Cyclohexanone
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Cyclohexanone is the organic compound with the formula (CH2)5CO. The molecule consists of six-carbon cyclic molecule with a ketone functional group. This colorless oily liquid[3] has a sweet odor reminiscent of benzaldehyde. Over time, samples of cyclohexanone assume a pale yellow color.[10] Cyclohexanone is slightly soluble in water and miscible with common organic solvents. Millions of tonnes are produced annually, mainly as a precursor to nylon.[11]
Not to be confused with Cyclexanone.
Quick Facts Names, Identifiers ...
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Names | |||
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Preferred IUPAC name
Cyclohexanone | |||
Other names
oxocyclohexane, pimelic ketone, ketohexamethylene, cyclohexyl ketone, ketocyclohexane, hexanon, Hydrol-O, Sextone, K, Anone | |||
Identifiers | |||
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3D model (JSmol) |
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ChEBI | |||
ChEMBL | |||
ChemSpider |
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DrugBank |
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ECHA InfoCard | 100.003.302 | ||
EC Number |
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KEGG |
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PubChem CID |
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UNII | |||
CompTox Dashboard (EPA) |
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Properties | |||
C6H10O | |||
Molar mass | 98.15 g/mol | ||
Appearance | Colorless liquid[3] | ||
Odor | peppermint or acetone-like | ||
Density | 0.9478 g/mL, liquid | ||
Melting point | −47 °C (−53 °F; 226 K)[4] | ||
Boiling point | 155.65 °C (312.17 °F; 428.80 K) | ||
8.6 g/100 mL (20 °C) | |||
Solubility in all organic solvents | Miscible | ||
log P | 0.81 | ||
Vapor pressure | 5 mmHg (20°C)[5] | ||
-62.04·10−6 cm3/mol | |||
Refractive index (nD) |
1.447 | ||
Viscosity | 2.02 cP at 25 °C[6] | ||
Thermochemistry | |||
Std molar entropy (S⦵298) |
+229.03 J.K−1.mol−1 | ||
Std enthalpy of formation (ΔfH⦵298) |
−270.7 kJ mol−1 | ||
Std enthalpy of combustion (ΔcH⦵298) |
−3519.3 kJmol−1 | ||
Hazards | |||
GHS labelling: | |||
Danger[7] | |||
H226, H302, H305, H312, H315, H318, H332[7] | |||
P280, P305+P351+P338[7] | |||
NFPA 704 (fire diamond) | |||
Flash point | 44 °C (111 °F; 317 K) | ||
420 °C (788 °F; 693 K) | |||
Explosive limits | 1.1–9.4% | ||
Lethal dose or concentration (LD, LC): | |||
LD50 (median dose) |
1200 mg/kg (cat, orally); 2362 mg/kg (rat, orally)[8] | ||
LC50 (median concentration) |
8000 ppm (rat, 4 hr)[9] | ||
LCLo (lowest published) |
4706 ppm (mouse, 1.5 hr)[9] | ||
NIOSH (US health exposure limits): | |||
PEL (Permissible) |
TWA 50 ppm (200 mg/m3)[5] | ||
REL (Recommended) |
TWA 25 ppm (100 mg/m3) [skin][5] | ||
IDLH (Immediate danger) |
700 ppm[5] | ||
Related compounds | |||
Related ketones |
Cyclopentanone, cycloheptanone | ||
Related compounds |
Cyclohexanol | ||
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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