1,3-Butanedione, 4,4,4-trifluoro-1-(2-thienyl)-

HCID 5601CAS 326-91-0

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Basic information

Standard SMILES
O=C(CC(=O)C(F)(F)F)c1cccs1
InChIKey
TXBBUSUXYMIVOS-UHFFFAOYSA-N
Molecular formula
C8H5F3O2S
Average molar mass
222.187 g/mol
Monoisotopic mass
221.99623506

Names & identifiers

Preferred name
1,3-Butanedione, 4,4,4-trifluoro-1-(2-thienyl)-
IUPAC
4,4,4-Trifluoro-1-(thiophen-2-yl)butane-1,3-dione
English name
Thenoyltrifluoroacetone
Molecular formula
C8H5F3O2S
Molecular weight
222.18

Names & synonyms

2-THENOYLTRIFLUOROACETONETTFA4,4,4-TRIFLUORO-1-(THIOPHEN-2-YL)BUTANE-1,3-DIONE2-Theonyltrifluoroacetone2-(4,4,4-TRIFLUOROACETOACETYL)THIOPHENE4,4,4-TRIFLUORO-1-(2-THIENYL)-1,3-BUTANEDIONE2-ThenoyLAKOS B010015AKOS MSC-0329TTA (extractant)

Database identifiers

CAS
326-91-0
PubChem CID
5601
DTXSID
DTXSID1059812
ChEMBL
CHEMBL1236433
UNII
MYQ9MNW7NI
EC Number
206-316-7
Nikkaji
J139.250F

Properties

Physicochemical properties

Melting point
40 · 40-44 °C(lit.)
Boiling point
96 · 96-98 °C8 mm Hg(lit.)
Density
1.4373 · 1.4373 (estimate)
Flash point
233 °F · 233 °F
storage temp.
2 · 2-8°C
solubility
40 · 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.

Safety & regulation

Safety data

F
10-23
PPE
dust mask type N95 (US), Eyeshields, Gloves
wgk
3
tsca
TSCA listed
hs_code
29349990
risk_code
36/37/38-22

Chemistry & industry

Applications · 3 items

DescriptionTTFA(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.1Inhibition of Complex II by TFA has been shown to cause a delay in overall cell cycle progression leading to oxidative stress.2,3TTFA also was found to inhibit porcine liver carboxylesterase (IC50= 0.54 μM).4

Uses2-Thenoyltrifluoroacetone is an inhibitor of respiration in animals and bacteria. TTFA binds at the quinone reduction site of succinate ubiquinone oxidoreductase.

UsesThenoyltrifluoroacetone 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.

Suppliers50 total

国药集团化学试剂有限公司86-21-63210123 · [email protected]
梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
衢州润东化工有限公司0570-8789886 18892685668 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
INTATRADE GmbH+49 3493/605464 · [email protected]

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