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| CAS No.: | 623-47-2 |
|---|---|
| Name: | Ethyl propiolate |
| 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; |

Xi,
F