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372-31-6

Basic Information
CAS No.: 372-31-6
Name: Ethyl 4,4,4-trifluoroacetoacetate
Molecular Structure:
Molecular Structure of 372-31-6 (Ethyl 4,4,4-trifluoroacetoacetate)
Formula: C6H7F3O3
Molecular Weight: 184.11
Synonyms: ethyl 4,4,4-trifluoro-3-oxo-butanoate;Ethyl trifluoroacetoacetate;Acetoacetic acid, 4,4,4-trifluoro-, ethyl ester;Ethyl (trifluoroacetyl)acetate;Butanoic acid, 4,4,4-trifluoro-3-oxo-, ethyl ester;4,4,4 trifluor-3-oxoethylester;ethyl-4,4,4-trifluoroaceto acetate;Ethyl 4,4,-Trifluoroacetoacetate;Ethyl 3-oxo-4,4,4-trifluoroacetoacetate;Trifluoroacetyl ethyl acetate;
EINECS: 206-750-7
Density: 1.273 g/cm3
Melting Point: -39 °C
Boiling Point: 129.5 °C at 760 mmHg
Flash Point: 28.9 °C
Solubility: 10 g/L (20 °C) in water
Appearance: Clear liquid
Hazard Symbols: HarmfulXn, FlammableF, CorrosiveC, IrritantXi
Risk Codes: 10-22-52/53
Safety: 61-16
Transport Information: UN 3272 3/PG 3
PSA: 43.37000
LogP: 1.07100
Synthetic route
383-63-1

ethyl trifluoroacetate,

141-78-6

ethyl acetate

372-31-6

ethyl 4,4,4-trifluoroacetoacetate

Conditions
ConditionsYield
With sodium hydride In diethyl ether; paraffin reflux, 2 h and r.t., 12 h;85%
Stage #1: ethyl acetate With sodium ethanolate at 0 - 5℃; for 1h;
Stage #2: ethyl trifluoroacetate, at 0 - 65℃; for 25h;
70.7%
With diethyl ether; sodium ethanolate
867-13-0

diethoxyphosphoryl-acetic acid ethyl ester

400-53-3

trimethylsilyl trifluoroacetate

372-31-6

ethyl 4,4,4-trifluoroacetoacetate

Conditions
ConditionsYield
Stage #1: diethoxyphosphoryl-acetic acid ethyl ester With n-butyllithium In tetrahydrofuran
Stage #2: trimethylsilyl trifluoroacetate In tetrahydrofuran
Stage #3: With hydrogenchloride In tetrahydrofuran Further stages.;
55%
With n-butyllithium 1.) THF, -78 deg C, 20 min, 2.) THF, RT, 5 h; Yield given. Multistep reaction;
459-72-3

ethyl 2-fluoroacetate

454-31-9

ethyl difluoroacetate

372-31-6

ethyl 4,4,4-trifluoroacetoacetate

Conditions
ConditionsYield
With sodium hydride
652-71-1

Trifluoracetyl-glyoxylsaeure-aethylester-α-hydrazon

372-31-6

ethyl 4,4,4-trifluoroacetoacetate

Conditions
ConditionsYield
With quinoline In ethanol
2707-65-5

3-acetoxy-4,4,4-trifluoro-but-2-enoic acid ethyl ester

372-31-6

ethyl 4,4,4-trifluoroacetoacetate

Conditions
ConditionsYield
With sodium tetrahydroborate In ethanol
383-63-1

ethyl trifluoroacetate,

141-78-6

ethyl acetate

A

197850-97-8

Aethyl-γ,γ,γ-trifluoracetoacetat-hydrat

B

372-31-6

ethyl 4,4,4-trifluoroacetoacetate

Conditions
ConditionsYield
With ethanol; sulfuric acid; sodium at 90℃; for 48h; Heating;
With sodium ethanolate In ethanol for 48h; Heating;
129657-54-1

3-tert-Butylperoxy-4,4,4-trifluoro-3-hydroxy-butyric acid ethyl ester

A

75-91-2

tert.-butylhydroperoxide

B

372-31-6

ethyl 4,4,4-trifluoroacetoacetate

Conditions
ConditionsYield
In tetrachloromethane at 20℃; Equilibrium constant; Rate constant;
64-17-5

ethanol

693817-83-3

2,2-Dimethyl-5-(2,2,2-trifluoro-1-hydroxy-ethylidene)-[1,3]dioxane-4,6-dione

372-31-6

ethyl 4,4,4-trifluoroacetoacetate

Conditions
ConditionsYield
at 70℃; for 6h; Ring cleavage; Decarboxylation;
141-78-6

ethyl acetate

sodium compound of orthotrifluoroacetic acid diethyl ester

sodium compound of orthotrifluoroacetic acid diethyl ester

372-31-6

ethyl 4,4,4-trifluoroacetoacetate

60-29-7

diethyl ether

383-63-1

ethyl trifluoroacetate,

sodium

sodium

372-31-6

ethyl 4,4,4-trifluoroacetoacetate

197850-97-8

Aethyl-γ,γ,γ-trifluoracetoacetat-hydrat

A

106260-08-6

ethyl 3-trifluoromethyl-3-oxo-propionate

B

372-31-6

ethyl 4,4,4-trifluoroacetoacetate

Conditions
ConditionsYield
In tetrahydrofuran-d8 Equilibrium constant;
106260-08-6

ethyl 3-trifluoromethyl-3-oxo-propionate

A

197850-97-8

Aethyl-γ,γ,γ-trifluoracetoacetat-hydrat

B

372-31-6

ethyl 4,4,4-trifluoroacetoacetate

Conditions
ConditionsYield
With water In tetrahydrofuran-d8 Equilibrium constant;
623-73-4

diazoacetic acid ethyl ester

433-27-2

Trifluoroacetaldehyde ethyl hemiacetal

372-31-6

ethyl 4,4,4-trifluoroacetoacetate

Conditions
ConditionsYield
Stage #1: ethyl trifluoroacetaldehyde hemiacetal With sulfuric acid at 70 - 150℃; for 0.133333h; microwave irradiation;
Stage #2: diazoacetic acid ethyl ester In dichloromethane at 20℃; for 0.25h; Further stages.;
15 % Chromat.
18955-75-4

ethyl 2-diazo-3-oxo-4,4,4-trifluorobutyrate

372-31-6

ethyl 4,4,4-trifluoroacetoacetate

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: diisopropyl ether
2: H2O; methanol / Heating
3: quinoline / ethanol
View Scheme
2559-41-3

Trifluoracetyl-glyoxylsaeure-aethylester-triphenylphosphazin-(2)

372-31-6

ethyl 4,4,4-trifluoroacetoacetate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: H2O; methanol / Heating
2: quinoline / ethanol
View Scheme
22466-45-1

sodium 4-ethoxy-1,1,1-trifluoro-4-oxobut-2-en-2-olate

372-31-6

ethyl 4,4,4-trifluoroacetoacetate

Conditions
ConditionsYield
With hydrogenchloride In water at 5 - 10℃; for 3h; pH=1 - 3;
421-50-1

1,1,1-trifluoro-2-propanone

105-58-8

Diethyl carbonate

372-31-6

ethyl 4,4,4-trifluoroacetoacetate

Conditions
ConditionsYield
With sodium hydride In toluene Inert atmosphere; Reflux;
372-31-6

ethyl 4,4,4-trifluoroacetoacetate

N-(4-hydroxy-6-trifluoromethyl-pyrimidin-2-yl)-guanidine

Conditions
ConditionsYield
Stage #1: biguanide sulfate With sodium hydroxide In ethanol at 0 - 20℃;
Stage #2: ethyl 4,4,4-trifluoroacetoacetate In ethanol for 2.5h; Heating; Further stages.;
100%
372-31-6

ethyl 4,4,4-trifluoroacetoacetate

100-51-6

benzyl alcohol

83097-87-4

benzyl 4,4,4-trifluoroacetoacetate

Conditions
ConditionsYield
In toluene at 120℃; for 5h; Dean-Stark;100%
In toluene Heating;
372-31-6

ethyl 4,4,4-trifluoroacetoacetate

68761-48-8

4-(2-hydroxy-benzylidene)-5-methyl-2-phenyl-2,4-dihydro-pyrazol-3-one

5-ethoxylcarbonyl-6-hydroxy-4-(2-hydroxyphenyl)-1-phenyl-3-methyl-6-(trifluoromethyl)-1,4,5,6-tetrahydropyrazolo[3,4-b]pyran

Conditions
ConditionsYield
With ammonium acetate In ethanol at 20℃; for 2h;100%
555-75-9

aluminum ethoxide

372-31-6

ethyl 4,4,4-trifluoroacetoacetate

123-54-6

acetylacetone

monoacetylacetonate aluminum bis(ethyl-4,4,4-trifluoroacetoacetate)

Conditions
ConditionsYield
In toluene at 20℃; for 24h;100%
372-31-6

ethyl 4,4,4-trifluoroacetoacetate

363-58-6

ethyl 2-chloro-4,4,4-trifluoro-3-oxobutanoate

Conditions
ConditionsYield
With sulfuryl dichloride In dichloromethane at -5 - 20℃;99.3%
With chlorine In acetone95%
With chlorine at 0 - 30℃; Cooling with acetone-dry ice;95%
372-31-6

ethyl 4,4,4-trifluoroacetoacetate

108-46-3

recorcinol

575-03-1

7-hydroxy-4-(trifluoromethyl)-2H-chromen-2-one

Conditions
ConditionsYield
With iodine In toluene at 80℃; Pechmann reaction;99%
With magnesium bis(trifluoromethane solfonyl)imide In neat (no solvent) at 80℃; for 0.416667h; Pechmann Condensation;97%
indium(III) chloride at 65℃; for 0.5h; von Pechmann reaction;96%
372-31-6

ethyl 4,4,4-trifluoroacetoacetate

372-30-5

ethyl 3-hydroxy-4,4,4-trifluorobutyrate

Conditions
ConditionsYield
With formic acid; C18H24ClIrN3 In water at 80℃; for 8h; Schlenk technique; Inert atmosphere; chemoselective reaction;99%
With sodium tetrahydroborate In diethyl ether 1.) 0-5 deg C, 1 h, 2.) r.t., overnight;98%
With sodium tetrahydroborate In diethyl ether97%
22867-74-9

7-ethyl-1H-indole

372-31-6

ethyl 4,4,4-trifluoroacetoacetate

ethyl 3-(7-ethyl-1H-indol-3-yl)-4,4,4-trifluoro-3-hydroxybutanoate

Conditions
ConditionsYield
With (S)-3,3'-bis(2,4,6-tri-iso-propylphenyl)-1,1'-binaphthyl-2,2'-diyl hydrogenphosphate In dichloromethane at 20℃; for 76h; Friedel-Crafts reaction; optical yield given as %ee; enantioselective reaction;99%
104-86-9

4-chlorobenzylamine

372-31-6

ethyl 4,4,4-trifluoroacetoacetate

1384849-55-1

ethyl 3-(4-chlorobenzyl)amino-4,4,4-trifluorobut-2-enoate

Conditions
ConditionsYield
Stage #1: 4-chlorobenzylamine With acetic acid In chloroform at 20℃; for 0.0833333h;
Stage #2: ethyl 4,4,4-trifluoroacetoacetate In chloroform for 5h; Reflux;
99%
2536-91-6

6-methylbenzothiazol-2-ylamine

372-31-6

ethyl 4,4,4-trifluoroacetoacetate

8-methyl-2-(trifluoromethyl)-4H-benzo[4,5]thiazolo[3,2-a]pyrimidin-4-one

Conditions
ConditionsYield
With indium(III) triflate In toluene at 100℃; for 16h; regioselective reaction;99%
17852-52-7, 27918-19-0

4-hydrazinobenzene-1-sulfonamide hydrochloride

372-31-6

ethyl 4,4,4-trifluoroacetoacetate

627094-59-1

4-(5-hydroxy-3-(trifluoromethyl)-1H-pyrazol-1-yl)benzenesulfonamide

Conditions
ConditionsYield
In ethanol at 24℃; Reflux; Inert atmosphere;99%
504-02-9

1,3-cylohexanedione

372-31-6

ethyl 4,4,4-trifluoroacetoacetate

4-(trifluoromethyl)-7,8-dihydro-2H-chromene-2,5(6H)-dione

Conditions
ConditionsYield
With 2-(Dimethylamino)pyridine In 1,2-dichloro-ethane at 120℃; for 16h; Catalytic behavior; Reagent/catalyst; Solvent; Temperature; Pechmann Condensation; Glovebox; Inert atmosphere;99%
4341-24-6

5-methylcyclohexan-1,3-dione

372-31-6

ethyl 4,4,4-trifluoroacetoacetate

7-methyl-4-(trifluoromethyl)-7,8-dihydro-2H-chromene-2,5(6H)-dione

Conditions
ConditionsYield
With 2-(Dimethylamino)pyridine In 1,2-dichloro-ethane at 120℃; for 16h; Pechmann Condensation; Glovebox; Inert atmosphere;99%
126-81-8

dimedone

372-31-6

ethyl 4,4,4-trifluoroacetoacetate

7,7-dimethyl-4-(trifluoromethyl)-7,8-dihydro-2H-chromene-2,5(6H)-dione

Conditions
ConditionsYield
With 2-(Dimethylamino)pyridine In 1,2-dichloro-ethane at 120℃; for 16h; Pechmann Condensation; Glovebox; Inert atmosphere;99%
493-72-1

5-phenyl-cyclohexane-1,3-dione

372-31-6

ethyl 4,4,4-trifluoroacetoacetate

7-phenyl-4-(trifluoromethyl)-7,8-dihydro-2H-chromene-2,5(6H)-dione

Conditions
ConditionsYield
With 2-(Dimethylamino)pyridine In 1,2-dichloro-ethane at 120℃; for 16h; Pechmann Condensation; Glovebox; Inert atmosphere;99%
372-31-6

ethyl 4,4,4-trifluoroacetoacetate

4392-54-5

4-aminosulfonylphenylhydrazine

627094-59-1

4-(5-hydroxy-3-(trifluoromethyl)-1H-pyrazol-1-yl)benzenesulfonamide

Conditions
ConditionsYield
In ethanol for 12h; Reflux;99%
122-51-0

orthoformic acid triethyl ester

372-31-6

ethyl 4,4,4-trifluoroacetoacetate

571-55-1

ethyl 2-(ethoxymethylidene)-4,4,4-trifluoro-3-oxobutanoate

Conditions
ConditionsYield
With acetic anhydride at 120 - 140℃; for 7h; Condensation;98%
With acetic anhydride at 135℃; for 18h;97.1%
In acetic anhydride for 8h; Reflux;95%
372-31-6

ethyl 4,4,4-trifluoroacetoacetate

76480-99-4

5-(trifluoromethyl)-4-pyrazolin-3-one

Conditions
ConditionsYield
With hydrazine hydrate In ethanol; water for 18h; Heating;98%
With water; hydrazine hydrate
With ethanol; hydrazine hydrate
28491-52-3

5-amino-1,2-dihydropyrazol-3-one

372-31-6

ethyl 4,4,4-trifluoroacetoacetate

4-trifluoromethyl-6-hydroxy-3-oxo-2,3-dihydropyrazolo<3,4-b>pyridine

Conditions
ConditionsYield
With acetic acid for 2h; Heating;98%
372-31-6

ethyl 4,4,4-trifluoroacetoacetate

591-27-5

m-Hydroxyaniline

53518-15-3

Coumarin 151

Conditions
ConditionsYield
With magnesium bis(trifluoromethane solfonyl)imide In neat (no solvent) at 80℃; for 0.416667h; Pechmann Condensation;98%
With sulfuric acid In ethanol at 80℃;83%
With zinc(II) chloride In ethanol for 12h; Heating;69%
With zinc(II) chloride In ethanol Reflux;12%
With zinc(II) chloride In ethanol for 12h; Reflux;
372-31-6

ethyl 4,4,4-trifluoroacetoacetate

141860-78-8

ethyl 3-amino-4,4,4-trifluorocrotonate

Conditions
ConditionsYield
With ammonium acetate In cyclohexane; isopropyl alcohol98%
With ammonium acetate In ethanol; water88%
With ammonia
20880-92-6

2,3;4,5-di-O-isopropylidene-β-D-fructopyranose

372-31-6

ethyl 4,4,4-trifluoroacetoacetate

4,4,4-Trifluoro-3-oxo-butyric acid (3aS,5aR,8aR,8bS)-2,2,7,7-tetramethyl-tetrahydro-bis[1,3]dioxolo[4,5-b;4',5'-d]pyran-3a-ylmethyl ester

Conditions
ConditionsYield
With vermiculite In toluene for 48h; Heating;98%
4099-85-8

((3aR,4R,6R,6aR)-6-methoxy-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)methanol

372-31-6

ethyl 4,4,4-trifluoroacetoacetate

4,4,4-Trifluoro-3-oxo-butyric acid (3aR,4R,6R,6aR)-6-methoxy-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-ylmethyl ester

Conditions
ConditionsYield
With vermiculite In toluene for 48h; Heating;98%
120-72-9

indole

372-31-6

ethyl 4,4,4-trifluoroacetoacetate

3-hydroxy-3-(indol-3-yl)-4,4,4-trifluorobutanoic acid ethyl ester

Conditions
ConditionsYield
With K-10 montmorillonite In toluene at 70℃; for 1h; Friedel-Crafts hydroxyalkylation;98%
95-20-5

2-methyl-1H-indole

372-31-6

ethyl 4,4,4-trifluoroacetoacetate

3-hydroxy-3-(2-methylindol-3-yl)-4,4,4-trifluorobutanoic acid ethyl ester

Conditions
ConditionsYield
With K-10 montmorillonite In toluene at 70℃; for 0.75h; Friedel-Crafts hydroxyalkylation;98%
109-97-7

pyrrole

372-31-6

ethyl 4,4,4-trifluoroacetoacetate

3-hydroxy-3-(pyrrol-2-yl)-4,4,4-trifluorobutanoic acid ethyl ester

Conditions
ConditionsYield
With K-10 montmorillonite In toluene at 70℃; for 0.5h; Friedel-Crafts hydroxyalkylation;98%
100-63-0

phenylhydrazine

372-31-6

ethyl 4,4,4-trifluoroacetoacetate

321-07-3

1-phenyl-3-(trifluoromethyl)-1H-pyrazol-5(4H)-one

Conditions
ConditionsYield
at 150 - 160℃; for 3h;98%
With acetic acid for 6h; Reflux;90%
With acetic acid Reflux;90%
372-31-6

ethyl 4,4,4-trifluoroacetoacetate

85571-85-3

ethyl (3R)-4,4,4-trifluoro-3-hydroxybutanoate

Conditions
ConditionsYield
With α-D-glucose 6-phosphate; permeabilized cells of Bacillus pumilus Phe-C3; NADPH In various solvent(s) at 25℃; for 24h; pH=7.0;98%
With glucose dehydrogenase; pET28-bmgdh-cgcr; sodium carbonate In aq. phosphate buffer; toluene at 30℃; for 12h; pH=6.5; Enzymatic reaction; enantioselective reaction;92%
With nicotinamide adenine dinucleotide phosphate; isopropyl alcohol In dimethyl sulfoxide at 30℃; for 24h; pH=7.5; Reagent/catalyst; Enzymatic reaction; enantioselective reaction;66%
100-63-0

phenylhydrazine

372-31-6

ethyl 4,4,4-trifluoroacetoacetate

96145-98-1

1-phenyl-3-trifluoromethyl-5-hydroxypyrazole

Conditions
ConditionsYield
With acetic acid at 10 - 80℃; for 6.5h;98%
In ethanol at 24℃; for 12h; Reflux; Inert atmosphere;92%
In ethanol for 12h; Reflux;92%
372-31-6

ethyl 4,4,4-trifluoroacetoacetate

74-89-5

methylamine

507448-65-9

3-methylamino-4,4,4-trifluorobut-2-enoic acid ethyl ester

Conditions
ConditionsYield
With acetic acid In ethanol; methyl cyclohexane at 80 - 90℃; under 760.051 Torr; for 3 - 4h; Product distribution / selectivity;98%
With acetic acid In methyl cyclohexane at 80 - 85℃; for 3 - 8h; Product distribution / selectivity;88.5%
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    ethyl 4,4,4-trifluoroacetoacetate

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    high purity lowest priceOverview Quick Details CAS No.: 372-31-6 Other Names: ETHYL 3-OXO-4,4,4-TRIFLU

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    Ethyl 3-oxo-4,4,4-trifluoroacetoacetate

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    Ethyl 4,4,4-trifluoroacetoacetate Formula C6H7 F3 O3 Molecular Formula 184.1 CAS No. 372-31-6

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    Ethyl 4,4,4-trifluoroacetoacetate

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Chemistry

Molecular Structure of Ethyl 4,4,4-trifluoroacetoacetate (CAS NO.372-31-6):

IUPAC Name: Ethyl 4,4,4-trifluoro-3-oxobutanoate
Canonical SMILES: CCOC(=O)CC(=O)C(F)(F)F
InChI: InChI=1S/C6H7F3O3/c1-2-12-5(11)3-4(10)6(7,8)9/h2-3H2,1H3
InChIKey: OCJKUQIPRNZDTK-UHFFFAOYSA-N
Molecular Weight: 184.11319 [g/mol]
Molecular Formula: C6H7F3O3
XLogP3: 1.4
H-Bond Donor: 0
H-Bond Acceptor: 6 
EINECS: 206-750-7 
Storage temp.: Flammables area
Water Solubility: 10 g/L (20 °C)
Appearance: Clear liquid
Melting Point: -39 °C 
Index of Refraction: 1.362
Molar Refractivity: 32.1 cm3
Molar Volume: 144.5 cm3
Surface Tension: 25.3 dyne/cm
Density: 1.273 g/cm3
Flash Point: 28.9 °C
Enthalpy of Vaporization: 36.72 kJ/mol
Boiling Point: 129.5 °C at 760 mmHg
Vapour Pressure: 10.1 mmHg at 25 °C
Product Categories: Pharmaceutical Intermediates; Aliphatics; Esters; Organic Fluorides; Fluorochemicals; Fluorinated Building Blocks; Fluorinating Reagents & Building Blocks for Fluorinated Biochemical Compounds; Synthetic Organic Chemistry

Uses

 Ethyl 4,4,4-trifluoroacetoacetate (CAS NO.372-31-6) is used as intermediate for agro chemicals and pharmaceuticals (mefloquine).

Safety Profile

Safety Information of Ethyl 4,4,4-trifluoroacetoacetate (CAS NO.372-31-6):
Hazard Codes: HarmfulXnFlammableFCorrosiveC,IrritantXi
Risk Statements: 10-22-52/53 
R10:Flammable. 
R22:Harmful if swallowed. 
R52/53:Harmful to aquatic organisms, may cause long-term adverse effects in the aquatic environment.
Safety Statements: 61-16 
S16:Keep away from sources of ignition. 
S61:Avoid release to the environment. Refer to special instructions / safety data sheets.
RIDADR: UN 3272 3/PG 3
WGK Germany: 2
Hazard Note: Flammable/Corrosive
TSCA: T
HazardClass: 3
PackingGroup: III

Specification

 Ethyl 4,4,4-trifluoroacetoacetate (CAS NO.372-31-6), its Synonyms are Ethyl trifluoroacetoacetate ; Ethyl (trifluoroacetyl)acetate ; Acetoacetic acid, 4,4,4-trifluoro-, ethyl ester ; Butanoic acid, 4,4,4-trifluoro-3-oxo-, ethyl ester .