3-Hexanone

3-Hexanone

Names
Preferred IUPAC name Hexan-3-one
Other names Ethyl propyl ketone
Identifiers
CAS Number	589-38-8  Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:89891  Y
ChemSpider	11025
ECHA InfoCard	100.008.770
PubChem CID	11509
UNII	P601A79G79  Y
CompTox Dashboard (EPA)	DTXSID2021608
InChI InChI=1S/C6H12O/c1-3-5-6(7)4-2/h3-5H2,1-2H3 Key: PFCHFHIRKBAQGU-UHFFFAOYSA-N InChI=1/C6H12O/c1-3-5-6(7)4-2/h3-5H2,1-2H3 Key: PFCHFHIRKBAQGU-UHFFFAOYAM
SMILES O=C(CC)CCC
Properties
Chemical formula	C6H12O
Molar mass	100.161 g·mol−1
Appearance	Colorless liquid [1]
Density	0.82 g/cm3 [1]
Melting point	−55.5 °C (−67.9 °F; 217.7 K)
Boiling point	123 °C (253 °F; 396 K) [1]
Solubility in water	14.7 g/L [1]
Vapor pressure	13.9 mmHg
Magnetic susceptibility (χ)	−69.03·10−6 cm3/mol
Refractive index (nD)	1.4
Hazards
Flash point	20 °C (68 °F; 293 K) [1]
Lethal dose or concentration (LD, LC):
LD50 (median dose)	2740 mg/kg (oral rat) [1] 2580 mg/kg (dermal, rabbit) [1]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

3-Hexanone (ethyl propyl ketone) is an organic compound with the formula C₆H₁₂O. It is a ketone used as a solvent and as a chemical intermediate. It is highly flammable. It has roles as a human urinary metabolite, a human xenobiotic metabolite, an insect trap, a plant metabolite and a bacterial xenobiotic metabolite. It derives from a hydride of hexane ^[2] .

According to IFF, it was described as having sweet, fruity, waxy, grape organoleptic properties. ^[3]

Preparation

3-Hexanone can be obtained by oxidation of 3-hexanol:

It is also the product of the Grignard reaction of propylmagnesium bromide with propionitrile:

Health effects

3-Hexanone can also act as a neurotoxin, causing chronic solvent-induced encephalopathy. Patients with this disease can experience difficulty sleeping, a decrease in intellectual capacity, dizziness, altered visual perception, impaired psychomotor skills, forgetfulness, and disorientation. Neurological signs include impaired vibratory sensation at extremities and an inability to maintain steady motion.

Isomers

• 2-Methyl-3-pentanone (Ethyl isopropyl ketone)

References

1. Record in the GESTIS Substance Database of the Institute for Occupational Safety and Health
2. "PubChem".
3. "Online Compendium".