471-25-0

Basic information

• Product Name: Propiolic Acid
• Synonyms: ACETYLENECARBOXYLIC ACID;2-PROPYNIOC ACID;2-PROPYNOIC ACID;PROPYNOIC ACID;PROPIOLIC ACID;Propiolic acidd;PROPARGYLIC ACID;Carboxyacetylene
• CAS NO: 471-25-0
• Molecular Formula: C₃H₂O₂
• Molecular Weight: 70.05
• EINECS: 207-437-8
• Product Categories: Aromatic Carboxylic Acids, Amides, Anilides, Anhydrides & Salts;Acetylenes;Acetylenic Carboxylic Acids & Their Derivatives;Diyne Compounds (LB Films);Functional Materials;LB Films;fine chemicals
• Mol File: 471-25-0.mol
• Article Data: 15

Chemical Properties

• Melting Point: 16-18 °C(lit.)
• Boiling Point: 102 °C200 mm Hg(lit.)
• Flash Point: 138 °F
• Appearance: Clear colorless to light brown/Liquid After Melting
• Density: 1.138 g/mL at 25 °C(lit.)
• Vapor Pressure: 3.65mmHg at 25°C
• Refractive Index: n20/D 1.431(lit.)
• Storage Temp.: 2-8°C
• PKA: 1.84(at 25℃)
• Water Solubility: miscible
• Stability: Stable. Incompatible with bases, oxidizing agents, reducing agents. Combustible.
• Merck: 14,7821
• BRN: 878176
• CAS DataBase Reference: Propiolic Acid(CAS DataBase Reference)
• NIST Chemistry Reference: Propiolic Acid(471-25-0)
• EPA Substance Registry System: Propiolic Acid(471-25-0)

Safety Data

• Hazard Codes: T
• Statements: 24/25-34-25-23/24/25
• Safety Statements: 26-36/37/39-45-24/25-7/9
• RIDADR: UN 2920 8/PG 2
• WGK Germany: 3
• RTECS: UD9300000
• F: 3-8
• TSCA: Yes
• HazardClass: 8
• PackingGroup: II
• Hazardous Substances Data: 471-25-0(Hazardous Substances Data)

Usage

Uses

Different sources of media describe the Uses of 471-25-0 differently. You can refer to the following data:
1. Propiolic acid is an intermediate in monohalogenated acetylene synthesis and a corrosion inhibitor for steel.
2. Propiolic acid is a reagent used in the preparation of transition metal complexes, haloalkyl propiolates and halopropenoates.
3. Reagent employed in the synthesis of transition metal complexes, haloalkyl propiolates, and halopropenoates.

Definition

ChEBI: A terminal acetylenic compound that is a 3-carbon, straight-chain, monounsaturated fatty acid having one acetylenic bond.

InChI:InChI=1/C3H2O2/c1-2-3(4)5/h1H,(H,4,5)/p-1

Synthetic route

Propargylamine (2450-71-7) → Propiolic acid (471-25-0)

Conditions	Yield
Stage #1: Propargylamine With sodium nitrate at 30 - 45℃; for 3.33h; Stage #2: With diethyleneglycol diacetate; antimonypentachloride at 56℃; for 0.833333h; Temperature;	94%

propargyl alcohol (107-19-7) → Propiolic acid (471-25-0)

Conditions	Yield
With tert.-butylhydroperoxide; copper(l) chloride In decane; acetonitrile at 20℃; for 5h;	93%
With sodium hydroxide; sodium hypochlorite; TEMPOL In water; ethyl acetate at 15 - 20℃; pH=8.5; Aqueous phophate buffer;	92%
With sodium hydroxide; sodium hypochlorite; disodium hydrogenphosphate; phosphoric acid; TEMPOL In water at 5 - 10℃; pH=7 - 10; Aqueous phophate buffer;	83%

propargyl alcohol (107-19-7) → Propiolsaeure-(2-propinyl)ester (4383-39-5) + Propiolic acid (471-25-0)

Conditions	Yield
With sodium hydroxide; sodium hypochlorite; sulfuric acid; TEMPOL In water at 5 - 10℃; pH=8 - 10;	A 0.9% B 83%
With sodium hydroxide; sodium hypochlorite; sulfuric acid; TEMPOL; tetra(n-butyl)ammonium hydrogensulfate In dichloromethane; water at 5 - 10℃; pH=8 - 10;	A 1.3% B 46%

trans-2-bromobutenedioic acid (584-99-6) → Propiolic acid (471-25-0)

Conditions	Yield
With water at 140℃;

cis-2-bromobutenedioic acid (644-80-4) → Propiolic acid (471-25-0)

Conditions	Yield
With water at 140℃;

sodium acetylide (1066-26-8) + methylammonium carbonate (15719-64-9, 15719-76-3, 97762-63-5) → Propiolic acid (471-25-0)

sodium acetylide (1066-26-8) → Propiolic acid (471-25-0)

Conditions	Yield
With carbon dioxide under 38000 - 45600 Torr;

Acetylenedicarboxylic acid (142-45-0) → Propiolic acid (471-25-0)

acetylenemagnesium bromide (4301-14-8) → Propiolic acid (471-25-0)

Conditions	Yield
With carbon dioxide
With diethyl ether; carbon dioxide

carbon dioxide (124-38-9) + sodium acetylide (1066-26-8) → Propiolic acid (471-25-0)

water (7732-18-5) + Acetylenedicarboxylic acid (142-45-0) → Propiolic acid (471-25-0)

Conditions	Yield
at 38 - 95℃; Rate constant; Das Eingangsprodukt ist die Saeure, der Mononatrium-Salz und der Dinatrium-Salz.Decarboxylation;

1,4-dioxane (123-91-1) + water (7732-18-5) + Acetylenedicarboxylic acid (142-45-0) → Propiolic acid (471-25-0)

Conditions	Yield
at 38 - 95℃; Rate constant; Das Eingangsprodukt ist die Saeure der Mononatrium-Salz und der Dinatrium-Salz.Decarboxylation;

methanol (67-56-1) + water (7732-18-5) + Acetylenedicarboxylic acid (142-45-0) → Propiolic acid (471-25-0)

Conditions	Yield
at 38 - 95℃; Rate constant; Das Eingangsprodukt ist die Saeure der Mononatrium-Salz und der Dinatrium-Salz.Decarboxylation;

ethanol (64-17-5) + water (7732-18-5) + Acetylenedicarboxylic acid (142-45-0) → Propiolic acid (471-25-0)

Conditions	Yield
at 38 - 95℃; Rate constant; Das Eingangsprodukt ist die Saeure der Mononatrium-Salz und der Dinatrium-Salz.Decarboxylation;

acidic potassium salt of/the/ acetylene-dicarboxylic acid → Propiolic acid (471-25-0)

acidic potassium salt of/the/ acetylenedicarboxylic acid → Propiolic acid (471-25-0)

Conditions	Yield
With water

dibromosuccinic acid → Propiolic acid (471-25-0)

Conditions	Yield
With ethanol ueber mehrere Stufen;

sulfuric acid (7664-93-9) + propargyl alcohol (107-19-7) → Propargylic aldehyde (624-67-9) + Propiolic acid (471-25-0)

Conditions	Yield
elektrochemische Oxydation an einer Bleidioxid-Anode;

water (7732-18-5) + Acetylenedicarboxylic acid (142-45-0) → carbon dioxide (124-38-9) + Propiolic acid (471-25-0)

water (7732-18-5) + Acetylenedicarboxylic acid (142-45-0) → methylammonium carbonate (15719-64-9, 15719-76-3, 97762-63-5) + Propiolic acid (471-25-0) + acetylene (74-86-2)

Conditions	Yield
at 130℃;

n-butyllithium (109-72-8, 29786-93-4) + Vinyl bromide (593-60-2) + carbon dioxide (124-38-9) + petroleum ether → Propiolic acid (471-25-0) + Acetylenedicarboxylic acid (142-45-0)

Conditions	Yield
at 14℃;

trans-2-bromobutenedioic acid (584-99-6) + water (7732-18-5) → carbon dioxide (124-38-9) + hydrogen bromide (10035-10-6, 12258-64-9) + Propiolic acid (471-25-0)

Conditions	Yield
at 140℃;

cis-2-bromobutenedioic acid (644-80-4) + water (7732-18-5) → carbon dioxide (124-38-9) + hydrogen bromide (10035-10-6, 12258-64-9) + Propiolic acid (471-25-0)

Conditions	Yield
at 140℃;

meso-2,3-dibromosuccinic acid (608-36-6) + concentrated NaOH-solution → hydrogen bromide (10035-10-6, 12258-64-9) + Propiolic acid (471-25-0) + Acetylenedicarboxylic acid (142-45-0)

trans-2-bromobutenedioic acid (584-99-6) + NaOH-solution (1 mol 0.1n) → carbon dioxide (124-38-9) + Propiolic acid (471-25-0) + NaBr

Conditions	Yield
at 140℃;

cis-2-bromobutenedioic acid (644-80-4) + NaOH-solution (1 mol 0.1n) → carbon dioxide (124-38-9) + Propiolic acid (471-25-0) + NaBr

Conditions	Yield
at 140℃;

trans-2-bromobutenedioic acid (584-99-6) + NaOH-solution (2 mol 0.1n) → carbon dioxide (124-38-9) + Propiolic acid (471-25-0) + NaBr

cis-2-bromobutenedioic acid (644-80-4) + NaOH-solution (2 mol 0.1n) → carbon dioxide (124-38-9) + Propiolic acid (471-25-0) + NaBr

trans-2-bromobutenedioic acid (584-99-6) + NaOH-solution (3 mol 0.1n) → carbon dioxide (124-38-9) + Propiolic acid (471-25-0) + NaBr

Conditions	Yield
entsteht Acetylendicarbonsaeure, die unter den Versuchsbedingungen teilweise in das Produkt2 und Produkt3 gespalten wird;

Propiolic acid (471-25-0) → (E)-3-iodoacrylic acid (6372-02-7)

Conditions	Yield
With sodium iodide In trifluoroacetic acid for 48h; Heating;	100%
With hydrogen iodide In water at 95℃; for 21h;	94%
With hydrogen iodide at 95℃; for 21h;	94%

(-)-menthol (2216-51-5) + Propiolic acid (471-25-0) → (1R,2S,5R)-2-isopropyl-5-methylcyclohexyl propiolate (65018-52-2)

Conditions	Yield
With toluene-4-sulfonic acid In toluene Reflux; Dean-Stark;	100%
With sulfuric acid
With sulfuric acid for 216h; Ambient temperature;
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 0 - 25℃; for 6h;

prenyl bromide (870-63-3) + Propiolic acid (471-25-0) → 3-methylbut-2-en-1-yl propiolate (118741-76-7)

Conditions	Yield
With sodium hydrogencarbonate In N,N-dimethyl-formamide at 20℃; for 18h; Inert atmosphere; Schlenk technique;	100%
With sodium hydrogencarbonate In N,N-dimethyl-formamide at 20℃; for 18h; Inert atmosphere;	100%
With sodium hydrogencarbonate In N,N-dimethyl-formamide for 20h; Ambient temperature;
With potassium carbonate In acetone

(E)-hept-4-en-1-ol (24469-79-2) + Propiolic acid (471-25-0) → Propynoic acid (E)-hept-4-enyl ester (79405-41-7)

Conditions	Yield
With sulfuric acid	100%

Propiolic acid (471-25-0) + hexan-1-ol (111-27-3) → acetylene carboxylic acid n-hexyl ester (68279-21-0)

Conditions	Yield
With toluene-4-sulfonic acid In benzene	100%
toluene-4-sulfonic acid In toluene for 18h; Heating / reflux;	96%
With toluene-4-sulfonic acid	84%
With toluene-4-sulfonic acid In benzene for 16h; Heating;	84%

(1R,4R)-3-(2-Benzenesulfinyl-ethyl)-4-[3-(tert-butyl-dimethyl-silanyloxy)-propyl]-4-methyl-cyclohex-2-enol + Propiolic acid (471-25-0) → Propynoic acid (1R,4R)-3-(2-benzenesulfinyl-ethyl)-4-[3-(tert-butyl-dimethyl-silanyloxy)-propyl]-4-methyl-cyclohex-2-enyl ester

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In toluene at 20℃; Acylation;	100%

Propiolic acid (471-25-0) + (1R,4R)-3-(2-Benzenesulfinyl-ethyl)-4-(tert-butyl-dimethyl-silanyloxymethyl)-4-methyl-cyclohex-2-enol (331627-36-2) → (1R,4R)-4-tert-butyldimethylsilyloxymethyl-4-methyl-3-(2-phenylsulfinylethyl)-2-cyclohexenyl propiolate (331627-29-3)

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In toluene at 0℃; for 1h;	100%

adamantane-2-thione (23695-65-0) + Propiolic acid (471-25-0) → spiro[6H-[1,3]oxathiin-2,2'-tricyclo[3.3.1.13,7]decan]-6-one (625820-15-7)

Conditions	Yield
In toluene Heating;	100%
In toluene for 5h; Heating;	100%
In toluene at 79.84℃; Kinetics; Further Variations:; Solvents; Temperatures;

bis(tri-n-butyltin)oxide (56-35-9) + Propiolic acid (471-25-0) → Propiolsaeure-tri-n-butylstannylester (7316-46-3)

Conditions	Yield
In benzene byproducts: H2O, dicarboxylate; mole ratio of (C4H9)3SnOSn(C4H9)3 and carboxylic acid 1:2; at 20°C or at reflux temp. to remove of water formed by azeotropic distn.;	100%

Phenyl azide (622-37-7) + Propiolic acid (471-25-0) → 1-phenyl-1H-[1,2,3]triazole-4-carboxylic acid (4600-04-8)

Conditions	Yield
With copper(ll) sulfate pentahydrate; sodium 2-(1,2-dihydroxyethyl)-4-hydroxy-5-oxo-2,5-dihydro-furan-3-olate In water; tert-butyl alcohol at 20℃; for 21h;	100%
Stage #1: Propiolic acid With 2-nitrophenylboronic acid In 1,2-dichloro-ethane at 25℃; for 0.166667h; Inert atmosphere; Stage #2: Phenyl azide In 1,2-dichloro-ethane at 25℃; for 24h; Huisgen cycloaddition; Inert atmosphere; regioselective reaction;	82%
With sodium L-ascorbate In water; ethylene glycol at 60℃; for 0.5h;	78%

9-(2-azidoethylamino)-N-(2-(dimethylamino)ethyl)acridine-4-carboxamide (1196472-27-1) + Propiolic acid (471-25-0) → 1-(2-(4-(2-(dimethylamino)ethylcarbamoyl)acridin-9-ylamino)ethyl)-1H-1,2,3-triazole-4-carboxylic acid (1374606-54-8)

Conditions	Yield
With copper(II) sulfate; sodium L-ascorbate In water; tert-butyl alcohol at 20℃;	100%

3C22H14N6O4(2-)*3Zr(4+)*2O(2-)*2HO(1-) + Propiolic acid (471-25-0) → 3C28H18N6O8(2-)*3Zr(4+)*2O(2-)*2HO(1-)

Conditions	Yield
With copper(l) iodide In N,N-dimethyl-formamide at 60℃; for 30h;	100%

Zr3O2(OH)2(2',3',5',6'-tetramethyl-[1,1':4',1''-terphenyl]-4,4''-dicarboxylate)3 + Propiolic acid (471-25-0) → 3Zr(4+)*2O(2-)*2HO(1-)*C36H26N12O12

Conditions	Yield
With copper(l) iodide In N,N-dimethyl-formamide at 60℃; for 30h;	100%

(1S)-1,3,3-trimethylbicyclo[2.2.1]heptane-2-selone (56956-24-2) + Propiolic acid (471-25-0) → C13H18O2Se (960398-74-7)

Conditions	Yield
With trifluoroacetic acid In chloroform at 20℃; for 48h; Wagner-Meerwein Rearrangement;	100%

(2-aminoxyethyl)carbamic acid tert-butyl ester (75051-55-7) + Propiolic acid (471-25-0) → tert-butyl N-[2-(prop-2-ynoylamino)oxyethyl]carbamate

Conditions	Yield
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 0 - 20℃;	100%

methyl (3'R,3aR,4S,4'S,6R,6aR)-dihydro-6-(azidomethyl)-2,2,2'-trimethyl-3'-phenylspiro[furo[3,4-d]-1,3-dioxole-4(3aH)-5'-isoxazolidine]-4'-carboxylate + Propiolic acid (471-25-0) → methyl (3'R,3aR,4S,4'S,6R,6aR)-dihydro-6-[(4-(hydroxycarbonyl)-1,2,3-triazol-1-yl)methyl]-2,2,2'-trimethyl-3'-phenyl-spiro[furo[3,4-d]-1,3-dioxole-4(3aH)-5'-isoxazolidine]-4'-carboxylate

Conditions	Yield
With copper(ll) sulfate pentahydrate; sodium L-ascorbate In water; tert-butyl alcohol at 25℃; for 18h;	100%

C34H58N3O14(1-)*Na(1+) + Propiolic acid (471-25-0) → C37H59N3O15

Conditions	Yield
Stage #1: Propiolic acid With oxalyl dichloride; N,N-dimethyl-formamide In dichloromethane at 15℃; for 0.333333h; Inert atmosphere; Stage #2: C34H58N3O14(1-)*Na(1+) With sodium hydrogencarbonate In methanol; dichloromethane at 20℃; for 0.5h; Inert atmosphere;	100%

1-tert-butyl 3-(4-aminophenyl)propionate (103790-48-3) + Propiolic acid (471-25-0) → C16H19NO3

Conditions	Yield
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at -30℃; for 0.5h; Inert atmosphere;	100%

Propiolic acid (471-25-0) + 1-dodecylthiol (112-55-0) → ammonium cis-β-(dodecylthio)acrylate

Conditions	Yield
In propan-1-ol; ammonia at -33 - -30℃; for 3h;	99.7%

2-N-morpholinopropanethiol (10220-25-4) + Propiolic acid (471-25-0) → β-(2-N-morpholinopropylthio)acrylic acid (121236-02-0, 121236-06-4)

Conditions	Yield
for 16h;	99.2%

2-(diethylamine)ethanethiol (100-38-9) + Propiolic acid (471-25-0) → β-(2-N,N-diethylaminoethylthio)acrylic acid (121236-00-8, 121236-04-2)

Conditions	Yield
With ammonia for 7h;	99%

pentamethylbenzene, (700-12-9) + Propiolic acid (471-25-0) → (Z)-3-(2,3,4,5,6-pentamethylphenyl)acrylic acid

Conditions	Yield
With gold(III) chloride; silver trifluoromethanesulfonate at 23℃; for 1h;	99%
With potassium tetrachloroplatinate; silver trifluoromethanesulfonate; trifluoroacetic acid In dichloromethane at 20℃; for 15h;	96%
With potassium tetrachloroplatinate; silver trifluoromethanesulfonate; trifluoroacetic acid at 20℃; for 15h;	96%

tris-(trimethylsilyl)silane (1873-77-4) + Propiolic acid (471-25-0) → (Z)-3-[tris(trimethylsilyl)silyl]propenoic acid (838852-54-3)

Conditions	Yield
With oxygen In water at 20℃; for 24h; optical yield given as %de; stereoselective reaction;	99%
With tris-(trimethylsilyl)silane; 2-hydroxyethanethiol In water at 100℃; for 4h;	95%
at 20℃;	90%

benzyl bromide (100-39-0) + Propiolic acid (471-25-0) → benzyl prop-2-ynoate (14447-01-9)

Conditions	Yield
Stage #1: Propiolic acid With caesium carbonate In N,N-dimethyl-formamide at 0℃; for 0.333333h; Inert atmosphere; Stage #2: benzyl bromide In N,N-dimethyl-formamide at 0 - 20℃; for 0.166667h; Inert atmosphere;	99%
Stage #1: Propiolic acid With potassium carbonate In N,N-dimethyl-formamide at 0℃; for 0.166667h; Stage #2: benzyl bromide In N,N-dimethyl-formamide at 20℃; for 2h;	94%
Stage #1: Propiolic acid With potassium hydroxide In methanol at 20℃; for 0.25h; Stage #2: benzyl bromide In dimethyl sulfoxide at 40℃; for 2h;	87%

3-azidopropan-1-ol (72320-38-8) + Propiolic acid (471-25-0) → 1-(3-hydroxypropyl)-1H-[1,2,3]triazole-4-carboxylic acid (1101852-31-6)

Conditions	Yield
With ascorbic acid; tris[1-(3-hydroxypropyl)-1H-1,2,3-triazol-4-ylmethyl]amine In water; tert-butyl alcohol at 20℃; for 10h;	99%

Propiolic acid (471-25-0) → sodium propargylate (920-38-7)

Conditions	Yield
With sodium hydroxide In methanol at 10 - 20℃; for 1h; Darkness;	99%
With sodium hydroxide In methanol at 10 - 20℃; for 1h; Darkness;	99%
With sodium hydroxide In methanol; water at 0 - 20℃; for 2h;	97%
With sodium hydroxide In methanol at 0 - 20℃; for 2h;	97%
With sodium hydride In tetrahydrofuran at 23℃; for 1h; Inert atmosphere; Darkness;

n-butyl isonitrile (2769-64-4) + 4-methoxy-benzylamine (2393-23-9) + isobutyraldehyde (78-84-2) + Propiolic acid (471-25-0) → C20H28N2O3

Conditions	Yield
Stage #1: 4-methoxy-benzylamine; isobutyraldehyde In methanol at 40℃; for 0.5h; Ugi Condensation; Stage #2: n-butyl isonitrile In methanol at 50℃; for 0.333333h; Ugi Condensation; Stage #3: Propiolic acid In methanol for 3h; Ugi Condensation; Reflux;	99%

2-bromonaphthalene (580-13-2) + Propiolic acid (471-25-0) → di(2-naphthyl)acetylene (20199-35-3)

Conditions	Yield
With bis-triphenylphosphine-palladium(II) chloride; 1,8-diazabicyclo[5.4.0]undec-7-ene; 1,4-di(diphenylphosphino)-butane In dimethyl sulfoxide at 110℃; for 16h;	99%
With bis-triphenylphosphine-palladium(II) chloride; 1,8-diazabicyclo[5.4.0]undec-7-ene; 1,2-bis-(diphenylphosphino)ethane In dimethyl sulfoxide at 80℃;
With bis-triphenylphosphine-palladium(II) chloride; 1,8-diazabicyclo[5.4.0]undec-7-ene; 1,4-di(diphenylphosphino)-butane In dimethyl sulfoxide at 80℃; for 32h;

O-methylresorcine (150-19-6) + Propiolic acid (471-25-0) → 3-methoxyphenyl propiolate (1123745-75-4)

Conditions	Yield
Stage #1: O-methylresorcine With sodium hydride In tetrahydrofuran; mineral oil at 0℃; Stage #2: Propiolic acid With dicyclohexyl-carbodiimide In tetrahydrofuran; mineral oil at 0 - 18℃; for 16h;	99%
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 0℃; for 3h;	67%

Cyclohexyl isocyanide (931-53-3) + 6-bromoimidazo[1,2-a]pyridine-2-carbaldehyde + Propiolic acid (471-25-0) + para-methylbenzylamine (104-84-7) → N-(1-(6-bromoimidazo[1,2-a]pyridin-2-yl)-2-(cyclohexylamino)-2-oxoethyl)-N-(4-methylbenzyl)propiolamide

Conditions	Yield
With sodium carbonate In methanol at 20℃; Ugi Condensation;	99%

Upstream product

• 584-99-6 trans-2-bromobutenedioic acid 
• 644-80-4 cis-2-bromobutenedioic acid 
• 1066-26-8 sodium acetylide 
• 15719-64-9 methylammonium carbonate 
• 142-45-0 Acetylenedicarboxylic acid 
• 124-38-9 carbon dioxide 
• 7732-18-5 water 
• 123-91-1 1,4-dioxane 
• 67-56-1 methanol 
• 64-17-5 ethanol 
• 7664-93-9 sulfuric acid 
• 107-19-7 propargyl alcohol 
• 109-72-8 n-butyllithium 
• 593-60-2 Vinyl bromide 

Downstream Products

• 102589-30-0 bicyclo<2.2.2>octa-2,5-diene-2-carboxylic acid 
• 14442-12-7 3-phenylisoxazole-5-carboxylic acid 
• 13831-02-2 3-(Z)-(benzylsulfanyl)propenoic acid 
• 13831-01-1 3-(benzylthio)acrylic acid 
• 74-85-1 ethene 
• 65-85-0 benzoic acid 
• 4315-35-9 cyclohexa-1,4-diene-1-carboxylic acid 
• 710-39-4 (Z)-3-(4-chlorophenylthio)acrylic acid 
• 98550-86-8 4-chloro-cyclohexa-1,4-dienecarboxylic acid 
• 13831-03-3 tert-butyl prop-2-ynoate 
• 922-67-8 propynoic acid methyl ester 
• 101724-25-8 3c-(2-chloro-phenylsulfanyl)-acrylic acid 
• 29262-25-7 4-hydroxy-4,4-diphenyl-but-2-ynoic acid 
• 714-32-9 (Z)-3-(4-methoxyphenylthio)acrylic acid 

Relevant articles and documents

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Environment-friendly preparation method of propiolic acid derivatives

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.

Gold-catalyzed formal [4π+2π]-cycloadditions of tert-butyl propiolates with aldehydes and ketones to form 4H-1,3-dioxine derivatives

Gold-catalyzed formal hetero-[4π+2π] cycloadditions of tert-butyl propiolates with carbonyl compounds proceeded efficiently to yield 4H-1,3-dioxine derivatives over a wide scope of substrates. With acetone as a promoter, gold-catalyzed cycloadditions of these propiolate derivatives with enol ethers led to the formation of atypical [4+2]-cycloadducts with skeletal rearrangement.