127223-93-2

Basic information

• Product Name: (E)-4-(diMethylaMino)-1,1,1-trifluorobut-3-en-2-one
• Synonyms: (E)-4-(diMethylaMino)-1,1,1-trifluorobut-3-en-2-one;(3E)-4-(Dimethylamino)-1,1,1-trifluorobut-3-en-2-one;OPFMBYIQGSJDOB-ONEGZZNKSA-N
• CAS NO: 127223-93-2
• Molecular Formula: C₆H₈F₃NO
• Molecular Weight: 167.1290296
• Mol File: 127223-93-2.mol

Chemical Properties

• Boiling Point: 103.4±40.0 °C(Predicted)
• Appearance: /
• Density: 1.177±0.06 g/cm3(Predicted)
• PKA: 3.43±0.70(Predicted)
• CAS DataBase Reference: (E)-4-(diMethylaMino)-1,1,1-trifluorobut-3-en-2-one(CAS DataBase Reference)
• NIST Chemistry Reference: (E)-4-(diMethylaMino)-1,1,1-trifluorobut-3-en-2-one(127223-93-2)
• EPA Substance Registry System: (E)-4-(diMethylaMino)-1,1,1-trifluorobut-3-en-2-one(127223-93-2)

Safety Data

• Hazardous Substances Data: 127223-93-2(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
DMADTFB is utilized as a key reagent for the synthesis of pharmaceuticals, where its trifluoromethyl group can enhance the bioactivity and metabolic stability of drug molecules. The introduction of this group can lead to improved pharmacokinetic properties, such as increased lipophilicity and resistance to metabolic degradation, which are crucial for the effectiveness and safety of medications.
Used in Agrochemical Industry:
In the agrochemical sector, DMADTFB serves as a precursor in the synthesis of compounds with enhanced pesticidal properties. The trifluoromethyl group can impart increased stability and efficacy to agrochemicals, making them more effective in controlling pests and diseases in agriculture.
Used in Materials Science:
DMADTFB is employed in the development of advanced materials with improved properties. The trifluoromethyl group can enhance the thermal stability, chemical resistance, and other physical properties of materials, making them suitable for various high-performance applications.

Upstream product

• 59938-06-6 (E)-4-Ethoxy-1,1,1-trifluoro-3-buten-2-one 
• 124-40-3 dimethyl amine 
• 120417-45-0 4-amino-1,1,1-trifluoro-3-buten-2-one 
• 202074-35-9 1,1,1-trifluoro-4-(phenylsulfonyl)but-3-ene-2,2-diol 
• 329915-02-8 1,1,1-trifluoro-4-(methylsulfonyl)but-3-ene-2,2-diol 
• 239437-47-9 3,3,4,4,4-Pentafluoro-butyraldehyde 
• 59938-06-6 4-ethoxy-1,1,1-trifluoro-3-butene-2-one 
• 109-92-2 ethyl vinyl ether 
• 407-25-0 trifluoroacetic anhydride 

Downstream Products

• 176722-74-0 7-methyl-2-(trifluoromethyl)quinoline 
• 41192-81-8 2-(trifluoromethyl)-7-quinolinol 
• 1860-46-4 8-methyl-2-(trifluoromethyl)quinoline 
• 177723-83-0 (E)-6-Phenyl-1,1,1-Trifluoro-3-hexen-5-yn-2-one 
• 96107-02-7 (E)-4-(4-methoxyphenyl)-1,1,1-trifluorobut-3-en-2-one 
• 3108-32-5 (E)-1,1,1-trifluoro-4-phenyl-3-buten-2-one 
• 204708-11-2 (E)-1,1,1-trifluoro-4-(3-methoxyphenyl)but-3-en-2-one 
• 1007105-55-6 1,1,1-trifluoro-4-(2,5-dimethoxyphenyl)but-3-en-2-one 
• 312615-59-1 2-oxo-6-trifluoromethyl-2H-pyran-3-yl-N-benzamide 

Relevant articles and documents

The conformational analysis of push-pull enaminones using Fourier transform IR and NMR spectroscopy, and quantum chemical calculations. V. α-Methyl-, fluorine-β-N,N-dimethylaminovinyl trifluoromethyl ketones

IR Fourier spectra of two enaminoketones with general formula F 3CCOCRCHN(CH3)2, R = F (DMTFBN); R = CH 3, (DMTMBN) were studied in various pure solvents. For comparison results of earlier investigated enaminoketone R = H (DMTBN) was also presented. On the basis of NMR and IR spectra it was shown that enaminoketones DMTBN, DMTFBN and DMTMBN presented in solutions as equilibrium of two conformers, (E-s-Z) (E-s-E) (for DMTFBN these conformers are denoted as (Z-s-Z) and (Z-s-E), respectively). DFT calculations were carried out to evaluate relative energy and dipole moment of each spatial form. It was shown that 'closed-ring' complex formation between (E-s-Z) and (E-s-E) conformers of DMTBN accounts for discrepancies between DFT calculations of conformer relative energies and experimentally evaluated enthalpies of (E-s-Z) (E-s-E) equilibrium. In α-substituted DMTFBN and DMTMBN, where formation of 'closed-ring' complex was impossible we did not observe such discrepancies. For both (E-s-Z) and (E-s-E) conformers of the DMTBN and DMTMBN the main influence on the ν (CO) vibrations has the solvent's hydrogen bond donor (HBD) acidity, whereas for the DMTFBN an influence of the solvent's polarity/polarizability dominated.

The conformational analysis of push-pull enaminones using Fourier transform IR and NMR spectroscopy, and quantum chemical calculations. IV. 4-(N,N-dimethylamino)-1,1,1-trifluoro-3-methylbut-3-en-2-one and 4-(N,N-dimethyl-amino)-1,1,1-trifluoropropen-3-en-2-one

IR Fourier spectra of two enaminoketones with general formula (CH 3)2NCR1CR2C(O)CF3, R 1H, R2CH3 (2); R1CH3, R2H (3) were investigated in various pure solvents. For comparison results of earlier investigated enaminoketone R1H, R2H (1) were also presented. On the basis of NMR and IR spectra it was shown that enaminoketones 1 and 2 presented in solutions as an equilibrium of two conformers, (E-s-Z) R (E-s-E), whereas the enaminoketone 3 presented as equilibrium of two isomers, (E-s-Z) R (Z-s-Z). Quantum chemical calculations by the DFT methods were carried out to evaluate relative energy and dipole moment of each spatial form. For both (E-s-Z) and (E-s-E) conformer of the 1 and 2 the main influence on the ν?(CO) vibrations has the solvent's hydrogen bond donor (HBD) acidity whereas for the 3 influence of the solvent's polarity/polarizability dominated. Both the solvent's polarity/polarizability and solvent's hydrogen bond donor (HBD) acidity influenced on the ν?(CC) mode of the conformers of the 1 and 2. Solvent influence on the ν?(CC) vibrations of the 3 depended substantially whether the solvent is aprotic or an alcohol. In the former case the main contribution made the solvent's hydrogen bond acceptor (HBA) basicity [(E-s-Z) isomer] or the solvent's polarity/polarizability with solvent's hydrogen bond donor (HBD) acidity [(Z-s-Z) isomer]. Alcohols influenced on the ν?(CC) vibrations of both isomers predominantly due to the solvent's polarity/polarizability. In aprotic solvents the greatest contribution in solvent influence on thermodynamic parameters of both (E-s-Z) R (E-s-E) and (E-s-Z) R (Z-s-Z) equilibrium made the solvent's hydrogen bond acceptor (HBA) basicity. Rotation around double CC bond is characterized by higher sensitivity to the solvent's hydrogen bond acceptor (HBA) basicity compared to the rotation around formally single CCO bond.

A novel synthesis of trifluoromethyl enones and enediones

Reactions of trifluoromethyl enamino ketones, (E)-4(dimethylamino)- 1,1,1-trifluorobut-3-en-2-one (2) and 3-(dimethylaminomethylene)- 1,1,1,5,5,5-hexafluoropentane-2,4-dione (3), with various types of lithium derivatives of aromatic or heteroaromatic comp

3-Trifloxy-3-trifluoromethylpropeniminium triflate: Reaction with aromatic amines - An efficient synthesis of 2-trifluoromethylquinolines

The reaction of iminium triflates 2 and 7 with various aromatic amines were investigated. The 2-R(f)-substituted quinolines 3 and 8 were prepared in excellent yields by the reaction of 2 and 7, respectively, with substituted anilines. The reactions of 2 a

Uncommon fluorination of enones with xenon difluoride

Readily available β-alkoxyvinylpolyfluoroalkyl ketones react with XeF2 to give the products of addition of two Fluorine atoms to the C[dbnd]C double bond - vic-difluoro ketones, which can be easily converted to α-F enones. We demonstrated chemical evaluation of these compounds by formation of new fluorocontaining enaminones and pyrazoles. In order to obtain new precursors for bioactive compounds we performed [4 + 2] hetero Diels-Alder reaction and obtained dihydropyranes which are perspective starting materials for fluorinated carbohydrates.

3-Trifloxy-3-(trifluoromethyl)prop-2-ene 1-Iminium Salts as Precursors for Elusive 3-(Trifluoromethyl)prop-2-yne 1-Iminium Salts

Abstract: 3-(Trifluoromethyl)prop-2-yne 1-iminium triflate salts were generated from 3-trifloxy-3-(trifluoromethyl)prop-2-ene 1-iminium salts by triethylamine-assisted elimination of triflic acid and trapped in situ in various cycloaddition reactions. The

Tetracyclic pyrimidinone compound, preparation method, composition and application thereof

A tetracyclic pyrimidinone compound represented by a formula (I) or a pharmaceutically acceptable salt thereof has a structure represented by a formula (I), is a brand new Lp-PLA2 inhibitor, and can be used for treating neurodegenerative related diseases such as Alzheimer's disease (AD), glaucoma, age-related macular degeneration (AMD), or cardiovascular diseases including atherosclerosis and thelike.

Reactions of 2,2-dihydropolyfluoroalkylaldehydes with amines: A facile synthetic method for fluoroalkyl enaminoketones

Reactions of 2,2-dihydropolyfluoroalkylaldehydes (1) with amines (2) were studied. Both aliphatic amines and electron-deficient aromatic amines readily reacted with 1 in acetonitrile and water under reflux to give fluoroalkyl enaminoketones (3) in high yields, while no condensed products were obtained by reactions of 1 with electron-rich aromatic amines under similar conditions. In the presence of triethylamine, however, the reaction of 1 with electron-rich aromatic amines at room temperature gave 3 in low yields.

A new method for the synthesis of CF3-containing aminovinyl ketones

A new method for the synthesis of aminovinyl trifluoroinethyl ketones was developed. The method is based on the reactions of 4-sulfonyl-1,1,1-trifluorobut-3-ene-2,2-diols with various alkyl-, aryl-, dialkyl-, and alkylarylamines. The stereochemistry of the compounds obtained was studied.

Synthesis of αβ-unsaturated trifluoromethyl ketones from 4-Dimethylamino-1,1,1-trifluorobut-3-ene-2-one by addition of grignard reagents

Enaminones are available by reaction of 4-ethoxy-1,1,1-trifluorobut-3-ene-2-one with amines such as dimethylamine and they react with Grignard reagents to give αβ-unsaturated trifluoromethyl ketones in good yield by 1,4-addition followed by elimination. The generality of this procedure is contrasted with reactions based either on the use of organolithium nucleophiles, or the use of 4-alkoxy-αβ-unsaturated trifluoromethyl ketones as electrophilic partners. (C) 2000 Elsevier Science Ltd.