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CAS No.: | 623-47-2 |
---|---|
Name: | Ethyl propiolate |
Article Data: | 32 |
Molecular Structure: | |
Formula: | C5H6O2 |
Molecular Weight: | 98.1014 |
Synonyms: | Propiolicacid, ethyl ester (6CI,7CI,8CI);(Ethoxycarbonyl)acetylene;Carboethoxyacetylene;Ethyl 2-propynoate;Ethyl acetylenecarboxylate;Ethylacetylenemonocarboxylate;Ethyl propargylate;Ethylpropynoate;NSC 60551;Propynoic acid ethyl ester; |
EINECS: | 210-795-8 |
Density: | 0.998 g/cm3 |
Melting Point: | 9 °C |
Boiling Point: | 119.999 °C at 760 mmHg |
Flash Point: | 23.333 °C |
Solubility: | miscible with water |
Appearance: | clear colorless to pale yellow liquid |
Hazard Symbols: | Xi,F |
Risk Codes: | 10-36/37/38-36-11 |
Safety: | 26-36-37/39-16-33-29-24-23 |
Transport Information: | UN 3272 3/PG 3 |
PSA: | 26.30000 |
LogP: | 0.18270 |
Conditions | Yield |
---|---|
With sulfuric acid; trimethyl orthoformate In dichloromethane at 40℃; for 24h; Reagent/catalyst; | 86.7% |
boron trifluoride diethyl etherate 1.) reflux, 1.5 h; 2.) rt., 4 h.; | 60% |
With sulfuric acid for 24h; Reflux; | 36% |
Ethyl half ester of acetylenedicarboxylic acid
toluene
propynoic acid ethyl ester
Conditions | Yield |
---|---|
at 100℃; Zeitlicher Verlauf der thermischen Zersetzung; |
(E)-4-(Triphenyl-λ5-phosphanylidene)-pent-2-enedioic acid diethyl ester
A
ethyl (triphenylphosphoranylidene)acetate
B
propynoic acid ethyl ester
Conditions | Yield |
---|---|
equil. react.; |
Ethyl half ester of acetylenedicarboxylic acid
water
propynoic acid ethyl ester
Conditions | Yield |
---|---|
at 100℃; Zeitlicher Verlauf der thermischen Zersetzung; |
Mesitol
chloroformic acid ethyl ester
Propiolic acid
A
Trifluoressigsaeure-(2,4,6-trimethyl-phenylester)
B
propynoic acid ethyl ester
Conditions | Yield |
---|---|
Stage #1: Propiolic acid With lithium hydride In tetrahydrofuran at 20℃; for 18h; Metallation; Stage #2: chloroformic acid ethyl ester In tetrahydrofuran at -10 - 20℃; Acylation; Stage #3: Mesitol In tetrahydrofuran at 20 - 45℃; Substitution; |
chloroformic acid ethyl ester
sodium 2,4,6-trimethylphenoxide
Propiolic acid
A
Trifluoressigsaeure-(2,4,6-trimethyl-phenylester)
D
propynoic acid ethyl ester
Conditions | Yield |
---|---|
Stage #1: Propiolic acid With lithium hydride In tetrahydrofuran at 20℃; for 18h; Metallation; Stage #2: chloroformic acid ethyl ester In tetrahydrofuran at -10 - 20℃; Acylation; Stage #3: sodium 2,4,6-trimethylphenoxide In tetrahydrofuran at 20 - 45℃; Substitution; |
methyl propargyl alcohol
diethylazodicarboxylate
phenol
A
but-2-ynyloxybenzene
B
propynoic acid ethyl ester
Conditions | Yield |
---|---|
With triphenylphosphine In tetrahydrofuran; benzene | A 2.18 g (70%) B n/a |
propargyl alcohol
diethylazodicarboxylate
5-bromo-2-[(4-hydroxy-benzenesulfonyl)-methyl-amino]-3-methyl-benzoic acid methyl ester
A
propynoic acid ethyl ester
B
5-bromo-3-methyl-2-[methyl-(4-prop-2-ynyloxy-benzenesulfonyl)-amino]-benzoic acid methyl ester
Conditions | Yield |
---|---|
With triphenylphosphine In tetrahydrofuran; benzene | A n/a B 0.389 g (71%) |
(hydrotris(3,5-diisopropylpyrazolyl)borato)CoCCC(O)OCH2CH3
water
B
propynoic acid ethyl ester
Conditions | Yield |
---|---|
In not given |
Conditions | Yield |
---|---|
Stage #1: acetylene With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.25h; Inert atmosphere; Stage #2: chloroformic acid ethyl ester In tetrahydrofuran; hexane at -78℃; for 8h; Inert atmosphere; | |
Stage #1: acetylene With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.5h; Inert atmosphere; Stage #2: chloroformic acid ethyl ester In tetrahydrofuran; hexane at -78 - 20℃; for 1.5h; Inert atmosphere; |