2,2,6-trimethyl-4H-1,3-dioxin-4-one
isopropyl alcohol
isopropyl acetoacetate
Conditions | Yield |
---|---|
With sodium acetate for 24h; Reflux; | 98% |
Esterification; | 92% |
In 5,5-dimethyl-1,3-cyclohexadiene at 150℃; for 3h; | 55% |
Conditions | Yield |
---|---|
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% |
4-methyleneoxetan-2-one
(E)-3-phenylpropenal
titanium(IV)isopropoxide
B
isopropyl acetoacetate
Conditions | Yield |
---|---|
In dichloromethane | A 88% B n/a |
Conditions | Yield |
---|---|
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% |
Conditions | Yield |
---|---|
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% |
isopropyl 4-bromo-3-oxobutanoate
triphenylphosphine
A
isopropyl acetoacetate
Conditions | Yield |
---|---|
In benzene for 24h; Ambient temperature; Yields of byproduct given; | A n/a B 82.9% |
Conditions | Yield |
---|---|
With triethylamine for 5h; Ambient temperature; | 77.5% |
Isopropyl acetate
methyl (2S)-N-tritylaziridine-2-carboxylate
A
isopropyl acetoacetate
B
(4S)-3-oxo-4,5-(N-triphenylmethylepimino)pentanoic acid isopropyl ester
Conditions | Yield |
---|---|
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% |
cycl-isopropylidene malonate
acetyl chloride
isopropyl alcohol
isopropyl acetoacetate
Conditions | Yield |
---|---|
Stage #1: cycl-isopropylidene malonate; acetyl chloride With pyridine In dichloromethane at 0 - 20℃; for 2h; Stage #2: isopropyl alcohol for 2h; Reflux; | 65% |
Isopropyl acetate
isopropylmagnesium chloride
A
isopropyl acetoacetate
B
3-hydroxy-3,4-dimethyl-valeric acid isopropyl ester
Conditions | Yield |
---|---|
With diethyl ether |
Conditions | Yield |
---|---|
Geschwindigkeit; |
Conditions | Yield |
---|---|
With sodium isopropylate at 87℃; | |
With diethyl ether; ammonia; sodium amide | |
With sodium | |
(i) LiNH2, liq. NH3, (ii) Ph2CO; Multistep reaction; |
Conditions | Yield |
---|---|
With triethylamine In diethyl ether |
1-<(Carboisopropoxy)methylthio>ethylidenyldimethylammonium Iodide
1-<(Carboethoxy)methylthio>pentylidenyldimethylammonium Iodide
A
Ethyl 3-oxoheptanoate
B
isopropyl acetoacetate
C
ethyl acetoacetate
D
Isopropyl 3-Oxoheptanoate
Conditions | Yield |
---|---|
With bis [3-dimethyl-amino-1-propyl] phenyl phosphine In acetonitrile Mechanism; Heating; |
isopropyl alcohol
2,4-dioxo-6-methyl-3,4-dihydro-2H-1,3-oxazine
isopropyl acetoacetate
Conditions | Yield |
---|---|
With triethylamine Heating; |
isopropyl 4-bromo-3-oxobutanoate
triphenylphosphine
A
isopropyl acetoacetate
Conditions | Yield |
---|---|
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 |
5-(1-hydroxyethylidene)-2,2-dimethyl-1,3-dioxane-4,6-dione
isopropyl alcohol
isopropyl acetoacetate
Conditions | Yield |
---|---|
In toluene Heating; |
4-methyleneoxetan-2-one
(E)-3-phenylpropenal
titanium(IV)isopropoxide
A
isopropyl acetoacetate
Conditions | Yield |
---|---|
With (S)-[1,1']-binaphthalenyl-2,2'-diol In dichloromethane at 20℃; for 24h; Title compound not separated from byproducts; |
S-phenyl thioacetate
S-phenyl 3-oxobutanethioate
isopropyl alcohol
A
Isopropyl acetate
B
isopropyl acetoacetate
Conditions | Yield |
---|---|
With silver trifluoroacetate In chloroform for 3h; |
isopropyl acetoacetate
isopropyl 3-aminocrotonate
Conditions | Yield |
---|---|
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% |
isopropyl acetoacetate
isopropyl ester of (R)-3-hydroxybutanoic acid
Conditions | Yield |
---|---|
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. |
isopropyl acetoacetate
2-chloro-benzaldehyde
2-[1-(2-Chloro-phenyl)-meth-(Z)-ylidene]-3-oxo-butyric acid isopropyl ester
Conditions | Yield |
---|---|
With piperdinium acetate In isopropyl alcohol at 45 - 55℃; | 100% |
isopropyl acetoacetate
N,N-dimethyl-formamide dimethyl acetal
isopropyl 2-((dimethylamino)methylene)-3-oxobutanoate
Conditions | Yield |
---|---|
at 20℃; | 100% |
at 20℃; | 100% |
at 20℃; | 100% |
In chloroform for 1h; Heating; |
isopropyl acetoacetate
methyl iodide
rac-isopropyl 2-methyl-3-oxobutanoate
Conditions | Yield |
---|---|
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% |
Conditions | Yield |
---|---|
With toluene-4-sulfonic acid In ethanol at 80℃; for 12h; Reagent/catalyst; Friedlaender Quinoline Synthesis; Schlenk technique; | 99% |
Conditions | Yield |
---|---|
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% |
Conditions | Yield |
---|---|
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; |
Conditions | Yield |
---|---|
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% |
Conditions | Yield |
---|---|
With 1-butyl-3-carboxymethyl-benzotriazolium trifluoroacetate In neat (no solvent) at 90℃; for 0.666667h; Biginelli Pyrimidone Synthesis; | 98% |
Conditions | Yield |
---|---|
With isopropyl alcohol In water at 60℃; for 48h; Biginelli Pyrimidone Synthesis; Enzymatic reaction; | 98% |
Conditions | Yield |
---|---|
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% |
Conditions | Yield |
---|---|
With [Ir(cod)2]SbF6; 2,2'-bis(diphenylphosphino)biphenyl for 24h; Reflux; diastereoselective reaction; | 98% |
Conditions | Yield |
---|---|
With pyridine; magnesium chloride In dichloromethane at 0 - 20℃; for 16h; | 97% |
isopropyl acetoacetate
thiourea
Conditions | Yield |
---|---|
With erythrosine B; oxygen In acetonitrile at 20℃; for 8h; Irradiation; Green chemistry; | 97% |
Conditions | Yield |
---|---|
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% |
isopropyl acetoacetate
anthranilic acid amide
2,2-dimethyl-2,3-dihydro-1H-quinazolin-4-one
Conditions | Yield |
---|---|
With Candida antarctica lipase B In hexane; water at 50℃; for 40h; Enzymatic reaction; | 97% |
isopropyl acetoacetate
iso-propyl (S)-(+)-3-hydroxybutyrate
Conditions | Yield |
---|---|
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 |
Conditions | Yield |
---|---|
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; |
Conditions | Yield |
---|---|
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; |
isopropyl acetoacetate
2-chloro-benzaldehyde
urea
(±)-isopropyl 4-(2-chlorophenyl)-6-methyl-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate
Conditions | Yield |
---|---|
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% |
isopropyl acetoacetate
(Z)-isopropyl 3-phenoxybut-2-enoate
Conditions | Yield |
---|---|
With copper(l) iodide; lithium carbonate In 1,4-dioxane at 70℃; for 60h; Inert atmosphere; Sealed tube; regioselective reaction; | 96% |
isopropyl acetoacetate
isopropyl 3-aminocrotonate
Conditions | Yield |
---|---|
With ammonia In dichloromethane | 95% |
With ammonia at 10℃; | 89% |
With ammonia In ethanol |
tryptamine
isopropyl acetoacetate
3-phenyl-propenal
(2S,12bS)-isopropyl 4-methyl-2-phenyl-1,2,6,7,12,12b-hexahydroindolo[2,3-a]quinolizine-3-carboxylate
Conditions | Yield |
---|---|
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% |
Conditions | Yield |
---|---|
With C23H3BF16N2O; ammonium acetate In toluene at 100℃; for 10h; Hantzsch Dihydropyridine Synthesis; | 95% |
Conditions | Yield |
---|---|
With C23H3BF16N2O; ammonium acetate In toluene at 100℃; for 10h; Hantzsch Dihydropyridine Synthesis; | 95% |
isopropyl acetoacetate
3-nitro-benzaldehyde
urea
Isopropyl 6-methyl-4-(3-nitrophenyl)-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate
Conditions | Yield |
---|---|
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; |
Conditions | Yield |
---|---|
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% |
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
Isopropyl acetoacetate (CAS NO.542-08-5) is used as intermediate for chemical synthesis.
Hazard Codes: Xi
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
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.
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