103-78-6

Basic information

• Product Name: CYCLOHEXYLACETONE
• Synonyms: CYCLOHEXYLACETONE;ACETONYLCYCLOHEXANE;1-cyclohexyl-2-propanon;Cyclohexyacetone;1-Cyclohexyl-2-propanone;1-Cyclohexylacetone;1-Cyclohexylpropane-2-one;1-cyclohexylpropan-2-one
• CAS NO: 103-78-6
• Molecular Formula: C₉H₁₆O
• Molecular Weight: 140.22
• EINECS: 203-143-9
• Mol File: 103-78-6.mol
• Article Data: 33

Chemical Properties

• Melting Point: 116℃
• Boiling Point: 198-200°C
• Flash Point: 198-200°C
• Appearance: Liquid
• Density: 0,905 g/cm3
• Vapor Pressure: 0.609mmHg at 25°C
• Refractive Index: 1.4528
• BRN: 1209723
• CAS DataBase Reference: CYCLOHEXYLACETONE(CAS DataBase Reference)
• NIST Chemistry Reference: CYCLOHEXYLACETONE(103-78-6)
• EPA Substance Registry System: CYCLOHEXYLACETONE(103-78-6)

Safety Data

• Hazard Codes: T
• Statements: 25-36-52
• Safety Statements: 24/25-45-26
• TSCA: Yes
• Hazardous Substances Data: 103-78-6(Hazardous Substances Data)

Usage

Uses

1-Cyclohexyl-2-propanone is a useful reagent for organic synthesis.

Synthesis Reference(s)

Journal of the American Chemical Society, 94, p. 4370, 1972 DOI: 10.1021/ja00767a072Tetrahedron, 51, p. 9917, 1995 DOI: 10.1016/0040-4020(95)00563-N

InChI:InChI=1/C9H16O/c1-8(10)7-9-5-3-2-4-6-9/h9H,2-7H2,1H3

Synthetic route

1-cyclohexyl-2-nitro-2(pyridine-2-thiyl)-propane (104543-13-7) → 4-cyclohexyl-butan-2-one (103-78-6)

Conditions	Yield
With titanium(III) chloride In tetrahydrofuran; water Ambient temperature;	100%

prop-2-ynylcyclohexane (17715-00-3) → 4-cyclohexyl-butan-2-one (103-78-6)

Conditions	Yield
With hexafluoroantimonic acid; AuOH(1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene); water at 120℃; for 24h;	94%

1-phenyl-acetone (103-79-7) → 4-cyclohexyl-butan-2-one (103-78-6)

Conditions	Yield
With hydrogen In tetrahydrofuran at 24.84℃; under 30003 Torr; chemoselective reaction;	92%
With hydrogen; K5PPdW11O39/C In various solvent(s) at 200℃; under 22502.3 Torr; for 4h;	100 % Chromat.

2-((E)-2-Cyclohexyl-1-methyl-vinyl)-[1,3,2]dioxaborinane (105763-14-2) → 4-cyclohexyl-butan-2-one (103-78-6)

Conditions	Yield
With sodium hydroxide; dihydrogen peroxide In tetrahydrofuran for 2h; Ambient temperature;	86%

allylcyclohexane (2114-42-3) → 4-cyclohexyl-butan-2-one (103-78-6)

Conditions	Yield
With tetrakis(acetonitrile)palladium(II) tetrafluoroborate; [bis(acetoxy)iodo]benzene; water; nitrobenzene; p-benzoquinone In dimethyl sulfoxide at 35℃; for 48h; Wacker Oxidation; Sealed tube; Darkness;	85%
With oxygen; copper(l) chloride; palladium dichloride In water; N,N-dimethyl-formamide at 55℃; under 760.051 Torr; for 24h; Wacker Oxidation; regioselective reaction;	68%

Cyclohexylacetic acid (5292-21-7) + methyllithium (917-54-4) → 4-cyclohexyl-butan-2-one (103-78-6)

Conditions	Yield
Stage #1: methyllithium With copper(l) cyanide In diethyl ether at 0℃; for 0.0833333h; Inert atmosphere; Stage #2: Cyclohexylacetic acid In diethyl ether at 0 - 20℃; for 15h; Inert atmosphere;	81%
In diethyl ether

cyclohexane (110-82-7) + percarbonate de O,O-tert-butyle et O-isopropyle (65700-06-3) → 4-cyclohexyl-butan-2-one (103-78-6)

Conditions	Yield
With tert-butyl peroxyacetate at 95℃; for 16h;	72%

allylcyclohexane (2114-42-3) → 4-cyclohexyl-butan-2-one (103-78-6) + 3-cyclohexylpropanal (4361-28-8)

Conditions	Yield
With bis(benzonitrile)palladium(II) dichloride; silver(I) nitrite; copper(II) choride dihydrate; nitromethane; oxygen; tert-butyl alcohol at 20℃; under 760.051 Torr; for 6h; Wacker Oxidation; Overall yield = 75 %;	A n/a B 60%
With ethanol; iodine; mercury(II) oxide Erwaermen mit alkoh. Kalilauge und verd. Schwefelsaeure;
With diethyl ether; iodine; mercury(II) oxide Behandeln mit Silbernitrat in Aether;
With methanol; iodine; mercury(II) oxide Erwaermen mit alkoh. Kalilauge und verd. Schwefelsaeure;

acetone (67-64-1) + cyclohexene (110-83-8) → 4-cyclohexyl-butan-2-one (103-78-6)

Conditions	Yield
With potassium permanganate; potassium acetate; manganese(II) acetate; acetic acid at 70℃; addition of KMnO4, 4-10 h;	56%
With sodium persulfate; silver nitrate In water for 8h; Heating;	40%
In water at 40℃; for 6h; Photoirradiation; Inert atmosphere;	43 %Chromat.
With potassium acetate; manganese(II) acetate; acetic anhydride; lead dioxide; acetic acid at 70℃; for 6h;	5.9 g

cyclohexane (110-82-7) + percarbonate de O,O-tert-butyle et O-isopropyle (65700-06-3) → 4-cyclohexyl-butan-2-one (103-78-6) + cyclohexylcyclohexane (92-51-3) + 2,5-hexanedione (110-13-4)

Conditions	Yield
at 130℃; for 2.5h;	A 55% B n/a C n/a

cyclohexane (110-82-7) + percarbonate de O,O-tert-butyle et O-isopropyle (65700-06-3) → 4-cyclohexyl-butan-2-one (103-78-6) + cyclohexylcyclohexane (92-51-3) + 2,5-hexanedione (110-13-4) + tert-butyl alcohol (75-65-0)

Conditions	Yield
at 130℃; for 2.5h; Further byproducts given;	A 55% B n/a C n/a D n/a

1-(1-phenylethyl)-2-methyleneaziridine + c-C6H11MgX → 4-cyclohexyl-butan-2-one (103-78-6)

Conditions	Yield
Stage #1: N-(1-Phenylethyl)-2-methyleneaziridine; c-C6H11MgX With copper(l) iodide; boron trifluoride diethyl etherate In tetrahydrofuran at -30 - 0℃; Ring cleavage; Stage #2: In tetrahydrofuran Hydrolysis; Further stages.;	50%

cyclohexylmagnesiumchloride (931-51-1) + 1-(1-phenylethyl)-2-methyleneaziridine → 4-cyclohexyl-butan-2-one (103-78-6)

Conditions	Yield
With copper(l) iodide; boron trifluoride diethyl etherate In tetrahydrofuran at -30 - 0℃; for 1h;	49%

3-cyclohexyl-2-methyl-1-nitro-2-propanol → (R)-3-cyclohexyl-2-methyl-1-nitro-2-propanol + 4-cyclohexyl-butan-2-one (103-78-6)

Conditions	Yield
With (S)-La-Li3-(binaphthoxide)3; C42H36LaLi3O12 In tetrahydrofuran at -20℃; for 15h; Retro-nitroaldol reaction; optical yield given as %ee; enantioselective reaction;	A 40% B n/a

cyclohexylallene (5664-17-5) → (E)-1,6-Dicyclohexyl-hex-5-en-2-one + 4-cyclohexyl-butan-2-one (103-78-6)

Conditions	Yield
With carbon monoxide; trifluoroacetic acid; dodecacarbonyl-triangulo-triruthenium In water; isopropyl alcohol at 120℃; under 760 Torr; for 12h;	A 17% B 8%

1-cyclohexenylacetone (768-50-3) → 4-cyclohexyl-butan-2-one (103-78-6)

Conditions	Yield
With hydrogen; palladium

1-iodocyclohexane (626-62-0) + sodium ethyl acetylacetate enolate (1007476-32-5) → 4-cyclohexyl-butan-2-one (103-78-6)

Conditions	Yield
With ethanol

1-iodocyclohexane (626-62-0) + sodium ethyl acetylacetate enolate (1007476-32-5) → 4-cyclohexyl-butan-2-one (103-78-6) + ethyl 2-cyclohexylacetoacetate (10547-56-5) + cyclohexene (110-83-8)

2-cyclohexylacetonitrile (4435-14-7) → 4-cyclohexyl-butan-2-one (103-78-6)

Conditions	Yield
With methyl magnesium iodide

1-cyclohexyl-2-propanol (76019-86-8) → 4-cyclohexyl-butan-2-one (103-78-6)

Conditions	Yield
With chromic acid

cyclohexanone (108-94-1) + isopropyl alcohol (67-63-0) → 4-cyclohexyl-butan-2-one (103-78-6)

Conditions	Yield
With aluminium oxide-zinc oxide-copper (II)-oxide contact at 350℃; under 15445.7 Torr;

methyl magnesium iodide (917-64-6) + cyclohexylacetic acid chloride (23860-35-7) → 4-cyclohexyl-butan-2-one (103-78-6)

Conditions	Yield
at -10℃;

ethyl 2-cyclohexylacetoacetate (10547-56-5) → 4-cyclohexyl-butan-2-one (103-78-6)

Conditions	Yield
at 525℃;

3-bromo-2-methoxypropene (26562-24-3) + 1-iodocyclohexane (626-62-0) → 4-cyclohexyl-butan-2-one (103-78-6)

Conditions	Yield
(i) Ni(CO)4, (ii) /BRN= 1900797/; Multistep reaction;

1-cyclohexylpropyne (18736-95-3) → 4-cyclohexyl-butan-2-one (103-78-6)

Conditions	Yield
(i) dicyclohexylborane, THF, (ii) aq. H2O2, aq. NaOH; Multistep reaction;

2-chloro-3-cyclohexylprop-1-ene (67894-88-6) → 4-cyclohexyl-butan-2-one (103-78-6)

Conditions	Yield
With mercury(II) diacetate In trifluoroacetic acid

chloroacetone (78-95-5) + cyclohexene (110-83-8) → 4-cyclohexyl-butan-2-one (103-78-6)

Conditions	Yield
Irradiation;

((Z)-2-Bromo-1-methyl-vinyloxy)-trimethyl-silane (61668-34-6) + cyclohexylmagnesium bromide (931-50-0) → 4-cyclohexyl-butan-2-one (103-78-6)

Conditions	Yield
(i) Ni catalyst, (ii) aq. HCl; Multistep reaction;

cyclohexane (110-82-7) + percarbonate de O,O-tert-butyle et O-isopropyle (65700-06-3) → 4-cyclohexyl-butan-2-one (103-78-6) + cyclohexylcyclohexane (92-51-3) + 2,5-hexanedione (110-13-4) + acetone (67-64-1) + tert-butyl alcohol (75-65-0)

Conditions	Yield
at 130℃; for 2.5h; Product distribution; Mechanism; variation of time and temperature;

4-cyclohexyl-butan-2-one (103-78-6) → 1-bromo-3-cyclohexyl-2-propanone (152757-52-3)

Conditions	Yield
With bromine In methanol at 15℃;	98%
With water; bromine In methanol at 15 - 20℃;	78%
With bromine In methanol at 15℃; Cooling with ice;

4-cyclohexyl-butan-2-one (103-78-6) → 1-cyclohexyl-2-propanol (76019-86-8)

Conditions	Yield
Stage #1: 4-cyclohexyl-butan-2-one With n-butyllithium; 1-(2-hydroxyethyl)-3-methyl-1H-imidazol-3-ium trifluoromethanesulfonate; iron(II) acetate In tetrahydrofuran at 65℃; for 3h; Inert atmosphere; Stage #2: With water; sodium hydroxide In tetrahydrofuran; methanol at 20℃; for 2h; Inert atmosphere;	85%
With methanol; sodium tetrahydroborate at 0 - 20℃; for 2.25h;	79%
Stage #1: 4-cyclohexyl-butan-2-one With n-butyllithium; iron(II) acetate; 1,3-bis[2,6-diisopropylphenyl]imidazolium chloride In tetrahydrofuran; hexane at 65℃; Inert atmosphere; Stage #2: With sodium hydroxide In tetrahydrofuran; methanol; hexane; water at 20℃; for 3h; Inert atmosphere;	66%

4-cyclohexyl-butan-2-one (103-78-6) → cyclohexane carbonitrile (766-05-2)

Conditions	Yield
With aluminum (III) chloride; sodium nitrite In N,N-dimethyl-formamide at 100℃; for 5h; Schlenk technique;	77%

4-cyclohexyl-butan-2-one (103-78-6) + diazomethyl-trimethyl-silane (18107-18-1) → C14H26Si (1266614-73-6)

Conditions	Yield
Stage #1: diazomethyl-trimethyl-silane With n-butyllithium In tetrahydrofuran; diethyl ether; hexane at -78℃; for 0.5h; Inert atmosphere; Stage #2: 4-cyclohexyl-butan-2-one In tetrahydrofuran; diethyl ether; hexane at -78 - 20℃; for 4h; Inert atmosphere; regioselective reaction;	61%

4-cyclohexyl-butan-2-one (103-78-6) + oxalic acid diethyl ester (95-92-1) → ethyl α,γ-dioxo-cyclohexanepentanoate (1561966-01-5)

Conditions	Yield
With sodium hydride In ethanol at 20℃; for 5.25h; Cooling with ice;	59%

4-cyclohexyl-butan-2-one (103-78-6) + oxalic acid diethyl ester (95-92-1) → 4-Cyclohexylacetessigsaeure-ethylester (64127-44-2)

Conditions	Yield
With sodium ethanolate In ethanol at 0 - 20℃; Inert atmosphere;	57%

4-cyclohexyl-butan-2-one (103-78-6) + diethyl 2-acetamido-2-(2-(aminomethyl)benzyl)malonate → diethyl 2-acetamido-2-(2-(((1-cyclohexylpropan-2-yl)amino)methyl)benzyl)malonate

Conditions	Yield
Stage #1: 4-cyclohexyl-butan-2-one; diethyl 2-acetamido-2-(2-(aminomethyl)benzyl)malonate In methanol at 100℃; for 2h; Stage #2: With methanol; sodium tetrahydroborate at 60℃; for 6h;	57%

4-cyclohexyl-butan-2-one (103-78-6) + (2-(cyclohexyloxy)phenyl)methanamine → 1-cyclohexyl-N-(2-(cyclohexyloxy)benzyl)propan-2-amine

Conditions	Yield
Stage #1: 4-cyclohexyl-butan-2-one; (2-(cyclohexyloxy)phenyl)methanamine In methanol at 100℃; for 2h; Stage #2: With methanol; sodium tetrahydroborate at 60℃; for 6h;	51%

4-cyclohexyl-butan-2-one (103-78-6) + (2-(aminomethyl)phenyl)methanesulfonamide → (2-(((1-cyclohexylpropan-2-yl)amino)methyl)phenyl)methanesulfonamide

Conditions	Yield
Stage #1: 4-cyclohexyl-butan-2-one; (2-(aminomethyl)phenyl)methanesulfonamide In methanol at 100℃; for 2h; Stage #2: With methanol; sodium tetrahydroborate at 60℃; for 6h;	51%

4-cyclohexyl-butan-2-one (103-78-6) + (2-((methylsulfonyl)methyl)phenyl)methanamine → 1-cyclohexyl-N-(2-((methylsulfonyl)methyl)benzyl)propan-2-amine

Conditions	Yield
Stage #1: 4-cyclohexyl-butan-2-one; (2-((methylsulfonyl)methyl)phenyl)methanamine In methanol at 100℃; for 2h; Stage #2: With methanol; sodium tetrahydroborate at 60℃; for 6h;	49%

4-cyclohexyl-butan-2-one (103-78-6) + methyl (1r,3r)-3-(((2-(aminomethyl)phenyl)methyl)sulfonamido)cyclobutane-1-carboxylate → methyl (1r,3r)-3-(((2-(((1-cyclohexylpropan-2-yl)amino)methyl)phenyl)methyl)sulfonamido)cyclobutane-1-carboxylate

Conditions	Yield
Stage #1: 4-cyclohexyl-butan-2-one; methyl (1r,3r)-3-(((2-(aminomethyl)phenyl)methyl)sulfonamido)cyclobutane-1-carboxylate In methanol at 100℃; for 3h; Stage #2: With methanol; sodium tetrahydroborate at 60℃; for 7h;	44%

4-cyclohexyl-butan-2-one (103-78-6) + (2-((3-methoxybenzyl)oxy)phenyl)methanamine → 1-cyclohexyl-N-(2-((3-methoxybenzyl)oxy)benzyl)propan-2-amine

Conditions	Yield
Stage #1: 4-cyclohexyl-butan-2-one; (2-((3-methoxybenzyl)oxy)phenyl)methanamine In methanol at 100℃; for 2h; Stage #2: With methanol; sodium tetrahydroborate at 60℃; for 6h;	44%

4-cyclohexyl-butan-2-one (103-78-6) + 1-(2-(aminomethyl)phenyl)-N-(1-methylpiperidin-4-yl)methanesulfonamide → 1-(2-(((1-cyclohexylpropan-2-yl)amino)methyl)phenyl)-N-(1-methylpiperidin-4-yl)methanesulfonamide

Conditions	Yield
Stage #1: 4-cyclohexyl-butan-2-one; 1-(2-(aminomethyl)phenyl)-N-(1-methylpiperidin-4-yl)methanesulfonamide In methanol at 100℃; for 3h; Stage #2: With methanol; sodium tetrahydroborate at 60℃; for 7h;	42%

4-cyclohexyl-butan-2-one (103-78-6) + (2-((3-methylcyclohexyl)oxy)phenyl)methanamine → 1-cyclohexyl-N-(2-((3-methylcyclohexyl)oxy)benzyl)propan-2-amine

Conditions	Yield
Stage #1: 4-cyclohexyl-butan-2-one; (2-((3-methylcyclohexyl)oxy)phenyl)methanamine In methanol at 100℃; for 2h; Stage #2: With methanol; sodium tetrahydroborate at 60℃; for 6h;	41%

4-cyclohexyl-butan-2-one (103-78-6) + methyl (1s,3s)-3-(((2-(aminomethyl)phenyl)methyl)sulfonamido)cyclobutane-1-carboxylate → methyl (1s,3s)-3-(((2-(((1-cyclohexylpropan-2-yl)amino)methyl)phenyl)methyl)sulfonamido)cyclobutane-1-carboxylate

Conditions	Yield
Stage #1: 4-cyclohexyl-butan-2-one; methyl (1s,3s)-3-(((2-(aminomethyl)phenyl)methyl)sulfonamido)cyclobutane-1-carboxylate In methanol at 100℃; for 3h; Stage #2: With methanol; sodium tetrahydroborate at 60℃; for 7h;	41%

Upstream product

• 110-82-7 cyclohexane 
• 67-64-1 acetone 
• 110-83-8 cyclohexene 
• 2043-61-0 cyclohexanecarbaldehyde 
• 18107-18-1 diazomethyl-trimethyl-silane 
• 931-51-1 cyclohexylmagnesiumchloride 
• 108-94-1 cyclohexanone 
• 626-62-0 Cyclohexyl iodide 
• 768-50-3 1-cyclohexenylacetone 
• 75-16-1 methylmagnesium bromide 
• 134560-43-3 2-cyclohexyl-N-methoxy-N-methylacetamide 
• 103-79-7 1-phenyl-acetone 
• 67-63-0 isopropyl alcohol 
• 108-95-2 phenol 

Downstream Products

• 5531-30-6 2-cyclohexyl-1,1-dimethyl ethanol 
• 100247-12-9 1-cyclohexyl-4-dimethylamino-butan-2-one 
• 6281-53-4 2-cyclohexyl-4-nitrophenol 
• 1266614-73-6 C₁₄H₂₆Si 
• 63418-36-0 (2-chloropropyl)cyclohexane 
• 916318-18-8 1-cyclohexyl-2-methyl-4-[(1-phenyl-1 H-tetrazol-5-yl)sulfonyl]-2-butanol 
• 916318-16-6 4-cyclohexyl-3-methyl-1,3-butanediol 

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