Conditions | Yield |
---|---|
With N-fluorobis<(trifluoromethyl)sulfonyl>imide In dichloromethane; water at 22℃; for 8h; | 86% |
With N-fluorobis<(trifluoromethyl)sulfonyl>imide In dichloromethane; water at 22℃; for 8h; | 86% |
With trifluoroamine oxide; tetra(n-butyl)ammonium hydroxide In acetonitrile at 20℃; for 12h; | 85% |
acetyl hypofluorite
sodium ethyl acetylacetate enolate
ethyl-2-fluoroacetoacetate
Conditions | Yield |
---|---|
In tetrahydrofuran; trichlorofluoromethane at -75℃; for 0.0166667h; | 81% |
ethyl acetoacetate
A
ethyl-2-fluoroacetoacetate
B
2,2-difluoro-3-oxobutyric acid ethyl ester
C
ethyl 2,4-difluoro-3-oxobutanoate
Conditions | Yield |
---|---|
With fluorine In formic acid at 10 - 15℃; | A 80% B 1% C 10% |
With fluorine In formic acid at 10 - 15℃; for 2h; Yield given. Yields of byproduct given; |
perfluorobutanesulfonic acid
ethyl 2-chloro-3-oxo-butyrate
ethyl-2-fluoroacetoacetate
Conditions | Yield |
---|---|
With hydrogen fluoride at -10 - 20℃; Temperature; Inert atmosphere; | 68.51% |
ethyl 3-trimethylsiloxy-2-butenoate
ethyl-2-fluoroacetoacetate
Conditions | Yield |
---|---|
With fluorine In trichlorofluoromethane at -78℃; | 48% |
Conditions | Yield |
---|---|
With diethyl ether; sodium hydride |
ethyl 2-fluoroacetate
acetyl chloride
formic acid ethyl ester
ethyl-2-fluoroacetoacetate
Conditions | Yield |
---|---|
(i) NaOEt, (ii) /BRN= 605303/; Multistep reaction; |
2-chloro-1,2,2-trifluoroethyl methyl ketone
ethanol
ethyl-2-fluoroacetoacetate
Conditions | Yield |
---|---|
With hydrogenchloride; sodium 1.) 2 h, r.t.; 2.) 15 h, r.t.; Yield given. Multistep reaction; |
Conditions | Yield |
---|---|
Yield given. Multistep reaction; |
ethyl acetoacetate
A
ethyl-2-fluoroacetoacetate
B
2,2-difluoro-3-oxobutyric acid ethyl ester
Conditions | Yield |
---|---|
With 1-fluoro-2,4,6-trimethylpyridinium trifluoromethanesulfonate; zinc(II) chloride In 1,2-dichloro-ethane at 60℃; for 24h; | A 69 % Spectr. B 12 % Spectr. |
With 1-fluoro-2,4,6-trimethylpyridinium trifluoromethanesulfonate; zinc(II) chloride In 1,2-dichloro-ethane at 60℃; for 12h; | A 32 % Spectr. B 64 % Spectr. |
With 1-(chloromethyl)-4-fluoro-1,4-diazabicyclo[2.2.2]octane-1,4-diium tetrafluoroborate; cyclopentadienyl titanium(IV) trichloride In acetonitrile at 20℃; |
ethyl-2-fluoroacetoacetate
Conditions | Yield |
---|---|
With sodium hydrogencarbonate In tetrahydrofuran; water for 6h; Ambient temperature; Yield given; |
Chlorotrifluoroethylene
ethyl acetate
A
ethyl-2-fluoroacetoacetate
B
1,1,2,4,5,5-Hexafluoro-3-methyl-penta-1,4-dien-3-ol
Conditions | Yield |
---|---|
With sec.-butyllithium 1.) isopentane, ether, -60 deg C, 15 min, 2.) ether, -50 deg C, 40 min; Yield given. Multistep reaction. Yields of byproduct given; |
ethyl-2-fluoroacetoacetate
Conditions | Yield |
---|---|
With hydrogen cation |
ethyl-2-fluoroacetoacetate
Conditions | Yield |
---|---|
With diethyl ether; magnesium; ethyl acetate |
Conditions | Yield |
---|---|
anschliessendes Behandeln mit Acetylchlorid; |
Conditions | Yield |
---|---|
With hydrogen fluoride; triethylamine In acetonitrile |
[bis(acetoxy)iodo]benzene
ethyl acetoacetate
A
ethyl-2-fluoroacetoacetate
B
2,2-difluoro-3-oxobutyric acid ethyl ester
C
2-acetoxy-acetoacetic acid ethyl ester
Conditions | Yield |
---|---|
With triethylamine tris(hydrogen fluoride) In acetonitrile at 75℃; for 20h; Temperature; Inert atmosphere; | |
With triethylamine tris(hydrogen fluoride) In acetonitrile at 75℃; for 20h; Inert atmosphere; |
Conditions | Yield |
---|---|
Stage #1: formaldehyd; diethylamine In dichloromethane at 20℃; for 2h; Stage #2: ethyl-2-fluoroacetoacetate With sodium hydride In dichloromethane for 16h; Mannich Aminomethylation; | 100% |
cyclohexenone
ethyl-2-fluoroacetoacetate
ethyl α-acetyl-α-fluoro-3-oxocyclohexaneacetate
Conditions | Yield |
---|---|
With potassium fluoride In sulfolane for 24h; | 99% |
4-penten-3-one
ethyl-2-fluoroacetoacetate
2-Acetyl-2-fluoro-5-oxo-heptanoic acid ethyl ester
Conditions | Yield |
---|---|
With potassium fluoride In sulfolane for 1h; | 99% |
ethyl-2-fluoroacetoacetate
methyl vinyl ketone
ethyl 2-fluoro-2-acetyl-5-oxohexanoate
Conditions | Yield |
---|---|
With potassium fluoride In sulfolane for 10h; | 99% |
Conditions | Yield |
---|---|
With 2,6-di-tert-butyl-2,3,5,6-tetrahydro-1H-imidazo[1,2-a]imidazole In dichloromethane at -50℃; for 24h; Mannich reaction; optical yield given as %de; diastereoselective reaction; | 99% |
ethyl-2-fluoroacetoacetate
acetoxy-benzyloxycarbonylamino-acetic acid ethyl ester
Conditions | Yield |
---|---|
With C8H20N2*CHF3O3S In chloroform at 60℃; for 48h; Mannich Aminomethylation; stereoselective reaction; | 99% |
Conditions | Yield |
---|---|
With trans-1,2-(1S,2S)-1,2-diaminocyclohexane-N,N’-bis(2’-diphenylphosphinobenzoyl); N-ethyl-N,N-diisopropylamine; bis(η3-allyl-μ-chloropalladium(II)) In dichloromethane at 0℃; for 1.16667h; Product distribution / selectivity; | 98% |
With trans-1,2-(1S,2S)-1,2-diaminocyclohexane-N,N’-bis(2’-diphenylphosphinobenzoyl); Tri-n-octylamine; bis(η3-allyl-μ-chloropalladium(II)) In dichloromethane at 0℃; for 1.16667h; Product distribution / selectivity; | 92% |
With trans-1,2-(1S,2S)-1,2-diaminocyclohexane-N,N’-bis(2’-diphenylphosphinobenzoyl); triethylamine; bis(η3-allyl-μ-chloropalladium(II)) In dichloromethane at 0℃; for 1.16667h; Product distribution / selectivity; | 90% |
With trans-1,2-(1S,2S)-1,2-diaminocyclohexane-N,N’-bis(2’-diphenylphosphinobenzoyl); tetrahexylammonium bromide; sodium hydride; bis(η3-allyl-μ-chloropalladium(II)) In dichloromethane at 0℃; for 1.16667h; Product distribution / selectivity; | 87% |
With trans-1,2-(1S,2S)-1,2-diaminocyclohexane-N,N’-bis(2’-diphenylphosphinobenzoyl); sodium hydride; bis(η3-allyl-μ-chloropalladium(II)) In dichloromethane at 0℃; for 1.16667h; Product distribution / selectivity; | 65% |
ethyl-2-fluoroacetoacetate
Conditions | Yield |
---|---|
Stage #1: 1,3-di(m-bromophenyl)allyl acetate With bis(η3-allyl-μ-chloropalladium(II)); (R)-N-tert-butylsulfinyl-2-hydroxybenzamide In tetrahydrofuran; 1,4-dioxane at 20℃; for 0.166667h; Inert atmosphere; Stage #2: ethyl-2-fluoroacetoacetate With potassium phosphate In tetrahydrofuran; 1,4-dioxane at 20℃; Reagent/catalyst; Solvent; | 98% |
ethyl-2-fluoroacetoacetate
(E)-1,3-bis(3-chlorophenyl)-2-propen-1-yl acetate
Conditions | Yield |
---|---|
Stage #1: (E)-1,3-bis(3-chlorophenyl)-2-propen-1-yl acetate With bis(η3-allyl-μ-chloropalladium(II)); (R)-N-tert-butylsulfinyl-2-hydroxybenzamide In tetrahydrofuran; 1,4-dioxane at 20℃; for 0.5h; Inert atmosphere; Schlenk technique; Stage #2: ethyl-2-fluoroacetoacetate With potassium phosphate In tetrahydrofuran; 1,4-dioxane at 20℃; Reagent/catalyst; Solvent; Temperature; Inert atmosphere; Schlenk technique; | 98% |
ethyl-2-fluoroacetoacetate
Conditions | Yield |
---|---|
Stage #1: rac-(E)-1,3-bis(4-bromophenyl)-2-propen-1-yl acetate With bis(η3-allyl-μ-chloropalladium(II)); (R)-N-tert-butylsulfinyl-2-hydroxybenzamide In tetrahydrofuran; 1,4-dioxane at 20℃; for 0.5h; Inert atmosphere; Schlenk technique; Stage #2: ethyl-2-fluoroacetoacetate With potassium phosphate In tetrahydrofuran; 1,4-dioxane at 20℃; Inert atmosphere; Schlenk technique; | 98% |
Conditions | Yield |
---|---|
Stage #1: pyrrolidine; formaldehyd In dichloromethane at 20℃; for 2h; Stage #2: ethyl-2-fluoroacetoacetate In dichloromethane for 16h; Mannich Aminomethylation; | 98% |
Conditions | Yield |
---|---|
Stage #1: formaldehyd; benzyl-methyl-amine In dichloromethane at 20℃; for 2h; Stage #2: ethyl-2-fluoroacetoacetate With sodium hydride In dichloromethane for 16h; Mannich Aminomethylation; | 98% |
Conditions | Yield |
---|---|
Stage #1: piperidine; formaldehyd In dichloromethane at 20℃; for 2h; Stage #2: ethyl-2-fluoroacetoacetate In dichloromethane for 16h; Mannich Aminomethylation; | 98% |
ethyl-2-fluoroacetoacetate
Conditions | Yield |
---|---|
Stage #1: rac-(E)-1,3-bis(4-chlorophenyl)-2-propen-1-yl acetate With bis(η3-allyl-μ-chloropalladium(II)); (R)-N-tert-butylsulfinyl-2-hydroxybenzamide In tetrahydrofuran; 1,4-dioxane at 20℃; for 0.5h; Inert atmosphere; Schlenk technique; Stage #2: ethyl-2-fluoroacetoacetate With potassium phosphate In tetrahydrofuran; 1,4-dioxane at 20℃; Inert atmosphere; Schlenk technique; | 97% |
ethyl-2-fluoroacetoacetate
2-methoxyresorcinol
3-fluoro-7-hydroxy-8-methoxy-4-methyl-2H-1-benzopyran-2-one
Conditions | Yield |
---|---|
With perchloric acid at 20℃; Pechmann condensation; | 96% |
In 1,4-dioxane at 20℃; Pechmann Condensation; Acidic conditions; |
Conditions | Yield |
---|---|
With copper(II) acetate hydrate; 2-ethyl-1,3-oxazoline; copper(l) chloride In isopropyl alcohol at 20℃; regioselective reaction; | 96% |
Conditions | Yield |
---|---|
With trifluorormethanesulfonic acid; (S)-N1-(2-adamantyl)-3,3-dimethylbutane-1,2-diamine; 4-nitro-benzoic acid In dichloromethane at 20℃; Michael Addition; enantioselective reaction; | 96% |
Conditions | Yield |
---|---|
Stage #1: formaldehyd; diisopropylamine In dichloromethane at 20℃; for 2h; Stage #2: ethyl-2-fluoroacetoacetate With sodium hydride In dichloromethane for 16h; Mannich Aminomethylation; | 95% |
ethyl-2-fluoroacetoacetate
trans-4'-(trifluoromethyl)chalcone
Conditions | Yield |
---|---|
With caesium carbonate In acetonitrile at 120℃; for 4h; | 94% |
ethyl-2-fluoroacetoacetate
Conditions | Yield |
---|---|
With caesium carbonate In acetonitrile at 70℃; for 0.5h; | 94% |
ethyl-2-fluoroacetoacetate
rac-(E)-1,3-bis(3-bromophenyl)-2-propen-1-yl acetate
Conditions | Yield |
---|---|
Stage #1: rac-(E)-1,3-bis(3-bromophenyl)-2-propen-1-yl acetate With bis(η3-allyl-μ-chloropalladium(II)); (R)-N-tert-butylsulfinyl-2-hydroxybenzamide In tetrahydrofuran; 1,4-dioxane at 20℃; for 0.5h; Inert atmosphere; Schlenk technique; Stage #2: ethyl-2-fluoroacetoacetate With potassium phosphate In tetrahydrofuran; 1,4-dioxane at 20℃; Inert atmosphere; Schlenk technique; | 94% |
ethyl-2-fluoroacetoacetate
benzalacetophenone
1-Fluor-6-oxo-2,4-diphenyl-cyclohexen-(4)-carbonsaeure-(1)-aethylester
Conditions | Yield |
---|---|
With caesium carbonate In acetonitrile at 20℃; for 24h; | 93% |
With N-benzyl-trimethylammonium hydroxide; triethylamine In ethanol |
ethyl-2-fluoroacetoacetate
1-iodo-2-phenylethyne
(E)-ethyl 2-ethanoyl-2-fluoro-4-iodo-3-phenylbut-3-enoate
Conditions | Yield |
---|---|
With indium(III) tris[bis(trifluoromethanesulfonyl)amide] In toluene at 70℃; for 16h; Darkness; regioselective reaction; | 93% |
ethyl-2-fluoroacetoacetate
4-fluorochalcone
4-fluoro-[1,1':3',1''-terphenyl]-5'-ol
Conditions | Yield |
---|---|
With caesium carbonate In acetonitrile at 120℃; for 4h; | 93% |
ethyl-2-fluoroacetoacetate
(E)-3-(4-nitrophenyl)-1-phenylprop-2-en-1-one
4-nitro-[1,1':3',1"-terphenyl]-5'-phenol
Conditions | Yield |
---|---|
With caesium carbonate In acetonitrile at 120℃; for 4h; | 93% |
ethyl-2-fluoroacetoacetate
trans-4'-(trifluoromethyl)chalcone
Conditions | Yield |
---|---|
With caesium carbonate In acetonitrile at 70℃; for 0.5h; | 93% |
ethyl-2-fluoroacetoacetate
(E)-1-Phenyl-3-pyrid-3-yl-propenon
Conditions | Yield |
---|---|
With caesium carbonate In acetonitrile at 120℃; for 4h; | 93% |
ethyl-2-fluoroacetoacetate
(Z)-2-fluoro-1-phenyl-3-(4-(trifluoromethyl)phenyl)prop-2-en-1-one
Conditions | Yield |
---|---|
With caesium carbonate In acetonitrile at 120℃; for 4h; | 93% |
ethyl-2-fluoroacetoacetate
Conditions | Yield |
---|---|
With caesium carbonate In acetonitrile at 120℃; for 4h; | 93% |
ethyl-2-fluoroacetoacetate
4-chlorochalcone
4-chloro-[1,1':3',1''-terphenyl]-5'-ol
Conditions | Yield |
---|---|
With caesium carbonate In acetonitrile at 120℃; for 4h; | 93% |
Molecular Formula: C6H9FO3
Molar mass: 148.1323 g/mol
Density: 1.105 g/cm3
Flash Point: 55.6 °C
Index of Refraction: 1.39
Boiling Point: 170.1 °C at 760 mmHg
Vapour Pressure: 1.5 mmHg at 25°C
Appearance: Clear colorless liquid
Product categories of Ethyl 2-fluoroacetoacetate (1522-41-4): Carbonyl Compounds;Esters
Structure of Ethyl 2-fluoroacetoacetate (1522-41-4):
XLogP3-AA: 0.8
H-Bond Donor: 0
H-Bond Acceptor: 4
Systematic Name: Ethyl 2-fluoro-3-oxo-butanoate
SMILES: O=C(C(F)C(=O)OCC)C
InChI: InChI=1/C6H9FO3/c1-3-10-6(9)5(7)4(2)8/h5H,3H2,1-2H3
InChIKey: SHTFQLHOTAJQRJ-UHFFFAOYAK
Std. InChI: InChI=1S/C6H9FO3/c1-3-10-6(9)5(7)4(2)8/h5H,3H2,1-2H3
Std. InChIKey: SHTFQLHOTAJQRJ-UHFFFAOYSA-N
Hazard Codes: Xi
Risk Statements:
36: Irritating to the eyes
37: Irritating to the respiratory system
38: Irritating to the skin
Safety Statements:
26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice
36: Wear suitable protective clothing
Ethyl 2-fluoroacetoacetate (1522-41-4) also can be called Butanoic acid, 2-fluoro-3-oxo-, ethyl ester and 3-Fluoropyridine-2-carboxylic acid .
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