109-93-3

Basic information

• Product Name: Divinyl ether
• Synonyms: Vinyl ether(6CI,8CI); Divinyl ether; Divinyl oxide; Vinesthene; Vinesthesin; Vinethen;Vinethene; Vinether; Vinidyl; Vinydan
• CAS NO: 109-93-3
• Molecular Formula: C₄H₆O
• Molecular Weight: 70.10
• EINECS: 203-720-5
• Mol File: 109-93-3.mol
• Article Data: 12

Chemical Properties

• Boiling Point: 28.3°Cat760mmHg
• Flash Point: °C
• Appearance: /
• Density: 0.769g/cm³
• Vapor Pressure: 676mmHg at 25°C
• Refractive Index: 1.393
• CAS DataBase Reference: Divinyl ether(CAS DataBase Reference)
• NIST Chemistry Reference: Divinyl ether(109-93-3)
• EPA Substance Registry System: Divinyl ether(109-93-3)

Safety Data

• Hazardous Substances Data: 109-93-3(Hazardous Substances Data)

Usage

General Description

Divinyl ether is a colorless, volatile liquid with a mildly sweet scent. It is an organic compound primarily used as a copolymerization reagent in the production of polymers. It is quite flammable and has the chemical formula C4H6O. Known for its rapid induction in anesthesia, divinyl ether was once widely used as an inhalational anesthetic. However, this usage has declined due to its flammability, volatility, and its tendency to undergo potentially explosive reactions. In its industrial applications, divinyl ether is usually stored and transported as a refrigerated liquid to minimize risk.

InChI:InChI=1/C4H6O/c1-3-5-4-2/h3-4H,1-2H2

Synthetic route

3-oxa-1,5-dichloropentane (111-44-4) + methylamine (74-89-5) → 4-methyl-morpholine (109-02-4) + 1,1'-oxybisethene (109-93-3)

Conditions	Yield
With sodium hydroxide In water at 90 - 95℃; for 4h;	A 50% B 10%

3-oxa-1,5-dichloropentane (111-44-4) + methylamine (74-89-5) → 1,4-dioxane (123-91-1) + 4-methyl-morpholine (109-02-4) + 1,1'-oxybisethene (109-93-3) + 2-chloroetyl vinyl ether (110-75-8)

Conditions	Yield
With sodium hydroxide In water at 90 - 95℃; for 4h;	A 12% B 25% C 20% D 7%

ethylene glycol divinyl ether (764-78-3) → 1,1'-oxybisethene (109-93-3)

Conditions	Yield
With potassium hydroxide at 105 - 110℃; for 5h;	15%
With potassium hydroxide at 105 - 110℃; for 5h;	15%

divinyl sulfide (627-51-0) → 1,1'-oxybisethene (109-93-3)

Conditions	Yield
With silver(l) oxide

3-oxa-1,5-dichloropentane (111-44-4) + 2-chloroetyl vinyl ether (110-75-8) → 1,1'-oxybisethene (109-93-3)

Conditions	Yield
With triethanolamine

3-oxa-1,5-dichloropentane (111-44-4) → 1,1'-oxybisethene (109-93-3)

Conditions	Yield
With potassium hydroxide
With potassium hydroxide; tert-Amyl alcohol
With potassium hydroxide; diethylene glycol

2-chloroetyl vinyl ether (110-75-8) → 1,1'-oxybisethene (109-93-3)

Conditions	Yield
With sodium hydroxide

tetrachloromethane (56-23-5) + sodium amide + 3-oxa-1,5-dichloropentane (111-44-4) → 1,1'-oxybisethene (109-93-3)

ammonia (7664-41-7) + 3-oxa-1,5-dichloropentane (111-44-4) + KOH → 1,4-dioxane (123-91-1) + 1,1'-oxybisethene (109-93-3) + acetaldehyde (75-07-0) + 2-chloroetyl vinyl ether (110-75-8)

Conditions	Yield
at 200 - 280℃; weitere Prod.: Acetylen, Wasserstoff und Aethylenoxyd;

3-oxa-1,5-dichloropentane (111-44-4) + sodium hydroxide → 1,4-dioxane (123-91-1) + 1,1'-oxybisethene (109-93-3) + acetaldehyde (75-07-0) + 2-chloroetyl vinyl ether (110-75-8)

Conditions	Yield
at 200 - 220℃;

2,2'-diiodoethyl ether (34270-90-1) + ammonia (7664-41-7) + potassium hydroxide → 1,1'-oxybisethene (109-93-3)

Conditions	Yield
at 190 - 200℃;

divinyl sulfide (627-51-0) + silver oxide → 1,1'-oxybisethene (109-93-3)

potassium 18-crown-6 benzene anion radical salt → 2-methyl-1,3-dioxolane (497-26-7) + 1,4-dioxane (123-91-1) + 1,1'-oxybisethene (109-93-3) + cyclohexa-1,4-diene (1165952-92-0) + cyclohexene (110-83-8) + benzene (71-43-2) + H2, K, methane, 15-crown-5

Conditions	Yield
at 320℃; for 0.00833333h; Product distribution; Mechanism; other temperatures;

C12H24O6*C6(2)H6(1-)*K(1+) → 2-methyl-1,3-dioxolane (497-26-7) + 1,4-dioxane (123-91-1) + 15-crown-5 (33100-27-5) + 1,1'-oxybisethene (109-93-3) + 1,2,3,4,5,6-hexadeuterio-1,4-cyclohexadiene (71092-65-4) + 1,2,3,4,5,6-hexadeuteriocyclohexene + H2, K, methane

Conditions	Yield
at 320℃; Product distribution; Mechanism;

potassium tert-butylate (865-47-4) + 3-oxa-1,5-dichloropentane (111-44-4) → 1,1'-oxybisethene (109-93-3)

Conditions	Yield
In tert-butyl alcohol

diethyl acetal (105-57-7) → 1,1'-oxybisethene (109-93-3)

Conditions	Yield
With acetal cracking catalyst at 200℃; Reagent/catalyst; Temperature; Molecular sieve;

1,1'-oxybisethene (109-93-3) + tributyltin chloride (1461-22-9) → 1-(tributhylstannyl)ethenyl ethenyl ether (183275-22-1)

Conditions	Yield
With n-butyllithium; potassium tert-butylate In tetrahydrofuran divinyl ether treated with n-BuLi and KO-t-Bu in THF at -78°C; reacted with (N-Bu)3SnCl;	98%

1,1'-oxybisethene (109-93-3) + 4-phenyl-1-(trifluoromethyl)-1H-1,2,3-triazole → 3-phenyl-1-(trifluoromethyl)-1H-pyrrole

Conditions	Yield
With rhodium (II) octanoate dimer In chloroform at 140℃; for 0.333333h; Microwave irradiation; Sealed tube;	96%

1,1'-oxybisethene (109-93-3) + 3-fluorophenol (372-20-3) → 1-(1-ethoxyethoxy)-3-fluorobenzene

Conditions	Yield
With hydrogenchloride In n-heptane; water at -10 - 5℃; for 0.5h;	95%

1,1'-oxybisethene (109-93-3) + trifluoroacetic acid (76-05-1) → 4-ethoxy-1,1,1-trifluoro-3-butene-2-one (59938-06-6, 17129-06-5)

Conditions	Yield
Stage #1: trifluoroacetic acid With pyridine In dichloromethane at -5℃; for 3.66667h; Autoclave; Large scale; Stage #2: 1,1'-oxybisethene With methanesulfonyl chloride In dichloromethane at -5 - 20℃; Temperature; Large scale;	94.2%

1,1'-oxybisethene (109-93-3) + 4-(4-methoxyphenyl)-1-(trifluoromethyl)-1H-1,2,3-triazole → 3-(4-methoxyphenyl)-1-(trifluoromethyl)-1H-pyrrole

Conditions	Yield
With rhodium (II) octanoate dimer In chloroform at 140℃; for 0.333333h; Microwave irradiation; Sealed tube;	93%

1,1'-oxybisethene (109-93-3) → bis-(1,2-dibromo-ethyl) ether (6304-35-4)

Conditions	Yield
With selenium(II) chloride In chloroform at -50℃;	92%
With chloroform; bromine
With bromine
With bromine In tetrachloromethane

1,1'-oxybisethene (109-93-3) + 2-fluoro-2,2-dinitroethanol (17003-75-7) → 2-fluoro-2,2-dinitroethoxy ethyl vinyl ether (52483-76-8) + [1-(2-Fluoro-2,2-dinitro-ethoxy)-ethoxy]-ethene (88934-27-4) + 1-Fluoro-2-{1-[1-(2-fluoro-2,2-dinitro-ethoxy)-ethoxy]-ethoxy}-1,1-dinitro-ethane (88934-25-2)

Conditions	Yield
With trifluoroacetic acid; mercury(II) sulfate In dichloromethane Heating;	A 11% B 5.3% C 83.7%

1,1'-oxybisethene (109-93-3) + 2-fluoro-2,2-dinitroethanol (17003-75-7) → [1-(2-Fluoro-2,2-dinitro-ethoxy)-ethoxy]-ethene (88934-27-4) + 1-Fluoro-2-{1-[1-(2-fluoro-2,2-dinitro-ethoxy)-ethoxy]-ethoxy}-1,1-dinitro-ethane (88934-25-2)

Conditions	Yield
mercury(II) sulfate In dichloromethane for 16h; Ambient temperature;	A 18% B 82%
mercury(II) sulfate In dichloromethane for 16h;	A 78% B 22%

1,1'-oxybisethene (109-93-3) + 4-(p-tolyl)-1-(trifluoromethyl)-1H-1,2,3-triazole → 3-(p-tolyl)-1-(trifluoromethyl)-1H-pyrrole

Conditions	Yield
With rhodium (II) octanoate dimer In chloroform at 140℃; for 0.333333h; Microwave irradiation; Sealed tube;	82%

1,1'-oxybisethene (109-93-3) + dimethyl 2,2-dicyanoethene-1,1-dicarboxylate (82849-49-8) → 2,2-dicyano-3-vinyloxy-cyclobutane-1,1-dicarboxylic acid dimethyl ester

Conditions	Yield
In [D3]acetonitrile at 20℃; for 48h;	80%

1,1'-oxybisethene (109-93-3) + 4-(4-fluorophenyl)-1-(trifluoromethyl)-1H-1,2,3-triazole → 3-(4-fluorophenyl)-1-(trifluoromethyl)-1H-pyrrole

Conditions	Yield
With rhodium (II) octanoate dimer In chloroform at 140℃; for 0.333333h; Microwave irradiation; Sealed tube;	80%

1,1-diethoxypropane (4744-08-5) + 1,1'-oxybisethene (109-93-3) → 1,1,3,5-tetraethoxyheptane

Conditions	Yield
at 0 - 50℃; for 2.5h; Time;	75%

1,1'-oxybisethene (109-93-3) → 4,4-dichloro-4H-1,4-oxaphosphorin-4-ium hexachlorophosphate

Conditions	Yield
With phosphorus pentachloride In benzene for 24h;	74.3%

1,1'-oxybisethene (109-93-3) + N-benzyl-3,4,5-trimethoxybenzamide (3940-84-9) → C19H21NO4

Conditions	Yield
With 8-quinolinol; copper(II) sulfate In toluene at 100℃; for 10h; Inert atmosphere; Sealed tube; Green chemistry;	74%

1,1'-oxybisethene (109-93-3) + N-benzyl-4-(tert-butyl)benzamide → N-benzyl-N-vinyl(4-tert-butylphenyl)formamide

Conditions	Yield
With 8-quinolinol; copper(II) sulfate In toluene at 100℃; for 10h; Inert atmosphere; Sealed tube; Green chemistry;	73%

1,1'-oxybisethene (109-93-3) + methyl difluoroiodoacetate (109872-87-9) → 2,2-Difluoro-3-(4-iodomethyl-tetrahydro-furan-3-yl)-propionic acid methyl ester (129377-86-2)

Conditions	Yield
copper In N,N-dimethyl-formamide for 15h;	72%

1,1'-oxybisethene (109-93-3) → 2,6-dichloro-1,4-oxathiane

Conditions	Yield
With sulfur dichloride In ethyl acetate at 35℃; for 1h; Product distribution; general reaction; different solvents and temperature; cis-trans ratio;	72%
With sulfur dichloride In dichloromethane at 40℃; for 0.25h;	72%

1,1'-oxybisethene (109-93-3) + 2,2-dinitropropanol (918-52-5) → 2,2-dinitropropyl vinyl ether (52434-64-7)

Conditions	Yield
With trifluoroacetic acid; mercury(II) oxide In dichloromethane for 17.5h; Heating;	64.2%

1,1'-oxybisethene (109-93-3) + 2-fluoro-2,2-dinitroethanol (17003-75-7) → 2-fluoro-2,2-dinitroethoxy ethyl vinyl ether (52483-76-8) + acetaldehyde (75-07-0)

Conditions	Yield
With trifluoroacetic acid; mercury(II) oxide In dichloromethane for 16.5h; Product distribution; Heating; other catalysts;	A 64% B n/a
With trifluoroacetic acid; mercury(II) oxide In dichloromethane for 16.5h; Heating;	A 64% B n/a

1,1'-oxybisethene (109-93-3) + 1-acetoxy-4-methyl-2-formylnaphthalene diethylacetal (82671-93-0) → 2-acetoxy-5-methyl-3,4-benzocinnamaldehyde (82671-96-3)

Conditions	Yield
With zinc(II) chloride In ethyl acetate	63%

ethoxydiethylsilane (4087-42-7) + 1,1'-oxybisethene (109-93-3) → diethylethoxy(2-vinylethyl)silane (60600-65-9)

Conditions	Yield
With dihydrogen hexachloroplatinate In isopropyl alcohol at 100℃; for 10h;	59%
dihydrogen hexachloroplatinate

1,1'-oxybisethene (109-93-3) + ethenetetracarbonitrile (670-54-2) → 3-vinyloxy-cyclobutane-1,1,2,2-tetracarbonitrile

Conditions	Yield
In [D3]acetonitrile at -42 - -22℃;	55%

1,1'-oxybisethene (109-93-3) + topotecan hydrochloride (1349511-12-1) + N,N-dimethyl-formamide (68-12-2, 33513-42-7) → 2'-ethoxydihydropyrano[3,2-i]camptothecin

Conditions	Yield
In water at 70℃; for 10h;	55%

dimethyl(ethoxy)silane (14857-34-2) + 1,1'-oxybisethene (109-93-3) → dimethylethoxy(2-vinyl)silane (142088-36-6)

Conditions	Yield
With dihydrogen hexachloroplatinate In isopropyl alcohol at 100℃; for 10h;	53%

1,1'-oxybisethene (109-93-3) + N-benzylbenzamide (1485-70-7) → N-benzyl-N-vinylbenzamide

Conditions	Yield
With 8-quinolinol; copper(II) sulfate In toluene at 100℃; for 4h; Inert atmosphere; Sealed tube; Green chemistry;	51%

1,1'-oxybisethene (109-93-3) + N-benzyl-p-chlorobenzamide (7461-34-9) → N-benzyl-N-vinyl(4-chlorophenyl)formamide

Conditions	Yield
With 8-quinolinol; copper(II) sulfate In toluene at 100℃; for 10h; Inert atmosphere; Sealed tube; Green chemistry;	49%

chloromethyldimethylsilane (3144-74-9) + 1,1'-oxybisethene (109-93-3) → chloromethyl(2-vinyloxyethyl)dimethylsilane (194015-04-8)

Conditions	Yield
With dihydrogen hexachloroplatinate In isopropyl alcohol at 80℃; for 13h;	46%

1,1'-oxybisethene (109-93-3) + 2-fluoro-2,2-dinitroethanol (17003-75-7) → 2-fluoro-2,2-dinitroethoxy ethyl vinyl ether (52483-76-8)

Conditions	Yield
mercury(II) oxide In dichloromethane Heating;	30%

Upstream product

• 111-44-4 3-oxa-1,5-dichloropentane 
• 110-75-8 2-chloroetyl vinyl ether 
• 764-78-3 ethylene glycol divinyl ether 
• 105-57-7 diethyl acetal 
• 74-89-5 methylamine 
• 865-47-4 potassium tert-butylate 
• 627-51-0 divinyl sulfide 
• 34270-90-1 2,2'-diiodoethyl ether 
• 7664-41-7 ammonia 
• 56-23-5 tetrachloromethane 

Downstream Products

• 6986-48-7 bis-1-chloroethyl ether 
• 6304-35-4 bis-(1,2-dibromo-ethyl) ether 
• 141-46-8 Glycolaldehyde 
• 2150-02-9 bis(2-mercaptoethyl)ether 
• 2188-15-0 acetaldehyde di-2-propynyl acetal 
• 103398-49-8 3.3'-Oxy-bis-<2.2-diphenylcyclobutan> 
• 52483-76-8 2-fluoro-2,2-dinitroethoxy ethyl vinyl ether 
• 75-07-0 acetaldehyde 
• 612-00-0 1,1'-ethylidenebis-benzene 
• 16545-67-8 cyclopropyl vinyl ether 
• 60-29-7 diethyl ether 
• 7596-29-4 acetaldehyde p-nitrophenylhydrazone 
• 34557-54-5 methane 
• 74-86-2 acetylene 

Related news

Oxylipin biosynthesis in spikemoss Selaginella moellendorffii: Molecular cloning and identification of Divinyl ether (cas 109-93-3) synthases CYP74M1 and CYP74M308/24/2019

Nonclassical P450s of CYP74 family control the secondary conversions of fatty acid hydroperoxides to bioactive oxylipins in plants. At least ten genes attributed to four novel CYP74 subfamilies have been revealed by the recent sequencing of the spikemoss Selaginella moellendorffii Hieron genome....detailed

Hydroperoxide lyase and Divinyl ether (cas 109-93-3) synthase08/23/2019

“Heterolytic” hydroperoxide lyase (HPL) and divinyl ether synthase (DES) are important enzymes of the plant lipoxygenase pathway. HPL cleaves fatty acid hydroperoxides into the aldehyde fragments. DES converts hydroperoxides into the divinyl ethers. The present paper is concerned with recent s...detailed

Detection of Divinyl ether (cas 109-93-3) synthase in Lily-of-the-Valley (Convallaria majalis) roots08/22/2019

Incubations of linoleic acid with cell-free preparations from Lily-of-the-Valley (Convallaria majalis L., Ruscaceae) roots revealed the presence of 13-lipoxygenase and divinyl ether synthase (DES) activities. Exogenous linoleic acid was metabolized predominantly into (9Z,11E,1′E)-12-(1′-hexeny...detailed

Relevant articles and documents

FORMATION OF VINYLOXYETHENE FROM 1,2-DIVINYLOXYETHANE IN THE KOH-DMSO SYSTEM

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Method for producing vinyl ether

The invention relates to a method for producing vinyl ether. The method comprises the following steps: (A) reacting excessive alcohol with acetaldehyde, and carrying out a continuous acetalation reaction by using immobilized superacid as a catalyst to obtain a first mixture; (B) carrying out oil-water separation and adsorption dehydration on the first mixture to obtain a second mixture; (C) carrying out acetal catalytic decomposition on the second mixture under the catalysis of a high-efficiency catalyst to obtain a third mixture; (D) rectifying the third mixture, and washing with water to obtain a vinyl ether product. According to the method, the high-temperature heating process of acetal is avoided, and the safety risk of operation is reduced; and an efficient acetal decomposition catalyst is adopted, and an acetal decomposition reaction is carried out at a low temperature, so that side reactions are few, and the selectivity of a main product is improved.

Waste-free technology for N-methylmorpholine synthesis

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Structural analogues of vitamin D

PCT No. PCT/EP94/02294 Sec. 371 Date Jun. 28, 1996 Sec. 102(e) Date Jun. 28, 1996 PCT Filed Jul. 7, 1994 PCT Pub. No. WO95/01960 PCT Pub. Date Jan. 19, 1995The present invention relates to analogues of vitamin D, which lack the combined presence of the trans-fused six-membered C-ring and of five-membered D-ring, but still possess a central part consisting of a substituted chain of five atoms, atoms which correspond to positions 8, 14, 13, 17 and 20 of vitamin D, and at the ends of which are connected, at position 20 a structural moiety representing part of the side-chain of vitamin D or of an analogue of vitamin D, and at position 8 the DELTA (5,7)-diene moiety connected to the A-ring of the active 1-alpha-hydroxy metabolite or of an established vitamin D analogue, to their preparation process, to preparation intermediates, to pharmaceutical preparations comprising these compounds and to their use in medicine.