928-55-2

Basic information

• Product Name: Ethyl propenyl ether
• Synonyms: PROPENYL ETHYL ETHER;(1E)-1-Ethoxy-1-propene;1-Propene, 1-ethoxy-;Ether, ethyl propenyl;ether,ethylpropenyl;ethylpropenylether,mixtureofcis-andtrans-isomers;1-ETHOXY-1-PROPENE;1-ethoxypropene
• CAS NO: 928-55-2
• Molecular Formula: C₅H₁₀O
• Molecular Weight: 86.13
• EINECS: 213-176-0
• Product Categories: Fine Chemicals;Intermediates
• Mol File: 928-55-2.mol
• Article Data: 21

Chemical Properties

• Melting Point: -140°C (estimate)
• Boiling Point: 67-76 °C(lit.)
• Flash Point: −2 °F
• Appearance: Clear colorless to light yellow/Liquid
• Density: 0.778 g/mL at 25 °C(lit.)
• Vapor Pressure: 153mmHg at 25°C
• Refractive Index: n20/D 1.398(lit.)
• Storage Temp.: Flammables area
• Water Solubility: soluble
• BRN: 1735974
• CAS DataBase Reference: Ethyl propenyl ether(CAS DataBase Reference)
• NIST Chemistry Reference: Ethyl propenyl ether(928-55-2)
• EPA Substance Registry System: Ethyl propenyl ether(928-55-2)

Safety Data

• Hazard Codes: F,Xi
• Statements: 11-36/37/38
• Safety Statements: 16-26-36/37/39-37/39
• RIDADR: UN 3271 3/PG 2
• WGK Germany: 3
• RTECS: KO0525000
• HazardClass: 3
• PackingGroup: II
• Hazardous Substances Data: 928-55-2(Hazardous Substances Data)

Usage

Chemical Properties

clear colorless to light yellow liquid

InChI:InChI=1/C5H10O/c1-3-5-6-4-2/h3,5H,4H2,1-2H3/b5-3+

Synthetic route

3-ethoxyprop-1-ene (557-31-3) → ethyl 1-propenyl ether (928-55-2)

Conditions	Yield
With diiron nonacarbonyl In benzene at 40 - 50℃; for 2.5h;	90%
With triiron dodecarbonyl at 25 - 30℃; for 1h; Irradiation;	85%
With potassium tert-butylate In dimethyl sulfoxide at 70℃; for 0.833333h; Inert atmosphere;	70%
(PMe3)2Rh(D2O)2*BF4 In water-d2 at 25℃; for 0.5h;	95 % Spectr.

1,1-diethoxypropane (4744-08-5) → ethyl 1-propenyl ether (928-55-2)

Conditions	Yield
2-ethyl-N-(2-ethylhexyl)-1-hexanamine; toluene-4-sulfonic acid	77.5%
With quinoline; phosphorus pentoxide distillation at a bath temp. 150 deg C;	75%
With quinoline; phosphorus pentoxide vermutlich entsteht als Gemisch von cis- und trans-Form;
With sodium hydrogen sulfate vermutlich entsteht als Gemisch von cis- und trans-Form;
With silver-asbestos at 280℃; vermutlich entsteht als Gemisch von cis- und trans-Form;

3-ethoxy-2-methyl-acrylic acid (23981-30-8) → ethyl 1-propenyl ether (928-55-2) + methylammonium carbonate (15719-64-9, 15719-76-3, 97762-63-5)

β-ethoxymethacrylic acid → ethyl 1-propenyl ether (928-55-2)

Conditions	Yield
bei vorsichtigem Kochen;

propene (187737-37-7) + ethyl vinyl ether (109-92-2) → ethyl 1-propenyl ether (928-55-2)

Conditions	Yield
With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride In benzene-d6 at 60℃; for 1h;

3-ethoxyprop-1-ene (557-31-3) + Triethoxysilane (998-30-1) → ethylpropylether (628-32-0) + ethyl 1-propenyl ether (928-55-2) + triethoxy(3-ethoxypropyl)silane (81518-55-0)

Conditions	Yield
With platinum(0)-1,3-divinyl-1,1,3,3-tetramethyldisiloxane complex In 5,5-dimethyl-1,3-cyclohexadiene; diethylene glycol dimethyl ether at 70℃; for 12h; Inert atmosphere;

3-ethoxyprop-1-ene (557-31-3) + tris(2-methoxyethoxy)silane (5700-39-0) → ethylpropylether (628-32-0) + ethyl 1-propenyl ether (928-55-2) + C14H32O7Si

Conditions	Yield
With platinum(0)-1,3-divinyl-1,1,3,3-tetramethyldisiloxane complex In 5,5-dimethyl-1,3-cyclohexadiene; toluene at 70℃; for 12h; Inert atmosphere;

ethyl 1-propenyl ether (928-55-2) + azidoformiate de methyle (1516-56-9) → [1-Ethoxy-prop-(Z)-ylidene]-carbamic acid methyl ester

Conditions	Yield
In benzene at 80℃; for 24h;	100%

5-iodo-6-methyl-N-[4-(methylsulfonyl)benzyl]-2-oxo-1-[3-(trifluoromethyl)phenyl]-1,2-dihydropyridine-3-carboxamide (694479-85-1) + ethyl 1-propenyl ether (928-55-2) → 6-methyl-N-[4-(methylsulfonyl)benzyl]-2-oxo-5-propionyl-1-[3-(trifluoromethyl)phenyl]-1,2-dihydropyridine-3-carboxamide

Conditions	Yield
Stage #1: 5-iodo-6-methyl-N-[4-(methylsulfonyl)benzyl]-2-oxo-1-[3-(trifluoromethyl)phenyl]-1,2-dihydropyridine-3-carboxamide; ethyl 1-propenyl ether With triethylamine; bis[1,2-bis(diphenylphosphino)ethane]palladium(0) In DMF (N,N-dimethyl-formamide) at 100℃; Stage #2: With hydrogenchloride; water In DMF (N,N-dimethyl-formamide) for 1.5h;	99%
Stage #1: 5-iodo-6-methyl-N-[4-(methylsulfonyl)benzyl]-2-oxo-1-[3-(trifluoromethyl)phenyl]-1,2-dihydropyridine-3-carboxamide; ethyl 1-propenyl ether With triethylamine; bis[1,2-bis(diphenylphosphino)ethane]palladium(0) In DMF (N,N-dimethyl-formamide) at 100℃; Stage #2: With hydrogenchloride; water In DMF (N,N-dimethyl-formamide) for 1.5h;	99%

ethyl 1-propenyl ether (928-55-2) + diphenyl ketene (525-06-4) → 3-ethoxy-4-methyl-2,2-diphenylcyclobutanone (32929-60-5, 32949-69-2, 55701-86-5)

Conditions	Yield
In diethyl ether at 20℃;	99%

monomethyl oxalyl chloride (5781-53-3) + ethyl 1-propenyl ether (928-55-2) → C8H12O4 (1240314-05-9)

Conditions	Yield
at 0 - 20℃; for 18.33h; Inert atmosphere;	97%

ethyl 1-propenyl ether (928-55-2) + 1,3-Dimethyl-6-bromopteridine-2,4(1H,3H)-dione (84689-48-5) → 1,3-Dimethyl-6-propionylpteridine-2,4(1H,3H)-dione (71014-17-0)

Conditions	Yield
Multistep reaction.;	96%

3-methoxy-N,N-dimethylaniline (15799-79-8) + ethyl 1-propenyl ether (928-55-2) → C21H30N2O2

Conditions	Yield
With tris(pentafluorophenyl)borate at 110℃; for 8h; Sealed tube;	96%

ethyl 1-propenyl ether (928-55-2) + (1R)-trans-5-methyl-cyclohex-2-enol (116783-31-4) → (3R,5S)-3-(2-Bromo-1-ethoxy-propoxy)-5-methyl-cyclohexene (208761-32-4)

Conditions	Yield
With N-Bromosuccinimide In diethyl ether	95%

ethanol (64-17-5) + ethyl 1-propenyl ether (928-55-2) + Trichloroacetyl chloride (76-02-8) → (E)-ethyl 3-ethoxy-2-methylacrylate

Conditions	Yield
Stage #1: ethyl 1-propenyl ether; trifluoroacetyl chloride With pyridine at -10 - 20℃; for 20h; Inert atmosphere; Stage #2: ethanol With sodium ethanolate for 0.5h;	95%
Stage #1: ethyl 1-propenyl ether; trifluoroacetyl chloride With pyridine at -10 - 23℃; for 20h; Inert atmosphere; Stage #2: ethanol With sodium ethanolate for 0.5h;

ethyl 1-propenyl ether (928-55-2) + sodium ethanolate (141-52-6) + Trichloroacetyl chloride (76-02-8) → ethyl (ethoxymethylene)methylacetate (92145-32-9)

Conditions	Yield
Stage #1: ethyl 1-propenyl ether; trifluoroacetyl chloride With pyridine at -10 - 23℃; for 20h; Inert atmosphere; Stage #2: sodium ethanolate In ethanol for 0.5h;	95%
Stage #1: ethyl 1-propenyl ether; trifluoroacetyl chloride With pyridine at -10 - 23℃; for 20h; Inert atmosphere; Stage #2: sodium ethanolate In ethanol for 0.5h;
Stage #1: ethyl 1-propenyl ether; trifluoroacetyl chloride With pyridine In dichloromethane at -10 - 23℃; for 20h; Inert atmosphere; Stage #2: sodium ethanolate for 0.5h;

ethyl 1-propenyl ether (928-55-2) + tetraphenyldiphosphine disulfide (1054-60-0) → (1-ethoxypropane-1,2-diyl)bis(diphenylphosphine sulfide)

Conditions	Yield
In dichloromethane for 10h; Sealed tube; Inert atmosphere; Irradiation;	95%

ethyl 1-propenyl ether (928-55-2) + (1R,5R)-5-methyl-2-cyclohexenol (73610-84-1) → (3R,5R)-3-(2-Bromo-1-ethoxy-propoxy)-5-methyl-cyclohexene (208761-34-6)

Conditions	Yield
With N-Bromosuccinimide In diethyl ether	94%

ethyl 1-propenyl ether (928-55-2) + isobutyryl chloride (79-30-1) → cis-3-ethyloxy-2,2,4-trimethylcyclobutanone (55701-92-3, 90511-10-7, 90511-11-8)

Conditions	Yield
With triethylamine In tetrahydrofuran at 80℃; for 3.5h; Cooling with ice;	94%

ethyl 1-propenyl ether (928-55-2) → Methyl (4α,5α)-4-ethoxy-5-methylcyclopent-1-ene-1-carboxylate (139955-15-0, 140928-61-6)

Conditions	Yield
diethylaluminium chloride In dichloromethane at -78℃;	93%

ethyl 1-propenyl ether (928-55-2) + (1-tosyl-1H-1,2,3-triazol-4-yl)methyl acetate → trans-6-ethoxy-5-methyl-1-tosyl-1,4,5,6-tetrahydropyridin-3-yl acetate

Conditions	Yield
With dirhodium tetraacetate In toluene at 80℃; for 7h; Diels-Alder Cycloaddition; Inert atmosphere; chemoselective reaction;	93%

pentaamminetrifluoromethanesulfonato osmium(III) trifluoromethanesulfonate (83781-30-0) + ethyl 1-propenyl ether (928-55-2) → [Os(NH3)5(η2-1-ethoxypropene)](OTf)2

Conditions	Yield
With Zn/Hg In methanol stirring (15 min), filtration; pptn. of filtrate (CH2Cl2,Et2O); elem. anal.;	92%

ethyl 1-propenyl ether (928-55-2) + 2,4,7,9-tetramethyl-4,7-dihydroperoxy-5,6-dioxadecane (53151-88-5) → 2,2-bis(1-ethoxypropylperoxy)-4-methylpentane

Conditions	Yield
With toluene-4-sulfonic acid In isododecane at 15 - 20℃; for 0.5h;	91%

2-chloro-8-methyl-quinoline-3-carbaldehyde (73568-26-0) + ethyl 1-propenyl ether (928-55-2) + 3-methyl-1-(4-methylphenyl)-2-pyrazolin-5-one (86-92-0) → C27H28ClN3O2

Conditions	Yield
With triethylammonium acetate for 0.166667h; Microwave irradiation; Green chemistry;	91%

ethyl 1-propenyl ether (928-55-2) + 2-(methylsulfanyl)benzaldehyde (7022-45-9) → 2-ethoxy-1-[2-(methylthio)phenyl]butan-1-one

Conditions	Yield
With C29H39FO2P2Rh(1+)*C32H12BF24(1-) In acetone at 55℃; for 3h; Inert atmosphere; Glovebox;	91%

dimethylketene (598-26-5) + ethyl 1-propenyl ether (928-55-2) → cis-3-ethyloxy-2,2,4-trimethylcyclobutanone (55701-92-3, 90511-10-7, 90511-11-8)

Conditions	Yield
With triethylamine In various solvent(s)	90%
In diethyl ether at 20℃;	88%

ethyl 1-propenyl ether (928-55-2) + 2-ethoxycarbonyl-1-cyclopentanone (611-10-9) → ethyl 1-(1-methyl-2-oxoethyl)-2-oxocyclopentanecarboxylate

Conditions	Yield
With copper diacetate; manganese triacetate In dichloromethane at 40℃;	90%
With copper diacetate; manganese triacetate In dichloromethane at 40℃; for 18h;	90%

ethyl 1-propenyl ether (928-55-2) + para-methylphenylmagnesium bromide (4294-57-9) → 1-methyl-4-(prop-1-enyl)benzene (2698-14-8)

Conditions	Yield
With C68H72Cl2N6NiP2 In tetrahydrofuran at 50℃; for 12h; Inert atmosphere;	90%

2-chloro-8-methyl-quinoline-3-carbaldehyde (73568-26-0) + ethyl 1-propenyl ether (928-55-2) + edaravone (89-25-8) → 4-(2-chloro-8-methylquinolin-3-yl)-6-ethoxy-3,5-dimethyl-1-phenyl-1,4,5,6-tetrahydropyrano[2,3-c]pyrazole

Conditions	Yield
With triethylammonium acetate for 0.183333h; Microwave irradiation; Green chemistry;	90%

ethyl 1-propenyl ether (928-55-2) + 3-chloro-1H-indole-2-carboxaldehyde (110912-15-7) + 3-methyl-1-(4-methylphenyl)-2-pyrazolin-5-one (86-92-0) → C25H28ClN3O2

Conditions	Yield
With triethylammonium acetate for 0.15h; Microwave irradiation; Green chemistry;	90%

diethyl acetal (105-57-7) + ethyl 1-propenyl ether (928-55-2) → 1,1,3-triethoxy-2-methyl-butane (36551-27-6)

Conditions	Yield
With aluminum (III) chloride at -10 - -5℃; for 0.166667h; Reagent/catalyst; Temperature; Inert atmosphere;	88%
With aluminum (III) chloride at -10 - 5℃; for 0.166667h; Reagent/catalyst; Temperature; Inert atmosphere;	88%
With iron(III) chloride
With diethyl ether; boron trifluoride at 45 - 50℃;
With boron trifluoride diethyl etherate at 65℃;

ethyl 1-propenyl ether (928-55-2) + orthoformic acid triethyl ester (122-51-0) → 1,1,3,3-tetraethoxy-2-methyl-propane (10602-37-6)

Conditions	Yield
Stage #1: ethyl 1-propenyl ether; orthoformic acid triethyl ester With boron trifluoride diethyl etherate at 45℃; for 1h; Stage #2: With sodium carbonate at 45℃; for 3h;	88%
Stage #1: ethyl 1-propenyl ether; orthoformic acid triethyl ester; boron trifluoride diethyl etherate at 25℃; for 1h; Stage #2: With sodium carbonate for 1h;	80%
unter Zusatz des Borfluorid-Aether-Addukts;

ethyl 1-propenyl ether (928-55-2) + S-diethoxycarbonylmethyl O-ethyl dithiocarbonate (218966-77-9) → diethyl 2-(1-ethoxypropan-2-yl)malonate (93430-76-3)

Conditions	Yield
With triethyl borane; 4-tert-Butylcatechol In hexane; dichloromethane at 20℃; Giese Free Radical Synthesis; Inert atmosphere;	88%

2-chloro-8-methyl-quinoline-3-carbaldehyde (73568-26-0) + ethyl 1-propenyl ether (928-55-2) + 1,3-diphenyl-5-oxo-4,5-dihydro-1H-pyrazole (4845-49-2) → C31H28ClN3O2

Conditions	Yield
With triethylammonium acetate for 0.15h; Microwave irradiation; Green chemistry;	87%

ethyl 1-propenyl ether (928-55-2) + 3-chloro-1H-indole-2-carboxaldehyde (110912-15-7) + edaravone (89-25-8) → 4-(3-chloro-1H-indol-2-yl)-6-ethoxy-3,5-dimethyl-1-phenyl-1,4,5,6-tetrahydropyrano[2,3-c]pyrazole

Conditions	Yield
With triethylammonium acetate for 0.166667h; Microwave irradiation; Green chemistry;	87%

ethyl 1-propenyl ether (928-55-2) + 2-diazo-1H-phenalene-1,3(2H)-dione (18931-19-6) → 9-ethoxy-8-methyl-8,9-dihydro-phenaleno[1,2-b]furan-7-one

Conditions	Yield
dirhodium tetraacetate Cyclization;	86%

Upstream product

• 92854-89-2 4-methyl-3-(2,2,2-trichloroethyl)phenyl benzoate 
• 92854-49-4 4-methyl-3-(2,2,2-trichloroethyl)phenyl 4-nitrobenzoate 
• 928-54-1 1,2-DIISOCYANOETHANE 
• 92854-06-3 1,1-BIS-(4-CHLOROPHENYL)-BUTA-1,3-DIENE 
• 92853-70-8 2-(2-[(4-CHLOROPHENYL)SULFANYL]ETHYL)-1H-ISOINDOLE-1,3(2H)-DIONE 
• 92853-19-5 2-bromo-2-[bromo(phenyl)methyl]-2,3-dihydro-1H-inden-1-one 
• 92853-00-4 2-[{2,4-bisnitrophenyl}(phenylmethyl)amino]ethanol 
• 928-53-0 (Z)-but-2-enedinitrile 
• 92-85-3 Thianthrene 
• 92852-97-6 N-[4-[[(4-oxo-1-cyclohexa-2,5-dienylidene)methylamino]sulfamoyl]phenyl ]acetamide 
• 92852-02-3 2,3-diphenyl-1,3-thiazolidine 
• 92851-98-4 2-propyl-10H-phenothiazine 
• 928-51-8 4-Chloro-1-butanol 
• 92851-13-3 Carbamic acid, (4-methoxyphenyl)-, phenylmethyl ester (9CI) 

Downstream Products

• 92855-23-7 7-methyl-2-phenyl-1H-indole-3-carbaldehyde 
• 92855-30-6 10-methylphenanthrene-9-carboxamide 
• 92855-35-1 2-Methyl-3-phenoxyquinoline 
• 92855-38-4 8-METHYL-2-PHENYL-4-QUINOLINOL 
• 92855-40-8 2-methyl-4-phenyl-quinolin-7-ol 
• 92855-57-7 9-nitro-9,10-dihydro-9,10-ethanoanthracene 
• 92855-64-6 6-Benzyloxyindole-3-carboxaldehyde 
• 92855-65-7 7-Benzyloxyindole-3-carbaldehyde 
• 92856-07-0 5,5-diphenyl-1,3-oxazinane-2,4-dione 
• 92856-23-0 3-(6-amino-1,3-benzodioxol-5-yl)-2-phenylprop-2-enoic acid 
• 928-56-3 1-Chloro-2-ethoxyethene 
• 92856-34-3 N-(2,5-DIOXO-5,6,7,8-TETRAHYDRO-2H-CHROMEN-3-YL)BENZENECARBOXAMIDE 
• 92856-71-8 5-methyl-2-(naphthalen-2-ylsulfanyl)pyridine 
• 92857-05-1 1-(2,8,8-trimethyldecahydronaphthalen-2-yl)ethanol 

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• 105-57-7  diethyl acetal 
• 109-63-7  trifluoroborane diethyl ether 
• 4744-08-5  1,1-diethoxypropane 
• 15719-64-9  methylammonium carbonate 
• 23981-30-8  3-ethoxy-2-methyl-acrylic acid 
• 64-17-5  ethanol 
• 1670-47-9  1,1-diethoxycyclohexane 
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