ethyl 3-hydroxy-4,4,4-trifluorobutyrate
ethyl 4,4,4-trifluorocrotonate
Conditions | Yield |
---|---|
With triphenylphosphine; diethylazodicarboxylate In diethyl ether Ambient temperature; | 96% |
With methanesulfonyl chloride; triethylamine In dichloromethane at -70 - 25℃; for 1h; Reagent/catalyst; | 87% |
With triethylamine; p-toluenesulfonyl chloride | 82% |
Togni's reagent II
(E)-4-ethoxy-4-oxobut-2-enoic acid
ethyl 4,4,4-trifluorocrotonate
Conditions | Yield |
---|---|
In N,N-dimethyl-formamide at 120℃; for 24h; Sealed tube; stereoselective reaction; | 93% |
ethyl 4,4,4-trifluoroacetoacetate
ethyl 4,4,4-trifluorocrotonate
Conditions | Yield |
---|---|
Stage #1: ethyl 4,4,4-trifluoroacetoacetate With sodium tetrahydroborate In diethyl ether Stage #2: With phosphorus pentoxide In diethyl ether | 70% |
Multi-step reaction with 2 steps 1: 94 percent / sodium borohydride / toluene / 4.5 h / 20 °C 2: 69 percent / phosphorus pentoxide / 1 h View Scheme |
ethanol
3-(trifluoromethyl)acrylic acid
ethyl 4,4,4-trifluorocrotonate
Conditions | Yield |
---|---|
With sulfuric acid Heating; |
2,2,2-Trifluoroacetaldehyde
diethyl malonate
ethyl 4,4,4-trifluorocrotonate
ethyl 3-hydroxy-4,4,4-trifluorobutyrate
A
ethyl 4,4,4-trifluorocrotonate
B
ethyl (Z)-β-trifluoromethylacrylate
Conditions | Yield |
---|---|
With phosphorus pentaoxide for 1h; Yield given. Yields of byproduct given. Title compound not separated from byproducts; |
ethyl 3-hydroxy-4,4,4-trifluorobutyrate
A
ethyl 4,4,4-trifluorocrotonate
B
ethyl 3,4,4,4-tetrafluorobutyrate
C
4,4,4-Trifluoro-3-fluorosulfinyloxy-butyric acid ethyl ester
Conditions | Yield |
---|---|
With sulfur tetrafluoride; sodium fluoride 1.) steel autoclave; 2.) 20 deg C, 60 h; Yield given. Multistep reaction. Yields of byproduct given; |
ethyl 3-hydroxy-4,4,4-trifluorobutyrate
ethyl 4,4,4-trifluorocrotonate
ethyl 3-hydroxy-4,4,4-trifluorobutyrate
A
(E)-4,4,4-trifluorobut-2-enoate
B
ethyl 4,4,4-trifluorocrotonate
Conditions | Yield |
---|---|
at 350℃; |
ethyl 4,4,4-trifluorocrotonate
Conditions | Yield |
---|---|
With sodium carbonate | 15.90 g (91%) |
With caesium carbonate | 13.47 g (87%) |
With sodium carbonate | 15.90 g (91%) |
With caesium carbonate | 13.47g (87%) |
diethoxyphosphoryl-acetic acid ethyl ester
2,2,2-Trifluoroacetaldehyde
ethyl 4,4,4-trifluorocrotonate
Conditions | Yield |
---|---|
Stage #1: diethoxyphosphoryl-acetic acid ethyl ester With triethylamine; lithium bromide In tetrahydrofuran at 20℃; for 0.166667h; Inert atmosphere; Stage #2: 2,2,2-Trifluoroacetaldehyde In tetrahydrofuran at 0 - 20℃; for 1.08333h; Inert atmosphere; |
ethyl 4,4,4-trifluorocrotonate
diethyl malonate
Conditions | Yield |
---|---|
With lithium diisopropyl amide In tetrahydrofuran; hexane 1.) -78 deg C, 30 min, 2.) r.t., 1 h; | 99% |
Stage #1: diethyl malonate With sodium hydride In tetrahydrofuran at 0℃; for 0.5h; Inert atmosphere; Stage #2: ethyl 4,4,4-trifluorocrotonate In tetrahydrofuran at 0 - 20℃; Inert atmosphere; Stage #3: With hydrogenchloride; water In tetrahydrofuran Inert atmosphere; |
ethyl 4,4,4-trifluorocrotonate
N-benzyl-N-(methoxymethyl)-N-[(trimethylsilyl)methyl]amine
ethyl (+/-)-(3R,4R)-1-benzyl-4-(trifluoromethyl)pyrrolidine-3-carboxylate
Conditions | Yield |
---|---|
With trifluoroacetic acid In dichloromethane for 16h; Inert atmosphere; Reflux; | 99% |
With trifluoroacetic acid In dichloromethane at 0 - 20℃; | 98% |
With trifluoroacetic acid In dichloromethane | 95% |
With trifluoroacetic acid In acetonitrile at 70℃; Continuous flow conditions; | 74% |
Conditions | Yield |
---|---|
With Cl4SnC2HNOBC6H5CH(CH3)2(C6H5)2CH2C10H7 In dichloromethane at -78℃; for 8h; Diels-Alder reaction; Inert atmosphere; optical yield given as %ee; stereoselective reaction; | 99% |
ethyl 4,4,4-trifluorocrotonate
propiophenone lithium enolate
(3R*,4R*)-Ethyl 3-(trifluoromethyl)-4-methyl-5-oxo-5-phenylpentanoate
Conditions | Yield |
---|---|
98% |
ethyl 4,4,4-trifluorocrotonate
1-phenyl-propan-1-one
(3R*,4R*)-Ethyl 3-(trifluoromethyl)-4-methyl-5-oxo-5-phenylpentanoate
Conditions | Yield |
---|---|
With lithium diisopropyl amide In tetrahydrofuran at -78℃; Product distribution; multistep reaction; diastereoselectivity; other lithium enolates of ketones, esters or amides; | 98% |
With lithium diisopropyl amide 1) THF, -78 deg C, 2) -78 deg C, 0.5 h; Yield given. Multistep reaction; | |
With lithium diisopropyl amide In tetrahydrofuran; hexane 1.) -78 deg C, 30 min, 2.) -78 deg C, 0.5 h; Yield given; |
nitromethane
ethyl 4,4,4-trifluorocrotonate
4,4,4-trifluoro-3-(nitromethyl)butyric acid ethyl ester
Conditions | Yield |
---|---|
With N,N,N',N'-tetramethylguanidine at 20℃; for 13h; Inert atmosphere; | 98% |
With N,N,N',N'-tetramethylguanidine at 20℃; for 13h; | 98% |
With lithium diisopropyl amide In tetrahydrofuran; hexane 1.) -78 deg C, 30 min, 2.) -78 deg C to r.t., 6.0 h; | 83% |
In acetonitrile for 0.5h; Michael addition; | 90 % Spectr. |
ethyl 4,4,4-trifluorocrotonate
Ethyl isobutyrate
Conditions | Yield |
---|---|
With lithium diisopropyl amide In tetrahydrofuran; hexane 1.) -78 deg C, 30 min, 2.) -78 deg C, 1.0 h; | 98% |
ethyl 4,4,4-trifluorocrotonate
2,4-Dihydroxybenzaldehyde
Conditions | Yield |
---|---|
With potassium carbonate In DMF (N,N-dimethyl-formamide) at 90℃; for 3h; | 98% |
ethyl 4,4,4-trifluorocrotonate
(RS)-5-(trifluoromethyl)pyrazolidin-3-one
Conditions | Yield |
---|---|
With hydrazine hydrate In ethanol for 18h; Reflux; | 98% |
ethyl 4,4,4-trifluorocrotonate
3-pentanone lithium enolate
(3R*,4R*)-Ethyl 3-(trifluoromethyl)-4-methyl-5-oxoheptanoate
Conditions | Yield |
---|---|
diastereoselective Michael addition reactions with other lithium enolates; | 97% |
97% |
ethyl 4,4,4-trifluorocrotonate
(E)-4,4,4-trifluorobut-2-enoate
Conditions | Yield |
---|---|
With sodium hydroxide In water | 96% |
With sodium hydroxide In tetrahydrofuran; water for 1.5h; Ambient temperature; | 93% |
With water; sodium hydroxide In ethanol at 20℃; for 19h; | 91% |
ethyl 4,4,4-trifluorocrotonate
1-methoxy-1,3-cyclohexadiene
Ethyl (1RS,2RS,3SR,4RS)-1-methoxy-3-trifluoromethylbicyclo<2.2.2>oct-5-ene-2-carboxylate
Conditions | Yield |
---|---|
With cis-2,3-dichlorobutenedioic acid; 2-tert-Butyl-4-methylphenol In benzene for 96h; Heating; | 96% |
ethyl 4,4,4-trifluorocrotonate
2-amino-benzenethiol
Conditions | Yield |
---|---|
With triethylamine In dichloromethane at 20℃; for 24h; | 95% |
ethyl 4,4,4-trifluorocrotonate
diethyl malonate
3-(trifluoromethyl)pentanedioic acid
Conditions | Yield |
---|---|
With hydrogenchloride; potassium hydroxide; tetrabutylammomium bromide In tetrahydrofuran; water; acetic acid | 95% |
ethyl 4,4,4-trifluorocrotonate
bis(pinacol)diborane
Conditions | Yield |
---|---|
With methanol; copper(l) iodide; potassium carbonate In tetrahydrofuran at 20℃; for 30h; Inert atmosphere; chemoselective reaction; | 95% |
ethyl 4,4,4-trifluorocrotonate
t-butoxycarbonylhydrazine
3-(N'-tert-butoxycarbonylhydrazino)-4,4,4-trifluorobutyric acid ethyl ester
Conditions | Yield |
---|---|
In methanol at 70℃; for 72h; Michael condensation; | 94% |
ethyl 4,4,4-trifluorocrotonate
sodium methylate
4,4,4-trifluoro-3-methoxybutanoic acid
Conditions | Yield |
---|---|
In methanol at 20℃; | 93.8% |
ethyl 4,4,4-trifluorocrotonate
cyclopentanone
Conditions | Yield |
---|---|
With lithium diisopropyl amide In tetrahydrofuran; hexane 1.) -78 deg C, 30 min, 2.) -40 deg C, 4.0 h; | 93% |
ethyl 4,4,4-trifluorocrotonate
3,5-dichlorosalicyclaldehyde
ethyl 6,8-dichloro-2-(trifluoromethyl)-2H-chromene-3-carboxylate
Conditions | Yield |
---|---|
With triethylamine In dimethyl sulfoxide at 85℃; for 72h; | 93% |
regiospecific reaction; |
ethyl 4,4,4-trifluorocrotonate
ethyl 2,3-dibromo-4,4,4-trifluorobutanoate
Conditions | Yield |
---|---|
With bromine In tetrachloromethane for 5h; Heating; | 92% |
With bromine In tetrachloromethane at 20℃; Reflux; Inert atmosphere; | |
With bromine In tetrachloromethane at 20℃; Inert atmosphere; Reflux; |
ethyl 4,4,4-trifluorocrotonate
1-trifluoromethylprop-1-en-3-ol
Conditions | Yield |
---|---|
With lithium aluminium tetrahydride; aluminium trichloride In diethyl ether | 90% |
With lithium aluminium tetrahydride; aluminium trichloride In diethyl ether at 0℃; for 2h; Hydrogenolysis; | 90% |
With diisobutylaluminium hydride In tert-butyl methyl ether; toluene at -70 - 25℃; for 1h; Inert atmosphere; | 90% |
4-butanolide
ethyl 4,4,4-trifluorocrotonate
Conditions | Yield |
---|---|
With lithium diisopropyl amide In tetrahydrofuran; hexane 1.) -78 deg C, 30 min, 2.) -78 deg C, 3.0 h; | 90% |
ethyl 4,4,4-trifluorocrotonate
dimethyl methane phosphonate
Conditions | Yield |
---|---|
With lithium diisopropyl amide In tetrahydrofuran; hexane 1.) -78 deg C, 30 min, 2.) -78 deg C, 2.0 h; | 90% |
2-hydroxy-3-iodo-5-(trifluoromethoxy) benzaldehyde
ethyl 4,4,4-trifluorocrotonate
ethyl 8-iodo-6-(trifluoromethoxy)-2-(trifluoromethyl)-2H-chromene-3-carboxylate
Conditions | Yield |
---|---|
With triethylamine at 85℃; for 66h; | 90% |
With triethylamine In N,N-dimethyl-formamide at 85℃; for 66h; | 90% |
With triethylamine In N,N-dimethyl-formamide at 85℃; for 48h; | 69% |
With triethylamine In N,N-dimethyl-formamide at 85℃; for 48h; | 69% |
With triethylamine In N,N-dimethyl-formamide at 85℃; for 48h; | 69% |
5-(benzyloxy)-4-bromo-2-hydroxybenzaldehyde
ethyl 4,4,4-trifluorocrotonate
Conditions | Yield |
---|---|
With potassium carbonate In DMF (N,N-dimethyl-formamide) at 65℃; for 4h; | 89% |
Conditions | Yield |
---|---|
With Cl4SnC2HNOBC6H5CH(CH3)2(C6H5)2CH2C10H7 In dichloromethane at -78℃; for 8h; Diels-Alder reaction; Inert atmosphere; optical yield given as %ee; stereoselective reaction; | 89% |
ethyl 4,4,4-trifluorocrotonate
N-isopropyl oxazolidinone
(3R,4R,4'S)-Ethyl 3-(trifluoromethyl)-4-methyl-5-<4'-(1''-methylethyl)-2'-oxazolidinon-3'-yl>-5-oxopentanoate
Conditions | Yield |
---|---|
With lithium diisopropyl amide In tetrahydrofuran at -78℃; Product distribution; multistep reaction; diastereoselectivity; other acyl oxazolidinones; | 88% |
With lithium diisopropyl amide In tetrahydrofuran; hexane 1.) -78 deg C, 30 min, 2.) -78 deg C; | 88% |
With lithium diisopropyl amide 1) THF, -78 deg C, 2) -78 deg C, 1.5 h; Yield given. Multistep reaction; |
ethyl 4,4,4-trifluorocrotonate
methylhydrazine
1-methyl-5-(trifluoromethyl)-2,3,4,5-tetrahydropyrazol-3-one
Conditions | Yield |
---|---|
at 20℃; | 88% |
IUPAC Name: Ethyl (E)-4,4,4-trifluorobut-2-enoate
Molecular Formula: C6H7 F3 O2
Molecular Weight: 168.1138
Density: 1.191 g/cm3
Boiling Point: 114.5 °C at 760 mmHg
Flash Point: 25 ºC
Appearance: colorless and clear liquid
Freely Rotating Bonds: 3
Polar Surface Area: 26.3 Å2
Index of Refraction: 1.372
Molar Refractivity: 32.13 cm3
Molar Volume: 141 cm3
Polarizability: 12.73 ×10-24 cm3
Surface Tension: 22.2 dyne/cm
Enthalpy of Vaporization: 35.29 kJ/mol
Vapour Pressure: 19.9 mmHg at 25°C
The Cas Register Number of 2-Butenoic acid,4,4,4-trifluoro-, ethyl ester, (2E)- is 25597-16-4 . The chemical synonyms of 2-Butenoic acid,4,4,4-trifluoro-, ethyl ester, (2E)- (CAS NO.25597-16-4) are 4.4.4-Trifluorocrotonic acid ethyl ester ; Ethyl 4,4,4-trifluorocrotonate ; Ethyl 4,4,4-Trifluoro-trans-2-butenoate ; Ethyl (2E)-4,4,4-trifluoro-2-butenoate ; Ethyl 4,4,4-trifluorocrotonate 98% ; Ethyl4,4,4-trifluorocrotonate98% ; 2-Butenoic acid, 4,4,4-trifluoro-, ethyl ester, (2E)- ; 4,4,4-trifluorocrotonate . The molecular structure of 2-Butenoic acid,4,4,4-trifluoro-, ethyl ester, (2E)- (CAS NO.25597-16-4) is.
2-Butenoic acid,4,4,4-trifluoro-, ethyl ester, (2E)- (CAS NO.25597-16-4) is used in organic reagent, pharmaceutical intermediate.
Hazard Codes: Xi ,F
Risk Statements: 10-36/37-36/37/38
R10: Flammable.
R36/37: Irritating to eyes and respiratory system.
R36/37/38: Irritating to eyes, respiratory system and skin.
Safety Statements: 16-26-27-28-36/37/39-37/39
S16: Keep away from sources of ignition.
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
S27: Take off immediately all contaminated clothing.
S28: After contact with skin, wash immediately with plenty of soap-suds.
S36/37/39: Wear suitable protective clothing, gloves and eye/face protection.
S37/39: Wear suitable gloves and eye/face protection.
RIDADR: UN 3272 3/PG 3
WGK Germany: 3
Hazard Note: Flammable
HazardClass: 3
PackingGroup: III
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