398241 Sigma-Aldrich


ACS reagent, ≥99.0%



Related Categories Building Blocks, C3 to C6, Carbonyl Compounds, Chemical Synthesis, Ketones,
grade   ACS reagent
vapor density   3.4 (vs air)
vapor pressure   3.4 mmHg ( 20 °C)
assay   ≥99.0%
autoignition temp.   788 °F
expl. lim.   1.1 %, 100 °F
  9.4 %
impurities   ≤0.05% water
evapn. residue   ≤0.05%
color   APHA: ≤10
refractive index   n20/D 1.450(lit.)
bp   155 °C(lit.)
mp   −47 °C(lit.)
density   0.947 g/mL at 25 °C(lit.)



2 L in glass bottle

25, 500 mL in glass bottle

General description

Cyclohexanone, a colorless liquid is a cyclic ketone. It is an important building block for the synthesis of a variety of organic compounds. Majority of the cyclohexanone synthesized is utilized as an intermediate in the synthesis of nylon.1 One of the methods reported for its synthesis is by the palladium catalyzed hydrogenation of phenol.2 The kinetics of the oxidation reaction of cyclohexanone has been studied in a fused silica jet stirred reactor.3 The Meerwein–Ponndorf–Verley reduction of cyclohexanone has been reported.4

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Safety & Documentation

Safety Information

Signal word 
Hazard statements 
Precautionary statements 
UN 1915 3 / PGIII
WGK Germany 
Flash Point(F) 
111.2 °F
Flash Point(C) 
44 °C


Certificate of Analysis

Certificate of Origin

Protocols & Articles


Baeyer-Villiger Oxidation Reaction

The Baeyer–Villiger reaction involves the oxidation of ketones to esters by C-C bond cleavage of the carbonyl group and the introduction of an oxygen atom adjacent to it.1 This reaction can be accomp...
Keywords: Asymmetric synthesis, Catalysis, Oxidations

Determination of Water Content in Cyclohexanone Using Karl Fischer Titration

Ketones have a tendency to form ketals. At the same time water is formed. Cyclohexanone and acetone react rapidly, long chain ketones react more slowly. Aromatically substituted ketones only react ve...
Keywords: Titrations

Peer-Reviewed Papers


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1. First Order Hyperpolarizabilities, NPA and Fukui Functions of Cyclohexanone by Density Functional Theory Method. Gangadharan RP and Krishnan SS. Acta Phys. Pol.A 127(3), 748-752, (2015)

2. Selective transfer hydrogenation of phenol to cyclohexanone on supported palladium catalyst using potassium formate as hydrogen source under open atmosphere. Patil RD and Sasson Y. Appl. Catal. A Gen. 499, 227-231, (2015)

3. Kinetics of oxidation of cyclohexanone in a jet-stirred reactor: Experimental and modeling. Serinyel Z, et al. Proc. Combust. Inst. 35(1), 507-514, (2015)

4. Supported zirconium-based continuous-flow microreactor for effective Meerwein-Ponndorf-Verley reduction of cyclohexanone. Koreniuk A, et al. Catal. Commun. 64, 48-51, (2015)

Conversion of Cyclohexanone to Adipic Acid Catalyzed by Heteropoly Compounds. Lesbani A, et al. Indo. J. Chem. 15(1), 64-69, (2015)

Synthesis of tetrasubstituted propargylamines from cyclohexanone by solvent-free copper (II) catalysis. Palchak ZL, et al. Green Chem. 17(3), 1802-1810, (2015)

Synthesis, characterization, and application of silica supported ionic liquid as catalyst for reductive amination of cyclohexanone with formic acid and triethyl amine as hydrogen source. Tamboli AH, et al. Chin. J. Catal. 36, (2015)

Green and Sustainable Heterogeneous Organo-Catalyst for Asymmetric Aldol Reactions. Sadiq M, et al. Mod. Res. Catal. 4(2), 43, (2015)

Palladium-catalyzed aerobic dehydrogenative aromatization of cyclohexanone imines to arylamines. Hajra A, Wei Y, and Yoshikai N Org. Lett. 14(21), 5488-91, (2012)


The substrate-bound crystal structure of a Baeyer-Villiger monooxygenase exhibits a Criegee-like conformation. Yachnin BJ, Sprules T, McEvoy MB, et al. J. Am. Chem. Soc. 134(18), 7788-95, (2012)


Hydromorphone metabolites: isolation and identification from pooled urine samples of a cancer patient. Zheng M, McErlane KM, and Ong MC Xenobiotica 32(5), 427-39, (2002)


Cyclohexanone. IARC Monogr. Eval. Carcinog. Risks Hum. 47, 157-69, (1989)


Cyclohexanone. IARC Monogr. Eval. Carcinog. Risks Hum. 71 Pt 3, 1359-64, (1999)


Curcumin and synthetic analogs induce reactive oxygen species and decreases specificity protein (Sp) transcription factors by targeting microRNAs. Gandhy SU, Kim K, Larsen L, et al. BMC Cancer 12, 564, (2012)


A method for rapid screening of ketone biotransformations: detection of whole cell Baeyer-Villiger monooxygenase activity. Linares-Pastén JA, Chávez-Lizárraga G, Villagomez R, et al. Enzyme Microb. Technol. 50(2), 101-6, (2012)


A role for solvents in the toxicity of agricultural organophosphorus pesticides. Eddleston M, Street JM, Self I, et al. Toxicology 294(2-3), 94-103, (2012)


Helical polymer as mimetic enzyme catalyzing asymmetric aldol reaction. Zhang D, Ren C, Yang W, et al. Macromol. Rapid Commun. 33(8), 652-7, (2012)


The role of the reactor wall in hydrothermal biomass conversions. Fábos V, Yuen AK, Masters AF, et al. Chem. Asian J. 7(11), 2638-43, (2012)


Exploring the myth of nascent hydrogen and its implications for biomass conversions. Fábos V, Yuen AK, Masters AF, et al. Chem. Asian J. 7(11), 2629-37, (2012)


Application of fragment screening and merging to the discovery of inhibitors of the Mycobacterium tuberculosis cytochrome P450 CYP121. Hudson SA, McLean KJ, Surade S, et al. Angew. Chem. Int. Ed. Engl. 51(37), 9311-6, (2012)


Design, synthesis and molecular docking of α,β-unsaturated cyclohexanone analogous of curcumin as potent EGFR inhibitors with antiproliferative activity. Xu YY, Cao Y, Ma H, et al. Bioorg. Med. Chem. 21(2), 388-94, (2013)


Effects of NADH kinase on NADPH-dependent biotransformation processes in Escherichia coli. Lee WH, Kim JW, Park EH, et al. Appl. Microbiol. Biotechnol. 97(4), 1561-9, (2013)


Novel thieno[2,3-d]pyrimidines: their design, synthesis, crystal structure analysis and pharmacological evaluation. Adepu R, Rambabu D, Prasad B, et al. Org. Biomol. Chem. 10(29), 5554-69, (2012)


Aldol reactions catalyzed by L-proline functionalized polymeric nanoreactors in water. Lu A, Cotanda P, Patterson JP, et al. Chem. Commun. (Camb.) 48(78), 9699-701, (2012)


Breath analysis during one-lung ventilation in cancer patients. Kischkel S, Miekisch W, Fuchs P, et al. Eur. Respir. J. 40(3), 706-13, (2012)


Chiral picolylamines for Michael and aldol reactions: probing substrate boundaries. Nugent TC, Bibi A, Sadiq A, et al. Org. Biomol. Chem. 10(46), 9287-94, (2012)


Synthesis of N(4)-(substituted phenyl)-N(4)-alkyl/desalkyl-9H-pyrimido[4,5-b]indole-2,4-diamines and identification of new microtubule disrupting compounds that are effective against multidrug resistant cells. Gangjee A, Zaware N, Devambatla RK, et al. Bioorg. Med. Chem. 21(4), 891-902, (2013)


Copolymer-supported heterogeneous organocatalyst for asymmetric aldol addition in aqueous medium. Zhou J, Wan J, Ma X, et al. Org. Biomol. Chem. 10(21), 4179-85, (2012)


D-Glucosamine in a chimeric prolinamide organocatalyst for direct asymmetric aldol addition. De Nisco M, Pedatella S, Bektaş S, et al. Carbohydr. Res. 356, 273-7, (2012)


Refined transition-state models for proline-catalyzed asymmetric Michael reactions under basic and base-free conditions. Sharma AK and Sunoj RB J. Org. Chem. 77(23), 10516-24, (2012)


Studies on percutaneous penetration of chemicals - Impact of storage conditions for excised human skin. Dennerlein K, Schneider D, Göen T, et al. Toxicol. In Vitro 27(2), 708-13, (2013)


Preparation of ceramic-corrosion-cell fillers and application for cyclohexanone industry wastewater treatment in electrobath reactor. Wu S, Qi Y, Gao Y, et al. J. Hazard. Mater. 196, 139-44, (2011)


Modulation of sensory irritation responsiveness by adenosine and malodorants. Willis DN and Morris JB Chem. Senses 38(1), 91-100, (2013)


Olfactory responses to explosives associated odorants are enhanced by zinc nanoparticles. Moore CH, Pustovyy O, Dennis JC, et al. Talanta 88, 730-3, (2012)


Carbenic vs. ionic mechanistic pathway in reaction of cyclohexanone with bromoform. Vitnik VD, Vitnik ZJ, and Juranić IO J. Mol. Model. 18(10), 4721-8, (2012)


Development and validation of a bioanalytical method for quantification of 2,6-bis-(4-hydroxy-3-methoxybenzylidene)-cyclohexanone (BHMC) in rat plasma. Lee YZ, Ming-Tatt L, Lajis NH, et al. Molecules 17(12), 14555-64, (2012)


Solid-phase microextraction: investigation of the metabolism of substances that may be abused by inhalation. Walker R, Flanagan RJ, Lennard MS, et al. J. Chromatogr. Sci. 44(7), 387-93, (2006)


[Toxic anosmia and rhinitis due to occupational solvent exposure]. Muttray A, Haxel B, Mann W, et al. HNO 54(11), 883-7, (2006)


Merck 14,2726

Beil. 7,IV,15

Fieser 1,178

Aldrich MSDS 1, 517:B / Corp MSDS 1 (1), 965:A / FT-IR 1 (1), 432:C / FT-IR 2 (1), 674:D / FT-NMR 1 (1), 669:A / IR-Spectra (2), 229:C / IR-Spectra (3), 256:B / NMR-Reference 2 (1), 394:C / RegBook 1 (1), 471:C / Sax 6, 831 / Sigma FT-IR 1 (2), 414:D / Structure Index 1, 67:D:2 / Vapor Phase 3, 517:C

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