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542-08-5

Basic Information
CAS No.: 542-08-5
Name: Isopropyl acetoacetate
Article Data: 59
Cas Database
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: N/A
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
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    Isopropyl acetoacetate Chemical Properties Melting point -27°C Boiling point 95 °C52 hPa(lit.) density 0.989 g/mL at 20 °C(lit.) refractive index n20/D 1.418 Fp 73°C pka 11.67±0.46(Predicted) Water Solubi

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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.