Hexane-2,5-dione

Not to be confused with Acetylacetone.

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.

Hexane-2,5-dione

Skeletal formula of 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 Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:85014 N
ChemSpider	7744 Y
ECHA InfoCard	100.003.400
EC Number	203-738-3
PubChem CID	8035
RTECS number	MO3150000
UNII	C0Z8884J3P Y
UN number	1224
CompTox Dashboard (EPA)	DTXSID8030138
InChI InChI=1S/C6H10O2/c1-5(7)3-4-6(2)8/h3-4H2,1-2H3 Y Key: OJVAMHKKJGICOG-UHFFFAOYSA-N Y 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). N verify (what is YN ?) Infobox references

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.