thenoyltrifluoroacetone

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| verifiedrevid = 470606076

| Name = Thenoyltrifluoroacetone[http://www.sigmaaldrich.com/catalog/search/ProductDetail/FLUKA/88302 Sigma-Aldrich product page]

| ImageFile = Thenoyltrifluoroacetone-2D-skeletal.png

| ImageSize =

| ImageFile1 = Thenoyltrifluoroacetone-3D-balls.png

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| PIN = 4,4,4-Trifluoro-1-(thiophen-2-yl)butane-1,3-dione

| OtherNames = 2-thenoyltrifluoroacetone

|Section1={{Chembox Identifiers

| Abbreviations = TTFA

| ChEMBL = 1236433

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| ChemSpiderID = 5399

| InChI = 1/C8H5F3O2S/c9-8(10,11)7(13)4-5(12)6-2-1-3-14-6/h1-3H,4H2

| InChIKey = TXBBUSUXYMIVOS-UHFFFAOYAR

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| StdInChI = 1S/C8H5F3O2S/c9-8(10,11)7(13)4-5(12)6-2-1-3-14-6/h1-3H,4H2

| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}

| StdInChIKey = TXBBUSUXYMIVOS-UHFFFAOYSA-N

| CASNo_Ref = {{cascite|correct|CAS}}

| CASNo = 326-91-0

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = MYQ9MNW7NI

| EINECS = 206-316-7

| PubChem = 5601

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| DrugBank = DB04795

| SMILES = O=C(c1sccc1)CC(=O)C(F)(F)F

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|Section2={{Chembox Properties

| Formula = C₈H₅F₃O₂S

| MolarMass = 222.18 g mol⁻¹

| Appearance = fine, slightly yellow crystals

| Density =

| MeltingPtC = 40 to 44

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| BoilingPtC = 96 to 98

| BoilingPt_notes = 8 mmHg

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|Section3={{Chembox Structure

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|Section4={{Chembox Thermochemistry

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|Section5={{Chembox Pharmacology

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|Section7={{Chembox Hazards

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| GHSPictograms = {{GHS07}}

| GHSSignalWord = Warning

| HPhrases = {{H-phrases|315|319|335}}

| PPhrases = {{P-phrases|}}

| FlashPtC = 12

| FlashPt_notes = (closed cup)

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|Section8={{Chembox Related

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Thenoyltrifluoroacetone (TTFA) is a chemical compound with the molecular formula C₈H₅F₃O₂S. It is used pharmacologically as a chelating agent. It is an inhibitor of cellular respiration by blocking the respiratory chain at complex II.

The first report of TTFA as an inhibitor of respiration was by A. L. Tappel in 1960.{{cite journal |author=Tappel|title=Inhibition of electron transport by antimycin A, alkyl hydroxy naphthoquinones and metal coordination compounds|pmid=13836892 | volume=3|issue=4|date=July 1960|journal=Biochem. Pharmacol.|pages=289–96|doi=10.1016/0006-2952(60)90094-0}} Tappel had the erroneous idea that inhibitors such as antimycin and alkyl hydroxyquinoline-N-oxide might work by chelating iron in the hydrophobic milieu of respiratory membrane proteins, so he tested a series of hydrophobic chelating agents. TTFA was a potent inhibitor, but not because of its chelating ability. TTFA binds at the quinone reduction site in Complex II, preventing ubiquinone from binding. The first x-ray structure of Complex II showing how TTFA binds was published in 2005.{{cite journal | title = Crystal Structure of Mitochondrial Respiratory Membrane Protein Complex II | year = 2005 | volume= 121 | pages = 1043–1047 | doi = 10.1016/j.cell.2005.05.025 | journal =Cell | pmid=15989954 | issue=7| last1 = Sun | first1 = Fei | last2 = Huo | first2 = Xia | last3 = Zhai | first3 = Yujia | last4 = Wang | first4 = Aojin | last5 = Xu | first5 = Jianxing | last6 = Su | first6 = Dan | last7 = Bartlam | first7 = Mark | last8 = Rao | first8 = Zihe | s2cid = 16697879 | doi-access = free }}{{PDB|1ZP0}}

Thenoyltrifluoroacetone can be made in by Claisen condensation of ethyl trifluoroacetate and 2-acetylthiophene.{{cite book|title=Excuse me sir, would you like to buy a kilo of isopropyl bromide?|first=Max G.|last=Gergel|author-link=Max Gergel|date=March 1977|publisher=Pierce Chemical|page=130}}{{cite journal |last1=Taydakov |first1=Ilya V |last2=Kreshchenova |first2=Yuliya M |last3=Dolotova |first3=Ekaterina P |title=A convenient and practical synthesis of β-diketones bearing linear perfluorinated alkyl groups and a 2-thienyl moiety |journal=Beilstein Journal of Organic Chemistry |date=27 December 2018 |volume=14 |pages=3106–3111 |doi=10.3762/bjoc.14.290|pmid=30643588 |pmc=6317410 }}