2,5-Hexanedione

2,5-Hexanedione Basic information
Synthesis Mechanism of Toxicity
Product Name:2,5-Hexanedione
Synonyms:2,5-Diketohexane;Acetone, acetonyl-;Acetonyl acetone 2,5-hexanedione;2,5-Dioxohexane;2,5-Hexanedione, Standard f GC;Acetonylacetone,97%;NSC 7621;1,2-Diacetylethane 2,5-Hexanedione
CAS:110-13-4
MF:C6H10O2
MW:114.14
EINECS:203-738-3
Product Categories:Aliphatics;Metabolites & Impurities;Mutagenesis Research Chemicals;ketone;Building Blocks;C3 to C6;Carbonyl Compounds;Chemical Synthesis;Ketones;Organic Building Blocks;Pharmaceutical Intermediates;110-13-4
Mol File:110-13-4.mol
2,5-Hexanedione Structure
2,5-Hexanedione Chemical Properties
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
PH6.1 (10g/l, H2O, 20℃)
explosive limit1.5%(V)
Water Solubility miscible
Merck 14,71
BRN 506525
Stability:Stable. Incompatible with strong bases, strong reducing agents, strong oxidizing agents. Flammable.
InChIKeyOJVAMHKKJGICOG-UHFFFAOYSA-N
LogP-0.270
CAS DataBase Reference110-13-4(CAS DataBase Reference)
NIST Chemistry ReferenceCH3COCH2CH2COCH3(110-13-4)
EPA Substance Registry System2,5-Hexanedione (110-13-4)
Safety Information
Hazard Codes Xn,Xi
Risk Statements 36/38-48/20/21/22-36/37/38
Safety Statements 23-26-36/37-37/39
WGK Germany 2
RTECS MO3150000
8
Autoignition Temperature400 °C
TSCA Yes
HS Code 29141990
ToxicityLD50 orally in rats: 2.7 g/kg (Smyth, Carpenter)
MSDS Information
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2,5-Hexanedione English
SigmaAldrich English
ACROS English
ALFA English
2,5-Hexanedione Usage And Synthesis
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 Propertiescolourless to pale yellow liquid
UsesIt was used as reference standard for the determination of 2,5HD in human urine using gas chromatography-electron capture detection and gas chromatography-mass selective detection.
Uses2,5-Hexanedione is used as a reagent in the preparation of trans-2,5-dimethylpyrrolidine. It is also used in the synthesis of 2,5-dimethylpyrroles. Further, it plays an important role as a reagent used for the protection of amino groups in amino sugars and nucleosides. In addition to this, it is used in the preparation of five-membered heterocycles like indane-type and benzannulated systems. It is also employed as a precursor in Diels-alder cycloaddition reactions.
UsesIt is the metabolite implicated in n-hexane neurotoxicity.
Application2,5-Hexanedione is a neurotoxic metabolite of n-hexanes and methyl n-butyl ketone. It is also used as the starting material for diels-alder cycloaddition reactions, such as a reactions with amines to form 2,5-dimethylpyrroles.
PreparationPreparation of 2,5-hexanedione.jpg
20 g of diethyl 2,3-diacetylbutanedioate are mechanically shaken for several days with 250 ml (excess) of 5% aqueous sodium hydroxide, and until no diethyl 2,3-diacetylbutanedioate separates on acidification of a sample with dilute hydrochloric acid. The solution is then saturated with potassium carbonate and extracted with ether, the extract is washed with brine to remove alcohol, dried over calcium chloride, and distilled, the fraction 192-198° C being retained. You can get 2,5-Hexanedione with a yield of 70%. Colourless liquid; agreeable odour; miscible with water, alcohol and ether; m.p. 9° C; b.p. 194° C; d=0.973 g/ml at 20° C.
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 DescriptionClear colorless to amber liquid with a sweet aromatic odor.
Air & Water ReactionsHighly flammable. Water soluble.
Reactivity ProfileAcetonylacetone is incompatible with oxidizing agents. Acetonylacetone is also incompatible with strong bases and strong reducing agents.
Fire HazardAcetonylacetone is combustible.
Purification MethodsPurify 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.]
3,4-DIACETYL-2,5-HEXANEDIONE 2-ACETYL-1,3-CYCLOHEXANEDIONE 4,4,5,5,6,6,6-HEPTAFLUORO-1-PHENYL-1,3-HEXANEDIONE Adrenosterone QUASSIN RHODIZONIC ACID DIHYDRATE 1-ACETOXY-8-HYDROXY-1,4,4A,9A-TETRAHYDROANTHRAQUINONE 5-PHENYLCYCLOHEXANE-1,3-DIONE RHODIZONIC ACID DIPOTASSIUM SALT 11-KETOANDROSTERONE TIMTEC-BB SBB006499 1-DEHYDROANDRENOSTERONE Diethyl succinosuccinate 2,3-DIHYDRO-9,10-DIHYDROXY-1,4-ANTHRACENEDIONE 4,7-DIOXO-7-PHENYLHEPTANOIC ACID 1,4,4A,9A-TETRAHYDROANTHRAQUINONE, TECH. , 90 TRIQUINOLYL BARIUM RHODIZONATE

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