Hexafluoroacetylacetone

Base Information

• Chemical Name: Hexafluoroacetylacetone
• CAS No.: 1522-22-1
• Deprecated CAS: 149182-28-5,28987-01-1
• Molecular Formula: C5H2F6O2
• Molecular Weight: 208.06
• Hs Code.: 29147000
• European Community (EC) Number: 216-191-0
• NSC Number: 174351
• UNII: MG8477QRV4
• DSSTox Substance ID: DTXSID4061753
• Nikkaji Number: J7.508F
• Wikipedia: Hexafluoroacetylacetone
• Wikidata: Q5748732
• Mol file: 1522-22-1.mol

Synonyms:Hexafluoroacetylacetone;1522-22-1;1,1,1,5,5,5-Hexafluoropentane-2,4-dione;1,1,1,5,5,5-Hexafluoroacetylacetone;1,1,1,5,5,5-Hexafluoro-2,4-pentanedione;2,4-Pentanedione, 1,1,1,5,5,5-hexafluoro-;MFCD00000426;Hexafluoro-2,4-pentanedione;MG8477QRV4;EINECS 216-191-0;NSC174351;HFAC;CF3COCH2COCF3;1,1,1,5,5,5-Hexafluoro-2,4-pentadione;UNII-MG8477QRV4;Hexafluoroacetylacetone, 98%;SCHEMBL183178;DTXSID4061753;STL185660;AKOS005063442;CS-W015241;NSC-174351;SC11827;CID 5386425;s12332;MS-20623;1,3-Bis(trifluoromethyl)propane-1,3-dione;FT-0626988;H0476;1,1,1,5,5,5-hexafluoro-pentan-2,4-dione;EN300-20458;1,1,1,5,5,5-hexafluoro-pentane-2,4-dione;1,1,1,5,5,5-HEXAFLUORO-2,4-PENTANDIONE;J-008904;Q5748732;1,1,1,5,5,5-Hexafluoro-2,4-pentanedione, 98+%;Q63398865;F1908-0182

Chemical Property of Hexafluoroacetylacetone

Chemical Property:

• Appearance/Colour: clear colorless to slightly yellow liquid
• Vapor Pressure: 6.813mmHg at 25°C
• Refractive Index: n20/D 1.332(lit.)
• Boiling Point: 70 °C at 760 mmHg
• PKA: 4.30±0.10(Predicted)
• Flash Point: 30.8 °C
• PSA: 34.14000
• Density: 1.506 g/cm³
• LogP: 1.63930
• Storage Temp.: Flammables area
• Sensitive.: Hygroscopic
• Water Solubility.: Not miscible in water.
• XLogP3: 2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 2
• Exact Mass: 207.99589827
• Heavy Atom Count: 13
• Complexity: 200

Purity/Quality:

98% min ^*data from raw suppliers

Hexafluoroacetylacetone ^*data from reagent suppliers

Safty Information:

• Pictogram(s): C, F, Xi
• Hazard Codes: C,F,Xi
• Statements: 10-20/21/22-34
• Safety Statements: 26-36/37/39-45

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Other Classes -> Halogenated Ketones
• Canonical SMILES: C(C(=O)C(F)(F)F)C(=O)C(F)(F)F
• General Description: **HEXAFLUOROACETYLACETONE (HFA)** is a fluorinated β-diketone commonly used as a ligand in coordination chemistry, particularly in the synthesis of metal complexes such as manganese(II) and cobalt(II) compounds. It serves as a chelating agent due to its ability to form stable complexes with transition metals, often contributing to the magnetic or cytotoxic properties of the resulting compounds. In the context of the provided literature, HFA is utilized in the preparation of antiferromagnetic manganese(II) complexes and cytotoxic cobalt(II) β-ketoaminato complexes, demonstrating its versatility in both materials science and medicinal chemistry applications.

Technology Process of Hexafluoroacetylacetone

There total 10 articles about Hexafluoroacetylacetone 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: 93.0%

1,1,1,5,5,5-hexafluoro-3-pentyn-2-one trimethylsilylethyl ketal → 1,1,1,5,5,5-hexafluoroacetylacetone (1522-22-1)

Guidance literature:

With sulfuric acid; In tetrahydrofuran; water; at 40 - 50 ℃; for 7.5h;

Reference yield:

1,1,1,5,5,5-hexafluoro-3-trifluoroacetyl-pentane-2,4-dione (72721-52-9) → 1,1,1,5,5,5-hexafluoroacetylacetone (1522-22-1) + trifluoroacetic acid (76-05-1)

Guidance literature:

With water; Title compound not separated from byproducts;

DOI:10.1016/S0022-1139(00)80922-7

Reference yield:

1,1,1,5,5,5-hexafluoro-3-trifluoromethyl-pentane-2,4-dione (69962-11-4) → trifluoromethyl 2,2,2-trifluororethyl ketone (400-49-7) + 1,1,1,5,5,5-hexafluoroacetylacetone (1522-22-1) + trifluoroacetic acid (76-05-1)

Guidance literature:

With water; Title compound not separated from byproducts; 1.) 20 deg C, 7 d, 2.) 100 - 110 deg C, 70 h;

DOI:10.1016/S0022-1139(00)80922-7

upstream raw materials:

1,1,1,5,5,5-hexafluoro-3-trifluoromethyl-pentane-2,4-dione

1,1,1,5,5,5-hexafluoro-3-trifluoroacetyl-pentane-2,4-dione

bis(gem-diol) 1,1,1,5,5,5-hexafluoropentane-2,2,4,4-tetraol

1,1,1-trifluoro-2-propanone

Downstream raw materials:

C₂₂H₁₆F₆P⁽¹⁺⁾*C₅HF₆O₂^(1-)

7-amino-2,4-bis(trifluoromethyl)-1,8-naphthyridine

4,6-ditrifluoromethyl-3-oxo-2,3-dihydropyrazolo<3,4-b>pyridine

N-benzoyl-3,5-bis(trifluoromethyl)pyrazole

Refernces

Antiferromagnetic spin-coupling between Mn^II and amminium radical cation ligands: Models for coordination polymer magnets

10.1016/j.poly.2007.09.020

The research focuses on the antiferromagnetic spin-coupling between MnII and amminium radical cation ligands within coordination polymer magnets. The study involves the synthesis and characterization of manganese(II) and copper(II) complexes with a triarylamine ligand, [L2Mn(hfac)2] and [L2Cu(hfac)2], respectively. The experiments conducted include one- and two-electron oxidation processes, which were analyzed using ultra violet/visible/near infra red spectroscopy, cyclic voltammetry, and magnetometry. The reactants used in the synthesis involve the triarylamine ligand and metal complexes with hexafluoroacetylacetonate (hfac). The analyses revealed that the spin-coupling between the metal and the ligand was weak, making these complexes unsuitable for coordination polymer magnets. The copper(II) complex was found to decompose upon attempted oxidation of the ligand. The research provides insights into the challenges of designing high-spin polymers and the limitations of using amminium radical cation ligands in coordination polymer magnets.

The synthesis and characterization of a series of cobalt(II) β-ketoaminato complexes and their cytotoxic activity towards human tumor cell lines

10.1016/j.jinorgbio.2011.03.005

The research focuses on the synthesis, characterization, and evaluation of the cytotoxic activity of a series of cobalt(II) β-ketoaminato complexes towards various human tumor cell lines. The purpose of the study was to investigate the potential of these cobalt compounds as novel cytotoxic drugs, selective towards certain types of tumors. The researchers prepared a series of square planar cobalt(II) compounds with tetradentate β-ketoaminato ligands, varying in the number of ―CF3 ligand substituents, and one tetrahedral cobalt compound with two bidentate ligands. The compounds were synthesized using a multistep reaction sequence involving chemicals such as CoCl2, sodium bis(trimethylsilyl)amide, sodium hydride, tert-butyldimethylchlorosilane, 1,2-diaminoethane, and various β-diketones, including hexafluoroacetylacetone and 4,4,4-trifluoro-1-phenyl-1,3-butanedione. The conclusions drawn from the study indicate that the cobalt complexes, particularly L2Co, exhibit significant cytotoxic activity against prostate cancer and leukemia cells, with activity mediated through mechanisms involving caspase-3, MAP kinases, and reactive oxygen species. These findings suggest that these cobalt complexes could be developed as a new class of cytotoxic drugs.