2-Thenoyltrifluoroacetone

Base Information

• Chemical Name: 2-Thenoyltrifluoroacetone
• CAS No.: 326-91-0
• Deprecated CAS: 2122854-03-7,365439-57-2
• Molecular Formula: C8H5F3O2S
• Molecular Weight: 222.188
• Hs Code.: 29349990
• European Community (EC) Number: 206-316-7
• NSC Number: 66544
• UNII: MYQ9MNW7NI
• DSSTox Substance ID: DTXSID1059812
• Nikkaji Number: J139.250F
• Wikipedia: Thenoyltrifluoroacetone
• Wikidata: Q5933755
• Metabolomics Workbench ID: 149226
• ChEMBL ID: CHEMBL1236433
• Mol file: 326-91-0.mol

Synonyms:4,4,4-trifluoro-1-(2-thienyl)-1,3-butanedione;Thenoyltrifluoroacetone;Trifluorothienylacetone;TTFA cpd

Chemical Property of 2-Thenoyltrifluoroacetone

Chemical Property:

• Appearance/Colour: light yellow to beige to brown crystalline powder
• Vapor Pressure: 43.693mmHg at 25°C
• Melting Point: 40-44 °C(lit.)
• Refractive Index: 1.326
• Boiling Point: 227.5 °C at 760 mmHg
• PKA: 5.60±0.23(Predicted)
• Flash Point: 111.7 °C
• PSA: 62.38000
• Density: 1.415 g/cm³
• LogP: 2.45230
• 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.
• Water Solubility.: INSOLUBLE
• XLogP3: 2.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 3
• Exact Mass: 221.99623506
• Heavy Atom Count: 14
• Complexity: 250

Purity/Quality:

98%, ^*data from raw suppliers

2-Thenoyltrifluoroacetone76-05-1 ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi,Xn
• Hazard Codes: Xi,Xn
• Statements: 36/37/38-22
• Safety Statements: 26-36-37/39

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Other Uses -> Chelating Agents
• Canonical SMILES: C1=CSC(=C1)C(=O)CC(=O)C(F)(F)F
• 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
• Uses: 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-Thenoyltrifluoroacetone is an inhibitor of respiration in animals and bacteria. TTFA binds at the quinone reduction site of succinate ubiquinone oxidoreductase.

Technology Process of 2-Thenoyltrifluoroacetone

There total 9 articles about 2-Thenoyltrifluoroacetone 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: 86.0%

2-Acetylthiophene (88-15-3,97511-16-5) + ethyl trifluoroacetate, (383-63-1) → 1,1,1-trifluoro-4-(2-thienyl)butane-2,4-dione (326-91-0)

Guidance literature:

With potassium tert-butylate; In benzene; for 15h; Ambient temperature;

DOI:10.1055/s-1997-1354

Reference yield: 82.0%

trifluoroacetic anhydride (407-25-0) + 2-acetylthiophene dimethoxy acetal → 1,1,1-trifluoro-4-(2-thienyl)butane-2,4-dione (326-91-0)

Guidance literature:

trifluoroacetic anhydride; 2-acetylthiophene dimethoxy acetal; With pyridine; In chloroform; at -10 - 35 ℃;

With sulfuric acid; In chloroform; at 50 ℃; for 2h;

DOI:10.1016/S0040-4039(02)02137-8

Reference yield: 66.0%

(E)-1,1,1-Trifluoro-4-methoxy-4-thiophen-2-yl-but-3-en-2-one → 1,1,1-trifluoro-4-(2-thienyl)butane-2,4-dione (326-91-0)

Guidance literature:

With sulfuric acid; In water; at 50 ℃; for 16h;

DOI:10.1002/ejoc.201201111

upstream raw materials:

2-Acetylthiophene

ethyl trifluoroacetate,

4,4,4-trifluoro-1-(2-thienyl)-1,3-butanedione enol

trifluoroacetic anhydride

Downstream raw materials:

4-thiophen-2-yl-6-trifluoromethyl-pyrimidin-2-ylamine

2-phenyl-6-(5-thiophen-2-yl-3-trifluoromethyl-pyrazol-1-yl)-4-trifluoromethyl-pyridine

6-(2'-Thienyl)-4-trifluoromethylpyrimidin-2(1H)-on

2-oxo-6-(thiophen-2-yl)-4-(trifluoromethyl)-1,2-dihydropyridine-3-carbonitrile

Refernces

• 1、 Sthalam, Vinay Kumar,Singh, Ajay K.,Pabbaraja, Srihari. "An Integrated Continuous Flow Micro-Total Ultrafast Process System (μ-TUFPS) for the Synthesis of Celecoxib and Other Cyclooxygenase Inhibitors". supporting information. p. 1892 - 1899. Retrieved 2019/10/11.
• 2、 -. "APOPTOSIS INHIBITORS". Paragraph 0122. . Retrieved 2018/02/27.