926-66-9

Basic information

• Product Name: 2-Ethoxypropene
• Synonyms: 2-ETHOXYPROPENE;2-ETHOXYPROPYLENE;ETHYL-ISO-PROPENYL ETHER;CH2=C(CH3)OC2H5;2-Ethoxy-1-propene;2-ETHYOXYPROPENE;2-ethoxyprop-1-ene
• CAS NO: 926-66-9
• Molecular Formula: C₅H₁₀O
• Molecular Weight: 86.13
• Mol File: 926-66-9.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 64.1 °C at 760 mmHg
• Appearance: /
• Density: 0.766 g/cm³
• Vapor Pressure: 179mmHg at 25°C
• Refractive Index: 1.388
• CAS DataBase Reference: 2-Ethoxypropene(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Ethoxypropene(926-66-9)
• EPA Substance Registry System: 2-Ethoxypropene(926-66-9)

Safety Data

• Hazardous Substances Data: 926-66-9(Hazardous Substances Data)

Usage

Chemical Properties

Colorless liquid

InChI:InChI=1/C5H10O/c1-4-6-5(2)3/h2,4H2,1,3H3

Synthetic route

2-Methoxypropene (116-11-0) + Ir(C5(CH3)5)(P(CH3)3)H(CHOC2H5)(1+)*B(C6H5)4(1-)=[Ir(C5(CH3)5)(P(CH3)3)H(CHOC2H5)]B(C6H5)4 → 2-ethoxyprop-1-ene (926-66-9) + Ir(C5(CH3)5)(P(CH3)3)H(CHOCH3)(1+)*B(C6H5)4(1-)=[Ir(C5(CH3)5)(P(CH3)3)H(CHOCH3)]B(C6H5)4

Conditions	Yield
	A 93% B 96%

2-chloropropene (557-98-2) + sodium ethanolate (141-52-6) → 2-ethoxyprop-1-ene (926-66-9)

Conditions	Yield
at 180℃;

1,2-Dichloropropane (26198-63-0, 78-87-5) + sodium ethanolate (141-52-6) → 2-ethoxyprop-1-ene (926-66-9)

Conditions	Yield
at 180℃;

1,2-Dibromopropane (78-75-1) → 2-ethoxyprop-1-ene (926-66-9)

Conditions	Yield
With potassium carbonate at 170℃;

1,2-propanediene (463-49-0) → 2-ethoxyprop-1-ene (926-66-9)

Conditions	Yield
With ethanol; potassium carbonate at 170 - 180℃;

1-bromo-2-ethoxy-propane (23465-32-9) → 2-ethoxyprop-1-ene (926-66-9)

Conditions	Yield
With potassium hydroxide

Δ2-3-ethoxybutenoic acid (38624-58-7) → 2-ethoxyprop-1-ene (926-66-9)

Conditions	Yield
at 160 - 165℃;
at 160℃;
at 160 - 165℃;

2,2-diethoxypropane (126-84-1) → 2-ethoxyprop-1-ene (926-66-9)

Conditions	Yield
With quinoline; toluene-4-sulfonic acid
With sodium trisilicate; magnesium hydrogen phosphate at 300℃;
With quinoline; phosphorus pentoxide

prop-1-yne (74-99-7) → 2-ethoxyprop-1-ene (926-66-9)

Conditions	Yield
With ethanol; potassium carbonate at 170 - 180℃;

1-chloro-2-ethoxy-propane (5390-74-9) → 2-ethoxyprop-1-ene (926-66-9)

Conditions	Yield
With potassium hydroxide In ethanol at 165℃; under 15960 Torr;

orthoformic acid triethyl ester (122-51-0) + acetone (67-64-1) → 2-ethoxyprop-1-ene (926-66-9)

Conditions	Yield
With quinoline; toluene-4-sulfonic acid Heating;

(E)-3-ethoxy-but-2-enoic acid (221647-72-9) → 2-ethoxyprop-1-ene (926-66-9)

Conditions	Yield
(decarboxylation);

3-ethoxycrotonic acid (38624-58-7) → 2-ethoxyprop-1-ene (926-66-9)

Conditions	Yield
at 160℃;

prop-1-yne (74-99-7) + alcoholic potash → 2-ethoxyprop-1-ene (926-66-9)

Conditions	Yield
at 170 - 180℃;

quinoline (91-22-5) + 2,2-diethoxypropane (126-84-1) + P2O5 → 2-ethoxyprop-1-ene (926-66-9)

β-ethoxy-crotonic acid → 2-ethoxyprop-1-ene (926-66-9)

Conditions	Yield
With calcium hydroxide

1,2-propanediene (463-49-0) + alcoholic potash → 2-ethoxyprop-1-ene (926-66-9)

Conditions	Yield
at 160 - 170℃;

3-ethoxycrotonic acid (38624-58-7) + lime/chalk/ hydrate → 2-ethoxyprop-1-ene (926-66-9)

Conditions	Yield
Destillation;

ethanol (64-17-5) + prop-1-yne (74-99-7) + potassium hydroxide → 2-ethoxyprop-1-ene (926-66-9)

Conditions	Yield
at 220℃;

hydrogenchloride (7647-01-0) + ethanol (64-17-5) + 2-phenoxypropene (698-91-9) → 2-ethoxyprop-1-ene (926-66-9) + 2,2-diethoxypropane (126-84-1) + phenol (108-95-2)

ethyl 3-ethoxy-2-butenoate (998-91-4) → 2-ethoxyprop-1-ene (926-66-9)

Conditions	Yield
Multi-step reaction with 2 steps 1: NaOH 2: 160 - 165 °C View Scheme

tetraphenylborate anion (4358-26-3) + {Pd(η3-2-C3H5)(Py-2-CHNC6H4OMe-4)}(1+) + dimethylfumarate (624-49-7) → allylbenzene (300-57-2) + 2-ethoxyprop-1-ene (926-66-9) + (CH3OC(O)CHCHCOOCH3)Pd(C5NH4CHNC6H4(OCH3))

Conditions	Yield
In methanol; water Kinetics; react. of Pd-compex with BPh4(1-) at 25°C in solvent in the presence of dimethylfumarate;	A n/a B 0% C n/a

trifluoracetyl chloride (354-32-5) + 2-ethoxyprop-1-ene (926-66-9) → 1,1,1-trifluoro-4-ethoxypent-3-en-2-one (144219-75-0)

Conditions	Yield
With diethylamine In cyclohexane at 5 - 10℃; for 3h; Reagent/catalyst; Solvent; Temperature; Large scale;	96%

2-ethoxyprop-1-ene (926-66-9) + 3,7-dimethyloct-6-en-1-yn-3-ol (29171-20-8) → pseudoionone (141-10-6)

Conditions	Yield
With sulfonic acid resin T239 at 90℃; for 8h; Reagent/catalyst; Autoclave; Inert atmosphere;	94.6%

4-toluenesulfonyl azide (941-55-9) + 2-ethoxyprop-1-ene (926-66-9) + carbon monoxide (201230-82-2) → (E)-3-ethoxy-N-tosylbut-2-enamide

Conditions	Yield
With palladium diacetate In acetonitrile at 80℃; under 760.051 Torr; for 12h; Schlenk technique;	87%

2-ethoxyprop-1-ene (926-66-9) + 1-Phenylethynyl-1H-1λ3-benzo[d][1,2]iodoxol-3-one → C20H19IO3

Conditions	Yield
With 1-acetoxy-1,2-benziodoxol-3-one; (2r,4s,5r)-2,4,5,6-Tetrakis(3,6-dichloro-9H-carbazol-9-yl)isophthalonitrile In dichloromethane at 25 - 28℃; for 18h; Irradiation;	82%

2-ethoxyprop-1-ene (926-66-9) + (1-tosyl-1H-1,2,3-triazol-4-yl)methyl acetate → 6-ethoxy-6-methyl-1-tosyl-1,4,5,6-tetrahydropyridin-3-yl acetate

Conditions	Yield
With dirhodium tetraacetate In toluene at 80℃; for 11h; Diels-Alder Cycloaddition; Inert atmosphere; chemoselective reaction;	73%

2-ethoxyprop-1-ene (926-66-9) + N-(benzylidene)-p-methylbenzenesulfonamide (51608-60-7) → N-(4-Ethoxy-1-phenyl-pent-4-enyl)-4-methyl-benzenesulfonamide (106419-27-6)

Conditions	Yield
In acetonitrile at 50℃; under 9000720 Torr; for 20h;	70%

2-ethoxyprop-1-ene (926-66-9) → ethyl acetate (141-78-6)

Conditions	Yield
With pyridinium chlorochromate In dichloromethane at 25℃; for 2h;	65%

2-ethoxyprop-1-ene (926-66-9) → ethoxy-3-methyl-1,2-dioxolane (97674-28-7) + 3-Ethoxy-3-methyl-[1,2,4]trioxolane (90150-49-5)

Conditions	Yield
With ozone In pentane at -78℃;	A 63% B 3%
With ozone In pentane at -78℃;	A 56% B 5%

2-ethoxyprop-1-ene (926-66-9) + hexafluoroacetone azine (1619-84-7) → 7-Ethoxy-1,1,1-trifluor-2,5,5-tris(trifluormethyl)-3,4-diazaocta-2,7-dien (82489-21-2) + N-((Z)-3-Ethoxy-1,1-bis-trifluoromethyl-but-2-enyl)-N'-(2,2,2-trifluoro-1-trifluoromethyl-ethylidene)-hydrazine

Conditions	Yield
In diethyl ether at 0 - 5℃; for 192h;	A 56% B n/a

salicylaldehyde diethyl acetal (6842-31-5) + 2-ethoxyprop-1-ene (926-66-9) → C14H20O3 + (2S,4S)-2,4-diethoxy-2-methylchromane

Conditions	Yield
Stage #1: salicylaldehyde diethyl acetal; 2-ethoxyprop-1-ene With C75H86O15 In benzene at 20℃; for 16h; Diels-Alder Cycloaddition; Stage #2: With sodium tetrahydroborate In methanol for 0.5h; Overall yield = 50 %; Overall yield = 24.1 mg; enantioselective reaction;	A n/a B 50%

2-ethoxyprop-1-ene (926-66-9) + malonoyl dichloride (1663-67-8) → 4-hydroxy-6-methyl-2-pyron (675-10-5) + Phloroglucinmonoethylether (28334-98-7)

Conditions	Yield
In diethyl ether	A 42% B 43%
With potassium hydroxide; N-benzyl-N,N,N-triethylammonium chloride 1) Et2O, -19 deg C, 2 h, 2) Et2O, r.t., 4 h; Yield given. Multistep reaction. Yields of byproduct given;

2-ethoxyprop-1-ene (926-66-9) + [(p-methylphenyl)sulfonylmethyl]isonitrile (38622-91-2, 36635-61-7) → 2-ethoxy-2-methyl-N-(tosylmethyl)propanamide

Conditions	Yield
With camphor-10-sulfonic acid In tetrahydrofuran at 20℃; for 30h;	41%

2-ethoxyprop-1-ene (926-66-9) + 7-(diethylamino)-3-iodo-4-methyl-2H-chromen-2-one (107995-74-4) → 7-diethylamino-4-methylcoumarin (91-44-1) + 7-Diethylamino-3-((Z)-2-ethoxy-propenyl)-4-methyl-chromen-2-one (132093-45-9)

Conditions	Yield
for 12h; Irradiation; Further byproducts given;	A n/a B 31%

2-ethoxyprop-1-ene (926-66-9) + 7-(diethylamino)-3-iodo-4-methyl-2H-chromen-2-one (107995-74-4) → 7-diethylamino-4-methylcoumarin (91-44-1) + 7-Diethylamino-3-((Z)-2-ethoxy-propenyl)-4-methyl-chromen-2-one (132093-45-9) + N-de-ethylation products

Conditions	Yield
for 12h; Quantum yield; Irradiation;	A n/a B 31% C n/a

N-phenyl piperidine (4096-20-2) + 2-ethoxyprop-1-ene (926-66-9) → C25H34N2

Conditions	Yield
With tris(pentafluorophenyl)borate at 110℃; for 8h; Sealed tube;	31%

2-ethoxyprop-1-ene (926-66-9) + N-(4-(4-(cyclopropylamino)-4-oxobutyl)-1-phenyl-1H-imidazol-2-yl)-3-(1H-pyrazol-4-yl)benzamide → N-(4-(4-(cyclopropylamino)-4-oxobutyl)-1-phenyl-1H-imidazol-2-yl)-3-(1-(2-ethoxypropan-2-yl)-1H-pyrazol-4-yl)benzamide

Conditions	Yield
Stage #1: 2-ethoxyprop-1-ene; N-(4-(4-(cyclopropylamino)-4-oxobutyl)-1-phenyl-1H-imidazol-2-yl)-3-(1H-pyrazol-4-yl)benzamide With toluene-4-sulfonic acid In chloroform at 0℃; for 1h; Stage #2: With triethylamine In chloroform at 0℃; for 0.5h;	30%

methanol (67-56-1) + 2-ethoxyprop-1-ene (926-66-9) → 2-ethoxy-2-methoxy-propane (29328-22-1)

Conditions	Yield
With Fuller's Earth

trans-Crotonaldehyde (123-73-9) + 2-ethoxyprop-1-ene (926-66-9) → (+/-)-4-ethoxy-hept-5t-en-2-one (103263-48-5)

Conditions	Yield
With boric acid; oxalic acid

2-ethoxyprop-1-ene (926-66-9) + 1,1-Diethoxyhexa-2,4-diene (94088-28-5) → nona-3t,5t,7t-trien-2-one (16326-91-3)

Conditions	Yield
With zinc(II) chloride und anschliessenden Erwaermen mit Natriumacetat enthaltender wss.Essigsaeure;

2-ethoxyprop-1-ene (926-66-9) + octa-2t,4t,6t-trienal-diethylacetal (63282-12-2) → 3,5,7,9-undecatetraen-2-one (75143-19-0)

Conditions	Yield
With zinc(II) chloride und Erwaermen des Reaktionsprodukts mit Natriumacetat enthaltender wss.Essigsaeure;

2-ethoxyprop-1-ene (926-66-9) + ethene (74-85-1) → isoprene (78-79-5)

Conditions	Yield
at 130 - 135℃; under 3677.5 Torr; ueber einen Mischkatalysator aus Aluminium, SiO2, Nb2O5, WO3, und AgNO3;

2-ethoxyprop-1-ene (926-66-9) + ethene (74-85-1) → penta-1,3-diene (504-60-9) + isoprene (78-79-5)

Conditions	Yield
at 150 - 160℃; beim Leiten ueber einen Mischkatalysator aus Aluminium und Oxiden des Bors, Wolframs, Urans und Silbers;
at 150 - 160℃; beim Leiten ueber einen Mischkatalysator aus Aluminium und Oxiden des Bors, Wolframs, Urans und Silbers;

2-ethoxyprop-1-ene (926-66-9) + oxalic acid monoethyl ester (617-37-8) → 2,4,6-trioxo-heptanedioic acid diethyl ester (68854-18-2)

Conditions	Yield
With diethyl ether; ethanol; potassium ethoxide

2-ethoxyprop-1-ene (926-66-9) + 1,1-diethoxy-3-methyl-2-butene (1740-74-5) → 4,6,6-triethoxy-2-methyl-hept-2-ene (106522-69-4)

Conditions	Yield
With diethyl ether; zinc(II) chloride

2-ethoxyprop-1-ene (926-66-9) + (diethoxymethyl)benzene (774-48-1) → 4-ethoxy-4-phenyl-butan-2-one-diethylacetal (93154-72-4)

Conditions	Yield
With diethyl ether; zinc(II) chloride

2-ethoxyprop-1-ene (926-66-9) + 1,3-diphenyl-2H-cyclopenta<1>phenanthren-2-one (5660-91-3) → 2-ethoxy-2-methyl-1,4-diphenyl-1,2,3,4-tetrahydro-1,4-methano-triphenylen-13-one

Conditions	Yield
With benzene

2-ethoxyprop-1-ene (926-66-9) → ethyl-(bromo-tert-butyl)-ether (29840-15-1)

Conditions	Yield
With diethyl ether; bromine at -30℃; anschliessendes Behandeln mit Methylmagnesiumbromid in Aether bei 0grad;

2-ethoxyprop-1-ene (926-66-9) → 2-ethoxy-1,2-dibromo-propane (412013-01-5)

Conditions	Yield
With bromine at -10℃;

Upstream product

• 557-98-2 2-chloropropene 
• 141-52-6 sodium ethanolate 
• 26198-63-0 1,2-Dichloropropane 
• 78-75-1 1,2-Dibromopropane 
• 23465-32-9 1-bromo-2-ethoxy-propane 
• 38624-58-7 Δ²-3-ethoxybutenoic acid 
• 126-84-1 2,2-diethoxypropane 
• 7647-01-0 hydrogenchloride 
• 64-17-5 ethanol 
• 698-91-9 2-phenoxypropene 
• 116-11-0 2-Methoxypropene 
• 38624-58-7 3-ethoxycrotonic acid 
• 221647-72-9 (E)-3-ethoxy-but-2-enoic acid 
• 122-51-0 orthoformic acid triethyl ester 

Downstream Products

• 78-79-5 isoprene 
• 504-60-9 penta-1,3-diene 
• 41616-93-7 1,1,3,3-tetraethoxy-butane 
• 86534-49-8 1-Chloro-4-(2-chloro-2-ethoxy-propylsulfanyl)-benzene 
• 41623-06-7 Benzoic acid (8R,9S,13S,14S,17S)-17-(1-ethoxy-1-methyl-ethoxy)-13-methyl-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthren-3-yl ester 
• 91-44-1 7-diethylamino-4-methylcoumarin 
• 132093-45-9 7-Diethylamino-3-((Z)-2-ethoxy-propenyl)-4-methyl-chromen-2-one 
• 87910-10-9 2-propyl-3-methyl-3-ethoxy-4-(4-chlorophenylthio)butanal 
• 87910-14-3 2-<1-methyl-1-ethoxy-2-(4-chlorophenylthio)>ethylcyclohexanone 
• 126-84-1 2,2-diethoxypropane 
• 13837-60-0 2-ethynyl-2,6,6-trimethyl-3,4,5,6-tetrahydro-(2H)-pyran 
• 16647-05-5 6,10-dimethylundeca-4,5,9-trien-2-one 
• 187737-37-7 propene 
• 597-67-1 ethoxytriethylsilane 

Relevant articles and documents

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