926-65-8

Basic information

• Product Name: Vinyl isopropyl ether
• Synonyms: 1-Isopropoxyethylene;2-(ethenyloxy)-propan;2-Vinyloxy-propane;CH2=CHOCH(CH3)2;Ether, isopropyl vinyl;Isopropoxyethene;isopropoxy-ethene;Isopropoxyethylene
• CAS NO: 926-65-8
• Molecular Formula: C₅H₁₀O
• Molecular Weight: 86.13
• EINECS: 213-142-5
• Mol File: 926-65-8.mol
• Article Data: 6

Chemical Properties

• Melting Point: -140°C
• Boiling Point: 68.84°C (estimate)
• Flash Point: °C
• Appearance: colorless and transparent liquid
• Density: 0.7534
• Vapor Pressure: 230mmHg at 25°C
• Refractive Index: 1.3840
• CAS DataBase Reference: Vinyl isopropyl ether(CAS DataBase Reference)
• NIST Chemistry Reference: Vinyl isopropyl ether(926-65-8)
• EPA Substance Registry System: Vinyl isopropyl ether(926-65-8)

Safety Data

• RIDADR: 3271
• HazardClass: 3.1
• PackingGroup: II
• Hazardous Substances Data: 926-65-8(Hazardous Substances Data)

Usage

General Description

Vinyl isopropyl ether is a chemical compound with the molecular formula C5H10O. It is a colorless liquid with a mild, sweet odor, and is highly flammable. Vinyl isopropyl ether is commonly used as a solvent in the manufacturing of paints, varnishes, and other coatings. It is also used as an intermediate in the synthesis of various organic compounds and as a reagent in organic chemistry reactions. Additionally, it can be used as a monomer in the production of polymers and copolymers. However, vinyl isopropyl ether presents some health hazards, as it can cause irritation to the eyes, skin, and respiratory system, and may have harmful effects if ingested or inhaled. Therefore, proper safety precautions should be taken when handling and using this chemical.

InChI:InChI=1/C5H10O/c1-4-6-5(2)3/h4-5H,1H2,2-3H3

Synthetic route

isopropyl alcohol (67-63-0) + acetylene (74-86-2) → vinyl isopropyl ether (926-65-8)

Conditions	Yield
With sodium hydroxide; cesium fluoride In dimethyl sulfoxide at 100℃; for 5.5h; atmospheric pressure;	86%
With potassium hydroxide In dimethyl sulfoxide at 120℃; for 2h;	53%
With potassium hydroxide at 150 - 155℃;

β-isopropoxyethyl vinyl sulfoxide (80857-63-2) → vinyl isopropyl ether (926-65-8) + ethenesulfenic acid (2492-74-2)

Conditions	Yield
With potassium hydroxide at 280 - 290℃;	A 65% B n/a

β-isopropoxyethyl vinyl sulfoxide (80857-63-2) → vinyl isopropyl ether (926-65-8)

Conditions	Yield
With potassium hydroxide at 60 - 70℃; for 1h;	62%
With potassium hydroxide at 60 - 70℃; under 1 Torr; for 1h; Product distribution;	62%

isobutyl vinyl ether (109-53-5) + isopropyl alcohol (67-63-0) → vinyl isopropyl ether (926-65-8)

Conditions	Yield
With mercury(II) diacetate at 55 - 56℃;	30%

1,1-diisopropoxy-ethane (4285-59-0) → vinyl isopropyl ether (926-65-8)

Conditions	Yield
With sodium hydrogen sulfate

1-chloro-1-(1-methyletoxy)ethane (84607-80-7) → vinyl isopropyl ether (926-65-8)

Conditions	Yield
With pyridine

2-isopropyloxyethyl bromide (54149-16-5) → vinyl isopropyl ether (926-65-8)

Conditions	Yield
With potassium hydroxide at 130℃;
With potassium tert-butylate In dimethyl sulfoxide at 90℃;

-butyl vinyl ether (111-34-2) + isopropyl alcohol (67-63-0) → vinyl isopropyl ether (926-65-8)

Conditions	Yield
With mercury(II) diacetate

sodium isopropylate (683-60-3) + acetylene (74-86-2) → vinyl isopropyl ether (926-65-8)

Conditions	Yield
at 150 - 155℃;

2-(1-methylethoxy)-ethanol (109-59-1) → vinyl isopropyl ether (926-65-8)

Conditions	Yield
Multi-step reaction with 2 steps 1: pyridine; phosphorus tribromoide 2: KOH / 130 °C View Scheme

vinyl isopropyl ether (926-65-8) + (4-bromo-3,5-dimethoxyphenyl)methanol (61367-62-2) → 2-bromo-5-[(1-isopropoxyethoxy)methyl]-1,3-dimethoxybenzene (1144100-25-3)

Conditions	Yield
With pyridinium p-toluenesulfonate In tetrahydrofuran at 20℃; for 2.5h;	99.6%

vinyl isopropyl ether (926-65-8) + (3E)-1-Phenylsulfonyl-2-oxo-3-pentene (96530-26-6) → (2R,4R)-6-Benzenesulfonylmethyl-2-isopropoxy-4-methyl-3,4-dihydro-2H-pyran (161420-34-4)

Conditions	Yield
With diisopropoxytitanium(IV) dibromide; 4 A molecular sieve; (R,R)-TADDOL In dichloromethane at -78℃; for 24h;	92%
Stage #1: (3E)-1-Phenylsulfonyl-2-oxo-3-pentene With titanium((4R,5R)-2,2-dimethyl-α,α,α',α'-tetraphenyl-1,3-dioxolane-4,5-dimethylate)Br2 In dichloromethane at -78℃; Hetero Diels-Alder cycloaddition; Molecular sieve; Inert atmosphere; Stage #2: vinyl isopropyl ether In dichloromethane Hetero Diels-Alder cycloaddition; Inert atmosphere; optical yield given as %ee; enantioselective reaction;

vinyl isopropyl ether (926-65-8) + 2-((E)-4,4,4-Trichloro-3-oxo-but-1-enyl)-isoindole-1,3-dione (110945-43-2) → 2-isopropyloxy-4-phthalimido-6-trichloromethyl-3,4-dihydro-2H-pyran (142362-49-0, 142362-50-3)

Conditions	Yield
With 2-tert-Butyl-4-methylphenol In toluene at 120℃; for 24h;	91%

carbon disulfide (75-15-0) + vinyl isopropyl ether (926-65-8) + diethylamine (109-89-7) → Diethyl-dithiocarbamic acid 1-isopropoxy-ethyl ester (112165-06-7)

Conditions	Yield
	89%

vinyl isopropyl ether (926-65-8) + 2,2-dimethyl-3,4-dihydro-2H-naphthalen-1-one (2977-45-9) → C17H24O2

Conditions	Yield
With Fe(PMe3)4 at 50℃; for 40h; Inert atmosphere; regioselective reaction;	89%

4-phenyl-1H-1,2,3-triazole (1680-44-0) + vinyl isopropyl ether (926-65-8) → 2-(1-isopropoxyethyl)-4-phenyl-2H-1,2,3-triazole

Conditions	Yield
With triphenylphosphine gold(I)chloride; silver(I) triflimide In 1,2-dichloro-ethane at 80℃; for 6h; Inert atmosphere; Schlenk technique; regioselective reaction;	88%

vinyl isopropyl ether (926-65-8) + diethyl 2-oxo-3-butenylphosphonate (67257-30-1) → (6-Isopropoxy-5,6-dihydro-4H-pyran-2-ylmethyl)-phosphonic acid diethyl ester

Conditions	Yield
zinc(II) chloride In dichloromethane for 3h; Ambient temperature;	87%

vinyl isopropyl ether (926-65-8) + hexafluorothioacetone (1490-33-1) → C8H10F6OS (1206485-04-2) + C8H10F6OS2 (1258730-51-6)

Conditions	Yield
With cesium fluoride In N,N-dimethyl-formamide at 25℃; for 48h; Inert atmosphere;	A 85% B n/a
With sulfur; cesium fluoride In N,N-dimethyl-formamide at 25 - 35℃; Inert atmosphere;	A n/a B 20%

vinyl isopropyl ether (926-65-8) + N,N,N’,N’-tetrabenzylmethanediamine (58288-30-5) + isopropyl alcohol (67-63-0) → N,N-dibenzyl-3,3-diisopropoxypropan-1-amine (1493780-01-0)

Conditions	Yield
With Pd(xantphos)(CH3CN)2(OTf)2 In toluene at 110℃; for 12h; Inert atmosphere; Schlenk technique;	84%
With C39H32OP2*2C2H3N*2CF3O3S(1-)*Pd(2+) In toluene at 110℃; for 12h; Reagent/catalyst; Inert atmosphere;	84%

vinyl isopropyl ether (926-65-8) + methyl 2-romo-2-(4,5-dihydrooxazol-2-yl)-3,3,3-trifluoropropanoate → methyl 1-(2-bromoethyl)-5-isopropoxy-2-oxo-3-(trifluoromethyl)-pyrrolidine-3-carboxylate

Conditions	Yield
With Ir(dF(CF3)ppy)2(dtbbpy)(PF6) In N,N-dimethyl-formamide at 20℃; for 1h; Schlenk technique; Inert atmosphere; Irradiation;	83%

vinyl isopropyl ether (926-65-8) + dibenzyl 2-vinylcyclopropane-1,1-dicarboxylate (182740-91-6) → C26H30O5

Conditions	Yield
With (4,4'-di-tert-butyl-2,2'-dipyridyl)-bis-(2-phenylpyridine(-1H))-iridium(III) hexafluorophosphate; toluene-4-sulfonic acid isopropylidenehydrazide; potassium carbonate In acetonitrile at 20℃; Irradiation; Inert atmosphere;	83%

vinyl isopropyl ether (926-65-8) + hexafluorothioacetone (1490-33-1) → C8H10F6OS (1206485-04-2)

Conditions	Yield
With potassium fluoride In N,N-dimethyl-formamide at 25℃; for 48h; Inert atmosphere;	82%

vinyl isopropyl ether (926-65-8) + C24H34O5 → C29H43IO6

Conditions	Yield
With N-iodo-succinimide In dichloromethane	79%

vinyl isopropyl ether (926-65-8) + (E)-4-phenyl-1-phenylsulfonyl-3-buten-2-one (32117-28-5) → (2R,4R)-6-Benzenesulfonylmethyl-2-isopropoxy-4-phenyl-3,4-dihydro-2H-pyran (161420-36-6)

Conditions	Yield
With diisopropoxytitanium(IV) dibromide; 4 A molecular sieve; (R,R)-TADDOL In dichloromethane at -70℃; for 20h;	77%

vinyl isopropyl ether (926-65-8) + senecioyl cyanide (38576-60-2) → 6-Isopropoxy-4,4-dimethyl-5,6-dihydro-4H-pyran-2-carbonitrile (83379-78-6)

Conditions	Yield
at 160℃; for 10h;	76%

vinyl isopropyl ether (926-65-8) + C16H17NO5 → 9-(tert-butyl) 4-methyl (2R,4R)-2-isopropoxy-3,4-dihydropyrano[2,3-b]indole-4,9(2H)-dicarboxylate

Conditions	Yield
Stage #1: C16H17NO5 With nickel(II) tetrafluoroborate hexahydrate; C33H48N4O4 In dichloromethane at 30℃; for 0.5h; Stage #2: vinyl isopropyl ether In dichloromethane at 0℃; for 12h; Diels-Alder Cycloaddition; enantioselective reaction;	75%

chloroform (67-66-3) + vinyl isopropyl ether (926-65-8) → 2,2-dichlorocyclopropyl isopropyl ether (13764-05-1)

Conditions	Yield
With potassium hydroxide; triethylamine; N-benzyl-N,N,N-triethylammonium chloride	73.5%

vinyl isopropyl ether (926-65-8) + 2-acetyl-1,4-naphthoquinone (5813-57-0) → 1-(5-hydroxy-2-isobutoxy-2,3-dihydronaphtho[1,2-b]furan-4-yl)ethanone (1452153-50-2)

Conditions	Yield
With ammonium cerium (IV) nitrate In acetonitrile at 20℃; for 0.333333h;	70%

vinyl isopropyl ether (926-65-8) + N-(p-toluenesulfonyl)-2-vinylaziridine (126690-80-0) → C16H23NO3S

Conditions	Yield
With (4,4'-di-tert-butyl-2,2'-dipyridyl)-bis-(2-phenylpyridine(-1H))-iridium(III) hexafluorophosphate; toluene-4-sulfonic acid isopropylidenehydrazide; potassium carbonate In acetonitrile at 20℃; Irradiation; Inert atmosphere;	67%

tert.-butylhydroperoxide (75-91-2) + vinyl isopropyl ether (926-65-8) + 2-((4-methoxyphenyl)amino)-1-phenylethanone (5883-82-9) → 4-tert-butoxy-3-isopropoxy-2-(4-methoxyphenylamino)-1-phenylbutan-1-one

Conditions	Yield
With copper(l) chloride In hexane at 50℃; for 12h; Inert atmosphere; regioselective reaction;	51%

vinyl isopropyl ether (926-65-8) + ((1-butoxy-2-methylprop-1-en-1-yl)oxy)trimethylsilane (158362-24-4) → butyl 2,2-dimethyl-3-butenoate

Conditions	Yield
With gallium(III) bromide In 1,2-dichloro-ethane at 80℃; for 2h; regioselective reaction;	50%
In 1,2-dichloro-ethane at 80℃;	50 %Chromat.

vinyl isopropyl ether (926-65-8) + phosphonic acid diethyl ester (762-04-9) → isopropyl diethylphosphonoacetate (50350-99-7)

Conditions	Yield
With pyridine; manganese(III) acetylacetonate In acetonitrile at 20℃; for 24h;	50%

pyridine-2-thione (2637-34-5) + vinyl isopropyl ether (926-65-8) → 2-<1-isopropoxy-2-(2-isopropoxyethylthio)ethyl>pyridine (114193-80-5) + bis<2-isopropoxy-2-(2-pyridyl)ethyl>disulfide (114193-85-0)

Conditions	Yield
In acetonitrile for 4h; Irradiation;	A 46% B 3%

Triethylsilanol (597-52-4) + vinyl isopropyl ether (926-65-8) → et3Si(Oet-1-Oi-pr) (18048-18-5)

Conditions	Yield
In hydrogenchloride (C2H5)3Si(OH) and CH2CHOCH(CH3)2 in presence of 30% HCl soln. at 50-90°C;;	42%

vinyl isopropyl ether (926-65-8) + orthoformic acid triethyl ester (122-51-0) → malondialdehyde bis(diethyl acetal) (122-31-6) + 1,3,3-triethoxy-1-(isopropoxy)propane (603151-68-4)

Conditions	Yield
iron(III) chloride at -30℃; for 6h; Product distribution / selectivity;	A 6.5% B 42%
iron(III) chloride at 0℃; for 6h; Product distribution / selectivity;	A 13.6% B 27%

vinyl isopropyl ether (926-65-8) + 5-phenylfuran-2,3-dione (55991-67-8) → 2-phenyl-4H-pyran-4-one (2397-79-7) + 3-benzoyl-4-hydroxy-6-phenyl-2H-pyran-2-one (14895-21-7)

Conditions	Yield
In benzene for 3h; Heating;	A 30% B n/a

Upstream product

• 84607-80-7 1-chloro-1-(1-methyletoxy)ethane 
• 54149-16-5 2-isopropyloxyethyl bromide 
• 111-34-2 -butyl vinyl ether 
• 67-63-0 isopropyl alcohol 
• 74-86-2 acetylene 
• 109-59-1 2-(1-methylethoxy)-ethanol 
• 109-53-5 isobutyl vinyl ether 
• 80857-63-2 β-isopropoxyethyl vinyl sulfoxide 
• 683-60-3 sodium isopropylate 
• 4285-59-0 1,1-diisopropoxy-ethane 

Downstream Products

• 1123-27-9 1-(1-hydroxycyclohexyl)ethan-1-one 
• 17902-91-9 diethyl-(1-isopropoxy-ethoxy)-phenyl-silane 
• 75-07-0 acetaldehyde 
• 104741-77-7 1-benzoyloxy-1-isopropoxy-ethane 
• 63777-09-3 6-isopropoxy-4,4-dimethyl-1,3-diphenyl-1,4,5,6-tetrahydro-pyrano[2,3-c]pyrazole 
• 63777-08-2 6-isopropoxy-4,4-dimethyl-1-phenyl-1,4,5,6-tetrahydro-pyrano[2,3-c]pyrazole 
• 187737-37-7 propene 
• 122-31-6 malondialdehyde bis(diethyl acetal) 
• 603151-68-4 1,3,3-triethoxy-1-(isopropoxy)propane 
• 19690-04-1 Cyclohexyliden-cyclopropyl-isopropylaether 
• 603151-66-2 1,3,3-trimethoxy-1-(isopropoxy)propane 
• 102-52-3 malonaldehydebis(dimethylacetal) 

Relevant articles and documents

NATURE AND CONCENTRATION OF ACTIVE SPECIES IN CATIONIC POLYMERIZATION OF VINYL ETHERS: A KINETIC INVESTIGATION

The Kinetics of the polymerization of isopropyl vinyl ether, isobutyl vinyl ether (IBVE) and chloroethyl vinyl ether initiated by HI in CH2Cl2, in the presence and in the absence of tetrabutylammonium iodide as common anion salt, were investigated.The polymerizations proceed directly through the carbon-iodide termini without any necessary electrophilic activator.As previously observed with cyclohexyl vinyl ether, it was found that the addition of small amounts of salt, (0.5-10percent with respect to initial , depending on the monomer) drastically reduces the polymerization rate and leads to living-type polymerizations.Higher amounts of salt have no influence on the polymerization rate which remains constant over a broad range of / ratios.This general behaviour, observed for the all vinyl ethers, suggests a common ion salt effect and therefore an ionic polymerization mechanism involving ion pairs and free ions.In the absence of salt, both ion pairs and free ions of higher reactivity participate in the propagation, whereas only ion pairs contribute to the propagation in the presence of a common ion salt.According to this scheme, the living character of the polymerization is assumed to result from a propagation reaction governed by undissociated ionic species.The validity and the implications of this reaction scheme, in terms of active centre concentrations, are also discussed.

Nucleophilic Addition to Acetylenes in Superbasic Catalytic Systems. VII. Vinylation of Lower Alcohols

Superbasic systems KOH-DMSO and KOH-HMPA with acetylene and alcohols form highly active catalytic complexes capable of sharply increasing the rate and selectivity of nucleophilic addition of alcohols to acetylene and allowing preparation of high-purity lower alkyl vinyl ethers in high yield under acetylene pressure equal to atmospheric.

VINYLATION OF ALCOHOLS WITH DIVINYL SULFOXIDE

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