Hexafluoroacetylacetone

clear colorless to slightly yellow liquidHEXAFLUOROACETYLACETONE acts as a chelating ligand. For example, it can forms metal-chelate complexes with Ca(II), Zn (II), Cu(II), Ni(II), Co(II), Nd(III), Rh(III), Fe(III) and Cr(III), making it be useful in extracting related metal ions. It can also be used as liquid crystal intermediate.

To 3.4 g (14 mmol, 1 eq) of the above-obtained 1, 1, 1, 5, 5, 5-hexafluoroacetone hydrate, 6.8 g (69 mmol, 4.9 eq) of concentrated sulfuric acid was added at 10° C. The resulting mixture was stirred for 3 hours and 35 minutes at room temperature (in a two-phase system). The thus-dehydrated solution was separated into two phases. By this, 2.7 g of 1, 1, 1, 5, 5, 5-hexafluoroacetylacetone of the following formula was yielded. The recovery rate was 93percent. The 1: Preparation of l, l.lExample 3 A solution I was prepared by adding 5.1 g (36 mmol, 1.2 eq) of ethyl trifluoroacetate of the following formula to 50 mL of tetrahydrofuran and cooling the resulting mixture to −30° C. while stirring. On the other hand, a solution II was prepared by adding 4.0 g (43 mmol, 1.4 eq) of 3, 3, 3-trifluoropropyne of the following formula to 50 mL of tetrahydrofuran at 0° C., further adding thereto 19 mL (30 mmol, 1.0 eq) of n-butyl lithium/n-hexane solution (1.6 M) at −30° C., and then, stirring the resulting mixture for 15 minutes at the same temperature as above. The solution I was mixed with the solution II. The mixed solution was stirred at −30° C. for 2 hours (as a reaction completed solution). The operation until this point was performed under a nitrogen atmosphere. The reaction completed solution was added to 78 g of aqueous sulfuric acid solution (prepared from 15 g (150 mmol, 5.0 eq) of concentrated sulfuric acid and 63 g of ice water) at 0° C. The thus-mixed solution was stirred at 50° C. for 10 hours (in a two-phase system) and separated into two phases. The aqueous layer was extracted with tert-butyl methyl ether. Then, the extract was combined with the organic phase. The recovered organic phase was subjected to F-NMR quantification by internal standard method (internal standard material: α, α, α-trifluorotoluene). It was confirmed that 25 mmol of 1, 1, 1, 5, 5, 5-hexafluoroacetylacetone dihydrate of the following formula and 0.60 mmol of 1, 1, 1, 5, 5, 5-hexafluoroacetylacetone monohydrate of the following formula were contained in the recovered organic phase. The total yield of the target product was 87percent. Further, the recovered organic phase was washed with 20 mL of water and concentrated under a vacuum (40° C./60 mmHg). To the concentration residue, 18 mL of toluene was added. The resulting mixture was stirred for 3 hours and 10 minutes under ice cooling, thereby forming a crystalline precipitate. The crystalline precipitate was filtered out and dried under a vacuum. By this, 4.0 g of 1, 1, 1, 5, 5, 5-hexafluoroacetone hydrate (dihydrate:monohydrate=97:3) was yielded. The total yield was 53percent. To 3.4 g (14 mmol, 1 eq) of the above-obtained 1, 1, 1, 5, 5, 5-hexafluoroacetone hydrate, 6.8 g (69 mmol, 4.9 eq) of concentrated sulfuric acid was added at 10° C. The resulting mixture was stirred for 3 hours and 35 minutes at room temperature (in a two-phase system). The thus-dehydrated solution was separated into two phases. By this, 2.7 g of 1, 1, 1, 5, 5, 5-hexafluoroacetylacetone of the following formula was yielded. The recovery rate was 93percent.

Molecular Weight:208.06
XLogP3:2
Hydrogen Bond Acceptor Count:8
Rotatable Bond Count:2
Exact Mass:207.99589827
Monoisotopic Mass:207.99589827
Topological Polar Surface Area:34.1
Heavy Atom Count:13
Complexity:200
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes