Ethene, 1,1-diethoxy- supplier

Name
KETENE DIETHYL ACETAL
EINECS
CAS No. 2678-54-8
Article Data28
CAS DataBase
Density 0.859 g/cm³
Solubility
Melting Point
Formula C₆H₁₂O₂
Boiling Point 105.645 °C at 760 mmHg
Molecular Weight 116.16
Flash Point 7.004 °C
Transport Information UN 1993 3/PG 3
Appearance
Safety 23
Risk Codes 10
Molecular Structure
Hazard Symbols
Synonyms Ketene,diethyl acetal (6CI,7CI,8CI);1,1-Diethoxyethylene;Diethylketene acetal;
PSA 18.46000
LogP 1.53060

Synthetic route

: 2032-35-1
Bromoacetaldehyde diethyl acetal

: 2678-54-8
ketene diethyl acetal

Conditions

Conditions	Yield
With potassium hydroxide In dimethyl sulfoxide at 130 - 140℃; under 100 Torr;	92%
With potassium tert-butylate for 0.1 - 0.183333h; Cooling with ice;	72%
With potassium tert-butylate at 20℃; Reflux; Inert atmosphere;	69.9%

XCH2CH(OCH2CH3)2: XCH2CH(OCH2CH3)2

: 2678-54-8
ketene diethyl acetal

Conditions

Conditions	Yield
With 18-crown-6 ether; potassium tert-butylate In tetrahydrofuran at 0℃; for 2h; Elimination;	70%

: 855175-05-2
β-(1,1-diethoxy-ethoxy)-chalcone

A: 2678-54-8
ketene diethyl acetal

B: 120-46-7
1,3-diphenylpropanedione

Conditions

Conditions	Yield
at 140℃; under 38 Torr;

: 78-39-7
Triethyl orthoacetate

: 2678-54-8
ketene diethyl acetal

Conditions

Conditions	Yield
With aluminium tert-butyl oleate at 180℃;

: 865-47-4
potassium tert-butylate

: 51806-20-3
1,1-diethoxy-2-iodoethane

: 2678-54-8
ketene diethyl acetal

: 51806-20-3
1,1-diethoxy-2-iodoethane

: 2678-54-8
ketene diethyl acetal

Conditions

Conditions	Yield
With potassium tert-butylate
With potassium tert-butylate

: 1,1-Diethoxy-ethylamine; hydrochloride

: 2678-54-8
ketene diethyl acetal

Conditions

Conditions	Yield
With sodium methylate for 0.666667h; Ambient temperature; Yield given;

orthobromoacetic acid triethyl ester: orthobromoacetic acid triethyl ester

: 2678-54-8
ketene diethyl acetal

Conditions

Conditions	Yield
With sodium; benzene

: 40070-39-1
triethyl bromoorthoacetate

: 71-43-2
benzene

sodium: sodium

: 2678-54-8
ketene diethyl acetal

...Expand

: 75-85-4
tert-Amyl alcohol

: 1634-04-4
tert-butyl methyl ether

: 107-21-1
ethylene glycol

: 621-62-5
chloroacetaldehyde diethyl acetal

: 2678-54-8
ketene diethyl acetal

Conditions

Conditions	Yield
With potassium hydroxide In Dimethyl ether

...Expand

: 75-85-4
tert-Amyl alcohol

: 107-21-1
ethylene glycol

: 621-62-5
chloroacetaldehyde diethyl acetal

: 2678-54-8
ketene diethyl acetal

Conditions

Conditions	Yield
With potassium hydroxide In Dimethyl ether; tert-butyl methyl ether

...Expand

: 127826-29-3
N-propylsulfonylchloralimine

: 2678-54-8
ketene diethyl acetal

: N-(1-trichloromethyl-3,3-diethoxy-2-propenyl)-1-propanesulfonamide

Conditions

Conditions	Yield
In dichloromethane Ambient temperature;	100%

: 2678-54-8
ketene diethyl acetal

: 2-ethynyl-N-methyl-cyclohex-1-enecarboximidic acid methyl ester

: 1-(2,2-diethoxy-cyclopropyl)-3-methoxy-2-methyl-4,5,6,7-tetrahydro-2H-isoindole

Conditions

Conditions	Yield
dirhodium tetraacetate In dichloromethane at 20℃; for 2h;	100%

: 2678-54-8
ketene diethyl acetal

: 436146-73-5
(2-ethynylcyclohex-1-en-1-yl)(phenyl)methanone

: 1-(2,2-diethoxy-cyclopropyl)-3-phenyl-4,5,6,7-tetrahydro-isobenzofuran

Conditions

Conditions	Yield
chromium(0) hexacarbonyl In tetrahydrofuran at 20℃; for 2h;	99%
With pentacarbonyl(tetrahydrofuran)chromium(0) In tetrahydrofuran at 20℃; for 2h;	99%

: 2678-54-8
ketene diethyl acetal

: methyl 1,2,3-triazine-5-carboxylate

: 74357-22-5
methyl 6-ethoxynicotinate

Conditions

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In 1,4-dioxane at 60℃; for 0.5h; Diels-Alder reaction; Inert atmosphere; regioselective reaction;	99%

: 2678-54-8
ketene diethyl acetal

: 100-52-7
benzaldehyde

: 4192-77-2
ethyl cinnamate

Conditions

Conditions	Yield
With (2,4,5-trifluorophenyl)boronic acid In tert-butyl methyl ether at 50℃; for 14h;	98%

: 104-87-0
4-methyl-benzaldehyde

: 2678-54-8
ketene diethyl acetal

: 97585-04-1, 20511-20-0, 24393-49-5
ethyl (E)-3-(4-methylphenyl)acrylate

Conditions

Conditions	Yield
With (2,4,5-trifluorophenyl)boronic acid In tert-butyl methyl ether at 50℃; for 14h;	97%

: 2678-54-8
ketene diethyl acetal

: 1122-91-4
4-bromo-benzaldehyde

: 24393-53-1, 136265-11-7, 15795-20-7
ethyl (E)-3-(4-bromophenyl)-2-propenoate

Conditions

Conditions	Yield
With (2,4,5-trifluorophenyl)boronic acid In tert-butyl methyl ether at 50℃; for 14h;	97%

: 70591-46-7
(S)-5-methoxycarbonylmethyl-6,6-dimethyl-2-cyclohexen-1-one

: 2678-54-8
ketene diethyl acetal

: 70591-47-8, 82509-28-2, 82509-31-7
4-carbomethoxymethyl-7,7-diethoxy-3,3-dimethylbicyclo<4.2.0>octan-2-one

Conditions

Conditions	Yield
for 3h; Ambient temperature; Irradiation;	96%

: 2678-54-8
ketene diethyl acetal

: 684-16-2
Hexafluoroacetone

: 63504-98-3
4,4-diethoxy-1,1,1-trifluoro-2-trifluoromethyl-but-3-en-2-ol

Conditions

Conditions	Yield
In methanol at 20℃;	95%

: 2678-54-8
ketene diethyl acetal

: 213320-13-9
6-[(benzyloxycarbonyl)amino]-3-(methylthio)-1,2,4,5-tetrazine

: 6-[(benzyloxycarbonyl)amino]-4-ethoxy-3-(methylthio)pyridazine

Conditions

Conditions	Yield
In 1,4-dioxane at 100℃; for 2h; Diels-Alder reaction;	95%

: 2678-54-8
ketene diethyl acetal

: 106636-96-8
5-phenyl-1,2,3-triazine

: 2-ethoxy-5-phenylpyridine

Conditions

Conditions	Yield
In 5,5-dimethyl-1,3-cyclohexadiene at 140℃; for 24h; Diels-Alder reaction; regioselective reaction;	95%

: 1270038-98-6
3,6-dimethyl-o-quinone monoacetal

: 2678-54-8
ketene diethyl acetal

: C16H24O5

Conditions

Conditions	Yield
In toluene at 150℃; for 17h; Diels-Alder Cycloaddition; Inert atmosphere; regioselective reaction;	95%

: 79-52-7
1,1,3-trichloro-1,3,3-trifluoroacetone

: 2678-54-8
ketene diethyl acetal

: 138351-94-7
1,1-Diethoxy-4,4-difluoro-4-chloro-3-fluorodichloromethyl-1-buten-3-ol

Conditions

Conditions	Yield
for 18h; Ambient temperature;	94%

: 2678-54-8
ketene diethyl acetal

: 123-11-5
4-methoxy-benzaldehyde

: 24393-56-4
ethyl (E)-3-(4-methoxyphenyl)prop-2-enoate

Conditions

Conditions	Yield
With (2,4,5-trifluorophenyl)boronic acid In tert-butyl methyl ether at 50℃; for 14h;	94%

: 66-77-3
1-naphthaldehyde

: 2678-54-8
ketene diethyl acetal

: 98978-43-9
(E)-ethyl 3-(naphthalen-1-yl)acrylate

Conditions

Conditions	Yield
With (2,4,5-trifluorophenyl)boronic acid In tert-butyl methyl ether at 50℃; for 14h;	93%

: 126685-93-6
1-(2-diazo-1,3-dioxobutyl)-2-pyrrolidinone

: 2678-54-8
ketene diethyl acetal

: 7-Acetyl-8,8-diethoxy-10-oxa-5-aza-tricyclo[5.2.1.01,5]decan-6-one

Conditions

Conditions	Yield
dirhodium tetraacetate In benzene for 2h; Heating;	92%

: 58303-62-1
5-(4-chlorophenyl)-2,3-dihydrofuran-2,3-dione

: 2678-54-8
ketene diethyl acetal

: 159107-87-6
[5-(4-Chloro-phenyl)-2-hydroxy-3-oxo-2,3-dihydro-furan-2-yl]-acetic acid ethyl ester

Conditions

Conditions	Yield
In dichloromethane at 40℃; for 1h;	91%

: 2678-54-8
ketene diethyl acetal

: methyl 3-(1-oxo-2-cyclohexen-2-yl)acrylate

: 3,3-diethoxy-8-oxo-2,3,4,4a,5,6,7,8-octahydro-naphthalene-2-carboxylic acid methyl ester

Conditions

Conditions	Yield
In toluene for 1.5h; Heating;	91%

: 2678-54-8
ketene diethyl acetal

: 84011-69-8
5-<<<(1,1-dimethylethyl)dimethylsilyl>oxy>methyl>-2-cyclohexen-1-one

: 84011-67-6
4-<<<(1,1-dimethylethyl)dimethylsilyl>oxy>methyl>-7,7-diethoxybicyclo<4.2.0>octane-2-one

Conditions

Conditions	Yield
In benzene for 3.5h; Irradiation;	90%

: 2678-54-8
ketene diethyl acetal

: 623-91-6
diethyl Fumarate

: 127696-10-0
trans-3,3-diethoxy-1,2-cyclobutanedicarboxylic acid diethyl ester

Conditions

Conditions	Yield
With diisobutylaluminum chloride; N-ethyl-N,N-diisopropylamine In toluene at -40℃;	90%
In tert-butyl alcohol at 84℃; for 72h;	54%
In tert-butyl alcohol at 84℃; for 72h;	53%
Stage #1: ketene diethyl acetal With diethylaluminium chloride In toluene at -45℃; for 0.166667h; Inert atmosphere; Stage #2: With N-ethyl-N,N-diisopropylamine In toluene at -45℃; for 0.166667h; Inert atmosphere; Stage #3: diethyl Fumarate In toluene at -45℃; for 3h; Inert atmosphere;	42.3%

: 2678-54-8
ketene diethyl acetal

: 55991-70-3
5-(4-bromo-phenyl)-furan-2,3-dione

: 159107-86-5
[5-(4-Bromo-phenyl)-2-hydroxy-3-oxo-2,3-dihydro-furan-2-yl]-acetic acid ethyl ester

Conditions

Conditions	Yield
In dichloromethane at 40℃; for 1h;	90%

: 37643-54-2
N-[(4-methylbenzene-1-sulfonyl)(phenyl)methyl]formamide

: 2678-54-8
ketene diethyl acetal

: 850011-53-9
3-formylamino-3-phenyl-propionic acid ethyl ester

Conditions

Conditions	Yield
With caesium carbonate In dichloromethane for 24h; Heating;	90%
With caesium carbonate In dichloromethane for 24h; Product distribution / selectivity; Heating / reflux;	90%
With triethylamine In dichloromethane for 24h; Product distribution / selectivity; Heating / reflux;	80%
With 1,8-diazabicyclo[5.4.0]undec-7-ene In dichloromethane for 24h; Product distribution / selectivity; Heating / reflux;	48%

: 141-97-9
ethyl acetoacetate

: 2678-54-8
ketene diethyl acetal

: 182916-87-6
Ethyl 2-acetyl-3-ethoxybut-2-enoate

Conditions

Conditions	Yield
With sodium ethanolate In ethanol at 22 - 90℃; for 8.5h;	89%

: 904731-83-5
5-chloro-2,2-dimethyl-1,3-dioxin-4-one

: 2678-54-8
ketene diethyl acetal

: 904731-84-6
5-chloro-2,2-diethoxy-2,3-dihydropyran-4-one

Conditions

Conditions	Yield
In toluene for 0.666667h; Product distribution / selectivity; Heating / reflux;	89%

: 2678-54-8
ketene diethyl acetal

: 2043-61-0
cyclohexanecarbaldehyde

: 17343-88-3
(E)-3-cyclohexyl-acrylic acid ethyl ester

Conditions

Conditions	Yield
With (2,4,5-trifluorophenyl)boronic acid In tert-butyl methyl ether at 50℃; for 14h;	89%

: C3H9B8F3O3S

: 2678-54-8
ketene diethyl acetal

: C11H30B16O2

Conditions

Conditions	Yield
With lithium hexamethyldisilazane In cyclohexane at 20℃; for 0.0833333h; Inert atmosphere;	89%

: 3888-00-4
nitropentafluoroacetone

: 2678-54-8
ketene diethyl acetal

: 40657-28-1
4,4-diethoxy-1,1-difluoro-1-nitro-2-trifluoromethyl-but-3-en-2-ol

Conditions

Conditions	Yield
at -30°C, then at 20°C 2 h;	88%
at -30°C, then at 20°C 2 h;	88%

: 2678-54-8
ketene diethyl acetal

: dicyano(7,7-dimethyl-2,5-di-p-tolyl-3,4-diaza-bicyclo[4.1.0]hepta-2,4-dien-3-ium-3-yl)methanide

: 5,5-diethoxy-1,1-dimethyl-2,6a-di-p-tolyl-1,1a,5,6,6a,6b-hexahydro-cis-1a-transoid-6a,6b-3,3a-diaza-cyclopropa[e]indene-4,4-dicarbonitrile

Conditions

Conditions	Yield
In acetonitrile at 20 - 50℃; for 19h; Cycloaddition;	87%

: 401-78-5
3-bromo-1-trifluoromethylbenzene

: 2678-54-8
ketene diethyl acetal

: 1017235-56-1
1,1-diethoxy-6-(trifluoromethyl)benzocyclobutene

Conditions

Conditions	Yield
With sodium amide In tetrahydrofuran for 22h; Heating;	87%

Ethene, 1,1-diethoxy- Specification

The Ethene, 1,1-diethoxy-, with the CAS registry number 2678-54-8, is also known as Ketene, diethyl acetal. This chemical's molecular formula is C₆H₁₂O₂ and molecular weight is 116.16. What's more, both its IUPAC name and systematic name are the same which is called 1,1-Diethoxyethene. When you are dealing with this chemical, you should be very careful. This chemical is flammable. Therefore, you can not breathe the gas/fumes/vapour/spray.

Physical properties about Ethene, 1,1-diethoxy- are: (1)ACD/LogP: 1.195; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 1.20; (4)ACD/LogD (pH 7.4): 1.20; (5)ACD/BCF (pH 5.5): 4.77; (6)ACD/BCF (pH 7.4): 4.77; (7)ACD/KOC (pH 5.5): 106.42; (8)ACD/KOC (pH 7.4): 106.42; (9)#H bond acceptors: 2; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 4; (12)Polar Surface Area: 18.46 Å²; (13)Index of Refraction: 1.402; (14)Molar Refractivity: 32.905 cm³; (15)Molar Volume: 135.196 cm³; (16)Polarizability: 13.044×10^-24cm³; (17)Surface Tension: 22.788 dyne/cm; (18)Density: 0.859 g/cm³; (19)Flash Point: 7.004 °C; (20)Enthalpy of Vaporization: 33.033 kJ/mol; (21)Boiling Point: 105.645 °C at 760 mmHg; (22)Vapour Pressure: 34.079 mmHg at 25 °C.

Preparation of Ethene, 1,1-diethoxy-: this chemical can be prepared by 2-bromo-1,1-diethoxy-ethane. This reaction needs reagent t-BuOK at temperature of 120-130 °C.

Ethene, 1,1-diethoxy- can be prepared by 2-bromo-1,1-diethoxy-ethane.

Uses of Ethene, 1,1-diethoxy-: it is used to produce other chemicals. For example, it can react with acrylic acid methyl ester to get 2.2-Diethoxy-cyclobutancarbonsaeuremethylester. The reaction occurs with solvent acetonitrile and other condition of heating for 8 days. The yield is 17 %.

Ethene, 1,1-diethoxy- can react with acrylic acid methyl ester to get 2.2-Diethoxy-cyclobutancarbonsaeuremethylester.

You can still convert the following datas into molecular structure:
(1) SMILES: CCOC(=C)OCC
(2) InChI: InChI=1S/C6H12O2/c1-4-7-6(3)8-5-2/h3-5H2,1-2H3
(3) InChIKey: VTGIVYVOVVQLRL-UHFFFAOYSA-N

Product Name

KETENE DIETHYL ACETAL

Synthetic route

Ethene, 1,1-diethoxy- Specification

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