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Topic summary

Cyclohexanone

Cyclohexanone
Names Preferred IUPAC name
Cyclohexanone
Other names
oxocyclohexane, pimelic ketone, ketohexamethylene, cyclohexyl ketone, ketocyclohexane, hexanon, Hydrol-O, Sextone, K, Anone
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard100.003.302EC Number
  • 203-631-1
KEGG
UNII
  • InChI=1S/C6H10O/c7-6-4-2-1-3-5-6/h1-5H2
    Key: JHIVVAPYMSGYDF-UHFFFAOYSA-N
  • InChI=1/C6H10O/c7-6-4-2-1-3-5-6/h1-5H2
    Key: JHIVVAPYMSGYDF-UHFFFAOYAY
  • C1CCC(=O)CC1
Properties C6H10OMolar mass98.145 g·mol Appearance Colorless liquid OdorPeppermint or acetone-like Density0.9478 g/mL, liquid Melting point−47 °C (−53 °F; 226 K) Boiling point155.65 °C (312.17 °F; 428.80 K) 8.6 g/100 mL (20 °C) Solubility in all organic solvents Miscible log P0.81 Vapor pressure5 mmHg (20 °C) −62.04·10 cm/mol 1.447 Viscosity2.02 cP at 25 °C Thermochemistry +229.03 J·K·mol −270.7 kJ·mol −3519.3 kJ·mol Hazards GHS labelling: DangerH226, H302, H305, H312, H315, H318, H332P280, P305+P351+P338NFPA 704 (fire diamond)
1
2
0
Flash point44 °C (111 °F; 317 K) 420 °C (788 °F; 693 K) Explosive limits1.1–9.4% Lethal dose or concentration (LD, LC): 1200 mg/kg (cat, orally); 2362 mg/kg (rat, orally) 8000 ppm (rat, 4 hr) 4706 ppm (mouse, 1.5 hr) NIOSH (US health exposure limits):
PEL (Permissible)
TWA 50 ppm (200 mg/m)
REL (Recommended)
TWA 25 ppm (100 mg/m) [skin]
IDLH (Immediate danger)
700 ppm 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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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 has a sweet odor reminiscent of benzaldehyde. Over time, samples of cyclohexanone assume a pale yellow color.

Cyclohexanone is slightly soluble in water and miscible with common organic solvents. Millions of tonnes are produced annually, mainly as a precursor to nylon.

Wikipedia source