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623-47-2

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623-47-2 Usage

Chemical Description

Ethyl propiolate is an ester with the formula C5H6O2, and pyridine is a basic heterocyclic organic compound with the formula C5H5N.

Chemical Properties

Ethyl propiolate is a clear colorless to pale yellow liquid that is soluble in ethanol, ether and chloroform. It an important organic chemical raw material and pharmaceutical intermediate. Ethyl propargylate is obtained by oxidation of propargyl alcohol to propargylic acid followed by esterification.

Uses

Different sources of media describe the Uses of 623-47-2 differently. You can refer to the following data:
1. Halogenated derivatives were used as substrates for direct, asymmetric alkynylation of cyclic ?-ketoesters using chiral phase-transfer catalysts. Also employed in a one-pot , four-component synthesis of benzene-1,2,3,5-tetracarboxylates promoted by Ph3P.
2. In organic synthesis; peptide coupling reagent.
3. Ethyl propiolate is used as a precursor in the preparation of substituted anthraquinones and pyrazolo[1,5-a]pyridine, which exhibits anti-inflammatory activity. Further, it is employed in the synthesis of benzene-1,2,3,5-tetracarboxylates promoted by triphenylphosphine. Its halogenated derivatives are used as a substrate for direct, asymmetric alkynylation of cyclic beta-ketoesters using chiral phase-transfer catalysts.

Definition

ChEBI: Ethyl propiolate is the ethyl ester of prop-2-ynoic acid. It is a ynoate ester, a terminal acetylenic compound and an ethyl ester.

Hazard

Flammable; lachrymator.

Check Digit Verification of cas no

The CAS Registry Mumber 623-47-2 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 6,2 and 3 respectively; the second part has 2 digits, 4 and 7 respectively.
Calculate Digit Verification of CAS Registry Number 623-47:
(5*6)+(4*2)+(3*3)+(2*4)+(1*7)=62
62 % 10 = 2
So 623-47-2 is a valid CAS Registry Number.
InChI:InChI=1/C5H6O2/c1-3-5(6)7-4-2/h1H,4H2,2H3

623-47-2 Well-known Company Product Price

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  • TCI America

  • (P0529)  Ethyl Propiolate  >98.0%(GC)

  • 623-47-2

  • 5mL

  • 290.00CNY

  • Detail
  • TCI America

  • (P0529)  Ethyl Propiolate  >98.0%(GC)

  • 623-47-2

  • 25mL

  • 920.00CNY

  • Detail
  • Alfa Aesar

  • (A15068)  Ethyl propiolate, 99%   

  • 623-47-2

  • 5g

  • 371.0CNY

  • Detail
  • Alfa Aesar

  • (A15068)  Ethyl propiolate, 99%   

  • 623-47-2

  • 25g

  • 1212.0CNY

  • Detail
  • Alfa Aesar

  • (A15068)  Ethyl propiolate, 99%   

  • 623-47-2

  • 100g

  • 3184.0CNY

  • Detail

623-47-2SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 12, 2017

Revision Date: Aug 12, 2017

1.Identification

1.1 GHS Product identifier

Product name ethyl propiolate

1.2 Other means of identification

Product number -
Other names ethyl prop-2-ynoate

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:623-47-2 SDS

623-47-2Synthetic route

ethanol
64-17-5

ethanol

Propiolic acid
471-25-0

Propiolic acid

propynoic acid ethyl ester
623-47-2

propynoic acid ethyl ester

Conditions
ConditionsYield
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
38391-86-5

Ethyl half ester of acetylenedicarboxylic acid

toluene
108-88-3

toluene

propynoic acid ethyl ester
623-47-2

propynoic acid ethyl ester

Conditions
ConditionsYield
at 100℃; Zeitlicher Verlauf der thermischen Zersetzung;
(E)-4-(Triphenyl-λ5-phosphanylidene)-pent-2-enedioic acid diethyl ester
119930-16-4

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

A

ethyl (triphenylphosphoranylidene)acetate
1099-45-2

ethyl (triphenylphosphoranylidene)acetate

B

propynoic acid ethyl ester
623-47-2

propynoic acid ethyl ester

Conditions
ConditionsYield
equil. react.;
Ethyl half ester of acetylenedicarboxylic acid
38391-86-5

Ethyl half ester of acetylenedicarboxylic acid

water
7732-18-5

water

propynoic acid ethyl ester
623-47-2

propynoic acid ethyl ester

Conditions
ConditionsYield
at 100℃; Zeitlicher Verlauf der thermischen Zersetzung;
Mesitol
527-60-6

Mesitol

chloroformic acid ethyl ester
541-41-3

chloroformic acid ethyl ester

Propiolic acid
471-25-0

Propiolic acid

A

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

Trifluoressigsaeure-(2,4,6-trimethyl-phenylester)

B

propynoic acid ethyl ester
623-47-2

propynoic acid ethyl ester

Conditions
ConditionsYield
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
541-41-3

chloroformic acid ethyl ester

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

sodium 2,4,6-trimethylphenoxide

Propiolic acid
471-25-0

Propiolic acid

A

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

Trifluoressigsaeure-(2,4,6-trimethyl-phenylester)

B

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

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

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

D

propynoic acid ethyl ester
623-47-2

propynoic acid ethyl ester

Conditions
ConditionsYield
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
764-01-2

methyl propargyl alcohol

diethylazodicarboxylate
1972-28-7

diethylazodicarboxylate

phenol
108-95-2

phenol

A

but-2-ynyloxybenzene
13610-09-8

but-2-ynyloxybenzene

B

propynoic acid ethyl ester
623-47-2

propynoic acid ethyl ester

Conditions
ConditionsYield
With triphenylphosphine In tetrahydrofuran; benzeneA 2.18 g (70%)
B n/a
propargyl alcohol
107-19-7

propargyl alcohol

diethylazodicarboxylate
1972-28-7

diethylazodicarboxylate

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

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

A

propynoic acid ethyl ester
623-47-2

propynoic acid ethyl ester

B

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

5-bromo-3-methyl-2-[methyl-(4-prop-2-ynyloxy-benzenesulfonyl)-amino]-benzoic acid methyl ester

Conditions
ConditionsYield
With triphenylphosphine In tetrahydrofuran; benzeneA n/a
B 0.389 g (71%)
(hydrotris(3,5-diisopropylpyrazolyl)borato)CoCCC(O)OCH2CH3
461695-81-8

(hydrotris(3,5-diisopropylpyrazolyl)borato)CoCCC(O)OCH2CH3

water
7732-18-5

water

A

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

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

B

propynoic acid ethyl ester
623-47-2

propynoic acid ethyl ester

Conditions
ConditionsYield
In not given
chloroformic acid ethyl ester
541-41-3

chloroformic acid ethyl ester

acetylene
74-86-2

acetylene

propynoic acid ethyl ester
623-47-2

propynoic acid ethyl ester

Conditions
ConditionsYield
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;
glyoxylic acid ethyl ester
924-44-7

glyoxylic acid ethyl ester

propynoic acid ethyl ester
623-47-2

propynoic acid ethyl ester

Conditions
ConditionsYield
With C7H13N2O4P; potassium carbonate In methanol at 20℃; Inert atmosphere;
piperidine
110-89-4

piperidine

propynoic acid ethyl ester
623-47-2

propynoic acid ethyl ester

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

ethyl (E)-3-(piperidin-1-yl)acrylate

Conditions
ConditionsYield
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
propynoic acid ethyl ester
623-47-2

propynoic acid ethyl ester

2-propynamide
7341-96-0

2-propynamide

Conditions
ConditionsYield
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%
pyrrolidine
123-75-1

pyrrolidine

propynoic acid ethyl ester
623-47-2

propynoic acid ethyl ester

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

ethyl (E)-3-(pyrrolidin-1-yl)acrylate

Conditions
ConditionsYield
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%
morpholine
110-91-8

morpholine

propynoic acid ethyl ester
623-47-2

propynoic acid ethyl ester

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

ethyl (E)-3-(morpholin-4-yl)acrylate

Conditions
ConditionsYield
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%
2-methoxy-phenylamine
90-04-0

2-methoxy-phenylamine

propynoic acid ethyl ester
623-47-2

propynoic acid ethyl ester

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

ethyl 3-<(2-methoxyphenyl)amino>acrylate

Conditions
ConditionsYield
In ethanol for 3h; Heating;100%
ethanol
64-17-5

ethanol

propynoic acid ethyl ester
623-47-2

propynoic acid ethyl ester

ethyl 3,3-diethoxypropanoate
10601-80-6

ethyl 3,3-diethoxypropanoate

Conditions
ConditionsYield
With potassium for 12h;100%
With copper(II) sulfate for 24h; Heating / reflux;37%
1-Azidoadamantane
24886-73-5

1-Azidoadamantane

propynoic acid ethyl ester
623-47-2

propynoic acid ethyl ester

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

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

Conditions
ConditionsYield
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%
ethyl N-hydroxybenzimidate
7340-17-2

ethyl N-hydroxybenzimidate

propynoic acid ethyl ester
623-47-2

propynoic acid ethyl ester

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

ethyl N-<(2'-ethoxycarbonylvinyl)oxy>benzimidate

Conditions
ConditionsYield
With triethylamine for 0.166667h; Ambient temperature;100%
C15H17N3O4
135907-85-6

C15H17N3O4

propynoic acid ethyl ester
623-47-2

propynoic acid ethyl ester

C20H23N3O6
135907-91-4

C20H23N3O6

Conditions
ConditionsYield
In acetonitrile for 24h; Ambient temperature;100%
propynoic acid ethyl ester
623-47-2

propynoic acid ethyl ester

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

ethyl (Z)-3-iodopropenoate

Conditions
ConditionsYield
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 iodide98%
phosphonic acid diethyl ester
762-04-9

phosphonic acid diethyl ester

propynoic acid ethyl ester
623-47-2

propynoic acid ethyl ester

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

ethyl β,β-bis(diethoxyphosphoryl)propionate

Conditions
ConditionsYield
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;
propynoic acid ethyl ester
623-47-2

propynoic acid ethyl ester

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

ethyl 1H-pyrazole-3-carboxylate

Conditions
ConditionsYield
In diethyl ether Ambient temperature;100%
(S)-2-[(4-methoxybenzyloxy)methyl]oxirane
80910-01-6, 108836-41-5, 134733-19-0, 144069-33-0

(S)-2-[(4-methoxybenzyloxy)methyl]oxirane

propynoic acid ethyl ester
623-47-2

propynoic acid ethyl ester

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

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

Conditions
ConditionsYield
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%
propynoic acid ethyl ester
623-47-2

propynoic acid ethyl ester

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

(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
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
ConditionsYield
With 4-methyl-morpholine In dichloromethane at 20℃;100%
With 4-methyl-morpholine In dichloromethane at 30℃; for 16h;100%
propynoic acid ethyl ester
623-47-2

propynoic acid ethyl ester

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

1-(benzyloxy)-3-(phenyltellanyl)propan-2-ol

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

(E)-3-(1-benzyloxymethyl-2-phenyltellurenyl-ethoxy)-acrylic acid ethyl ester

Conditions
ConditionsYield
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%
1-Phenyl-3-buten-1-ol
80735-94-0

1-Phenyl-3-buten-1-ol

propynoic acid ethyl ester
623-47-2

propynoic acid ethyl ester

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

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

Conditions
ConditionsYield
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%
1-benzylidene-4,4-dimethyl-3-oxopyrazolidin-1-ium-2-ide
606123-85-7

1-benzylidene-4,4-dimethyl-3-oxopyrazolidin-1-ium-2-ide

propynoic acid ethyl ester
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

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

Conditions
ConditionsYield
With copper(l) iodide; phosphaferrocene-4-(S)-i-Pr-oxazoline; N-Methyldicyclohexylamine In dichloromethane at 20℃; for 20h;100%
2-(dimethylamino)-4-oxo-4H-pyrido<1,2-a>pyrimidine-3-carbaldehyde
111680-71-8

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

propynoic acid ethyl ester
623-47-2

propynoic acid ethyl ester

C15H15NO4

C15H15NO4

Conditions
ConditionsYield
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%
2-methoxy-phenylamine
90-04-0

2-methoxy-phenylamine

propynoic acid ethyl ester
623-47-2

propynoic acid ethyl ester

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

ethyl 3-(2-methoxyphenylamino)acrylate

Conditions
ConditionsYield
In ethanol100%
bis(pinacol)diborane
73183-34-3

bis(pinacol)diborane

propynoic acid ethyl ester
623-47-2

propynoic acid ethyl ester

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

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

Conditions
ConditionsYield
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%
C13H16O4
1021700-66-2

C13H16O4

propynoic acid ethyl ester
623-47-2

propynoic acid ethyl ester

C18H22O6

C18H22O6

Conditions
ConditionsYield
With 4-methyl-morpholine at 20℃; for 12h; Michael addition; Inert atmosphere;100%
trans-Crotonaldehyde
123-73-9

trans-Crotonaldehyde

propynoic acid ethyl ester
623-47-2

propynoic acid ethyl ester

C9H12O3

C9H12O3

Conditions
ConditionsYield
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%
2-azidoethanol
1517-05-1

2-azidoethanol

propynoic acid ethyl ester
623-47-2

propynoic acid ethyl ester

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

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

Conditions
ConditionsYield
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%
pyrrolidine
123-75-1

pyrrolidine

propynoic acid ethyl ester
623-47-2

propynoic acid ethyl ester

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

ethyl-3-(pyrrolidin-1-yl)prop-2-enoate

Conditions
ConditionsYield
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
N-benzyl-α-diazoacetamide
105310-97-2

N-benzyl-α-diazoacetamide

propynoic acid ethyl ester
623-47-2

propynoic acid ethyl ester

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

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

Conditions
ConditionsYield
In water; acetonitrile at 22℃; under 760.051 Torr;100%
C31H36Cl2O8S

C31H36Cl2O8S

propynoic acid ethyl ester
623-47-2

propynoic acid ethyl ester

C36H42Cl2O10S

C36H42Cl2O10S

Conditions
ConditionsYield
With 4-methyl-morpholine In dichloromethane at 0 - 20℃; for 4h;100%
C10H16N2O4
95239-02-4

C10H16N2O4

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

2-(1-methyl-1H-indol-3-yl)ethylamine

propynoic acid ethyl ester
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

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

Conditions
ConditionsYield
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%
propynoic acid ethyl ester
623-47-2

propynoic acid ethyl ester

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

triethyl benzene-1,3,5-tricarboxylate

Conditions
ConditionsYield
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%
propynoic acid ethyl ester
623-47-2

propynoic acid ethyl ester

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

(Z)-ethyl 2,3-dibromoprop-2-enoate

Conditions
ConditionsYield
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;
Phenyl azide
622-37-7

Phenyl azide

propynoic acid ethyl ester
623-47-2

propynoic acid ethyl ester

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

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

Conditions
ConditionsYield
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%

623-47-2Relevant articles and documents

Asymmetric synthesis of dihydrocarbazoles through a Friedel-Crafts alkylation/annulation sequential reaction of indoles

Hu, Linfeng,Cao, Weidi,Wang, Kaixuan,Liu, Xiaohua,Feng, Xiaoming

supporting information, p. 13138 - 13141 (2021/12/16)

An enantioselective tandem Friedel-Crafts alkylation/annulation of indoles with diazoacetoacetate enones is realized in one pot. A series of dihydrocarbazoles were obtained in moderate yields with good to excellent ee values by using a RhII/ScIII dual-metallic catalyst system. Control experiments revealed that ScIII is critical to both the alkylation and annulation.

Environment-friendly preparation method of propiolic acid derivatives

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Paragraph 0035-0038, (2020/02/14)

The invention discloses an environment-friendly preparation method of propiolic acid derivatives. The preparation method comprises the following steps: (1) with 2,3-dibromosuccinic acid as a raw material, generating a butynedioic acid salt under alkaline conditions; (2) under an acidic condition, carrying out high-temperature decarboxylation to obtain propiolic acid; and (3) adding corresponding methanol or ethanol into propiolic acid in an extraction solvent, and preparing high-yield propiolate under acidic catalytic conditions under the condition that trimethyl orthoformate or triethyl orthoformate participates in dehydration. In the invention, the propiolic acid preparation method is friendly to environment and high in safety coefficient; and the method provided by the invention can beused for preparing methyl propiolate and ethyl propiolate, and has the advantages of small alcohol consumption, thorough reaction, high yield and easiness in separation.

Production Of Terephthalic Acid Via Reductive Coupling Of Propiolic Acid Or Propiolic Acid Derivatives

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Paragraph 0035, (2016/10/04)

A method of making terephthalic acid via reductive coupling of two molecules of propiolic acid or propiolic acid derivatives is presented. The reductive coupling can be catalyzed by compounds comprising metals, and propiolic acid or propiolic acid derivatives can be produced from acetylene and carbon dioxide. At least 4 of the 8 carbons in the terephthalic acid are non-fossil-derived.

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