221915-87-3

Basic information

• Product Name: 1,1,1-trifluoro-4-(4-methoxy-phenyl)-butan-2-one
• Synonyms: 1,1,1-trifluoro-4-(4-methoxy-phenyl)-butan-2-one
• CAS NO: 221915-87-3
• Molecular Weight: 232.202
• Mol File: 221915-87-3.mol

Chemical Properties

• CAS DataBase Reference: 1,1,1-trifluoro-4-(4-methoxy-phenyl)-butan-2-one(CAS DataBase Reference)
• NIST Chemistry Reference: 1,1,1-trifluoro-4-(4-methoxy-phenyl)-butan-2-one(221915-87-3)
• EPA Substance Registry System: 1,1,1-trifluoro-4-(4-methoxy-phenyl)-butan-2-one(221915-87-3)

Safety Data

• Hazardous Substances Data: 221915-87-3(Hazardous Substances Data)

Upstream product

• 15893-42-2 3-(4-methoxyphenyl)propionyl chloride 
• 407-25-0 trifluoroacetic anhydride 
• 383-63-1 ethyl trifluoroacetate, 
• 1669-49-4 3-(4-methoxyphenyl)-1-phenylpropan-1-one 
• 1094348-31-8 3-(4-methoxyphenyl)-1-(thiophen-2-yl)propan-1-one 
• 1929-29-9 3-(4-methoxyphenyl)propanoic acid 
• 22767-72-2 ethyl 3-(4-methoxyphenyl)propanoate 
• 18357-74-9 O-ethyl S-4-methoxybenzyl carbonodithioate 
• 15823-04-8 methyl 3-(4-methoxyphenyl)propionate 

Downstream Products

• 117896-99-8 1,1,1-trifluoro-4-(4-hydroxyphenyl)-2-butanone 
• 96107-02-7 (E)-4-(4-methoxyphenyl)-1,1,1-trifluorobut-3-en-2-one 

Relevant articles and documents

Efficient Asymmetric Biomimetic Aldol Reaction of Glycinates and Trifluoromethyl Ketones by Carbonyl Catalysis

The direct asymmetric aldol reaction of glycinates represents an intriguing and straightforward strategy to make biologically significant chiral β-hydroxy-α-amino-acid derivatives. But it is not easy to realize the transformation due to the disruption of the reactive NH2 group of glycinates. Inspired by the enzymatic aldol reaction of glycine, we successfully developed an asymmetric aldol reaction of glycinate 5 and trifluoromethyl ketones 4 with 0.1–0.0033 mol % of chiral N-methyl pyridoxal 7 a as the catalyst, producing chiral β-trifluoromethyl-β-hydroxy-α-amino-acid esters 6 in 55–82 % yields (for the syn-diastereomers) with up to >20:1 dr and 99 % ee under very mild conditions. The reaction proceeds via a catalytic cycle similar to the enzymatic aldol reaction of glycine. Pyridoxal catalyst 7 a activates both reactants at the same time and brings them together in a specific spatial orientation, accounting for the high efficiency as well as excellent diastereo- and enantioselectivities.

A Dual-Modal Molecular Probe for Near-Infrared Fluorescence and Photoacoustic Imaging of Peroxynitrite

Peroxynitrite (ONOO-), a reactive and short-lived biological oxidant, is closely related with many pathological conditions such as cancer. However, real-time in vivo imaging of ONOO- in tumors remains to be challenging. Herein, we de

Near-infrared fluorescence probes to detect reactive oxygen species for keloid diagnosis

Development of molecular probes for the detection of reactive oxygen and nitrogen species (RONS) is important for the pathology and diagnosis of diseases. Although an abnormally high RONS level has been identified in keloids-a benign dermal tumour develop

A Convergent Radical Based Route to Trifluoromethyl Ketones and to α,β-Unsaturated Trifluoromethyl Ketones

A convergent synthesis of trifluoromethyl ketones and α,β-unsaturated trifluoromethyl ketones is described, starting with aliphatic iodides and dithiocarbonates (xanthates) and exploiting both the α- and β-fragmentations of a sulfonyl radical. The transfo

Highly selective trifluoroacetic ester/ketone metathesis: An efficient approach to trifluoromethyl ketones and esters

A highly selective and atom efficient 'trifluoroacetic ester/ketone metathesis' has been sincerely witnessed. Enolizable alkyl (at least two non-hydrogen atoms) aryl ketones were found to react readily with ethyl trifluoroacetate under the promotion of NaH to afford trifluoroacetic ester/ketone exchange products, trifluoromethyl ketones (TFMKs), and aromatic acid esters, which were quite different from the general Claisen condensation products, 1,3-diketones. The outcome of the reaction between ketone and ethyl trifluoroacetate is strongly related to the structures of substrates, the steric congestion caused by alkyl group is in favor of the C-C bond cleavage. DFT investigation further disclosed that the metathesis reaction was a kinetically favored pathway. Using only a slight excess of cheap trifluoromethylation reagent, simple operation and mild conditions make it a practical method for preparation of TFMKs on large scale, as well as a new choice of converting aryl alkyl ketones to aromatic acid esters.

Synthesis of trifluoromethyl ketones via tandem Claisen condensation and retro-Claisen C-C bond-cleavage reaction

A highly efficient, operationally simple approach to trifluoromethyl ketones has been developed that builds on the use of a tandem process involving Claisen condensation and retro-Claisen C-C bond cleavage reaction. Enolizable alkyl phenyl ketones were found to react readily with ethyl trifuoroacetate under the promotion of NaH to afford trifluoroacetic ester/ketone exchange products, trifluoromethyl ketones, which were quite different from the general Claisen condensation products, β-diketones. This procedure uses readily available starting materials and can be extended to the preparation of perfluoroalkyl ketones in excellent yield.

A Weinreb amide approach to the synthesis of trifluoromethylketones

A novel route to access trifluoromethylketones (TFMKs) from Weinreb amides is reported. This represents the first documented case of the Ruppert-Prakash reagent (TMS-CF3) reacting in a constructive manner with an amide and enables synthesis of TMFKs without risk of over-trifluoromethylation.

Trifluoromethyl ketone analogs as selective cPLA2 inhibitors

Selective inhibitors of the cPLA2enzymes are provided which are of use in controlling a wide variety of inflammatory diseases. The inhibitors of the present invention have the general formula where (R′), p, D, Y, Z, Ra, Rband A are as defined in the specification.

Trifluoromethyl ketone analogs as selective cPLA2 inhibitors

Selective inhibitors of the cPLA2enzymes are provided which are of use in controlling a wide variety of inflammatory diseases. The inhibitors of the present invention have the general formula

Regioselective intramolecular oxidation of phenols and anisoles by dioxiranes generated in situ

A novel method for regioselective oxidation of phenols and anisoles has been developed in which dioxiranes, generated in situ from ketones and Ozone, oxidize phenol derivatives in an intramolecular fashion. A series of ketones with electron-withdrawing groups, such as CF3, COOMe, and CH2Cl, were attached to phenols, anisoles, or aryl rings via a C2 or C3 methylene linker. In a homogeneous solvent system of CH3CN and H2O, oxidation of phenol derivatives 1-10 afforded spiro 2-hydroxydienones in 24-55% yields regardless of the presence of other substituents (ortho Me, meta Me or Br) on the aryl ring and the length of the linker. Experimental evidences were provided to support the mechanism that involves a regioselective π bond epoxidation of aryl rings followed by epoxide rearrangement and hemiketal formation.