting apoptos is in cerebellar granule neurons. 2,2,2-Trifluoroacetophenone is a fluorinated acetophenone with inhibitory activity of acetylcholinesterase. 2,2,2-Trifluoroacetophenone was shown to have neuroprotective activity by inhibiting apoptosis in cerebellar granule neurons.

Technology Process of 2,2,2-Trifluoroacetophenone

There total 143 articles about 2,2,2-Trifluoroacetophenone which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 97.0%

1-phenyl-2,2,2-trifluoromethylethanol (340-04-5,340-05-6) → 2,2,2-Trifluoroacetophenone (434-45-7)

Guidance literature:

With sodium hypochlorite pentahydrate; 4-acetamido-2,2,6,6-tetramethylpiperidine-N-hydroxyammonium tetrafluoroborate; In water; acetonitrile; at 20 ℃; for 1.5h;

DOI:10.1002/ejoc.201801718

Reference yield: 96.0%

Adamantan-1-yl-[2,2,2-trifluoro-1-phenyl-eth-(Z)-ylidene]-amine (141903-89-1) → 2,2,2-Trifluoroacetophenone (434-45-7) + 1-Adamantanamine (768-94-5)

Guidance literature:

With water; boric acid; In ethanol; at 80 ℃; for 8h;

DOI:10.1021/ja00071a017

Reference yield: 95.0%

benzoic acid methyl ester (93-58-3,5705-52-2,80226-58-0) + (trifluoromethyl)trimethylsilane (81290-20-2) → 2,2,2-Trifluoroacetophenone (434-45-7)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; toluene; for 18h; Ambient temperature;

DOI:10.1002/(SICI)1521-3773(19980403)37:6<820::AID-ANIE820>3.0.CO;2-M

upstream raw materials:

trifluoroacetonitrile

diethyl ether

phenyllithium

trifluoroacetic acid

Downstream raw materials:

1,1,1-trifluoro-2,2-dichloro-2-phenylethane

1-(3-chlorophenyl)-2,2,2-trifluoroethanone

S(+)-1-phenyl-2,2,2-trifluoroethanol

1-phenyl-2,2,2-trifluoromethylethanol

Refernces

One-Pot Synthesis of O-Allylhydroxylamines through the Organocatalytic Oxidation of Tertiary Allylic Amines Followed by a [2,3]-Meisenheimer Rearrangement

10.1002/chem.201406173

The study presents a green and efficient one-pot method for synthesizing O-protected allylic alcohols through the organocatalytic oxidation of tertiary allylic amines, followed by a [2,3]-Meisenheimer rearrangement. The key chemicals used in the study include 2,2,2-trifluoroacetophenone as the organocatalyst, hydrogen peroxide (H2O2) as the oxidant, and a variety of solvents such as dichloromethane, THF, methanol, ethyl acetate, and tert-butanol, which were tested to optimize the reaction conditions. The purpose of these chemicals is to facilitate the conversion of allylic amine N-oxides to O-allylhydroxylamines in a sustainable manner, reducing waste generation and simplifying the purification process compared to traditional methods that use stoichiometric amounts of oxidants. The study also explored the substrate scope, demonstrating the method's tolerance for various substituents on the amine and allylic moiety, and leading to products in moderate to high yields.

Asymmetric reduction of perfluoroalkyl ketones with chiral lithium alkoxides

10.1016/j.tetlet.2006.02.078

The research discusses the asymmetric reduction of perfluoroalkyl ketones using chiral lithium alkoxides, with the aim of synthesizing chiral α-perfluoroalkyl alcohols in high enantiomeric excesses. The study focuses on the reaction of various perfluoroalkyl ketones with lithium (S)-1-phenylethoxide, yielding chiral alcohols with either (S) or (R) configuration, depending on the size of the perfluoroalkyl group. The researchers concluded that chiral lithium 1-phenylethoxide is effective in reducing aromatic perfluoroalkyl ketones with large perfluoroalkyl groups to (R)-perfluoroalkyl alcohols in good yields and high enantioselectivity, while trifluoromethyl ketones yield (S)-alcohols. This reduction method is particularly useful for perfluoroalkyl ketones that do not yield good results with the CBS reduction. The chemicals used in the process include 2,2,2-trifluoroacetophenone, perfluorooctan-1-one, and lithium (S)-1-phenylethoxide, among others.