Methyl 2-Fluoro-3-(4-toluenesulfonyloxy)propanoate
methyl 2-fluoroprop-2-enoate
Conditions | Yield |
---|---|
With potassium phtalimide at -78 - 150℃; under 0.01 Torr; | 97% |
Methyl 3-chloro-2-fluoropropanoate
methyl 2-fluoroprop-2-enoate
Conditions | Yield |
---|---|
With 2,6-di-tert-butyl-4-methyl-phenol; sodium phosphate In 1-methyl-pyrrolidin-2-one at 150℃; under 112.511 - 225.023 Torr; | 95% |
With dimethyl amine In diethyl ether; benzene |
Conditions | Yield |
---|---|
With thionyl chloride at 5 - 35℃; for 2h; Concentration; Reagent/catalyst; | 93% |
methyl 2-fluoroprop-2-enoate
Conditions | Yield |
---|---|
With 2,6-di-tert-butyl-4-methyl-phenol; sodium carbonate In 1-methyl-pyrrolidin-2-one at 150℃; under 225.023 Torr; for 4h; | 92% |
methanol
1-chloro-1-fluoroethane
carbon monoxide
methyl 2-fluoroprop-2-enoate
Conditions | Yield |
---|---|
With dichloro[ferrocene-1,1'-diylbis(diisopropylphosphine-P)]palladium(II); triethylamine at 100℃; under 5250.53 Torr; for 8h; Reagent/catalyst; Autoclave; | 91.8% |
With bis(tri-t-butylphosphine)palladium(0) at 100℃; for 18h; Reagent/catalyst; Time; Autoclave; | 77.4% |
methanol
1-bromo-1-fluoroethylene
carbon monoxide
methyl 2-fluoroprop-2-enoate
Conditions | Yield |
---|---|
With bis-triphenylphosphine-palladium(II) chloride; lithium carbonate; triethylamine at 90℃; for 6h; Reagent/catalyst; Temperature; Autoclave; | 90.7% |
With dichloro[4,5-bis(diphenylphosphino)-9,9’-dimethylxanthene]palladium(II); triethylamine at 100℃; under 7500.75 Torr; for 8h; Reagent/catalyst; Autoclave; | 90.1% |
With bis-triphenylphosphine-palladium(II) chloride; tributyl-amine; lithium carbonate at 90℃; under 7500.75 Torr; for 6h; Reagent/catalyst; Autoclave; | 71.8 g |
methyl 2-fluoroprop-2-enoate
Conditions | Yield |
---|---|
With 2,6-di-tert-butyl-4-methyl-phenol; methoxybenzene at 120 - 130℃; under 500 Torr; Reagent/catalyst; Temperature; | 89.5% |
With 2,6-di-tert-butyl-4-methyl-phenol at 145℃; under 360 Torr; | 12.3 g |
Conditions | Yield |
---|---|
With 10H-phenothiazine; sulfuric acid; zinc In water at 82 - 86℃; for 0.333333h; | 85% |
With hydrogen sulfide; sodium N-nitroso-N-phenylhydroxylaminate; zinc In water at 100℃; | 82% |
With zinc | 80% |
With sulfuric acid; zinc |
methyl 2-fluoroprop-2-enoate
Conditions | Yield |
---|---|
With 10H-phenothiazine In sulfolane at 180℃; for 6h; | 83.9% |
methyl 2-fluoroprop-2-enoate
Conditions | Yield |
---|---|
With 4-methoxy-phenol at 170℃; for 9h; | 81.2% |
methyl 2-fluoroprop-2-enoate
Conditions | Yield |
---|---|
With 10H-phenothiazine at 170℃; for 15h; | 81.2% |
Conditions | Yield |
---|---|
Stage #1: methyl fluoroacetate With Dimethyl oxalate; sodium methylate In dimethyl sulfoxide at 15 - 25℃; for 1h; Inert atmosphere; Stage #2: formaldehyd With 2,6-di-tert-butyl-4-methyl-phenol In dimethyl sulfoxide at 20 - 35℃; for 1h; Temperature; Reagent/catalyst; Inert atmosphere; | 79.3% |
Stage #1: methyl fluoroacetate With Dimethyl oxalate; sodium methylate In methanol; pentane at 20 - 25℃; for 24.25h; Claisen Condensation; Stage #2: formaldehyd In pentane at 5 - 10℃; for 5h; Concentration; Reagent/catalyst; Temperature; Time; | 58% |
methyl 2R,3S-2,3-difluoro-2,3-dichloropropionate
A
methyl 2-fluoroprop-2-enoate
B
methyl Z-α,β-difluoropropenoate
Conditions | Yield |
---|---|
With sulfuric acid; zinc at 100℃; | A 10% B 75% |
methyl α,β-dibromo-α-fluoropropionate
A
methyl 2-fluoroprop-2-enoate
B
acrylic acid methyl ester
Conditions | Yield |
---|---|
With thiourea; zinc In diphenylether at 95℃; under 20 Torr; | A 74% B n/a |
methyl 2-fluoroprop-2-enoate
Conditions | Yield |
---|---|
With 2,6-di-tert-butyl-4-methyl-phenol In sulfolane at 140℃; for 17h; | 73.8% |
A
methyl 2-fluoroprop-2-enoate
B
methyl 2,2-difluoropropanoate
Conditions | Yield |
---|---|
With 2,6-di-tert-butyl-4-methyl-phenol; hydrogen fluoride; 1,8-diazabicyclo[5.4.0]undec-7-ene In toluene at 50℃; for 48h; Solvent; Temperature; Reagent/catalyst; Cooling with ice; | A 23% B 73% |
methanol
1-bromo-1-fluoroethylene
carbon monoxide
A
2-fluoroacrylic acid
B
methyl 2-fluoroprop-2-enoate
Conditions | Yield |
---|---|
With dichloro[bis(2-(diphenylphosphino)phenyl)ether]palladium(ll); triethylamine at 100℃; under 7500.75 Torr; for 13h; Autoclave; | A 14.1% B 70.9% |
A
methyl 2-fluoroprop-2-enoate
B
2,2-difluoropropanoic acid
C
methyl 2,2-difluoropropanoate
Conditions | Yield |
---|---|
With 2,6-di-tert-butyl-4-methyl-phenol; hydrogen fluoride; 1,8-diazabicyclo[5.4.0]undec-7-ene In acetonitrile at 50℃; for 72h; Reagent/catalyst; Solvent; Temperature; Cooling with ice; | A 18% B 5% C 70% |
dimethyl 2-fluoro-2-(hydroxymethyl)malonate
methyl 2-fluoroprop-2-enoate
Conditions | Yield |
---|---|
With sulfolane; potassium fluoride; 2,6-di-tert-butyl-4-methyl-phenol at 90 - 105℃; under 760.051 Torr; for 1.25h; | 70% |
With 2,6-di-tert-butyl-4-methyl-phenol; sodium carbonate In 1-methyl-pyrrolidin-2-one at 150℃; under 225.023 Torr; | 24 g |
methyl (2R,3R)-2,3-difluoro-2,3-dichloropropionate
A
methyl 2-fluoroprop-2-enoate
B
methyl Z-α,β-difluoropropenoate
C
methyl α,β-difluoroacrylate
Conditions | Yield |
---|---|
With sulfuric acid; zinc at 100℃; | A 10% B 64% C 10% |
2,3-Dichlor-2-fluor-propansaeuremethylester
methyl 2-fluoroprop-2-enoate
Conditions | Yield |
---|---|
With sulfuric acid; water; zinc at 100 - 110℃; | 52% |
Conditions | Yield |
---|---|
With sodium fluoride at 30℃; for 3h; | 46.9% |
methanol
Vinylidene fluoride
carbon monoxide
methyl 2-fluoroprop-2-enoate
Conditions | Yield |
---|---|
Stage #1: methanol With bis-triphenylphosphine-palladium(II) chloride; triethylamine; triphenylphosphine; lithium iodide In 1,4-dioxane at -78 - 30℃; for 1.5h; Autoclave; Sealed tube; Inert atmosphere; Stage #2: Vinylidene fluoride; carbon monoxide In 1,4-dioxane at 90℃; under 3000.3 Torr; for 24h; Concentration; Solvent; Temperature; Autoclave; Sealed tube; | 5% |
Conditions | Yield |
---|---|
With dimethyl amine In diethyl ether; benzene |
Conditions | Yield |
---|---|
With thiourea; zinc 1.) diphenyl ether, 95 deg C, 20 Torr, 2.) room temperature; Yield given. Multistep reaction. Yields of byproduct given; |
methyl 2-fluoroprop-2-enoate
Conditions | Yield |
---|---|
With 10H-phenothiazine; potassium carbonate; 1,8-diazabicyclo[5.4.0]undec-7-ene In N,N-dimethyl-formamide at 70℃; for 5h; Product distribution / selectivity; |
Conditions | Yield |
---|---|
Stage #1: C6H6FO5(1-)*Na(1+) In dimethyl sulfoxide for 0.333333h; Molecular sieve; Stage #2: formaldehyd In dimethyl sulfoxide at 40℃; for 1.5h; Molecular sieve; | 19 g |
Conditions | Yield |
---|---|
Stage #1: 1,1-dimethoxyethylene; Dichlorofluoromethane With tetrabutylammomium bromide; potassium hydroxide In hexane; water at 5 - 10℃; Stage #2: With 2,6-di-tert-butyl-4-methyl-phenol at 0 - 145℃; under 360 Torr; |
methyl 2-fluoroprop-2-enoate
Conditions | Yield |
---|---|
With 2,6-di-tert-butyl-4-methyl-phenol; sodium carbonate In 1-methyl-pyrrolidin-2-one at 130℃; under 225.023 Torr; for 4h; |
Conditions | Yield |
---|---|
With palladium(II) trifluoroacetate; silver carbonate In 1,4-dioxane at 90℃; for 4h; Heck Reaction; stereospecific reaction; | 99% |
Conditions | Yield |
---|---|
With palladium(II) trifluoroacetate; silver carbonate In 1,4-dioxane at 90℃; for 4h; Heck Reaction; stereospecific reaction; | 99% |
Conditions | Yield |
---|---|
With palladium(II) trifluoroacetate; silver carbonate In 1,4-dioxane at 90℃; for 4h; Heck Reaction; stereospecific reaction; | 99% |
methyl 2-fluoroprop-2-enoate
2-iodonaphthalene
(Z)-methyl 2-fluoro-3-(naphth-2-yl)acrylate
Conditions | Yield |
---|---|
With palladium(II) trifluoroacetate; silver carbonate In 1,4-dioxane at 90℃; for 4h; Heck Reaction; stereospecific reaction; | 99% |
iodobenzene
methyl 2-fluoroprop-2-enoate
methyl (Z)-2-fluoro-3-phenylpropenoate
Conditions | Yield |
---|---|
With palladium(II) trifluoroacetate; silver carbonate In 1,4-dioxane at 90℃; for 4h; Reagent/catalyst; Temperature; Heck Reaction; stereospecific reaction; | 99% |
With palladium(II) trifluoroacetate; silver carbonate In 1,4-dioxane at 90℃; for 4h; Sealed tube; Inert atmosphere; |
Conditions | Yield |
---|---|
With palladium(II) trifluoroacetate; silver carbonate In 1,4-dioxane at 90℃; for 4h; Heck Reaction; stereospecific reaction; | 99% |
methyl 2-fluoroprop-2-enoate
4-Iodobenzotrifluoride
methyl Z-2-fluoro-3-(4-trifluoromethylphenyl)prop-2-enoate
Conditions | Yield |
---|---|
With palladium(II) trifluoroacetate; silver carbonate In 1,4-dioxane at 90℃; for 4h; Heck Reaction; stereospecific reaction; | 99% |
Conditions | Yield |
---|---|
With palladium(II) trifluoroacetate; silver carbonate In 1,4-dioxane; dimethyl sulfoxide at 120℃; for 12h; Sealed tube; diastereoselective reaction; | 98% |
Conditions | Yield |
---|---|
With [1,3-bis(2,4,6-trimethylphenyl)-2-imidazolidinylidene]dichloro-(3-phenyl-1H-inden-1-ylidene)(tricyclohexylphosphine)ruthenium(II) In dichloromethane at 80℃; for 15h; Cross Metathesis; Inert atmosphere; Sealed tube; diastereoselective reaction; | 98% |
propylamine
methyl 2-fluoroprop-2-enoate
N-(n-propyl)-α-fluoroacrylamide
Conditions | Yield |
---|---|
In methanol at 20℃; for 24h; | 96.14% |
methyl 2-fluoroprop-2-enoate
N-benzyl-N-(methoxymethyl)-N-[(trimethylsilyl)methyl]amine
methyl 1-benzyl 3-fluoropyrrolidine-3-carboxylate
Conditions | Yield |
---|---|
With trifluoroacetic acid In dichloromethane at 0 - 20℃; for 4h; | 95% |
With trifluoroacetic acid In dichloromethane at 20℃; for 4h; Inert atmosphere; | 80% |
With trifluoroacetic acid In dichloromethane at 0 - 20℃; for 16h; Inert atmosphere; |
methyl 2-fluoroprop-2-enoate
1-(1,1-dimethylethyl)-1H-indole-1,2-dicarboxylic acid 2-methyl ester
Conditions | Yield |
---|---|
With [Ir(dF(Me)ppy)2dtbbpy]PF6 In tetrahydrofuran at 28℃; Inert atmosphere; Glovebox; Irradiation; | 93% |
methyl 2-fluoroprop-2-enoate
(R)-N-(1-phenylethyl)-N-(methoxymethyl)-N-(trimethylsilylmethyl)amine
methyl 3-fluoro-1-[(1R)-1-phenylethyl]pyrrolidine-3-carboxylate
Conditions | Yield |
---|---|
With trifluoroacetic acid In dichloromethane at 0 - 20℃; for 5h; Inert atmosphere; | 92% |
Conditions | Yield |
---|---|
With palladium(II) trifluoroacetate; silver carbonate In 1,4-dioxane; dimethyl sulfoxide at 120℃; for 12h; Catalytic behavior; Reagent/catalyst; Solvent; Temperature; Time; Sealed tube; diastereoselective reaction; | 92% |
Conditions | Yield |
---|---|
With Quinuclidine; (4,4'-di-tert-butyl-2,2'-dipyridyl)-bis-(2-phenylpyridine(-1H))-iridium(III) hexafluorophosphate In acetonitrile for 16h; Sealed tube; Inert atmosphere; Irradiation; | 92% |
methyl 2-fluoroprop-2-enoate
3,5-difluoro-N-hydroxybenzenecarboximidoyl chloride
Conditions | Yield |
---|---|
With sodium hydrogencarbonate In isopropyl alcohol at 40℃; for 1h; | 91% |
methyl 2-fluoroprop-2-enoate
4-iodobenzonitrile
methyl Z-3-(4-cyanophenyl)-2-fluoroprop-2-enoate
Conditions | Yield |
---|---|
With palladium(II) trifluoroacetate; silver carbonate In 1,4-dioxane at 90℃; for 4h; Heck Reaction; stereospecific reaction; | 90% |
With palladium(II) trifluoroacetate; silver carbonate In 1,4-dioxane at 90℃; for 4h; Sealed tube; Inert atmosphere; |
Conditions | Yield |
---|---|
With palladium(II) trifluoroacetate; silver carbonate In 1,4-dioxane at 90℃; for 4h; Heck Reaction; chemoselective reaction; | 89% |
Conditions | Yield |
---|---|
With palladium(II) trifluoroacetate; silver carbonate In 1,4-dioxane; dimethyl sulfoxide at 120℃; for 12h; Sealed tube; diastereoselective reaction; | 89% |
Conditions | Yield |
---|---|
Stage #1: methyl 2-fluoroprop-2-enoate With sodium hydroxide In ethanol; water for 0.5h; pH=11; Inert atmosphere; Stage #2: With hydrogenchloride In diethyl ether; water Inert atmosphere; | 87% |
methyl 2-fluoroprop-2-enoate
4-Phenyl-1-butene
A
(Z)-methyl 2-fluoro-4-phenyl-2-butenoate
Conditions | Yield |
---|---|
With [1,3-bis(2,4,6-trimethylphenyl)-2-imidazolidinylidene]dichloro-(3-phenyl-1H-inden-1-ylidene)(tricyclohexylphosphine)ruthenium(II) In chloroform at 80℃; for 15h; Reagent/catalyst; Solvent; Cross Metathesis; Inert atmosphere; Sealed tube; diastereoselective reaction; | A n/a B 87% |
methyl 2-fluoroprop-2-enoate
1-(but-3-en-1-yl)-2-methoxybenzene
Conditions | Yield |
---|---|
With [1,3-bis(2,4,6-trimethylphenyl)-2-imidazolidinylidene]dichloro-(3-phenyl-1H-inden-1-ylidene)(tricyclohexylphosphine)ruthenium(II) In dichloromethane at 80℃; for 15h; Cross Metathesis; Inert atmosphere; Sealed tube; diastereoselective reaction; | 87% |
Conditions | Yield |
---|---|
With [1,3-bis(2,4,6-trimethylphenyl)-2-imidazolidinylidene]dichloro-(3-phenyl-1H-inden-1-ylidene)(tricyclohexylphosphine)ruthenium(II) In dichloromethane at 80℃; for 15h; Cross Metathesis; Inert atmosphere; Sealed tube; diastereoselective reaction; | 87% |
The cas register number of Methyl 2-fluoroacrylate is 2343-89-7. In addition, the molecular formula is C4H5FO2 and the molecular weight is 104.08. The systematic name about this chemical is methyl 2-fluoroprop-2-enoate. Besides, it is a irritating chemical and should be stored in a cool and dry place.
Physical properties about Methyl 2-fluoroacrylate are: (1)ACD/LogP: 0.68; (2)ACD/LogD (pH 5.5): 0.68; (3)ACD/LogD (pH 7.4): 0.68; (4)ACD/BCF (pH 5.5): 1.95; (5)ACD/BCF (pH 7.4): 1.95; (6)ACD/KOC (pH 5.5): 56.12; (7)ACD/KOC (pH 7.4): 56.12; (8)#H bond acceptors: 2; (9)#Freely Rotating Bonds: 2; (10)Polar Surface Area: 26.3 Å2; (11)Index of Refraction: 1.366; (12)Molar Refractivity: 22.08 cm3; (13)Molar Volume: 98.3 cm3; (14)Polarizability: 8.75 ×10-24cm3; (15)Surface Tension: 21 dyne/cm; (16)Density: 1.057 g/cm3; (17)Flash Point: 1.1 °C; (18)Enthalpy of Vaporization: 31.7 kJ/mol; (19)Boiling Point: 75.9 °C at 760 mmHg; (20)Vapour Pressure: 103 mmHg at 25°C.
When you are using this chemical, please be cautious about it as the following:
This chemical is flammable and it is irritating to eyes, respiratory system and skin. When you are using it, wear suitable protective clothing. And you should keep away from sources of ignition. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
You can still convert the following datas into molecular structure:
(1)SMILES: F/C(=C)C(=O)OC
(2)Std. InChI: InChI=1S/C4H5FO2/c1-3(5)4(6)7-2/h1H2,2H3
(3)Std. InChIKey: ZTZJVAOTIOAZGZ-UHFFFAOYSA-N
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