Conditions | Yield |
---|---|
In ethanol | 95% |
Conditions | Yield |
---|---|
With trifluoroacetic acid at 0℃; | 85% |
With trifluoroacetic acid at 0℃; Mechanism; | 85% |
With hydrogen; hydrotalcite-supported palladium nanoparticles; palladium In toluene at 60℃; under 760 Torr; for 1h; |
Conditions | Yield |
---|---|
Stage #1: ethyl 2-cyanoacetate With sodium hydride In tetrahydrofuran; paraffin oil at 0℃; for 0.25h; Inert atmosphere; Stage #2: methyl iodide In tetrahydrofuran; paraffin oil at 0 - 20℃; for 3h; Inert atmosphere; | 83% |
Stage #1: ethyl 2-cyanoacetate With potassium carbonate In acetonitrile at 20℃; for 0.25h; Stage #2: methyl iodide In acetonitrile at 20℃; for 6h; | 41% |
With potassium hydroxide In ethanol at 0℃; for 4h; |
N,N,N',N',N'',N''-Hexamethylguanidiniumcyanid
Ethyl 2-bromopropionate
A
ethyl 2-cyanopropionate
B
1,1,2,2,3,3-Hexamethylguanidiniumbromid
Conditions | Yield |
---|---|
In dichloromethane at 40℃; for 18h; | A 73% B n/a |
ethanol
carbon monoxide
acrylonitrile
1-Phenylbut-1-en-3-one
A
ethyl 3-cyanopropionate
B
2,4-dicyano-2-methylbutanoic acid ethyl ester
C
2-cyano-5-oxo-3-phenyl-2-methylhexanoic acid ethyl ester
D
ethyl 2-cyanopropionate
Conditions | Yield |
---|---|
With pyridine; dicobalt octacarbonyl at 110℃; under 75005.9 Torr; Further byproducts given; | A n/a B 59% C 10% D n/a |
ethanol
carbon monoxide
acrylonitrile
ethyl acrylate
A
ethyl 3-cyanopropionate
B
2,4-dicyano-2-methylbutanoic acid ethyl ester
C
2-cyano-2-methyl-1,5-pentanedioic acid bis(ethyl ester)
D
ethyl 2-cyanopropionate
Conditions | Yield |
---|---|
With pyridine; dicobalt octacarbonyl at 110℃; under 75005.9 Torr; Further byproducts given; | A n/a B 44% C 5% D n/a |
sodium cyanide
Ethyl 2-bromopropionate
ethyl 2-cyanopropionate
Conditions | Yield |
---|---|
In water; N,N-dimethyl-formamide at 23℃; for 12h; | 30% |
Conditions | Yield |
---|---|
With sulfuric acid |
ethanol
potassium cyanide
Ethyl 2-bromopropionate
A
diethyl 2,3-dimethyl-2-cyanosuccinate
B
ethyl 2-cyanopropionate
Conditions | Yield |
---|---|
With diethyl ether; sodium |
sodium cyanoacetic acid ethyl ester
dimethyl sulfate
ethyl 2-cyanopropionate
Conditions | Yield |
---|---|
With ethanol |
sodium cyanoacetic acid ethyl ester
dimethyl sulfate
A
2-cyano-2-methyl-propionic acid ethyl ester
B
ethyl 2-cyanopropionate
Conditions | Yield |
---|---|
With benzene |
potassium cyanide
Ethyl 2-bromopropionate
ethyl 2-cyanopropionate
Conditions | Yield |
---|---|
With ethanol | |
With ethanol at 100℃; im geschlossenen Rohr; |
sodium cyanoacetic acid ethyl ester
methyl iodide
ethyl 2-cyanopropionate
Conditions | Yield |
---|---|
With diethyl ether | |
analog reagiert mit Aethyljodid und mit Allyljodid; |
sodium cyanoacetic acid ethyl ester
methyl iodide
A
2-cyano-2-methyl-propionic acid ethyl ester
B
ethyl 2-cyanopropionate
Conditions | Yield |
---|---|
With diethyl ether |
Conditions | Yield |
---|---|
(i) NaOEt, EtOH, (ii) /BRN= 1209223/; Multistep reaction; | |
Stage #1: ethyl 2-cyanoacetate With sodium hydride In tetrahydrofuran at 0℃; for 0.5h; Inert atmosphere; Stage #2: methyl bromide In tetrahydrofuran at 0℃; for 8h; Inert atmosphere; |
tetraethylammoniumcyanide
Ethyl 2-bromopropionate
ethyl 2-cyanopropionate
Conditions | Yield |
---|---|
In dichloromethane |
2-oxo-propionic acid ethyl ester
trimethylsilyl cyanide
ethyl 2-cyanopropionate
Conditions | Yield |
---|---|
In tetrahydrofuran for 8h; Heating; |
ethanol
carbon monoxide
acrylonitrile
A
ethyl 3-cyanopropionate
B
2,4-dicyano-2-methylbutanoic acid ethyl ester
C
ethyl 2-cyanopropionate
Conditions | Yield |
---|---|
With pyridine; dicobalt octacarbonyl In toluene at 110℃; under 75005.9 - 90007.2 Torr; for 6h; | A 6.0 % Chromat. B 75 % Chromat. C 17.7 % Chromat. |
2-hydroxy-2-methylpropanenitrile
Ethyl 2-bromopropionate
A
diethyl 2,3-dimethyl-2-cyanosuccinate
B
ethyl 2-cyanopropionate
Conditions | Yield |
---|---|
With tetra(n-butyl)ammonium hydroxide In acetonitrile Yield given. Yields of byproduct given; | |
With tetra(n-butyl)ammonium hydroxide Yield given. Yields of byproduct given; |
sodium cyanoacetic acid ethyl ester
dimethyl sulfate
A
ethyl 2-cyanopropionate
Conditions | Yield |
---|---|
With benzene |
methyl iodide
A
2-cyano-2-methyl-propionic acid ethyl ester
B
ethyl 2-cyanopropionate
Conditions | Yield |
---|---|
Stage #1: formaldehyd; ethyl 2-cyanoacetate; hydrotalcite; palladium In water; N,N-dimethyl-formamide at 80℃; for 3h; Stage #2: With hydrogen; hydrotalcite; palladium In water; N,N-dimethyl-formamide at 60℃; under 760 Torr; for 1h; | 91 % Chromat. |
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: hydrotalcite-supported palladium nanoparticles / dimethylformamide / 3 h / 80 °C 2: hydrogen / hydrotalcite-supported palladium nanoparticles / toluene / 1 h / 60 °C / 760 Torr View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: diethyl ether; sodium 2: analog reagiert mit Aethyljodid und mit Allyljodid View Scheme |
piperidine
formaldehyd
ethyl 2-cyanoacetate
ethyl 2-cyanopropionate
Conditions | Yield |
---|---|
With acetic acid; palladium on charcoal catalyst In water |
Conditions | Yield |
---|---|
With hydroquinone; palladium on charcoal catalyst In acetic acid; toluene |
Conditions | Yield |
---|---|
With zinc diacetate; paraformaldehyde; palladium In water; acetic acid |
Conditions | Yield |
---|---|
Stage #1: diethyl malonate With sodium hydride In tetrahydrofuran; mineral oil at 20℃; for 0.166667h; Stage #2: bromopropionitrile In tetrahydrofuran; mineral oil at 20℃; for 24h; |
ethyl 2-cyanopropionate
acrylonitrile
2,4-dicyano-2-methylbutanoic acid ethyl ester
Conditions | Yield |
---|---|
With triethylamine In chloroform at 20℃; for 8h; Michael Addition; enantioselective reaction; | 99% |
With [2,6-bis(4',4'-dimethyl-2'-oxazolinyl)phenyl](acetonitrile)nickel(II) tetrafluoroborate; N-ethyl-N,N-diisopropylamine In tetrahydrofuran at 20℃; for 4.5h; Michael addition; | 95% |
With 3-(diethylamino)propyltrimethoxysilane supported on silica-alumina In toluene at 60℃; for 24h; Michael reaction; | 95% |
ethyl 2-cyanopropionate
acrylic acid methyl ester
Conditions | Yield |
---|---|
With dihydridotetrakis(triphenylphosphine)ruthenium In tetrahydrofuran for 24h; Ambient temperature; | 99% |
Ru(+)Cp(NCC(Me)HCO2Et)(-)*(PPh3)2 In tetrahydrofuran at 25℃; for 5h; Addition; Michael reaction; | 99% |
Conditions | Yield |
---|---|
With [2,6-bis(4',4'-dimethyl-2'-oxazolinyl)phenyl](acetonitrile)nickel(II) tetrafluoroborate; N-ethyl-N,N-diisopropylamine In tetrahydrofuran at 20℃; for 4.5h; Michael addition; | 99% |
With BF4(1-)*C34H40N5Ni(1+); N-ethyl-N,N-diisopropylamine In toluene at 20℃; for 5h; Michael addition; Inert atmosphere; | 99% |
With triethylamine In chloroform at 20℃; for 8h; Reagent/catalyst; Solvent; Michael Addition; enantioselective reaction; | 99% |
Conditions | Yield |
---|---|
With triphenylphosphine; acetylacetonatodicarbonylrhodium(l) In tetrahydrofuran at 20℃; for 1h; | 99% |
Conditions | Yield |
---|---|
With lithium hydroxide In tetrahydrofuran; methanol; water for 1h; | 98% |
With lithium hydroxide; water In methanol at 20℃; for 36h; | 89% |
With water; potassium hydroxide In methanol at 0 - 40℃; for 2h; | 85% |
ethyl 2-cyanopropionate
2-cyanopropionamide
Conditions | Yield |
---|---|
With ammonia In ethanol at 20℃; for 15h; | 98% |
With ammonia; water |
ethyl 2-cyanopropionate
ethyl 2-bromo-2-cyano-propionate
Conditions | Yield |
---|---|
With bromine; sodium acetate; acetic acid at 20℃; for 3h; | 98% |
With bromine; sodium acetate; acetic acid at 20 - 30℃; for 1h; | |
With bromine; sodium acetate; acetic acid at 20℃; for 3h; Inert atmosphere; |
Conditions | Yield |
---|---|
With triphenylphosphine; acetylacetonatodicarbonylrhodium(l) In tetrahydrofuran; water at 20℃; for 1h; | 97% |
With triethylamine In acetonitrile at 50℃; | 80.9% |
With potassium carbonate In ethanol at 20℃; for 2.5h; | 59% |
With potassium carbonate In ethanol for 18h; | 48% |
With potassium carbonate In ethanol at 25℃; for 12h; | 16 g |
ethyl 2-cyanopropionate
propargyl bromide
ethyl 2-cyano-2-methylpent-4-ynoate
Conditions | Yield |
---|---|
Stage #1: ethyl 2-cyanopropionate With potassium carbonate In tetrahydrofuran at 20℃; for 0.5h; Stage #2: propargyl bromide In tetrahydrofuran for 24h; Reflux; | 96.4% |
Conditions | Yield |
---|---|
96% |
ethyl 2-cyanopropionate
Conditions | Yield |
---|---|
tetrakis(triphenylphosphine) palladium(0) In tetrahydrofuran at 100℃; | 95% |
tetrakis(triphenylphosphine) palladium(0) In tetrahydrofuran at 100℃; Addition; ring cleavage; | 95% |
Conditions | Yield |
---|---|
Stage #1: ethyl 2-cyanopropionate With C45H40N4O5 In tetrahydrofuran at -78℃; for 0.25h; Michael Addition; Stage #2: dibenzyl azodicarboxylate In tetrahydrofuran for 3h; Michael Addition; enantioselective reaction; | 95% |
Conditions | Yield |
---|---|
With trifluorormethanesulfonic acid; water; palladium diacetate; 2-(3,5-dimethyl-1H-pyrazol-1-yl)pyridine at 60℃; for 5h; | 95% |
ethanol
ethyl 2-cyanopropionate
3-ethoxy-3-imino-2-methylpropionate ethyl hydrochloride
Conditions | Yield |
---|---|
With hydrogenchloride In diethyl ether at 0℃; for 120h; | 94% |
With hydrogenchloride In diethyl ether at 0℃; for 72h; | 92% |
With hydrogenchloride at 0℃; for 4.5h; | |
With hydrogenchloride In toluene at 0 - 20℃; for 24.6667h; | 14.01 g |
ethyl 2-cyanopropionate
1,1-dibromomethane
ethyl 3-bromo-2-cyano-2-methylpropanoate
Conditions | Yield |
---|---|
With potassium carbonate In N,N-dimethyl-formamide for 20h; | 94% |
With sodium hydride In N,N-dimethyl-formamide; benzene for 2h; Ambient temperature; | 68% |
ethyl 2-cyanopropionate
ethyl acrylate
2-cyano-2-methyl-1,5-pentanedioic acid bis(ethyl ester)
Conditions | Yield |
---|---|
With 3-(diethylamino)propyltrimethoxysilane supported on silica-alumina In toluene at 90℃; for 24h; Michael reaction; | 94% |
Conditions | Yield |
---|---|
In tetrahydrofuran (N2); addn. of NCCH(CH3)CO2C2H5 to Ru complex and P(CH3)(C6H5)2 in THF, stirring (55°C, 30 h); pptn. by addn. of hexane, washing (hexane; Et2O); elem. anal.; | 93% |
ethyl 2-cyanopropionate
potassium 2-cyanopropanoate
Conditions | Yield |
---|---|
With potassium tert-butylate In ethanol; water at 60℃; for 0.5h; Schlenk technique; Inert atmosphere; | 93% |
With potassium tert-butylate In ethanol; water Inert atmosphere; Heating; | 92% |
With potassium tert-butylate; water In ethanol | |
With potassium tert-butylate; water In ethanol at 20℃; Inert atmosphere; |
N-(bis(4-fluorophenyl)methyl)-4-methylbenzenesulfonamide
ethyl 2-cyanopropionate
Conditions | Yield |
---|---|
With aluminum (III) chloride In chloroform at 80℃; for 12h; Sealed tube; | 93% |
ethyl 2-cyanopropionate
1,1,5-Trimethoxy-4-oxo-1,4-dihydronaphthalene
Ethyl 2-(1,1,5-Trimethoxy-4-oxo-1,2,3,4-tetrahydro-2-naphthyl)-2-cyanopropionate
Conditions | Yield |
---|---|
With sodium ethanolate In ethanol Ambient temperature; | 92% |
Diphenyliodonium triflate
ethyl 2-cyanopropionate
cyano-methyl-phenyl-acetic acid ethyl ester
Conditions | Yield |
---|---|
Stage #1: ethyl 2-cyanopropionate With potassium tert-butylate In dichloromethane at 0℃; for 0.0833333h; Schlenk technique; Inert atmosphere; Stage #2: Diphenyliodonium triflate In dichloromethane at 0℃; for 0.333333h; Reagent/catalyst; Solvent; Schlenk technique; Inert atmosphere; | 92% |
Conditions | Yield |
---|---|
With tris-(dibenzylideneacetone)dipalladium(0); 2,5-di-tert-butyl-p-benzoquinone; O,O'-(1,1'-biphenyl-2,2'-diyl)-N,N'-diisopropylphosphoramidite In 1,4-dioxane at 50℃; for 24h; Reagent/catalyst; Schlenk technique; Inert atmosphere; | 92% |
4-bromo-1,1'-biphenyl
ethyl 2-cyanopropionate
2-([1,1'-biphenyl]-4-yl)propanenitrile
Conditions | Yield |
---|---|
Stage #1: 4-bromo-1,1'-biphenyl; ethyl 2-cyanopropionate With C22H17N3O2; copper(I) bromide; sodium t-butanolate In isopropyl alcohol at 60℃; for 24h; Schlenk technique; Inert atmosphere; Stage #2: With water; sodium hydroxide In isopropyl alcohol at 60℃; for 4h; Schlenk technique; Inert atmosphere; Cooling; | 92% |
thienyl vinyl ketone
ethyl 2-cyanopropionate
Conditions | Yield |
---|---|
With 4 A molecular sieve; 1-{3,5-bis(trifluoromethyl)phenyl}-3-{(1R,2R)-2-(dimethylamino)cyclohexyl}thiourea In toluene at -60℃; for 96h; Michael addition; | 91% |
ethyl 2-cyanopropionate
diphenyliodonium hexafluorophosphate
cyano-methyl-phenyl-acetic acid ethyl ester
Conditions | Yield |
---|---|
Stage #1: ethyl 2-cyanopropionate With potassium tert-butylate In dichloromethane at 0℃; for 0.0833333h; Schlenk technique; Inert atmosphere; Stage #2: diphenyliodonium hexafluorophosphate In dichloromethane at 0℃; for 0.333333h; Schlenk technique; Inert atmosphere; | 91% |
Conditions | Yield |
---|---|
With C54H82N6NiO3 In chloroform at 20℃; for 8h; Reagent/catalyst; Michael Addition; Schlenk technique; | 91% |
allenyltributylstannane
ethyl 2-cyanopropionate
Conditions | Yield |
---|---|
With 1,4-di(diphenylphosphino)-butane; tris(dibenzylideneacetone)dipalladium(0) chloroform complex In tetrahydrofuran for 48h; Heating; | 90% |
ethyl 2-cyanopropionate
Conditions | Yield |
---|---|
tris(dibenzylideneacetone)dipalladium(0) chloroform complex; 1,1'-bis-(diphenylphosphino)ferrocene In tetrahydrofuran at 65℃; for 43h; | 90% |
With tris(dibenzylideneacetone)dipalladium(0) chloroform complex; 1,1'-bis-(diphenylphosphino)ferrocene In tetrahydrofuran at 65℃; for 43h; | 90% |
Molecular Structure:
Molecular Formula: C6H9NO2
Molecular Weight: 127.1412
IUPAC Name: Ethyl 2-cyanopropanoate
Synonyms of Ethyl 2-cyanopropionate (CAS NO.1572-99-2): AI3-05609 ; EINECS 216-393-9 ; Propanoic acid, 2-cyano-, ethyl ester
CAS NO: 1572-99-2
Index of Refraction: 1.418
Molar Refractivity: 31.49 cm3
Molar Volume: 124.8 cm3
Surface Tension: 33.9 dyne/cm
Density: 1.018 g/cm3
Flash Point: 78.9 °C
Enthalpy of Vaporization: 43.06 kJ/mol
Boiling Point: 194.5 °C at 760 mmHg
Vapour Pressure of Ethyl 2-cyanopropionate (CAS NO.1572-99-2): 0.441 mmHg at 25°C
Risk Statements of Ethyl 2-cyanopropionate (CAS NO.1572-99-2): 20/21/22-36/37/38
R20/21/22: Harmful by inhalation, in contact with skin and if swallowed.
R36/37/38: Irritating to eyes, respiratory system and skin.
Safety Statements: 23-36/37/39
S23: Do not breathe vapour.
S36/37/39: Wear suitable protective clothing, gloves and eye/face protection.
RIDADR: 3276
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