butanedioic acid, monoethyl ester
ethyl 3-(chloroformyl)propionate
Conditions | Yield |
---|---|
With thionyl chloride In dichloromethane Heating; | 100% |
With thionyl chloride for 1.5h; Heating; | 97% |
With thionyl chloride In dichloromethane; N,N-dimethyl-formamide at 38℃; for 5h; Inert atmosphere; | 95% |
Conditions | Yield |
---|---|
Stage #1: succinic acid anhydride; ethanol for 2h; Reflux; Stage #2: With thionyl chloride for 2h; Reflux; | 82% |
With thionyl chloride Yield given. Multistep reaction; |
(E)-4-ethoxy-4-oxobut-2-enoic acid
ethyl 3-(chloroformyl)propionate
Conditions | Yield |
---|---|
With thionyl chloride for 5h; Heating; | 68% |
ethyl 3-(chloroformyl)propionate
Conditions | Yield |
---|---|
With trichlorophosphate |
succinic acid diethyl ester
ethyl 3-(chloroformyl)propionate
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 60 percent / KOH / ethanol / 16 h / 0 °C 2: 97 percent / SOCl2 / 1.5 h / Heating View Scheme |
ethyl 3-(chloroformyl)propionate
ethyl cinnamate
Conditions | Yield |
---|---|
With magnesium In N,N-dimethyl-formamide at 20℃; for 15h; | 100% |
ethyl 3-(chloroformyl)propionate
amonafide
Conditions | Yield |
---|---|
In acetonitrile at 20℃; for 1h; | 100% |
In acetonitrile at 20℃; for 1h; | 100% |
ethyl 3-(chloroformyl)propionate
2,6-di-tert-butyl-4-{4-[3,5-di-tert-butyl-4-(4-hydroxybutoxy)phenylsulfanyl]piperidin-4-ylsulfanyl}phenol
4-[4-[3,5-di-tert-butyl-4-(4-hydroxybutoxy)phenylsulfanyl]-4-(3,5-di-tert-butyl-4-hydroxyphenyl-sulfanyl)piperidin-1-yl]-4-oxobutyric acid ethyl ester
Conditions | Yield |
---|---|
With N-ethyl-N,N-diisopropylamine In tetrahydrofuran at 20℃; for 0.25h; | 100% |
ethyl 3-(chloroformyl)propionate
diazomethyl-trimethyl-silane
ethyl 5-bromo-4-oxopentanoate
Conditions | Yield |
---|---|
Stage #1: ethyl 3-(chloroformyl)propionate; diazomethyl-trimethyl-silane In diethyl ether; acetonitrile at 20℃; for 1h; Stage #2: With hydrogen bromide In diethyl ether; acetic acid; acetonitrile at -20 - 20℃; for 16.33h; | 99% |
Stage #1: ethyl 3-(chloroformyl)propionate; diazomethyl-trimethyl-silane In hexane; acetonitrile for 2h; Stage #2: With hydrogen bromide; acetic acid In hexane; acetonitrile for 1h; | 64% |
ethyl 3-(chloroformyl)propionate
methyl 2-amino-5-iodobenzoate
2-(3-ethoxycarbonyl-propionylamino)-5-iodo-benzoic acid methyl ester
Conditions | Yield |
---|---|
With dmap; N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; | 99% |
ethyl 3-(chloroformyl)propionate
(S)-(5-methoxy-1,2,3,4-tetrahydro-naphthalen-2-yl)-propylamine hydrochloride
(S)-ethyl 4-((5-methoxy-1,2,3,4-tetrahydronaphthalen-2-yl)(propyl)amino)-4-oxobutanoate
Conditions | Yield |
---|---|
With triethylamine In dichloromethane at 0 - 20℃; for 3h; | 99% |
4-hydroxy-2,5-diphenyl-1,3-thiazole
ethyl 3-(chloroformyl)propionate
2,5-diphenyl-4-<(ethyloxysuccinyl)oxy>thiazole
Conditions | Yield |
---|---|
With dmap In dichloromethane at 23℃; for 2h; | 97% |
ethyl 3-(chloroformyl)propionate
bisdemethoxycurcumin
Conditions | Yield |
---|---|
With dmap In dichloromethane at 20℃; for 2h; Inert atmosphere; | 97% |
ethyl 3-(chloroformyl)propionate
(tert-Butoxycarbonylmethylene)triphenylphosphorane
t-butyl 5-ethoxycarbonyl-3-oxo-2-(triphenylphosphoranylidine)-pentanoate
Conditions | Yield |
---|---|
In benzene | 96% |
In benzene at 8 - 20℃; for 1.5h; | 87% |
In benzene 1.) 8 deg C, 5 min, 2.) r.t., 1.5 h; | 87% |
ethyl 3-(chloroformyl)propionate
2-carboethoxy-4,5-dimethoxyaniline
4,5-dimethoxy-2-[(4-ethoxy-1,4-dioxobutyl)amino]benzoic acid ethyl ester
Conditions | Yield |
---|---|
With pyridine In tetrahydrofuran at 20℃; for 2h; | 96% |
With pyridine In toluene at 20℃; for 4h; | 70% |
ethyl 3-(chloroformyl)propionate
demethoxycurcumin
Conditions | Yield |
---|---|
With dmap In dichloromethane at 20℃; for 2h; Inert atmosphere; | 96% |
Conditions | Yield |
---|---|
In dichloromethane at 60℃; for 1h; | 96% |
With sodium hydroxide In dichloromethane at 60℃; for 1h; | 96% |
Conditions | Yield |
---|---|
Stage #1: pyrrolidine With triethylamine In dichloromethane at 0℃; for 0.25h; Inert atmosphere; Stage #2: ethyl 3-(chloroformyl)propionate In dichloromethane at 0 - 20℃; for 1h; Inert atmosphere; | 96% |
With triethylamine In dichloromethane at 0 - 20℃; for 1h; Inert atmosphere; | 96% |
ethyl 3-(chloroformyl)propionate
4-amino-2,2,6,6-tetramethyl-1-piperidine-1-oxyl
A
triethylamine hydrochloride
B
C15H27N2O4
Conditions | Yield |
---|---|
With triethylamine In benzene 1.) 0 degC, 2.) R.T. 12 h; | A n/a B 95% |
ethyl 3-(chloroformyl)propionate
curcumin
Conditions | Yield |
---|---|
With dmap In dichloromethane at 20℃; for 2h; Inert atmosphere; | 95% |
ethyl 3-(chloroformyl)propionate
n-octylmagnesium chloride
4-Oxododecansaeure-ethylester
Conditions | Yield |
---|---|
With copper(l) iodide In tetrahydrofuran at 0 - 20℃; | 95% |
With copper(l) iodide In tetrahydrofuran at 0 - 20℃; for 3h; Inert atmosphere; |
ethyl 3-(chloroformyl)propionate
1,6,8-trihydroxy-3-methyl-9,10-anthraquinone
Conditions | Yield |
---|---|
With pyridine In dichloromethane at 0 - 20℃; for 3h; | 94.7% |
tryptamine
ethyl 3-(chloroformyl)propionate
ethyl 4-{[2-(1H-Indol-3-yl)ethyl]amino}-4-oxobutanoate
Conditions | Yield |
---|---|
Stage #1: ethyl 3-(chloroformyl)propionate With triethylamine In dichloromethane at 20℃; Stage #2: tryptamine In methanol; chloroform at 20℃; | 94% |
ethyl 3-(chloroformyl)propionate
1,1-dimethylethyl -<2-<<2-amino-3-(1H-indol-3-yl)-2-methyl-1-oxopropyl>amino>-1-phenylethyl>carbamate
ethyl -4-<<2-<<2-<<(1,1-dimethylethoxy)carbonyl>amino>-2-phenylethyl>amino>-1-(1H-indol-3-ylmethyl)-1-methyl-2-oxoethyl>amino>-4-oxobutanoate
Conditions | Yield |
---|---|
With triethylamine In tetrahydrofuran for 2h; Ambient temperature; | 93% |
ethyl 3-(chloroformyl)propionate
Bis(trimethylsilyl)ethyne
4-Oxo-6-trimethylsilanyl-hex-5-ynoic acid ethyl ester
Conditions | Yield |
---|---|
With aluminium trichloride In dichloromethane 1) 0 deg C, 15 min, 2) rt, 3 h; | 93% |
With aluminium trichloride In dichloromethane at 0 - 20℃; for 4h; Acylation; |
tetrakis-5,10,15,20-(o-aminophenyl)porphyrin
ethyl 3-(chloroformyl)propionate
Conditions | Yield |
---|---|
Acylation; | 93% |
With triethylamine In tetrahydrofuran at 0℃; | 93% |
thiophene
ethyl 3-(chloroformyl)propionate
ethyl 4-oxo-4-(thiophen-2-yl)butanoate
Conditions | Yield |
---|---|
With tin(IV) chloride In dichloromethane at 20℃; for 2h; Cooling; | 93% |
With tin(IV) chloride In dichloromethane at 20℃; Friedel-Crafts; | 83% |
With tin(IV) chloride In dichloromethane at 0 - 20℃; Friedel Crafts acylation; | |
With tin(IV) chloride at 20℃; Friedel-Crafts Acylation; |
ethyl 3-(chloroformyl)propionate
Conditions | Yield |
---|---|
With triethylamine In tetrahydrofuran at 20℃; for 12h; | 93% |
ethyl 3-(chloroformyl)propionate
2-aminoacetophenone hydrochloride
N-(3-Carbethoxypropanoyl)-ω-aminoacetophenone
Conditions | Yield |
---|---|
In pyridine at 25℃; for 96h; | 92% |
ethyl 3-(chloroformyl)propionate
1'-[3-(3-ethoxycarbonyl-propionyl)-3-aza-spiro[5.5]undecane-9-carbonyl]-[4,4']bipiperidinyl-1-carboxylic acid benzyl ester
Conditions | Yield |
---|---|
With N-ethyl-N,N-diisopropylamine In dichloromethane | 92% |
ethyl 3-(chloroformyl)propionate
Conditions | Yield |
---|---|
With triethylamine In tetrahydrofuran at 0℃; | 92% |
ethyl 3-(chloroformyl)propionate
Conditions | Yield |
---|---|
With sodium hydroxide In dichloromethane; water at 0 - 20℃; for 2h; | 92% |
ethyl 3-(chloroformyl)propionate
(2-aminophenyl)-(3-methoxyphenyl)methanone
Conditions | Yield |
---|---|
In dichloromethane at 60℃; for 1h; | 92% |
In dichloromethane at 60℃; for 1h; | 92% |
ethyl 3-(chloroformyl)propionate
2-amino-3-methylbenzamide
Conditions | Yield |
---|---|
With pyridine In tetrahydrofuran for 16h; | 92% |
With pyridine In tetrahydrofuran for 16h; | 92% |
Molecular Structure of Butanoic acid, 4-chloro-4-oxo-, ethyl ester (CAS NO.14794-31-1):
IUPAC Name: ethyl 4-chloro-4-oxobutanoate
Empirical Formula: C6H9ClO3
Molecular Weight: 164.5869
Sensitive: Moisture Sensitive
BRN: 1766126
EINECS: 238-855-9
H bond acceptors: 3
H bond donors: 0
Freely Rotating Bonds: 5
Polar Surface Area: 43.37Å2
Index of Refraction: 1.436
Molar Refractivity: 36.49 cm3
Molar Volume: 139.5 cm3
Surface Tension: 34.8 dyne/cm
Density: 1.179 g/cm3
Flash Point: 84.4 °C
Enthalpy of Vaporization: 44.41 kJ/mol
Boiling Point: 207.8 °C at 760 mmHg
Vapour Pressure: 0.22 mmHg at 25°C
InChI
InChI=1/C6H9ClO3/c1-2-10-6(9)4-3-5(7)8/h2-4H2,1H3
Smiles
O=C(OCC)CCC(Cl)=O
Hazard Codes: C
Risk Statements: 34-36/37-14
R34:Causes burns.
R36/37:Irritating to eyes and respiratory system.
R14 :Reacts violently with water.
Safety Statements: 26-27-36/37/39-45-24/25
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
S27:Take off immediately all contaminated clothing.
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection.
S45:In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.)
S24/25:Avoid contact with skin and eyes.
RIDADR: UN 3265 8/PG 2
WGK Germany: 3
HazardClass: 8
PackingGroup: II
Butanoic acid, 4-chloro-4-oxo-, ethyl ester , with CAS number of 14794-31-1, can be called Ethyl 3-(chloroformyl)propionate ; 3-Carbethoxypropionyl chloride ; 3-Chlorocarbonylpropionic acid ethyl ester ; 4-Chloro-4-oxobutanoic acid ethylester ; 4-Ethoxy-4-oxobutanoic acid chloride ; Monoethylsuccinoyl chloride ; b-Ethoxycarbonylpropionyl chloride ; b-Carbethoxypropionyl chloride . It is a clear colourless to yellow liquid.
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