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18545

Sigma-Aldrich

3-Bromo-1,1,1-trifluoroacetone

purum, ≥95.0% (GC)

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About This Item

Linear Formula:
CF3COCH2Br
CAS Number:
Molecular Weight:
190.95
Beilstein:
1703387
EC Number:
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
Pricing and availability is not currently available.

grade

purum

Assay

≥95.0% (GC)

refractive index

n20/D 1.376 (lit.)

bp

87 °C/743 mmHg (lit.)

density

1.839 g/mL at 25 °C (lit.)

SMILES string

FC(F)(F)C(=O)CBr

InChI

1S/C3H2BrF3O/c4-1-2(8)3(5,6)7/h1H2

InChI key

ONZQYZKCUHFORE-UHFFFAOYSA-N

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General description

3-Bromo-1,1,1-trifluoroacetone reacts with potassium enolate of ethyl 4,4,4-trifluoroacetoacetate to yield ethyl 2,4-bis(trifluoromethyl)-4-hydroxydihydro-3-furoate[1].

Application

3-Bromo-1,1,1-trifluoroacetone was used in the synthesis of:
  • 3-nonylthio-1,1,1-trifluoropropan-2-one[2]
  • cyclic tetrapeptides containing trifluoromethyl and pentafluoroethyl ketone as zinc binding functional group[3]
  • perfluoroalkylated trans-allylic alcohols[4]

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M Brauer et al.
Biochemistry, 25(8), 2187-2191 (1986-04-22)
G-Actin is a globular protein (Mr 42 300) known to have three cysteine residues that are at least partially exposed and chemically reactive (Cys-10, -284, and -374). When G-actin was reacted with 3-bromo-1,1,1-trifluoropropanone, three resolvable 19F resonances were observed in
W A McGee et al.
Analytical biochemistry, 189(2), 267-273 (1990-09-01)
A combined NMR and absorbance stopped-flow has been developed for monitoring the kinetics of biochemical reactions. We demonstrate its usefulness in following the alkaline denaturation of human hemoglobin. No glassblowing is required in the fabrication of the apparatus. Commercially available
Binoy Jose et al.
Bioorganic & medicinal chemistry letters, 14(21), 5343-5346 (2004-09-30)
Cyclic tetrapeptides containing trifluoromethyl and pentafluoroethyl ketone as zinc binding functional group were synthesized as potent HDAC inhibitors. Evaluation by human HDAC inhibition assay and p21 promoter assay showed that these inhibitors are promising anticancer agents.
Effect of magnetic susceptibility on nuclear magnetic resonance signals arising from red cells: a warning.
M E Fabry et al.
Biochemistry, 22(17), 4119-4125 (1983-08-16)
Novel reductive olefination mediated by Ti (Oi-Pr) 4 and Ph3P. One-pot synthesis of trifluoromethylated trans-allylic alcohols.
Shen Y, et al.
Chemical Communications (Cambridge, England), 20, 2195-2196 (1998)

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