Ethyl 4,4,4-trifluoroacetoacetate supplier

Name
Ethyl 4,4,4-trifluoroacetoacetate
EINECS 206-750-7
CAS No. 372-31-6
Article Data34
CAS DataBase
Density 1.273 g/cm³
Solubility 10 g/L (20 °C) in water
Melting Point -39 °C
Formula C₆H₇F₃O₃
Boiling Point 129.5 °C at 760 mmHg
Molecular Weight 184.115
Flash Point 28.9 °C
Transport Information UN 3272 3/PG 3
Appearance Clear liquid
Safety 61-16
Risk Codes 10-22-52/53
Molecular Structure
Hazard Symbols Xn, F, C, Xi
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;
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
With sodium hydride

: 652-71-1
Trifluoracetyl-glyoxylsaeure-aethylester-α-hydrazon

: 372-31-6
ethyl 4,4,4-trifluoroacetoacetate

Conditions

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
With ethanol; sulfuric acid; sodium at 90℃; for 48h; Heating;
With sodium ethanolate In ethanol for 48h; Heating;

...Expand

: 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

Conditions	Yield
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

Conditions	Yield
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

...Expand

: 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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
With sodium hydride In toluene Inert atmosphere; Reflux;

: 2583-53-1, 6945-23-9, 49719-55-3
biguanide sulfate

: 372-31-6
ethyl 4,4,4-trifluoroacetoacetate

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

Conditions

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
In toluene at 20℃; for 24h;	100%

...Expand

: 372-31-6
ethyl 4,4,4-trifluoroacetoacetate

: 363-58-6
ethyl 2-chloro-4,4,4-trifluoro-3-oxobutanoate

Conditions

Conditions	Yield
With sulfuryl dichloride In dichloromethane at -5 - 20℃;	99.3%
With chlorine In acetone	95%
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

Conditions	Yield
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

Conditions	Yield
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 ether	97%

: 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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
With ammonium acetate In cyclohexane; isopropyl alcohol	98%
With ammonium acetate In ethanol; water	88%
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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%

Ethyl 4,4,4-trifluoroacetoacetate Chemical Properties

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

Ethyl 4,4,4-trifluoroacetoacetate Uses

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

Ethyl 4,4,4-trifluoroacetoacetate Safety Profile

Safety Information of Ethyl 4,4,4-trifluoroacetoacetate (CAS NO.372-31-6):
Hazard Codes: Harmful XnF Corrosive C, Irritant Xi
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

Ethyl 4,4,4-trifluoroacetoacetate 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 .

Product Name

Ethyl 4,4,4-trifluoroacetoacetate

Synthetic route

Ethyl 4,4,4-trifluoroacetoacetate Chemical Properties

Ethyl 4,4,4-trifluoroacetoacetate Uses

Ethyl 4,4,4-trifluoroacetoacetate Safety Profile

Ethyl 4,4,4-trifluoroacetoacetate Specification

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