Ethyl propiolate supplier | CasNO.623-47-2

Name
Ethyl propiolate
EINECS 210-795-8
CAS No. 623-47-2
Article Data32
CAS DataBase
Density 0.998 g/cm³
Solubility miscible with water
Melting Point 9 °C
Formula C₅H₆O₂
Boiling Point 119.999 °C at 760 mmHg
Molecular Weight 98.1014
Flash Point 23.333 °C
Transport Information UN 3272 3/PG 3
Appearance clear colorless to pale yellow liquid
Safety 26-36-37/39-16-33-29-24-23
Risk Codes 10-36/37/38-36-11
Molecular Structure
Hazard Symbols Xi,F
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;
PSA 26.30000
LogP 0.18270

Synthetic route

: 64-17-5
ethanol

: 471-25-0
Propiolic acid

: 623-47-2
propynoic acid ethyl ester

Conditions

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%

: 38391-86-5
Ethyl half ester of acetylenedicarboxylic acid

: 108-88-3
toluene

: 623-47-2
propynoic acid ethyl ester

Conditions

Conditions	Yield
at 100℃; Zeitlicher Verlauf der thermischen Zersetzung;

: 119930-16-4
(E)-4-(Triphenyl-λ5-phosphanylidene)-pent-2-enedioic acid diethyl ester

A: 1099-45-2
ethyl (triphenylphosphoranylidene)acetate

B: 623-47-2
propynoic acid ethyl ester

Conditions

Conditions	Yield
equil. react.;

: 38391-86-5
Ethyl half ester of acetylenedicarboxylic acid

: 7732-18-5
water

: 623-47-2
propynoic acid ethyl ester

Conditions

Conditions	Yield
at 100℃; Zeitlicher Verlauf der thermischen Zersetzung;

: 527-60-6
Mesitol

: 541-41-3
chloroformic acid ethyl ester

: 471-25-0
Propiolic acid

A: 1737-55-9
Trifluoressigsaeure-(2,4,6-trimethyl-phenylester)

B: 623-47-2
propynoic acid ethyl ester

Conditions

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;

...Expand

: 541-41-3
chloroformic acid ethyl ester

: 51114-00-2
sodium 2,4,6-trimethylphenoxide

: 471-25-0
Propiolic acid

A: 1737-55-9
Trifluoressigsaeure-(2,4,6-trimethyl-phenylester)

B: carbonic acid ethyl ester 2,4,6-trimethyl-phenyl ester

C: (E)-3-(2,4,6-Trimethyl-phenoxy)-acrylic acid 2,4,6-trimethyl-phenyl ester

D: 623-47-2
propynoic acid ethyl ester

Conditions

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;

...Expand

: 764-01-2
methyl propargyl alcohol

: 1972-28-7
diethylazodicarboxylate

: 108-95-2
phenol

A: 13610-09-8
but-2-ynyloxybenzene

B: 623-47-2
propynoic acid ethyl ester

Conditions

Conditions	Yield
With triphenylphosphine In tetrahydrofuran; benzene	A 2.18 g (70%) B n/a

...Expand

: 107-19-7
propargyl alcohol

: 1972-28-7
diethylazodicarboxylate

: 287108-60-5
5-bromo-2-[(4-hydroxy-benzenesulfonyl)-methyl-amino]-3-methyl-benzoic acid methyl ester

A: 623-47-2
propynoic acid ethyl ester

B: 287108-61-6
5-bromo-3-methyl-2-[methyl-(4-prop-2-ynyloxy-benzenesulfonyl)-amino]-benzoic acid methyl ester

Conditions

Conditions	Yield
With triphenylphosphine In tetrahydrofuran; benzene	A n/a B 0.389 g (71%)

...Expand

: 461695-81-8
(hydrotris(3,5-diisopropylpyrazolyl)borato)CoCCC(O)OCH2CH3

: 7732-18-5
water

A: [Co(hydrotris(3,5-diisopropyl-1-pyrazolyl)borate)]2(OH)2

B: 623-47-2
propynoic acid ethyl ester

Conditions

Conditions	Yield
In not given

...Expand

: 541-41-3
chloroformic acid ethyl ester

: 74-86-2
acetylene

: 623-47-2
propynoic acid ethyl ester

Conditions

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;

: 924-44-7
glyoxylic acid ethyl ester

: 623-47-2
propynoic acid ethyl ester

Conditions

Conditions	Yield
With C7H13N2O4P; potassium carbonate In methanol at 20℃; Inert atmosphere;

: 110-89-4
piperidine

: 623-47-2
propynoic acid ethyl ester

: 81239-00-1
ethyl (E)-3-(piperidin-1-yl)acrylate

Conditions

Conditions	Yield
at 20℃; for 0.0333333h; Michael addition;	100%
With water at 20℃; for 0.0833333h; optical yield given as %de; stereoselective reaction;	96%
With benzene

: 623-47-2
propynoic acid ethyl ester

: 7341-96-0
2-propynamide

Conditions

Conditions	Yield
With ammonia at -78 - 20℃; for 5h;	100%
With ammonia at -55℃; for 9h;	83%
With ammonium hydroxide at -10℃; for 1h; Inert atmosphere;	74%

: 123-75-1
pyrrolidine

: 623-47-2
propynoic acid ethyl ester

: 65651-80-1
ethyl (E)-3-(pyrrolidin-1-yl)acrylate

Conditions

Conditions	Yield
In toluene at 20℃; for 16h;	100%
With water In neat (no solvent) at 20℃; for 0.166667h; Michael Addition; Sealed tube; Green chemistry; stereoselective reaction;	99%
With water at 20℃; for 0.0833333h; optical yield given as %de; stereoselective reaction;	91%

: 110-91-8
morpholine

: 623-47-2
propynoic acid ethyl ester

: 81239-01-2
ethyl (E)-3-(morpholin-4-yl)acrylate

Conditions

Conditions	Yield
at 20℃; for 0.0333333h; Michael addition;	100%
With water In neat (no solvent) at 20℃; for 0.166667h; Michael Addition; Sealed tube; Green chemistry; stereoselective reaction;	99%
With water at 20℃; for 0.0833333h; optical yield given as %de; stereoselective reaction;	94%

: 90-04-0
2-methoxy-phenylamine

: 623-47-2
propynoic acid ethyl ester

: 115607-78-8
ethyl 3-<(2-methoxyphenyl)amino>acrylate

Conditions

Conditions	Yield
In ethanol for 3h; Heating;	100%

: 64-17-5
ethanol

: 623-47-2
propynoic acid ethyl ester

: 10601-80-6
ethyl 3,3-diethoxypropanoate

Conditions

Conditions	Yield
With potassium for 12h;	100%
With copper(II) sulfate for 24h; Heating / reflux;	37%

: 24886-73-5
1-Azidoadamantane

: 623-47-2
propynoic acid ethyl ester

: 76599-43-4
1-(1-adamantyl)-4-(ethyoxycarbonyl)-1H-1,2,3-triazole

Conditions

Conditions	Yield
With tetrakis(acetonitrile)copper(I)tetrafluoroborate; tris[(1-benzyl-1H-1,2,3-triazol-4yl)methyl]amine In tetrahydrofuran at 20℃; for 24h; Inert atmosphere;	100%
With 2,6-dimethylpyridine In water at 20℃; for 8h; Huisgen 1,3-dipolar cycloaddition; regioselective reaction;	96%
With C22H28CuIN2 In neat (no solvent) at 20℃; for 72h;	81%
In toluene at 110℃; for 50h;	77%

: 7340-17-2
ethyl N-hydroxybenzimidate

: 623-47-2
propynoic acid ethyl ester

: 139172-68-2, 144946-63-4
ethyl N-<(2'-ethoxycarbonylvinyl)oxy>benzimidate

Conditions

Conditions	Yield
With triethylamine for 0.166667h; Ambient temperature;	100%

: 135907-85-6
C15H17N3O4

: 623-47-2
propynoic acid ethyl ester

: 135907-91-4
C20H23N3O6

Conditions

Conditions	Yield
In acetonitrile for 24h; Ambient temperature;	100%

: 623-47-2
propynoic acid ethyl ester

: 31930-36-6
ethyl (Z)-3-iodopropenoate

Conditions

Conditions	Yield
With acetic acid; sodium iodide at 70℃; for 16h; Inert atmosphere;	100%
With acetic acid; sodium iodide at 70℃; for 16h; Inert atmosphere;	99%
With acetic acid; sodium iodide	98%

: 762-04-9
phosphonic acid diethyl ester

: 623-47-2
propynoic acid ethyl ester

: 1112-29-4
ethyl β,β-bis(diethoxyphosphoryl)propionate

Conditions

Conditions	Yield
With aluminum oxide; potassium hydroxide In dichloromethane at 20℃; for 0.0833333h;	100%
With sodium hexamethyldisilazane 1) THF, -50 deg C, 15 min; 2) THF, -50 deg C, 10 min; Yield given. Multistep reaction;
With aluminum oxide; potassium hydroxide at 20℃; for 0.0833333h; Yield given;

: 186581-53-3, 908094-01-9
diazomethane

: 623-47-2
propynoic acid ethyl ester

: 5932-27-4
ethyl 1H-pyrazole-3-carboxylate

Conditions

Conditions	Yield
In diethyl ether Ambient temperature;	100%

: 80910-01-6, 108836-41-5, 134733-19-0, 144069-33-0
(S)-2-[(4-methoxybenzyloxy)methyl]oxirane

: 623-47-2
propynoic acid ethyl ester

: 302554-85-4
ethyl (5S)-5-hydroxy-6-(4-methoxybenzyloxy)hex-2-ynoate

Conditions

Conditions	Yield
With n-butyllithium; boron trifluoride diethyl etherate In tetrahydrofuran at -78℃; for 0.5h; Ring cleavage;	100%
Stage #1: propynoic acid ethyl ester With n-butyllithium In tetrahydrofuran; hexane at -90℃; for 0.333333h; Stage #2: (S)-2-[(4-methoxybenzyloxy)methyl]oxirane With boron trifluoride diethyl etherate In tetrahydrofuran; hexane at -90 - 0℃;	100%

: 623-47-2
propynoic acid ethyl ester

: 370884-58-5
1-[(2R,3S,6R,7S)-3-Hydroxy-6-(4-methoxy-benzyloxy)-7-(4-methoxy-benzyloxymethyl)-2-methyl-oxepan-2-yl]-propan-2-one

: 370884-60-9
(E)-3-[(2R,3S,6R,7S)-6-(4-Methoxy-benzyloxy)-7-(4-methoxy-benzyloxymethyl)-2-methyl-2-(2-oxo-propyl)-oxepan-3-yloxy]-acrylic acid ethyl ester

Conditions

Conditions	Yield
With 4-methyl-morpholine In dichloromethane at 20℃;	100%
With 4-methyl-morpholine In dichloromethane at 30℃; for 16h;	100%

: 623-47-2
propynoic acid ethyl ester

: 396714-80-0
1-(benzyloxy)-3-(phenyltellanyl)propan-2-ol

: 396714-84-4
(E)-3-(1-benzyloxymethyl-2-phenyltellurenyl-ethoxy)-acrylic acid ethyl ester

Conditions

Conditions	Yield
With 4-methyl-morpholine In dichloromethane at 20℃; hetero-Michael addition reaction;	100%
With 4-methyl-morpholine In dichloromethane at 20℃; hetero-Michael addition;	80%

: 80735-94-0
1-Phenyl-3-buten-1-ol

: 623-47-2
propynoic acid ethyl ester

: ethyl (E)-3-(1-phenyl-3-buten-1-yl)oxy-2-propenoate

Conditions

Conditions	Yield
Stage #1: propynoic acid ethyl ester With triethylamine In diethyl ether for 0.25h; Inert atmosphere; Stage #2: 1-Phenyl-3-buten-1-ol In diethyl ether for 28h; Inert atmosphere;	100%
Stage #1: propynoic acid ethyl ester With triethylamine In diethyl ether at 20℃; for 0.166667h; Stage #2: 1-Phenyl-3-buten-1-ol In diethyl ether at 20℃; for 48h;	97%

: 606123-85-7
1-benzylidene-4,4-dimethyl-3-oxopyrazolidin-1-ium-2-ide

: 623-47-2
propynoic acid ethyl ester

: 6,6-dimethyl-5-oxo-1-phenyl-6,7-dihydro-1H,5H-pyrazolo[1,2-a]pyrazole-2-carboxylic acid ethyl ester

Conditions

Conditions	Yield
With copper(l) iodide; phosphaferrocene-4-(S)-i-Pr-oxazoline; N-Methyldicyclohexylamine In dichloromethane at 20℃; for 20h;	100%

: 111680-71-8
2-(dimethylamino)-4-oxo-4H-pyrido<1,2-a>pyrimidine-3-carbaldehyde

: 623-47-2
propynoic acid ethyl ester

: 24461-61-8, 26682-99-5, 37760-98-8, 6591-61-3
phenylglycine methyl ester

: C15H15NO4

Conditions

Conditions	Yield
Stage #1: 2-(dimethylamino)-4-oxo-4H-pyrido<1,2-a>pyrimidine-3-carbaldehyde; phenylglycine methyl ester In toluene at 85℃; for 1h; Stage #2: propynoic acid ethyl ester In toluene at 85℃; for 3.5h; Stage #3: With pyridinium p-toluenesulfonate In toluene Further stages.;	100%

...Expand

: 90-04-0
2-methoxy-phenylamine

: 623-47-2
propynoic acid ethyl ester

: 142781-90-6
ethyl 3-(2-methoxyphenylamino)acrylate

Conditions

Conditions	Yield
In ethanol	100%

: 73183-34-3
bis(pinacol)diborane

: 623-47-2
propynoic acid ethyl ester

: 1009307-13-4
ethyl (2E)-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)acrylate

Conditions

Conditions	Yield
Stage #1: bis(pinacol)diborane With 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; copper(l) chloride; sodium t-butanolate In tetrahydrofuran at 20℃; for 0.166667h; Schlenk technique; Inert atmosphere; Stage #2: propynoic acid ethyl ester In tetrahydrofuran; methanol Sealed tube; Schlenk technique; Inert atmosphere;	100%
Stage #1: bis(pinacol)diborane With 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; copper(l) chloride; sodium t-butanolate In tetrahydrofuran at 25℃; for 0.166667h; Schlenk technique; Inert atmosphere; Stage #2: propynoic acid ethyl ester In tetrahydrofuran; methanol at 25℃; Schlenk technique; Inert atmosphere; Sealed tube;	95%
Stage #1: bis(pinacol)diborane With 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; copper(l) chloride; sodium t-butanolate In tetrahydrofuran at 25℃; for 0.166667h; Inert atmosphere; Stage #2: propynoic acid ethyl ester In tetrahydrofuran; methanol at 25℃; for 11.4h; Inert atmosphere;	85.3%

: 1021700-66-2
C13H16O4

: 623-47-2
propynoic acid ethyl ester

: C18H22O6

Conditions

Conditions	Yield
With 4-methyl-morpholine at 20℃; for 12h; Michael addition; Inert atmosphere;	100%

: 123-73-9
trans-Crotonaldehyde

: 623-47-2
propynoic acid ethyl ester

: C9H12O3

Conditions

Conditions	Yield
Stage #1: propynoic acid ethyl ester With n-butyllithium; diisopropylamine In tetrahydrofuran; hexane at -78℃; for 0.5h; Stage #2: trans-Crotonaldehyde In tetrahydrofuran; hexane at -78℃; for 1.5h;	100%

: 1517-05-1
2-azidoethanol

: 623-47-2
propynoic acid ethyl ester

: 1-(2-hydroxyethyl)-4-ethoxycarbonyl-1H-1,2,3-triazole

Conditions

Conditions	Yield
With supported Cu(I) bis-2-pyridiylamine functionalized silica Si-BPA*Cu+ In water; tert-butyl alcohol for 1h; Microwave irradiation; regiospecific reaction;	100%
With copper(II) loaded mesoporous SBA-15 In dichloromethane at 20℃; Huisgen Cycloaddition; regioselective reaction;	64%

: 123-75-1
pyrrolidine

: 623-47-2
propynoic acid ethyl ester

: 53927-12-1
ethyl-3-(pyrrolidin-1-yl)prop-2-enoate

Conditions

Conditions	Yield
In tetrahydrofuran at 10 - 25℃; for 1h;	100%
In acetonitrile at 20℃; for 10h;	98%
In acetonitrile at 20℃; Inert atmosphere;
In acetonitrile at 20℃;	9.47 g

: 105310-97-2
N-benzyl-α-diazoacetamide

: 623-47-2
propynoic acid ethyl ester

: ethyl 5-(benzylcarbamoyl)-1H-pyrazole-3-carboxylate

Conditions

Conditions	Yield
In water; acetonitrile at 22℃; under 760.051 Torr;	100%

: C31H36Cl2O8S

: 623-47-2
propynoic acid ethyl ester

: C36H42Cl2O10S

Conditions

Conditions	Yield
With 4-methyl-morpholine In dichloromethane at 0 - 20℃; for 4h;	100%

: 95239-02-4
C10H16N2O4

: 7518-21-0
2-(1-methyl-1H-indol-3-yl)ethylamine

: 623-47-2
propynoic acid ethyl ester

: 4-ethyl 3-methyl 2-methyl-1-[2-(1-methyl-1H-indol-3-yl)ethyl]-1H-pyrrole-3,4-dicarboxylate

Conditions

Conditions	Yield
Stage #1: 2-(1-methyl-1H-indol-3-yl)ethylamine; propynoic acid ethyl ester In dichloromethane at 20℃; Stage #2: C10H16N2O4 In dichloromethane; toluene for 2h; Reflux; Stage #3: With trifluoroacetic acid In dichloromethane; toluene Reflux;	100%

...Expand

: 623-47-2
propynoic acid ethyl ester

: 4105-92-4
triethyl benzene-1,3,5-tricarboxylate

Conditions

Conditions	Yield
With chloro-trimethyl-silane In butan-1-ol; benzene at 40℃; for 8h; regioselective reaction;	99.1%
With ClO4 In methanol Ambient temperature;	87%
With piperazine; LACTIC ACID In N,N-dimethyl-formamide at 90℃; for 12h;	78%

: 623-47-2
propynoic acid ethyl ester

: 26631-66-3
(Z)-ethyl 2,3-dibromoprop-2-enoate

Conditions

Conditions	Yield
With bromine In tetrachloromethane at 70℃; for 0.5h;	99%
With bromine In tetrachloromethane at 70℃; for 2.5h;	90%
With bromine In tetrachloromethane at 70℃; for 1.5h;	83%
With bromine In tetrachloromethane Irradiation;
With bromine In tetrachloromethane at 70℃; for 1.5h; Yield given;

: 622-37-7
Phenyl azide

: 623-47-2
propynoic acid ethyl ester

: 4915-97-3
1-phenyl-1H-[1,2,3]triazole-4-carboxylic acid ethyl ester

Conditions

Conditions	Yield
With C30H23Cl2N7O4Ru(1+)*Cl(1-) In water at 23℃; for 0.0666667h; Huisgen Cycloaddition; Sonication; Green chemistry; regioselective reaction;	99%
In ethanol for 20h; Heating;	95%
With copper(I) oxide In water at 25℃; for 0.0833333h; Inert atmosphere;	95%

Ethyl propiolate Chemical Properties

The Molecular formula of Ethyl propiolate(623-47-2): C₅H₆O₂
The Molecular Weight of Ethyl propiolate(623-47-2): 98.1
Molecular Structure :

EINECS: 210-795-8
Boiling Point: 120 °C at 760 mmHg
Flash Point: 23.3 °C
Water Solubility miscible
Index of Refraction: 1.418
Molar Refractivity: 24.81 cm³
Molar Volume: 98.3 cm³
Polarizability: 9.83 10^-24 cm³
Surface Tension: 32.5 dyne/cm
Density: 0.997 g/cm³
Enthalpy of Vaporization: 35.81 kJ/mol
Vapour Pressure: 15.5 mmHg at 25°C
storage temp.: 2-8°C
IUPAC Name: ethyl prop-2-ynoate
Synonyms: ACETYLENECARBOXYLIC ACID ETHYL ESTER;ETHYL PROPIOLATE;2-Propynoic acid, ethyl ester;Ethyl 2-propynoate;Ethyl propynoate;ETHYL ACETYLENECARBOXYLATE;EPL;(Ethoxycarbonyl)acetylene;

Ethyl propiolate Uses

Ethyl propiolate(623-47-2) is a kind of reagents for Organic Synthesis.

Ethyl propiolate Safety Profile

The Hazard Codes of Ethyl propiolate(623-47-2):

Xi,

F
Hazard Note: Irritant
HazardClass: 3
The Risk Statements information of Ethyl propiolate(623-47-2):
10: Flammable
11: Highly Flammable
36: Irritating to the eyes
36/37/38: Irritating to eyes, respiratory system and skin
The Safety Statements information of Ethyl propiolate(623-47-2):
16: Keep away from sources of ignition - No smoking
23: Do not breathe gas/fumes/vapor/spray (appropriate wording to be specified by the manufacturer)
24: Avoid contact with skin
26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice
36: Wear suitable protective clothing
37/39: Wear suitable gloves and eye/face protection
RIDADR: UN 3272 3/PG 3
WGK Germany: 3
PackingGroup: II

Product Name

Ethyl propiolate

Synthetic route

Ethyl propiolate Chemical Properties

Ethyl propiolate Uses

Ethyl propiolate Safety Profile

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