326-91-0

Basic information

• Product Name: Thenoyltrifluoroacetone
• Synonyms: 1-(Thenoyl-(2'))-3,3,3-trifluoroacetone;1,1,1-trifluoro-3-(2-theonyl)acetone;1-Thenoyl-3,3,3-trifluoroacetone;1-theonyl-3,3,3-trifluoroacetone;3-Butanedione,4,4,4-trifluoro-1-(2-thienyl)-1;4,4,4-trifluoro-1-(2-thienyl)-3-butanedione;alpha-Thenoyltrifluoroacetone;perfluoroacetyl-(2-theonyl)methane
• CAS NO: 326-91-0
• Molecular Formula: C₈H₅F₃O₂S
• Molecular Weight: 222.18
• EINECS: 206-316-7
• Product Categories: Thiophenes;Aromatic Ketones (substituted);organofluorine compounds;Achiral Oxygen
• Mol File: 326-91-0.mol
• Article Data: 21

Chemical Properties

• Melting Point: 40-44 °C(lit.)
• Boiling Point: 96-98 °C8 mm Hg(lit.)
• Flash Point: 233 °F
• Appearance: Light yellow or beige to brown/Crystalline Powder, Crystals and/or Chunks
• Density: 1.4373 (estimate)
• Vapor Pressure: 43.693mmHg at 25°C
• Refractive Index: 1.326
• Storage Temp.: 2-8°C
• Solubility: sparingly soluble in water, readily soluble in organic solvents. Distribution ratio between acidic water and benzene is about 40. In alkaline aqueous medium it exists in the enolate form, this being relatively more soluble in water. The equilibrium distribution ratio between benzene and alkaline aqueous medium (about pH 8) is about 1. In alkaline aqueous medium of pH > 9 TTA decomposes to trifluoroacetone and acetylthiophen.
• PKA: 5.60±0.23(Predicted)
• Water Solubility: INSOLUBLE
• Stability: Stable for 1 year from date of purchase as supplied. Solutions in DMSO or ethanol may be stored at -20°C for up to 1 month.
• BRN: 168645
• CAS DataBase Reference: Thenoyltrifluoroacetone(CAS DataBase Reference)
• NIST Chemistry Reference: Thenoyltrifluoroacetone(326-91-0)
• EPA Substance Registry System: Thenoyltrifluoroacetone(326-91-0)

Safety Data

• Hazard Codes: Xi,Xn
• Statements: 36/37/38-22
• Safety Statements: 26-36-37/39
• WGK Germany: 3
• F: 10-23
• TSCA: T
• HazardClass: IRRITANT
• Hazardous Substances Data: 326-91-0(Hazardous Substances Data)

Usage

Description

TTFA?(326-91-0) blocks the respiratory chain complex II causing inhibition of mitochondrial respiration.? Respiratory chain complex II inhibition is caused via binding of TTFA to two ubiquinone binding sites, Qp and Qd.1?Inhibition of Complex II by TFA has been shown to cause a delay in overall cell cycle progression leading to oxidative stress.2,3?TTFA also was found to inhibit porcine liver carboxylesterase (IC50?= 0.54 μM).4

Chemical Properties

light yellow to beige to brown crystalline powder,

Uses

Different sources of media describe the Uses of 326-91-0 differently. You can refer to the following data:
1. Thenoyltrifluoroacetone is one of the most proved extracting agents in solventextraction analysis. It is equally suitable for the separation and selective enrichment of metal ions. 2-Thenoyltrifluoroacetone (TTFA) is an inhibitor of respiration in animals and bacteria. In animals, TTFA binds at the quinone reduction site of succinate:ubiquinone oxidoreductase (SQR; Complex II), preventing ubiquinone from binding. It inhibits NADH fumarate reductase in bacteria. TTFA also inhibits photosystem II in plants and NADH-ubiquinone oxidoreductase of the virus Vibrio cholerae, decreasing cholera toxin production. This compound is also a chelator of metals, including lanthanum, zirconium, hafnium, and neodymium. Reagent for the determination of actinides and lanthanides. 2-Thenoyltrifluoroacetone is used for the extractive spectrophotometric determination of ruthenium at ph 4.0 (acetate buffer). Thenoyltrifluoroacetone has also been used as an alternative β-diketone for in-house assay development since NTA was not, until recently, commercially available.
2. 2-Thenoyltrifluoroacetone is an inhibitor of respiration in animals and bacteria. TTFA binds at the quinone reduction site of succinate ubiquinone oxidoreductase.

Purification Methods

Crystallise the dione from hexane or *benzene. (Anaqueous solutions slowly decompose it). It has 1638(C=O), 1657(C=C)cm-1 . The oxime crystallises from H2O or aqueous EtOH. It is used for the determination of Actinides and Lanthanides. [Chaston et al. Aust J Chem 18 673 1956, Jeffrey et al. In Vogel’s Textbook of Qunatitative Chemical Analysis 5thedn J Wiley & Sons, p170 1989, Beilstein 17 III/IV 5989, 17/11 V 128.]

References

1) Sun?et al.?(2005),?Crystal Structure of Mitochondrial Respiratory Membrane Protein Complex II; Cell?121?1043 2) Byon?et al.?(2008),?Mitochondrial dysfunction by complex II inhibition delays overall cell cycle progression via reactive oxygen species production; J. Cell Biochem.?104?1747 3) Siebels and Dr?se (2013),?Q-site inhibitor induced ROS production of mitochondrial complex II is attenuated by TCA cycle dicarboxylates; Biochim. Biophys. Acta?1827?1156 4) Zhang and Fariss (2002),?Thenoyltrifluoroacetone, a potent inhibitor of carboxylesterase activity; Biochem. Pharmacol.?63?751

InChI:InChI=1/C4H3F3O2/c5-4(6,7)3(9)1-2-8/h2H,1H2

Upstream product

• 407-25-0 trifluoroacetic anhydride 
• 88-15-3 2-Acetylthiophene 
• 407-38-5 2,2,2-trifluoroethyl trifluoroacetate 
• 615-07-6 sodium 2-thenoyltrifluoroacetylacetonate 
• 148-24-3 8-quinolinol 
• 59354-21-1 4,4,4-trifluoro-1-(2-thienyl)-1,3-butanedione enol 
• 15788-02-0 1,1,1-trifluoro-4-hydroxy-4-(2-thienyl)-3-buten-2-one 
• 383-63-1 ethyl trifluoroacetate, 

Downstream Products

• 128228-83-1 2-(5-(2-thienyl)-3-trifluoromethylpyrazol-1-yl)-4-phenylthiazole 
• 128228-97-7 2-<3-trifluoromethyl-5-(2-thienyl)pyrazol-1-yl>-4-p-chlorophenylthiazole 
• 476172-19-7 2-(5-hydroxy-3-(2-thienyl)-5-trifluoromethylpyrazolin-1-yl)-4-(4-chlorophenyl)thiazole 
• 128228-96-6 3-(thien-2-yl)-5-trifluoromethyl-1H-pyrazole 

Relevant articles and documents

Studies on the adsorption and photocatalytic degradation of an EuIII(TTFA)3(MePhTerpy) complex on the TiO2 surface

The luminescent dye EuropiumIII(thenoyltrifluoroacetone)(4′-(4-methylphenyl)-2,2′:6′,2′′-terpyridine) (EuIII(TTFA)3(MePhTerpy)) has been proposed as a probe molecule for a fast photocatalytic test of TiO2-materials. For an industrial application of this test method the underlying photocatalytic reaction mechanism and the degradation products of the dye need to be known. Hence, in this study the adsorption and the photocatalytic degradation of the luminescent dye on the TiO2 surface were investigated by means of ATR-FTIR spectroscopy and GC/MS analysis. The dye is adsorbed by the thenoyltrifluoroacetone (TTFA) ligand on the TiO2 surface as evinced by the respective ATR-FTIR spectra. It is assumed that TTFA and TiO2 form hydrogen bonds. Upon UV illumination the ATR-FTIR spectra reveal a degradation of the TTFA ligand forming trifluoroacetic acid (TFAA) and 2-thiophenecarboxylic acid (TCA). GC/MS analysis confirms the ATR-FTIR results because TCA and TFAA are also detected here. Additionally, 2-thiophenecarboxaldehyde is observed, which is proposed to be an intermediate that is further oxidized to TCA.

Discovery and structure-resistance relationship study of new thieno[2,3-b] pyridine HCV NS4B inhibitors

The non-structural protein 4B (NS4B) of hepatitis C virus (HCV) has emerged as a promising target for chronic hepatitis C treatment. The thieno[2,3-b]pyridine HCV inhibitor 2 has demonstrated properties as a NS4B inhibitor. Subsequent hybridization of 2 with our recently published imidazo[2,1-b]thiazole NS4B inhibitor 3 resulted in the discovery of several more potent compounds with sub-micromolar EC50 against HCV genotype 1b replicon. More importantly, the resistant profile study of the new synthesized HCV inhibitors illustrated that the bicyclic scaffold would mediate the resistance of H3R and Q26R mutations, while the piperazinone motif would mediate the resistance of H94R, F98C and V105M mutations, and the C3- amino group would disrupt the interaction between piperazinone motif and NS4B. This structure-resistance relationship detail could help us to develop new NS4B inhibitors with higher resistant barrier in the future.

Design and synthesis of novel benzenesulfonamide containing 1,2,3-triazoles as potent human carbonic anhydrase isoforms I, II, IV and IX inhibitors

In a quest to discover new biologically active compounds, a series of twenty novel heterocyclic derivatives substituted at position 5 with -H (7a-7j) or -CF3 (8a-8j), bearing benzenesulfonamide at N-1 position and various aroyl groups at position 4 of the 1,2,3-triazole ring was synthesized and screened for their carbonic anhydrase (CA, EC 4.2.1.1) inhibition potential against four human (h) isoforms hCA I, II, IV and IX. All the compounds (7a-7j and 8a-8j) were synthesized via [3+2] cycloaddition reaction from 4-azidobenzenesulfonamide. Interestingly, compounds 7a-7j were prepared in one pot manner via enaminone intermediate using novel methodology. All the newly synthesized compounds (7a-7j & 8a-8j) were found to be excellent inhibitors of edema related isoform hCA I with their inhibition constant (Ki) ranging from 30.1 to 86.8 nM as compared to standard drug acetazolamide (AAZ) with Ki = 250 nM. Further it was found that most of tested compounds were weaker inhibitors of isoform, hCA II although compounds 7b, 7d-7e, 8a, 8d-8f, 8i (mostly with electron withdrawing substituents) have shown better inhibition potential (Ki i = 52.4 nM) than AAZ (Ki = 74 nM) while against tumor associated hCA IX, all the compounds have shown moderate inhibition potential. Present study have added one more step in exploring the 1,2,3-triazlole moiety in the medicinal field.