Acetonylacetone CAS NO.110-13-4

Product Name:    Acetonylacetone
Synonyms:    2,5-Diketohexane;2,5-Hexadione;Acetone, acetonyl-;Acetonyl acetone 2,5-hexanedione;2,5-Dioxohexane;2,5-Hexanedione, Standard f GC;Acetonylacetone,97%;NSC 7621
CAS:    110-13-4
MF:    C6H10O2
MW:    114.14
EINECS:    203-738-3
Product Categories:    Aliphatics;Metabolites & Impurities;ketone;Mutagenesis Research Chemicals;Building Blocks;C3 to C6;Pharmaceutical Intermediates;Carbonyl Compounds;Chemical Synthesis;Ketones;Organic Building Blocks
Mol File:    110-13-4.mol

Melting point     -6--5 °C (lit.)
Boiling point     191 °C (lit.)
density     0.973 g/mL at 25 °C (lit.)
vapor pressure     0.43 mm Hg ( 20 °C)
refractive index     n20/D 1.425(lit.)
Fp     174 °F
storage temp.     Store below +30°C.
solubility     alcohol: miscible
form     Liquid
color     Clear yellow to brown
PH    6.1 (10g/l, H2O, 20℃)
explosive limit    1.5%(V)
Water Solubility     miscible
Merck     14,71
BRN     506525
Stability:    Stable. Incompatible with strong bases, strong reducing agents, strong oxidizing agents. Flammable.
InChIKey    OJVAMHKKJGICOG-UHFFFAOYSA-N

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Synthesis    
2,5-Hexanedione has been prepared in several ways. A common method involves hydrolysis of 2,5-dimethylfuran, a glucose derived heterocycle.

Mechanism of Toxicity    
Identification of 2,5-hexanedione as the major neurotoxic metabolite of n-hexane proceeded rapidly after its discovery as a urinary metabolite. 2,5-Hexanedione has been found to produce a polyneuropathy indistinguishable from n-hexane. 2,5-Hexanedione is many times more potent than n-hexane, the parent compound, in causing neurotoxicity in experimental animals. It appears that the neurotoxicity of 2,5-hexanedione resides in its γ-diketone structure since 2,3-, 2,4-hexanedione and 2,6-heptanedione are not neurotoxic, while 2,5-heptanedione and 3,6-octanedione and other γ-diketones are neurotoxic.

Chemical Properties    colourless to pale yellow liquid
Uses    It is the metabolite implicated in n-hexane neurotoxicity.
Definition    
ChEBI: A diketone that is hexane substituted by oxo groups at positions 2 and 5. It is a toxic metabolite of hexane and of 2-hexanone

Synthesis Reference(s)    Canadian Journal of Chemistry, 59, p. 945, 1981 DOI: 10.1139/v81-137
Journal of the American Chemical Society, 105, p. 7200, 1983 DOI: 10.1021/ja00362a047
Tetrahedron Letters, 15, p. 4149, 1974
General Description    Clear colorless to amber liquid with a sweet aromatic odor.
Air & Water Reactions    Highly flammable. Water soluble.
Reactivity Profile    Acetonylacetone is incompatible with oxidizing agents. Acetonylacetone is also incompatible with strong bases and strong reducing agents.
Fire Hazard    Acetonylacetone is combustible.
Purification Methods    Purify it by dissolving in Et2O, stiring with K2CO3 (a quarter of the weight of dione), filtering, drying over anhydrous Na2SO4 (not CaCl2), filtering again, evaporating the filtrate and distilling it in a vacuum. It is then redistilled through a 30cm Vigreux column (p 11, oil bath temperature 150o). It is miscible with H2O and EtOH. The dioxime has m 137o (plates from *C6H6), the mono-oxime has b 130o/11mm, and the 2,4-dinitrophenylhydrazone has m 210-212o (red needles from EtOH). It forms complexes with many metals. [Werner et al. Chem Ber 22 2100 1989, for enol content see Gero J Org Chem 19 1960 1954, Beilstein 1 IV 3688.]
Acetonylacetone Preparation Products And Raw materials
Raw materials    Potassium carbonate-->2,3-Butanedione-->2,5-Dimethylfuran-->ETHYL ACETOACETATE SODIUM SALT-->IODINE PURE-->3-HEXENE-2,5-DIONE-->(2R,3S,4S,5R)-2,5-Bis(hydroxymethyl)-oxolane-2,3,4-triol-->5-Chloromethylfurfural-->5-Methyl furfural-->2,5-Hexanediol
Preparation Products    L(+)-Ascorbic acid-->Methyl 3-methyl-2-butenoate-->2,5-Dimethyl-1H-pyrrole-->1-[2,6-DICHLORO-4-(TRIFLUOROMETHYL)PHENYL]-2,5-DIMETHYL-1H-PYRROLE-3-CARBALDEHYDE-->2,5-Dimethylthiophene-->5-Methylisoxazole-3-carboxylic acid