563-80-4

Basic information

• Product Name: 2-Acetylpropane
• Synonyms: 2-Acetylpropane;2-Methylbutan-3-one;Isopropyl methyl ketone;MIPK;Methylisopropyl ketone
• CAS NO: 563-80-4
• Molecular Formula: C₅H₁₀O
• Molecular Weight: 86.1323
• EINECS: 209-264-3
• Mol File: 563-80-4.mol
• Article Data: 132

Chemical Properties

• Melting Point: -92℃
• Boiling Point: 78.3 °C at 760 mmHg
• Flash Point: 6 °C
• Appearance: clear colourless liquid
• Density: 0.793 g/cm³
• Vapor Pressure: 93.3mmHg at 25°C
• Refractive Index: 1.38
• Water Solubility: 6 g/L (20℃)
• CAS DataBase Reference: 2-Acetylpropane(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Acetylpropane(563-80-4)
• EPA Substance Registry System: 2-Acetylpropane(563-80-4)

Safety Data

• Hazard Codes: F:Flammable
• Statements: R11:
• Safety Statements: S16:; S33:; S9:
• Hazardous Substances Data: 563-80-4(Hazardous Substances Data)

Usage

General Description

2-Acetylpropane, also known as pentane-2,4-dione, is a chemical compound with the molecular formula C5H8O. It is a colorless, flammable liquid with a sweet, fruity odor, and is primarily used as a precursor for the synthesis of other organic compounds. 2-Acetylpropane is commonly used as a flavoring agent in food and beverages, and as a fragrance in cosmetic and personal care products. It is also used in the production of pharmaceuticals and as a solvent in various chemical reactions. Additionally, it has been investigated for its potential applications in the field of medicine, such as in the treatment of neurodegenerative diseases and as an anti-inflammatory agent.

InChI:InChI=1/C5H10O/c1-4(2)5(3)6/h4H,1-3H3

Synthetic route

pivalaldehyde (630-19-3) → 3-methyl-butan-2-one (563-80-4)

Conditions	Yield
With fluoroboric acid Rearrangement;	100%
With gallium(III) trichloride; methyl cyclohexane In 1,2-dichloro-ethane at 20℃; for 1h;	61%
With hydrogenchloride In water at 250℃; under 37503.8 Torr; for 1h; Sealed tube; Inert atmosphere;	59%

benzaldehyde (100-52-7) + 1-bromo-3-methyl-2-butanone (19967-55-6) → 3-methyl-butan-2-one (563-80-4) + 4-methyl-1-phenyl-1-penten-3-one (3160-32-5)

Conditions	Yield
With tributylstibine at 50℃; for 9h;	A n/a B 98%

4-methyl-N'-(3-methylbutan-2-ylidene)benzenesulfonohydrazide (5508-40-7) → 3-methyl-butan-2-one (563-80-4)

Conditions	Yield
With silica gel; copper(II) nitrate In tetrachloromethane for 1h; Heating;	97%

3-methyl-2-butanol (598-75-4) → 3-methyl-butan-2-one (563-80-4)

Conditions	Yield
With water; dihydrogen peroxide; tetra(n-butyl)ammonium hydrogensulfate; sodium tungstate at 100℃; for 0.166667h; Oxidation; microwave irradiation;	94%
With potassium permanganate; Rexyn 101 H ion exchange resin In dichloromethane for 4.3h; Heating;	92%
In neat (no solvent) at 20℃; for 0.0666667h; Microwave irradiation;	89%

hexanal (66-25-1) + 1-bromo-3-methyl-2-butanone (19967-55-6) → 3-methyl-butan-2-one (563-80-4) + 3-methyl-4E-decen-3-one (122657-49-2)

Conditions	Yield
With tributylstibine at 90℃; for 8h;	A n/a B 94%

3-bromo-2-thiophenecarboxaldehyde (930-96-1) + 1-bromo-3-methyl-2-butanone (19967-55-6) → 3-methyl-butan-2-one (563-80-4) + 1-(3-bromo-2-thiophenyl)-4-methyl-1E-penten-3-one (122657-50-5)

Conditions	Yield
With tributylstibine at 70℃; for 5h;	A n/a B 92%

3-methyl-butan-2-one semicarbazone (617-67-4) → 3-methyl-butan-2-one (563-80-4)

Conditions	Yield
With (Bu4N)2S2O8 In 1,2-dichloro-ethane at 80℃; for 1.5h; oxidative cleavage;	92%
With potassium carbonate In water at 9.9℃; Kinetics; Mechanism; Thermodynamic data; E(activ.), ΔG(excit.), ΔH(excit.), ΔS(excit.); other temperatures;

3-methyl-3-buten-2-ol (10473-14-0) → 3-methyl-butan-2-one (563-80-4)

Conditions	Yield
With diiron nonacarbonyl In benzene at 40 - 50℃; for 2.5h;	90%
With triiron dodecarbonyl at 25 - 30℃; for 2h; Irradiation;	88%
With sulfuric acid at 100℃;

molybdenum naphthenate + water (7732-18-5) + 2-Methyl-1-butene (563-46-2) → 3-methyl-butan-2-one (563-80-4)

Conditions	Yield
With tert.-butylhydroperoxide	90%

pivalaldehyde (630-19-3) → 3-methyl-butan-2-one (563-80-4)

Conditions	Yield
With fluoroboric acid Rearrangement;	100%
With gallium(III) trichloride; methyl cyclohexane In 1,2-dichloro-ethane at 20℃; for 1h;	61%
With hydrogenchloride In water at 250℃; under 37503.8 Torr; for 1h; Sealed tube; Inert atmosphere;	59%

benzaldehyde (100-52-7) + 1-bromo-3-methyl-2-butanone (19967-55-6) → 3-methyl-butan-2-one (563-80-4) + 4-methyl-1-phenyl-1-penten-3-one (3160-32-5)

Conditions	Yield
With tributylstibine at 50℃; for 9h;	A n/a B 98%

4-methyl-N'-(3-methylbutan-2-ylidene)benzenesulfonohydrazide (5508-40-7) → 3-methyl-butan-2-one (563-80-4)

Conditions	Yield
With silica gel; copper(II) nitrate In tetrachloromethane for 1h; Heating;	97%

3-methyl-2-butanol (598-75-4) → 3-methyl-butan-2-one (563-80-4)

Conditions	Yield
With water; dihydrogen peroxide; tetra(n-butyl)ammonium hydrogensulfate; sodium tungstate at 100℃; for 0.166667h; Oxidation; microwave irradiation;	94%
With potassium permanganate; Rexyn 101 H ion exchange resin In dichloromethane for 4.3h; Heating;	92%
In neat (no solvent) at 20℃; for 0.0666667h; Microwave irradiation;	89%

hexanal (66-25-1) + 1-bromo-3-methyl-2-butanone (19967-55-6) → 3-methyl-butan-2-one (563-80-4) + 3-methyl-4E-decen-3-one (122657-49-2)

Conditions	Yield
With tributylstibine at 90℃; for 8h;	A n/a B 94%

3-bromo-2-thiophenecarboxaldehyde (930-96-1) + 1-bromo-3-methyl-2-butanone (19967-55-6) → 3-methyl-butan-2-one (563-80-4) + 1-(3-bromo-2-thiophenyl)-4-methyl-1E-penten-3-one (122657-50-5)

Conditions	Yield
With tributylstibine at 70℃; for 5h;	A n/a B 92%

3-methyl-butan-2-one semicarbazone (617-67-4) → 3-methyl-butan-2-one (563-80-4)

Conditions	Yield
With (Bu4N)2S2O8 In 1,2-dichloro-ethane at 80℃; for 1.5h; oxidative cleavage;	92%
With potassium carbonate In water at 9.9℃; Kinetics; Mechanism; Thermodynamic data; E(activ.), ΔG(excit.), ΔH(excit.), ΔS(excit.); other temperatures;

3-methyl-3-buten-2-ol (10473-14-0) → 3-methyl-butan-2-one (563-80-4)

Conditions	Yield
With diiron nonacarbonyl In benzene at 40 - 50℃; for 2.5h;	90%
With triiron dodecarbonyl at 25 - 30℃; for 2h; Irradiation;	88%
With sulfuric acid at 100℃;

molybdenum naphthenate + water (7732-18-5) + 2-Methyl-1-butene (563-46-2) → 3-methyl-butan-2-one (563-80-4)

Conditions	Yield
With tert.-butylhydroperoxide	90%

isoprene (78-79-5) → 3-methyl-butan-2-one (563-80-4)

Conditions	Yield
With water at 180 - 250℃; under 750.075 Torr;	89.4%
With oxygen; Amberlyst 15 acid resin at 20℃; for 12h; Product distribution / selectivity; Gas phase;

2-Methylbutyraldehyde (96-17-3, 57456-98-1) + isoprene (78-79-5) → 3-methyl-butan-2-one (563-80-4) + 2-methyl-but-2-ene (513-35-9) + 3-Methyl-1-butene (563-45-1) + pivalaldehyde (630-19-3) + C2-C4 hydrocarbons

Conditions	Yield
With steam; calcium phosphate catalyst TU 103-134-72 at 380℃; Product distribution; Rate constant; Kinetics; other conditions - var. space velocity of adding reagent, var. dilution with steam, var. temp., var. contact time, other object - activation energy data;;	A 8.2% B n/a C n/a D 0.6% E n/a

acetylacetone (123-54-6) → 3-methyl-butan-2-one (563-80-4) + 2-Pentanone (107-87-9)

Conditions	Yield
With hydrogenchloride; acetic acid; zinc for 2h; Heating;	A 79% B 21%
With hydrogenchloride; acetic acid; zinc for 2h; Product distribution; Mechanism; Heating; further co-reagents: LiCl, TFA; also amalgamated zinc; further β-dicarbonal substrates;	A 79% B 21%

ethyl 2,2-dimethyl-3-oxobutanoate (597-04-6) → 3-methyl-butan-2-one (563-80-4)

Conditions	Yield
Stage #1: ethyl 2,2-dimethyl-3-oxobutanoate With sodium hydroxide In water at 20℃; for 2.5h; Stage #2: With sulfuric acid In water for 1h; Heating;	77%
With water at 250℃; unter Druck;
With potassium hydroxide

(CH2C(OSi(CH3)3)C(CH3)2)Fe(CO)2NO + rac-3-bromocyclohexene (1521-51-3) → 3-methyl-butan-2-one (563-80-4) + (π-cyclohexenyl)dicarbonylnitrosyl iron

Conditions	Yield
In dichloromethane Refluxing of Fe-complex (prepd. in situ) and ((CH2)3)CCHCH2Br with stirring for 2 h.; Cooling, chromy. (silica gel, hexane-ethylacetate) gives iron complex and 3-methyl-2-butanone.;	A n/a B 76%

(CH2C(OSi(CH3)3)C(CH3)2)Fe(CO)2NO + allyl bromide (106-95-6) → 3-methyl-butan-2-one (563-80-4) + (ϖ-allyl)(dicarbonylnitrosyl)iron

Conditions	Yield
In dichloromethane Refluxing of Fe-complex (prepd. in situ) and allybromide with stirring for 2 h.; Cooling, chromy. (silica gel, hexane-ethylacetate) gives iron complex and 3-methyl-2-butanone.;	A n/a B 75%

trimethyloxirane (5076-19-7) → 3-methyl-butan-2-one (563-80-4) + 3-methyl-3-buten-2-ol (10473-14-0)

Conditions	Yield
With magnesium bromide In N,N-dimethyl-formamide at 130℃; for 0.5h;	A 72.3% B 27.7%
With 3-chlorobenzoate; methanesulfonic acid In dichloromethane-d2 at 26.5℃; Product distribution; various conc. of methanesulfonic acid in the presence and absence of 3-chlorobenzoic acid;	A 15% B 55%
With 3-chlorobenzoate; methanesulfonic acid In dichloromethane-d2 at 26.5℃;	A 15% B 55%
With magnesium bromide In dimethyl sulfoxide at 130℃; for 3.5h; Product distribution; Kinetics; Further Variations:; Solvents;
With magnesium bromide In chloroform at 130℃; Kinetics; Further Variations:; Solvents; Temperatures;	A 94.1 % Chromat. B 5.9 % Chromat.

3-Methyl-1-trimethylsilanyl-butan-2-one (69561-99-5) → 3-methyl-butan-2-one (563-80-4) + 1-bromo-3-methyl-2-butanone (19967-55-6)

Conditions	Yield
With bromine In tetrachloromethane 1.) -20 deg C, 2.) room temperature; Yields of byproduct given;	A n/a B 70%

methylbutane (78-78-4) → 3-methyl-butan-2-one (563-80-4) + tert-Amyl alcohol (75-85-4) + 2-Methylbutyraldehyde (96-17-3, 57456-98-1) + 3-methyl-2-butanol (598-75-4)

Conditions	Yield
With [2,2]bipyridinyl; Ba; trifluoroacetic acid In dichloromethane at 20℃; for 0.0333333h;	A 11% B 70% C 4.5% D n/a
With [2,2]bipyridinyl; Ba; trifluoroacetic acid In dichloromethane at 20℃; for 0.0333333h; Product distribution;	A 11% B 70% C 4.5% D n/a

isopropylmagnesium bromide (920-39-8) + 3-methylthio-3-N-piperidino-1-phenyl-2-propen-1-one (185245-65-2) → 3-methyl-butan-2-one (563-80-4) + phenyl isopropyl ketone (611-70-1)

Conditions	Yield
In tetrahydrofuran; diethyl ether for 4h; Ambient temperature;	A n/a B 69%

2-methyl-2,3-butanediol (5396-58-7) → 3-methyl-butan-2-one (563-80-4) + isobutyraldehyde (78-84-2)

Conditions	Yield
With poly(3,4-ethylenedioxythiophene) In n-heptane Reflux; Inert atmosphere;	A 69% B 14%

(CH2C(OSi(CH3)3)C(CH3)2)Fe(CO)2NO + 3-bromo-1-phenyl-1-propenyl bromide (4392-24-9) → 3-methyl-butan-2-one (563-80-4) + (1-phenyl-π-allyl)dicarbonylnitrosyl iron

Conditions	Yield
In dichloromethane Refluxing of Fe-complex (prepd. in situ) and phenylallybromide with stirring for 2 h.; Cooling, chromy. (silica gel, hexane-ethylacetate) gives iron complex and 3-methyl-2-butanone.;	A n/a B 68%

((2R,3S)-3-Isopropyl-oxiranyl)-trimethyl-silane (86553-87-9, 86554-05-4) → 3-methyl-butan-2-one (563-80-4) + 3-Methyl-2-trimethylsilanyloxy-butyraldehyde (112969-05-8)

Conditions	Yield
With 4-nitraminopyridine N-oxide; trimethylsilyl trifluoromethanesulfonate for 4.5h; Ambient temperature;	A 66% B 33%
With 4-nitraminopyridine N-oxide; trimethylsilyl trifluoromethanesulfonate for 2h; Ambient temperature;	A 56% B 34%

3-methyl-4,4-bis(methylthio)but-3-en-2-one (17649-87-5) → 3-methyl-butan-2-one (563-80-4)

Conditions	Yield
With dichloro(N,N,N’,N‘-tetramethylethylenediamine)zinc; zinc In ethanol for 25h; Heating;	65%

3-Methyl-1-trimethylsilanyl-butan-2-one (69561-99-5) → 3-methyl-butan-2-one (563-80-4) + 1-chloro-3-methylbutan-2-one (17687-63-7)

Conditions	Yield
With sulfuryl dichloride; triethylamine In dichloromethane 1.) 0 deg C, 2.) room temperature; Yields of byproduct given;	A n/a B 64%

3-Hydroxy-3-methyl-2-butanone (115-22-0) → 3-methyl-butan-2-one (563-80-4)

Conditions	Yield
With lithium diphenylphosphide In tetrahydrofuran Product distribution; Ambient temperature; other α-hydroxy ketones;	60%
Multi-step reaction with 2 steps 1: Raney nickel; water / 70 °C / 56634.1 Torr / Hydrogenation 2: aluminium oxide / 275 °C View Scheme
Multi-step reaction with 2 steps 1: 485 °C / Pyrolysis.Reaktion des Essigsaeureesters 2: Raney nickel; ethanol / 20 - 32 °C / Hydrogenation.unter Druck View Scheme
Multi-step reaction with 2 steps 1: p-toluenesulfonic acid / 150 °C 2: nickel; kieselguhr; pentane / 25 °C View Scheme
Multi-step reaction with 2 steps 1: sodium; ethanol 2: H2SO4 / beim Destillieren View Scheme

1-(3,4-dimethoxyphenyl)-2,2-dimethyl-1-propanol (213267-13-1) → 3-methyl-butan-2-one (563-80-4) + benzene-1,2-diol (120-80-9)

Conditions	Yield
With hydrogenchloride; water at 250℃; under 37503.8 Torr; for 3h; Sealed tube; Inert atmosphere;	A 24% B 53%

2-isopropyloxirane (1438-14-8) → 3-methyl-butan-2-one (563-80-4) + 2-methyl-1-buten-4-ol (763-32-6) + 2-isopropyl-5-methyl-hex-2-enal (35158-25-9) + 3-methyl-2-buten-1-ol

Conditions	Yield
With magnesium bromide In N,N-dimethyl-formamide at 130℃; for 0.666667h; Further byproducts given;	A 52.2% B 23.2% C 8.7% D 13.7%

+ methyl iodide → 3-methyl-butan-2-one (563-80-4) + butanone (78-93-3)

Conditions	Yield
With N,N,N,N,N,N-hexamethylphosphoric triamide In tetrahydrofuran for 12h; Ambient temperature;	A 21% B 51%

isopropyl methyl ketone thiosemicarbazone (7410-52-8) → 3-methyl-butan-2-one (563-80-4)

Conditions	Yield
With nickel(II) perchlorate In ethanol for 5h; Heating;	46.93%

Upstream product

• 5076-19-7 trimethyloxirane 
• 1117-96-0 Diazoethan 
• 67-64-1 acetone 
• 513-35-9 2-methyl-but-2-ene 
• 598-23-2 3-methyl-but-1-yne 
• 497-02-9 2-methyl-2-buten-1-ol 
• 5166-35-8 3-chloro-2-methylbut-1-ene 
• 875853-51-3 3-butyloxy-2-methyl-butanol-⁽²⁾ 
• 4465-04-7 2-iso-propyl acrylic acid 
• 62-54-4 calcium acetate 
• 39250-87-8 3-methoxy-3-methyl-butan-2-ol 
• 108-24-7 acetic anhydride 
• 67382-30-3 3-methoxy-2-methyl-butan-2-ol 
• 75-16-1 methylmagnesium bromide 

Downstream Products

• 594-82-1 tetramethyl-2,2,3,3 butane 
• 75-28-5 Isobutane 
• 54862-89-4 5-hydroxy-2,5,6-trimethyl-heptan-3-one 
• 115-11-7 isobutene 
• 4111-10-8 (+/-)-2-hydroxy-2,3-dimethylbutanenitrile 
• 17312-77-5 2,3-dimethyl-undecane 
• 617-67-4 3-methyl-butan-2-one semicarbazone 
• 61868-04-0 2,3-dimethyl-octadecane 
• 75163-99-4 2,3-dimethyl-nonadecane 
• 19781-10-3 2,3-dimethyl-octan-3-ol 
• 1482-15-1 3,4-dimethylpent-1-yn-3-ol 
• 18435-23-9 2,3-dimethyltetradecane 
• 61868-03-9 2,3-dimethylheptadecane 
• 598-75-4 3-methyl-2-butanol 

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