Hexane-2,5-dione

Hexane-2,5-dione
Names
	Preferred IUPAC name Hexane-2,5-dione
	Other names 1,2-Diacetylethane; 'α','β'-Diacetylethane; Acetonyl acetone; Diacetonyl; 2,5-Dioxohexane; 2,5-Diketohexane; 2,5-Hexanedione
Identifiers
CAS Number	110-13-4 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:85014 ;
ChemSpider	7744 ;
ECHA InfoCard	100.003.400
EC Number	203-738-3;
PubChem CID	8035;
RTECS number	MO3150000;
UNII	C0Z8884J3P ;
UN number	1224
CompTox Dashboard (EPA)	DTXSID8030138 ;
	InChI InChI=1S/C6H10O2/c1-5(7)3-4-6(2)8/h3-4H2,1-2H3 Key: OJVAMHKKJGICOG-UHFFFAOYSA-N ; InChI=1/C6H10O2/c1-5(7)3-4-6(2)8/h3-4H2,1-2H3 Key: OJVAMHKKJGICOG-UHFFFAOYAH;
	SMILES O=C(C)CCC(=O)C;
Properties
Chemical formula	C6H10O2
Molar mass	114.1438 g mol−1
Appearance	colorless liquid
Density	0.973 g cm−3, liquid
Melting point	−5.5 °C (22.1 °F; 267.6 K)
Boiling point	191.4 °C (376.5 °F; 464.5 K)
Solubility in water	≥ 10 g/100 mL (22 °C)
Magnetic susceptibility (χ)	-62.51·10−6 cm3/mol
Structure
Molecular shape	trigonal planar at carbonyl; tetrahedral elsewhere
Hazards
	GHS labelling:
Pictograms
Signal word	Warning
Hazard statements	H315, H319, H373
Precautionary statements	P260, P264, P280, P302+P352, P305+P351+P338, P314, P321, P332+P313, P337+P313, P362, P501
Flash point	78 °C (172 °F; 351 K)
Related compounds
Related diketones	acetylacetone
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

2,5-Hexanedione (Acetonylacetone) is an aliphatic diketone. It is a colorless liquid.^[1] In humans, it is a toxic metabolite of hexane and of 2-hexanone.

Symptoms of poisoning

The chronic toxicity of hexane is attributed to hexane-2,5-dione. The symptoms are tingling and cramps in the arms and legs, followed by general muscular weakness. In severe cases, atrophy of the skeletal muscles is observed, along with a loss of coordination and vision problems.^[2]

Similar symptoms are observed in animal models. They are associated with a degeneration of the peripheral nervous system (and eventually the central nervous system), starting with the distal portions of the longer and wider nerve axons.

Mechanism of action

2,5-Hexanedione reacts with lysine residues in axonal proteins by Schiff base formation followed by cyclization to give pyrroles. Oxidation of the pyrrole residues then causes cross-linking and denaturation of proteins, which perturbs axonal transport and function and causes damage to nerve cells.^[3]

Synthesis

2,5-Hexanedione has been prepared in several ways.^[4] A common method involves hydrolysis of 2,5-dimethylfuran, a glucose derived heterocycle.^[1]

Uses

Acetonylacetone can be used in the synthesis of isocarboxazid,^[5] rolgamidine,^[6] and mopidralazine. Treatment with P₄S₁₀ gives 2,5-dimethylthiophene.

References

^ ^a ^b Young, D. M.; Allen, C. F. H. (1936). "2,5-Dimethylpyrrole". Organic Syntheses. 16: 25. doi:10.15227/orgsyn.016.0025.
^ Couri D, Milks M. "Toxicity and metabolism of the neurotoxic hexacarbons n-hexane, 2-hexanone, and 2,5-hexanedione" Annu. Rev. Pharmacol. Toxicol. 1982;22:145-66.
^ Wolfgang Dekant; Spiridon Vamvakas (2007). "Toxicology". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. p. 23. ISBN 978-3527306732.
^ http://www.prepchem.com/synthesis-of-2-5-hexanedione/ Primary: Systematic organic chemistry, by W. M. Cumming, 194, 1937.
^ U.S. patent 2,908,688
^ U.S. patent 4,140,793

[OS-1] Young, D. M.; Allen, C. F. H. (1936). "2,5-Dimethylpyrrole". Organic Syntheses. 16: 25. doi:10.15227/orgsyn.016.0025.

[2] Couri D, Milks M. "Toxicity and metabolism of the neurotoxic hexacarbons n-hexane, 2-hexanone, and 2,5-hexanedione" Annu. Rev. Pharmacol. Toxicol. 1982;22:145-66.

[ulltox-3] Wolfgang Dekant; Spiridon Vamvakas (2007). "Toxicology". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. p. 23. ISBN 978-3527306732.

[4] ttp://www.prepchem.com/synthesis-of-2-5-hexanedione/ Primary: Systematic organic chemistry, by W. M. Cumming, 194, 1937.

[5] U.S. patent 2,908,688

[6] U.S. patent 4,140,793

[1]

[2]

[3]

[4]

[5]

[6]