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542-08-5

Basic Information
CAS No.: 542-08-5
Name: Isopropyl acetoacetate
Molecular Structure:
Molecular Structure of 542-08-5 (Isopropyl acetoacetate)
Formula: C7H12O3
Molecular Weight: 144.17
Synonyms: Acetoaceticacid, isopropyl ester (6CI,8CI);3-Oxobutanoic acid 1-methylethyl ester;3-Oxobutanoic acid isopropyl ester;Isopropyl 3-oxobutanoate;Isopropyl3-oxobutyrate;Butanoic acid, 3-oxo-, 1-methylethyl ester;
EINECS: 208-798-4
Density: 0.993 g/cm3
Melting Point: -27 °C
Boiling Point: 185.8 °C at 760 mmHg
Flash Point: 68.9 °C
Solubility: Slightly miscible with water.
Appearance: Colourless liquid
Hazard Symbols: IrritantXi
Risk Codes: 38
Safety: 26-36
Transport Information:
PSA: 43.37000
LogP: 0.91710
Synthetic route
5394-63-8

2,2,6-trimethyl-4H-1,3-dioxin-4-one

67-63-0

isopropyl alcohol

542-08-5

isopropyl acetoacetate

Conditions
ConditionsYield
With sodium acetate for 24h; Reflux;98%
Esterification;92%
In 5,5-dimethyl-1,3-cyclohexadiene at 150℃; for 3h;55%
674-82-8

4-methyleneoxetan-2-one

67-63-0

isopropyl alcohol

542-08-5

isopropyl acetoacetate

Conditions
ConditionsYield
With 1,4-diaza-bicyclo[2.2.2]octane at 50 - 90℃; for 2h; Reagent/catalyst; Temperature;95.5%
With triethylamine at 95℃; for 3h;89.6%
With sodium acetate at 115℃; for 2.5h;86%
674-82-8

4-methyleneoxetan-2-one

14371-10-9

(E)-3-phenylpropenal

546-68-9

titanium(IV)isopropoxide

A

isopropyl E-5-hydroxy-3-oxo-7-phenyl-6-heptenoate

B

542-08-5

isopropyl acetoacetate

Conditions
ConditionsYield
In dichloromethaneA 88%
B n/a
105-45-3

acetoacetic acid methyl ester

67-63-0

isopropyl alcohol

542-08-5

isopropyl acetoacetate

Conditions
ConditionsYield
With boron trifluoride diethyl etherate In toluene for 5h; Reflux;87%
With iodine In toluene for 7h; Heating;63%
niobium(V) oxide In toluene for 8h; Heating;63%
141-97-9

ethyl acetoacetate

67-63-0

isopropyl alcohol

542-08-5

isopropyl acetoacetate

Conditions
ConditionsYield
With 1,3,5-trichloro-2,4,6-triazine; N,N-dimethyl-formamide for 0.0116667h; Reagent/catalyst; Microwave irradiation;83%
With Prussian blue In toluene for 0.183333h; Microwave irradiation;82%
With silver trifluoromethanesulfonate In toluene at 110℃; for 10h;77%
With iodine In toluene for 6h; Ionic liquid; Reflux;68%
134969-44-1

isopropyl 4-bromo-3-oxobutanoate

603-35-0

triphenylphosphine

A

542-08-5

isopropyl acetoacetate

B

(3-Isopropoxycarbonyl-2-oxopropyl)triphenylphosphonium bromide

Conditions
ConditionsYield
In benzene for 24h; Ambient temperature; Yields of byproduct given;A n/a
B 82.9%
15159-48-5

2,4-oxetanedione

67-63-0

isopropyl alcohol

542-08-5

isopropyl acetoacetate

Conditions
ConditionsYield
With triethylamine for 5h; Ambient temperature;77.5%
108-21-4

Isopropyl acetate

75154-68-6

methyl (2S)-N-tritylaziridine-2-carboxylate

A

542-08-5

isopropyl acetoacetate

B

236742-98-6

(4S)-3-oxo-4,5-(N-triphenylmethylepimino)pentanoic acid isopropyl ester

Conditions
ConditionsYield
Stage #1: Isopropyl acetate With n-butyllithium; diisopropylamine In tetrahydrofuran; hexane at -78℃; for 1h; Metallation;
Stage #2: methyl (2S)-N-tritylaziridine-2-carboxylate In tetrahydrofuran; hexane at -78℃; for 12h; Claisen condensation;
A n/a
B 70%
2033-24-1

cycl-isopropylidene malonate

75-36-5

acetyl chloride

67-63-0

isopropyl alcohol

542-08-5

isopropyl acetoacetate

Conditions
ConditionsYield
Stage #1: cycl-isopropylidene malonate; acetyl chloride With pyridine In dichloromethane at 0 - 20℃; for 2h;
Stage #2: isopropyl alcohol for 2h; Reflux;
65%
108-21-4

Isopropyl acetate

1068-55-9

isopropylmagnesium chloride

A

542-08-5

isopropyl acetoacetate

B

54074-71-4

3-hydroxy-3,4-dimethyl-valeric acid isopropyl ester

Conditions
ConditionsYield
With diethyl ether
108-21-4

Isopropyl acetate

683-60-3

sodium isopropylate

542-08-5

isopropyl acetoacetate

Conditions
ConditionsYield
Geschwindigkeit;
108-21-4

Isopropyl acetate

542-08-5

isopropyl acetoacetate

Conditions
ConditionsYield
With sodium isopropylate at 87℃;
With diethyl ether; ammonia; sodium amide
With sodium
(i) LiNH2, liq. NH3, (ii) Ph2CO; Multistep reaction;
2343-88-6

Acetoacetylfluorid

67-63-0

isopropyl alcohol

542-08-5

isopropyl acetoacetate

Conditions
ConditionsYield
With triethylamine In diethyl ether
73200-00-7

1-<(Carboisopropoxy)methylthio>ethylidenyldimethylammonium Iodide

73200-01-8

1-<(Carboethoxy)methylthio>pentylidenyldimethylammonium Iodide

A

7737-62-4

Ethyl 3-oxoheptanoate

B

542-08-5

isopropyl acetoacetate

C

141-97-9

ethyl acetoacetate

D

73200-02-9

Isopropyl 3-Oxoheptanoate

Conditions
ConditionsYield
With bis [3-dimethyl-amino-1-propyl] phenyl phosphine In acetonitrile Mechanism; Heating;
67-63-0

isopropyl alcohol

2911-21-9

2,4-dioxo-6-methyl-3,4-dihydro-2H-1,3-oxazine

542-08-5

isopropyl acetoacetate

Conditions
ConditionsYield
With triethylamine Heating;
134969-44-1

isopropyl 4-bromo-3-oxobutanoate

603-35-0

triphenylphosphine

A

542-08-5

isopropyl acetoacetate

B

(3-Isopropoxycarbonyl-2-oxopropyl)triphenylphosphonium bromide

C

((Z)-2-Bromo-3-isopropoxycarbonyl-allyl)-triphenyl-phosphonium; bromide

D

(3-Bromo-1-isopropoxycarbonyl-2-oxo-propyl)-triphenyl-phosphonium; bromide

Conditions
ConditionsYield
In benzene for 24h; Product distribution; Ambient temperature; various solvents;
In chloroform-d1 Ambient temperature;A 18 % Spectr.
B 60.5 % Spectr.
C n/a
D n/a
85920-63-4

5-(1-hydroxyethylidene)-2,2-dimethyl-1,3-dioxane-4,6-dione

67-63-0

isopropyl alcohol

542-08-5

isopropyl acetoacetate

Conditions
ConditionsYield
In toluene Heating;
674-82-8

4-methyleneoxetan-2-one

14371-10-9

(E)-3-phenylpropenal

546-68-9

titanium(IV)isopropoxide

A

542-08-5

isopropyl acetoacetate

B

(S,E)-5-hydroxy-3-oxo-7-phenyl-6-heptenoic acid isopropyl ester

C

(R)-(E)-isopropyl 5-hydroxy-7-phenyl-3-oxo-6-heptenoate

Conditions
ConditionsYield
With (S)-[1,1']-binaphthalenyl-2,2'-diol In dichloromethane at 20℃; for 24h; Title compound not separated from byproducts;
934-87-2

S-phenyl thioacetate

40053-29-0

S-phenyl 3-oxobutanethioate

67-63-0

isopropyl alcohol

A

108-21-4

Isopropyl acetate

B

542-08-5

isopropyl acetoacetate

Conditions
ConditionsYield
With silver trifluoroacetate In chloroform for 3h;
542-08-5

isopropyl acetoacetate

14205-46-0

isopropyl 3-aminocrotonate

Conditions
ConditionsYield
With ammonium acetate In ethanol for 24h; Reflux;100%
With ammonia In water at 25℃; for 3h; Temperature; Reagent/catalyst;91.7%
With ammonium hydroxide; ammonium acetate at -5 - 5℃; for 18h;86%
542-08-5

isopropyl acetoacetate

87128-49-2

isopropyl ester of (R)-3-hydroxybutanoic acid

Conditions
ConditionsYield
With hydrogen; C50H44Cl2N2O8P4Ru(4-)*Zr(4+) In methanol at 20℃; under 72402.6 Torr; for 20h; Product distribution / selectivity;100%
With C50H46Cl2N2O2P2Ru; hydrogen In methanol at 50℃; under 30003 Torr; for 24h; Catalytic behavior; Reagent/catalyst; Autoclave; enantioselective reaction;99%
With hydrogen; [(R)-BINAP]RuBr2 In methanol at 23 - 30℃; under 55480 Torr; for 34h;93 % Chromat.
542-08-5

isopropyl acetoacetate

89-98-5

2-chloro-benzaldehyde

139471-96-8

2-[1-(2-Chloro-phenyl)-meth-(Z)-ylidene]-3-oxo-butyric acid isopropyl ester

Conditions
ConditionsYield
With piperdinium acetate In isopropyl alcohol at 45 - 55℃;100%
542-08-5

isopropyl acetoacetate

4637-24-5

N,N-dimethyl-formamide dimethyl acetal

329363-90-8

isopropyl 2-((dimethylamino)methylene)-3-oxobutanoate

Conditions
ConditionsYield
at 20℃;100%
at 20℃;100%
at 20℃;100%
In chloroform for 1h; Heating;
542-08-5

isopropyl acetoacetate

74-88-4

methyl iodide

919771-62-3

rac-isopropyl 2-methyl-3-oxobutanoate

Conditions
ConditionsYield
With potassium carbonate at 0 - 40℃; for 3h;99%
Stage #1: isopropyl acetoacetate With potassium carbonate In acetone for 0.0833333h; Inert atmosphere;
Stage #2: methyl iodide In acetone for 18h; Inert atmosphere; Reflux;
81%
Stage #1: isopropyl acetoacetate With potassium carbonate In acetone for 0.0833333h; Inert atmosphere;
Stage #2: methyl iodide In acetone for 18h; Inert atmosphere; Reflux;
81%
542-08-5

isopropyl acetoacetate

551-93-9

2-aminoacetophenone

iso-propyl 2,4-dimethylquinoline-3-carboxylate

Conditions
ConditionsYield
With toluene-4-sulfonic acid In ethanol at 80℃; for 12h; Reagent/catalyst; Friedlaender Quinoline Synthesis; Schlenk technique;99%
542-08-5

isopropyl acetoacetate

100-52-7

benzaldehyde

(±)-isopropyl 6-methyl-2-oxo-4-phenyl-1,2,3,4-tetrahydropyrimidine-5-carboxylate

Conditions
ConditionsYield
With calcium fluoride In ethanol at 40℃; for 1.3h; Biginelli reaction;98%
With strontium (III) chloride hexahydrate In ethanol at 40℃; for 2h; Biginelli pyrimidine synthesis;96%
With silica-supported Cu(I) In ethanol for 5h; Biginelli pyrimidine synthesis; Reflux;93%
542-08-5

isopropyl acetoacetate

104-88-1

4-chlorobenzaldehyde

5-isopropoxycarbonyl-4-(4'-chlorophenyl)-6-methyl-3,4-dihydropyrimidin-2(1H)-one

Conditions
ConditionsYield
With calcium fluoride In ethanol at 40℃; for 2h; Biginelli reaction;98%
With strontium (III) chloride hexahydrate In ethanol at 40℃; for 2h; Biginelli pyrimidine synthesis;94%
With Amberlyst 15-supported ytterbium(III) reagent at 120℃; for 48h; Biginelli reaction;
542-08-5

isopropyl acetoacetate

123-11-5

4-methoxy-benzaldehyde

5-isopropyloxycarbonyl-6-methyl-4-(4-methoxyphenyl)-3,4-dihydropyrimidin-2(1H)-one

Conditions
ConditionsYield
With calcium fluoride In ethanol at 40℃; for 1.3h; Biginelli reaction;98%
With strontium (III) chloride hexahydrate In ethanol at 40℃; for 2h; Biginelli pyrimidine synthesis;94%
With hexaaquaaluminium(III) tetrafluoroborate In acetonitrile for 20h; Biginelli pyrimidine synthesis; Reflux;83%
With Amberlyst 15-supported ytterbium(III) reagent at 120℃; for 48h; Biginelli reaction;75%
542-08-5

isopropyl acetoacetate

123-08-0

4-hydroxy-benzaldehyde

5-isopropoxycarbonyl-6-methyl-4-(3-methoxyphenyl)-3,4-dihydropyrimidin-2(1H)-thione

Conditions
ConditionsYield
With 1-butyl-3-carboxymethyl-benzotriazolium trifluoroacetate In neat (no solvent) at 90℃; for 0.666667h; Biginelli Pyrimidone Synthesis;98%
108-05-4

vinyl acetate

96-31-1

N,N'-Dimethylurea

542-08-5

isopropyl acetoacetate

isopropyl 1,3,4,6-tetramethyl-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate

Conditions
ConditionsYield
With isopropyl alcohol In water at 60℃; for 48h; Biginelli Pyrimidone Synthesis; Enzymatic reaction;98%
542-08-5

isopropyl acetoacetate

7646-85-7

zinc(II) chloride

2C7H11O3(1-)*Zn(2+)

Conditions
ConditionsYield
Stage #1: isopropyl acetoacetate With sodium methylate In isopropyl alcohol at 80℃; for 1h;
Stage #2: zinc(II) chloride In isopropyl alcohol at 70 - 90℃; for 4.5h;
98%
111-66-0

oct-1-ene

542-08-5

isopropyl acetoacetate

isopropyl 2-acetyl-3-methylnonanoate

Conditions
ConditionsYield
With [Ir(cod)2]SbF6; 2,2'-bis(diphenylphosphino)biphenyl for 24h; Reflux; diastereoselective reaction;98%
542-08-5

isopropyl acetoacetate

75-36-5

acetyl chloride

365212-62-0

isopropyl diacetylacetate

Conditions
ConditionsYield
With pyridine; magnesium chloride In dichloromethane at 0 - 20℃; for 16h;97%
542-08-5

isopropyl acetoacetate

17356-08-0

thiourea

isopropyl 2-amino-4-methylthiazole-5-carboxylate

Conditions
ConditionsYield
With erythrosine B; oxygen In acetonitrile at 20℃; for 8h; Irradiation; Green chemistry;97%
542-08-5

isopropyl acetoacetate

87-48-9

5-Bromo-1H-indole-2,3-dione

isopropyl (R)-4-(5-bromo-3-hydroxy-2-oxoindolin-3-yl)-3-oxobutanoate

Conditions
ConditionsYield
With 1-(3,5-bis(trifluoromethyl)phenyl)-3-((R)-(6-methoxyquinolin-4-yl)((1S,2R,4S,5R)-5-vinylquinuclidin-2-yl)methyl)thiourea In tetrahydrofuran at 4℃; for 96h; Aldol Addition; enantioselective reaction;97%
542-08-5

isopropyl acetoacetate

28144-70-9

anthranilic acid amide

77726-78-4

2,2-dimethyl-2,3-dihydro-1H-quinazolin-4-one

Conditions
ConditionsYield
With Candida antarctica lipase B In hexane; water at 50℃; for 40h; Enzymatic reaction;97%
542-08-5

isopropyl acetoacetate

111970-49-1

iso-propyl (S)-(+)-3-hydroxybutyrate

Conditions
ConditionsYield
With yeast Saccharomyces cerevisiae; water In Petroleum ether Ambient temperature;96%
With hydrogen In isopropyl alcohol at 80℃; under 15001.5 Torr; for 10h; enantioselective reaction;96.5%
With dichloro(benzene)ruthenium(II) dimer; C49H52O2P2; hydrogen In methanol at 80℃; under 38002.6 Torr; for 12h; optical yield given as %ee; enantioselective reaction;
With D-Glucose; cobalt(II); BaSDR1 reductase variant Q139G; NADH In aq. phosphate buffer at 35℃; pH=7.5; Kinetics; Reagent/catalyst; Enzymatic reaction; enantioselective reaction;n/a
542-08-5

isopropyl acetoacetate

459-57-4

4-fluorobenzaldehyde

5-isopropoxycarbonyl-4-(4'-fluorophenyl)-6-methyl-3,4-dihydropyrimidin-2(1H)-one

Conditions
ConditionsYield
With calcium fluoride In ethanol at 40℃; for 2h; Biginelli reaction;96%
With strontium (III) chloride hexahydrate In ethanol at 40℃; for 2h; Biginelli pyrimidine synthesis;94%
With Amberlyst 15-supported ytterbium(III) reagent at 120℃; for 48h; Biginelli reaction;
542-08-5

isopropyl acetoacetate

555-16-8

4-nitrobenzaldehdye

5-isopropoxycarbonyl-6-methyl-4-(4'-nitrophenyl)-3,4-dihydropyrimidin-2(1H)-one

Conditions
ConditionsYield
With calcium fluoride In ethanol at 40℃; for 3h; Biginelli reaction;96%
With strontium (III) chloride hexahydrate In ethanol at 40℃; for 4h; Biginelli pyrimidine synthesis;90%
With Amberlyst 15-supported ytterbium(III) reagent at 120℃; for 48h; Biginelli reaction;
542-08-5

isopropyl acetoacetate

89-98-5

2-chloro-benzaldehyde

312596-19-3

(±)-isopropyl 4-(2-chlorophenyl)-6-methyl-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate

Conditions
ConditionsYield
With calcium fluoride In ethanol at 40℃; for 1.3h; Biginelli reaction;96%
With strontium (III) chloride hexahydrate In ethanol at 40℃; for 2h; Biginelli pyrimidine synthesis;96%
With zinc(II) chloride In tetrahydrofuran at 70℃; for 12h; Biginelli Pyrimidone Synthesis;92%

diphenyl(trifluoromethanesulfonato)-λ3-iodane

542-08-5

isopropyl acetoacetate

1613614-14-4

(Z)-isopropyl 3-phenoxybut-2-enoate

Conditions
ConditionsYield
With copper(l) iodide; lithium carbonate In 1,4-dioxane at 70℃; for 60h; Inert atmosphere; Sealed tube; regioselective reaction;96%
542-08-5

isopropyl acetoacetate

40100-28-5

isopropyl 3-aminocrotonate

Conditions
ConditionsYield
With ammonia In dichloromethane95%
With ammonia at 10℃;89%
With ammonia In ethanol
61-54-1

tryptamine

542-08-5

isopropyl acetoacetate

104-55-2

3-phenyl-propenal

1225230-86-3

(2S,12bS)-isopropyl 4-methyl-2-phenyl-1,2,6,7,12,12b-hexahydroindolo[2,3-a]quinolizine-3-carboxylate

Conditions
ConditionsYield
Stage #1: isopropyl acetoacetate; 3-phenyl-propenal With (2S)-2-{diphenyl[(trimethylsilyl)oxy]methyl}pyrrolidine; benzoic acid In toluene at -15℃; for 24h; Inert atmosphere;
Stage #2: tryptamine With benzoic acid In toluene at 50℃; for 24h; optical yield given as %ee; enantioselective reaction;
95%
542-08-5

isopropyl acetoacetate

104-87-0

4-methyl-benzaldehyde

C22H29NO4

Conditions
ConditionsYield
With C23H3BF16N2O; ammonium acetate In toluene at 100℃; for 10h; Hantzsch Dihydropyridine Synthesis;95%
542-08-5

isopropyl acetoacetate

123-11-5

4-methoxy-benzaldehyde

C22H29NO5

Conditions
ConditionsYield
With C23H3BF16N2O; ammonium acetate In toluene at 100℃; for 10h; Hantzsch Dihydropyridine Synthesis;95%
542-08-5

isopropyl acetoacetate

99-61-6

3-nitro-benzaldehyde

131275-78-0

Isopropyl 6-methyl-4-(3-nitrophenyl)-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate

Conditions
ConditionsYield
With polyphosphate ester for 0.00833333h; Cyclization; Biginelli condensation; Irradiation;94%
With polyphosphonate ester In tetrahydrofuran for 24h; Biginelli cyclocondensation; Heating;94%
With ytterbium(III) triflate In toluene at 100℃; Biginelli Pyrimidone Synthesis;
542-08-5

isopropyl acetoacetate

591-31-1

3-methoxy-benzaldehyde

5-isopropoxycarbonyl-6-methyl-4-(3-methoxyphenyl)-3,4-dihydropyrimidin-2(1H)-thione

Conditions
ConditionsYield
With 1-butyl-3-carboxymethyl-benzotriazolium trifluoroacetate In neat (no solvent) at 90℃; for 0.666667h; Biginelli Pyrimidone Synthesis;94%
With Amberlyst 15-supported ytterbium(III) reagent at 120℃; for 48h; Biginelli reaction;73%
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    542-08-5

    Isopropyl Acetoacetate

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    542-08-5

    Isopropyl acetoacetate

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    542-08-5 Isopropyl acetoacetate

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    Acetoacetic acid isopropyl ester

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  • Isopropyl acetoacetate CAS NO 542-08-5

  • Casno:

    542-08-5

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Chemistry


IUPAC Name: Propan-2-yl 3-oxobutanoate
Molecular Formula: C7H12O3
Molecular Weight: 144.17 g/mol
Canonical SMILES: O=C(OC(C)C)CC(=O)C
InChI: InChI=1/C7H12O3/c1-5(2)10-7(9)4-6(3)8/h5H,4H2,1-3H3
EINECS: 208-798-4
Product Categories: Miscellaneous Reagents; C6 to C7; Carbonyl Compounds; Esters
XLogP3-AA: 0.8
H-Bond Acceptor: 3
Index of Refraction: 1.413
Molar Refractivity: 36.24 cm3
Molar Volume: 145 cm3
Polarizability: 14.36×10-24 cm3
Surface Tension: 29.4 dyne/cm
Density: 0.993 g/cm3
Flash Point: 68.9 °C
Enthalpy of Vaporization: 42.2 kJ/mol
Boiling Point: 185.8 °C at 760 mmHg
Melting Point: -27 °C
Vapour Pressure of Isopropyl acetoacetate (CAS NO.542-08-5): 0.686 mmHg at 25 °C

Uses

  Isopropyl acetoacetate (CAS NO.542-08-5) is used as intermediate for chemical synthesis.

Safety Profile

Hazard Codes: IrritantXi
Risk Statements: 38 
R38: Irritating to skin.
Safety Statements: 26-36 
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. 
S36: Wear suitable protective clothing.
WGK Germany of Isopropyl acetoacetate (CAS NO.542-08-5): 1

Specification

 Isopropyl acetoacetate (CAS NO.542-08-5), its Synonyms are Butanoic acid, 3-oxo-, 1-methylethyl ester ; 3-Oxo-butanoicaci1-methylethylester; Acetoaceticacid,isopropylester ; Acetoaceticacidisopropylester ; Isopropyl3-oxobutanoate . It is colourless liquid.