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2,5-Hexanedione

Synthesis Mechanism of Toxicity

2,5-Hexanedione

CAS No.110-13-4
Chemical Name:2,5-Hexanedione
CBNumber:CB2455570
Molecular Formula:C6H10O2
Formula Weight:114.14
MOL File:110-13-4.mol

2,5-Hexanedione Property

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.)
Flash point 174 °F
storage temp. Store below +30°C.
solubility alcohol: miscible; Miscible with water, ethylalcohol and ether,ess. oils and perfume materials.
form Liquid
color Clear yellow to brown
PH 6.1 (10g/l, H2O, 20℃)
Odor Pleasant, sweet-ethereal odor.
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
LogP -0.270
CAS DataBase Reference 110-13-4(CAS DataBase Reference)
EWG's Food Scores 1
FDA UNII C0Z8884J3P
Proposition 65 List 2,5-Hexanedione
NIST Chemistry Reference CH3COCH2CH2COCH3(110-13-4)
EPA Substance Registry System 2,5-Hexanedione (110-13-4)
UNSPSC Code 12352115
NACRES NA.22

Safety

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
F :8
Autoignition Temperature :400 °C
TSCA :Yes
HS Code :29141990
Toxicity :LD50 orally in rats: 2.7 g/kg (Smyth, Carpenter)

NFPA 704:

	2
1		0

Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal wordWarning
Hazard statements H302-H315-H319-H361f-H373
Precautionary statements P202-P260-P301+P312-P302+P352-P305+P351+P338-P308+P313

2,5-Hexanedione Price More Price(11)

Brand: Sigma-Aldrich(India)
Product number: 8.00105
Product name : 2,5-Hexanedione
Purity: for synthesis
Packaging: 100ML
Price: ₹7180
Updated: 2022/06/14
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Brand: Sigma-Aldrich(India)
Product number: 8.00105
Product name : 2,5-Hexanedione
Purity: for synthesis
Packaging: 250ML
Price: ₹11920.01
Updated: 2022/06/14
Buy: Buy

Brand: Sigma-Aldrich(India)
Product number: 165131
Product name : 2,5-Hexanedione
Purity: ≥98%
Packaging: 25G
Price: ₹2045.93
Updated: 2022/06/14
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Brand: Sigma-Aldrich(India)
Product number: 165131
Product name : 2,5-Hexanedione
Purity: ≥98%
Packaging: 100G
Price: ₹4081.03
Updated: 2022/06/14
Buy: Buy

Brand: Sigma-Aldrich(India)
Product number: 15972
Product name : 2,5-Hexanedione
Purity: analytical standard
Packaging: 5ML
Price: ₹13715.28
Updated: 2022/06/14
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2,5-Hexanedione Chemical Properties,Usage,Production

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.
Description 2, 5-hexadione (2,5HD) is a flammable, transparent colorless to amber water-soluble liquid that is a multifunctional platform chemical, a major metabolite of n-hexane, and a key intermediate for the production of high energy density aviation fuels from biomass resources. It has a sweet aromatic smell and neurotoxic effects. It can be used as a high energy density fuel additive of platform chemicals, and can induce ovarian granulosa cell cycle arrest to establish ovarian injury model. It can also be used for biological monitoring of 2, 5-hexanedione exposure to n-hexane^[1-2].
Chemical Properties colourless to pale yellow liquid
Uses It 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.
Uses 2,5-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.
Uses It is the metabolite implicated in n-hexane neurotoxicity.
Application 2,5-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.
Preparation
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 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.]
References [1] KAIXUAN ZHOU, Xin L, Chenggong Sun. Directed glycerol conversion to 2,5-hexanedione and more advanced poly-oxygenates as platform chemicals and high energy–density fuel additives[J]. Chemical Engineering Journal, 2022, 430: Article 132981. DOI:10.1016/j.cej.2021.132981.
[2] XUEMING XU. The Wnt/β-catenin pathway is involved in 2,5-hexanedione-induced ovarian granulosa cell cycle arrest[J]. Ecotoxicology and Environmental Safety, 2023, 268: Article 115720. DOI:10.1016/j.ecoenv.2023.115720.