Tetraethyl orthocarbonate supplier

Name
Tetraethyl orthocarbonate
EINECS 201-082-2
CAS No. 78-09-1
Article Data27
CAS DataBase
Density 0.948 g/cm³
Solubility insoluble in water
Melting Point 222 °C
Formula C₉H₂₀O₄
Boiling Point 159.5 °C at 760 mmHg
Molecular Weight 192.255
Flash Point 52.8 °C
Transport Information UN 3272 3/PG 3
Appearance clear colorless liquid
Safety 37/39-26-16-36
Risk Codes 10-36/37/38
Molecular Structure
Hazard Symbols Xi,F
Synonyms Tetraethylorthocarbonate;Orthocarbonicacid, tetraethyl ester (6CI,7CI,8CI);NSC 28574;Tetraethoxymethane;(triethoxymethoxy)ethane;Ethane, 1,1',1'',1'''-(methanetetrayltetrakis(oxy))tetrakis-;
PSA 36.92000
LogP 1.74370

Synthetic route

: 64-17-5
ethanol

: 76-06-2
chloropicrin

: 78-09-1
orthocarbonic acid tetraethyl ester

Conditions

Conditions	Yield
With sodium ethanolate at 65 - 70℃; for 3h; Temperature; Large scale;	91%
With sodium Darst.;

: 23213-96-9
ethyl 2,2,2-trichloroacetimidate

: 124-41-4
sodium methylate

: 78-09-1
orthocarbonic acid tetraethyl ester

Conditions

Conditions	Yield
In ethanol for 1h; Heating;	85%

: 141-52-6
sodium ethanolate

: 545-06-2
trichloroacetonitrile

: 78-09-1
orthocarbonic acid tetraethyl ester

Conditions

Conditions	Yield
In ethanol for 3.5h; Heating / reflux;	83%
In ethanol Heating;

: 56-23-5
tetrachloromethane

: 64-17-5
ethanol

: 141-52-6
sodium ethanolate

: 78-09-1
orthocarbonic acid tetraethyl ester

Conditions

Conditions	Yield
at 80 - 95℃; for 5h; Temperature;	83%

...Expand

: 64-17-5
ethanol

: 68714-37-4
triethoxyacetonitrile

: 78-09-1
orthocarbonic acid tetraethyl ester

Conditions

Conditions	Yield
With toluene-4-sulfonic acid Heating;	71%

: 68714-37-4
triethoxyacetonitrile

: 141-52-6
sodium ethanolate

A: 78-09-1
orthocarbonic acid tetraethyl ester

B: 81759-13-9
Triethylmethylorthocarbonat

C: 81759-14-0
Trimethylethylorthocarbonat

Conditions

Conditions	Yield
In ethanol 1.) 5 min, 60 deg C, 2.) 30 min, to room temperature; Title compound not separated from byproducts;	A 70% B 58% C 2%

...Expand

: 75-15-0
carbon disulfide

: 64-17-5
ethanol

: 78-09-1
orthocarbonic acid tetraethyl ester

Conditions

Conditions	Yield
With silver trifluoroacetate; triethylamine for 5h; Ambient temperature;	61%
Yield given. Multistep reaction;

: 68714-37-4
triethoxyacetonitrile

: 109-73-9
N-butylamine

A: 78-09-1
orthocarbonic acid tetraethyl ester

B: 81759-28-6
Diethyl(butylimido)carbonat

C: 81759-30-0
1,3-Dibutyl-2-ethylisoharnstoff

Conditions

Conditions	Yield
at 120℃; Yield given. Yields of byproduct given. Title compound not separated from byproducts;	A n/a B n/a C 59%
at 120℃; Heating; Yields of byproduct given;	A n/a B n/a C 59%

...Expand

: 76-06-2
chloropicrin

: 141-52-6
sodium ethanolate

: 78-09-1
orthocarbonic acid tetraethyl ester

Conditions

Conditions	Yield
In ethanol at 57 - 64℃; for 2h; Heating / reflux; Industry scale;	58.3%

: 68714-37-4
triethoxyacetonitrile

: 124-41-4
sodium methylate

A: 78-09-1
orthocarbonic acid tetraethyl ester

B: 81759-13-9
Triethylmethylorthocarbonat

C: 81759-14-0
Trimethylethylorthocarbonat

Conditions

Conditions	Yield
In methanol at 60℃; Title compound not separated from byproducts;	A 8 % Chromat. B 58% C 2 % Chromat.

...Expand

: 36749-09-4
3,3-diethoxypentane

A: 78-09-1
orthocarbonic acid tetraethyl ester

B: 1128-76-3
3-chloro-benzoic acid ethyl ester

C: 105-37-3
Ethyl propionate

D: 105-58-8
Diethyl carbonate

Conditions

Conditions	Yield
With 3-chloro-benzenecarboperoxoic acid In dichloromethane at 15 - 30℃; for 0.5h; Further byproducts given;	A 18% B n/a C n/a D 50%

...Expand

: 68714-37-4
triethoxyacetonitrile

: 100-46-9
benzylamine

A: 78-09-1
orthocarbonic acid tetraethyl ester

B: 6263-03-2
Diethyl(benzylimido)carbonat

C: 81759-29-7
1,3-Dibenzyl-2-ethylisoharnstoff

Conditions

Conditions	Yield
at 120℃;	A n/a B 45% C 14%
at 120℃; Heating;	A n/a B 45% C 14%

...Expand

: 115-80-0
Triethyl orthopropionate

A: 78-09-1
orthocarbonic acid tetraethyl ester

B: 105-58-8
Diethyl carbonate

Conditions

Conditions	Yield
With 3-chloro-benzenecarboperoxoic acid In dichloromethane at 15 - 30℃; for 0.5h;	A 25% B 45%

: 124-41-4
sodium methylate

: 545-06-2
trichloroacetonitrile

A: 78-09-1
orthocarbonic acid tetraethyl ester

B: 23213-96-9
ethyl 2,2,2-trichloroacetimidate

C: 68714-37-4
triethoxyacetonitrile

D: 77388-04-6
Ethyl-triethoxyacetimidat

Conditions

Conditions	Yield
In n-heptane at 94℃; for 2h;	A n/a B n/a C n/a D 5.5%

...Expand

: 56-23-5
tetrachloromethane

: 141-52-6
sodium ethanolate

A: 78-09-1
orthocarbonic acid tetraethyl ester

B: 122-51-0
orthoformic acid triethyl ester

...Expand

: 60-29-7
diethyl ether

: 558-13-4
carbon tetrabromide

: 141-52-6
sodium ethanolate

: 78-09-1
orthocarbonic acid tetraethyl ester

...Expand

: 558-13-4
carbon tetrabromide

: 141-52-6
sodium ethanolate

: 78-09-1
orthocarbonic acid tetraethyl ester

Conditions

Conditions	Yield
With diethyl ether

: 13029-05-5
trichloro-methanesulfenic acid ethyl ester

: 141-52-6
sodium ethanolate

: 78-09-1
orthocarbonic acid tetraethyl ester

: 60-29-7
diethyl ether

: 64-17-5
ethanol

: 141-52-6
sodium ethanolate

: 594-42-3
chlorothio-trichloro-methane

: 78-09-1
orthocarbonic acid tetraethyl ester

Conditions

Conditions	Yield
bei Einw.;

...Expand

: 141-52-6
sodium ethanolate

: 594-42-3
chlorothio-trichloro-methane

: 78-09-1
orthocarbonic acid tetraethyl ester

Conditions

Conditions	Yield
With diethyl ether

: 75-15-0
carbon disulfide

: 3173-69-1, 14791-99-2, 24126-00-9, 96473-13-1
tin(II) ethoxide

: 78-09-1
orthocarbonic acid tetraethyl ester

: 64-17-5
ethanol

: 15146-36-8
N-(di-ethoxymethylene)-benzamide

: 78-09-1
orthocarbonic acid tetraethyl ester

: 64-17-5
ethanol

: 1122-85-6
phenyl cyanate

: 78-09-1
orthocarbonic acid tetraethyl ester

Conditions

Conditions	Yield
With hydrogenchloride

: 64-17-5
ethanol

: 4885-03-4
dichlorodiphenoxymethane

: 78-09-1
orthocarbonic acid tetraethyl ester

Conditions

Conditions	Yield
With pyridine Ambient temperature;

: 631-57-2
Acetyl cyanide

: 73708-97-1
N,N-Dimethyl-orthocarbamidsaeure-triethylester

A: 127-19-5
N,N-dimethyl acetamide

B: 78-09-1
orthocarbonic acid tetraethyl ester

C: 68714-37-4
triethoxyacetonitrile

D: 34644-32-1
2,2-diethoxy-2-dimethylaminoacetonitrile

Conditions

Conditions	Yield
In diethyl ether for 5h; Ambient temperature; Yield given;
In diethyl ether for 5h; Ambient temperature;

...Expand

: 124-41-4
sodium methylate

: triethoxycarbenium tetrafluoroborate

A: 1850-14-2
tetramethoxymethane

B: 78-09-1
orthocarbonic acid tetraethyl ester

C: 81759-13-9
Triethylmethylorthocarbonat

D: 81759-14-0
Trimethylethylorthocarbonat

E: Diethyldimethylorthocarbonat

Conditions

Conditions	Yield
In methanol for 12h; Product distribution; Ambient temperature; also with other sodium-alcoholates;

...Expand

: 58137-35-2
methyl 2-(trifluoroacetamido)acrylate

: 2678-54-8
ketene diethyl acetal

A: C12H16F3NO5

B: 1-trifluoroacetamido-2-ethoxy-4-oxocyclohex-2-ene-1-carboxylic acid methyl ester

C: 7737-40-8
ethyl 2-ethoxypropionate

D: 78-09-1
orthocarbonic acid tetraethyl ester

Conditions

Conditions	Yield
In chloroform-d1 at 25℃; Product distribution; Michael-Dieckmann type reaction;

...Expand

: 78-09-1
orthocarbonic acid tetraethyl ester

: 62-53-3
aniline

: 101-01-9
N,N',N''-triphenylguanidine

Conditions

Conditions	Yield
at 160 - 170℃; for 10h;	98%
at 120℃; for 3h; Product distribution; other times and temperatures;	21%
at 160℃;

: 1122-28-7
4,5-dicyano-1H-imidazole

: 78-09-1
orthocarbonic acid tetraethyl ester

: 133123-67-8
1-ethyl-4,5-dicyanoimidazole

Conditions

Conditions	Yield
1) 0.5 h, 100 deg C 2) 2 h, 150 deg C;	96%

: 78-09-1
orthocarbonic acid tetraethyl ester

: 402-14-2
2-nitro-5-(trifluoromethyl)aniline

: 1060705-50-1
C10H9F3N2O

Conditions

Conditions	Yield
With 10% Pd/C; hydrogen; acetic acid In methanol at 20℃; under 760.051 Torr;	96%

: 78-09-1
orthocarbonic acid tetraethyl ester

: 95-54-5
1,2-diamino-benzene

: 22219-23-4
2-ethoxy-1H-benzo[d]imidazole

Conditions

Conditions	Yield
Stage #1: orthocarbonic acid tetraethyl ester; 1,2-diamino-benzene With acetic acid at 70℃; for 2h; Stage #2: With potassium hydroxide In water at 20℃; for 1h;	94%
Stage #1: orthocarbonic acid tetraethyl ester; 1,2-diamino-benzene With acetic acid at 70℃; for 3h; Large scale; Stage #2: With potassium hydroxide for 1h; Large scale;	94.2%
In neat (no solvent) at 70℃; for 2h;	93%

: 78-09-1
orthocarbonic acid tetraethyl ester

: 6972-71-0
4,5-dimethyl-2-nitrobenzenamine

: C11H14N2O

Conditions

Conditions	Yield
With 10% Pd/C; hydrogen; acetic acid In methanol at 20℃; under 760.051 Torr;	94%

: 78-09-1
orthocarbonic acid tetraethyl ester

: 2369-11-1
5-fluoro-2-nitroaniline

: 1060705-58-9
C9H9FN2O

Conditions

Conditions	Yield
With 10% Pd/C; hydrogen; acetic acid In methanol at 20℃; under 760.051 Torr;	94%

: 78-09-1
orthocarbonic acid tetraethyl ester

: 1236156-65-2
2-(((2'-(1H-tetrazol-5-yl)-[1,1'-biphenyl]-4-yl)methyl)amino)-3-aminobenzoic acid-1-(((cyclohexyloxy)carbonyl)oxy)ethyl ester

: 145040-37-5
candesartan cilexetil

Conditions

Conditions	Yield
With acetic acid In ethyl acetate at 30℃; Temperature;	93.9%
With acetic acid In toluene at 60℃; for 2h;	81%

: 78-09-1
orthocarbonic acid tetraethyl ester

: tert-butyl 3,4-diaminopyrrolidine-1-carboxylate hydrochloride

: tert-butyl 2-ethoxy-3a,4,6,6a-tetrahydropyrrolo[3,4-d]imidazole-5(1H)-carboxylate

Conditions

Conditions	Yield
at 20℃; for 17h;	93.4%

: 78-09-1
orthocarbonic acid tetraethyl ester

: 1066-54-2
trimethylsilylacetylene

: 91022-26-3
trimethyl(3,3,3-triethoxyprop-1-yn-1-yl)silane

Conditions

Conditions	Yield
Stage #1: trimethylsilylacetylene With magnesium; isopropyl bromide In diethyl ether at 10℃; for 1h; Inert atmosphere; Cooling with ice; Stage #2: orthocarbonic acid tetraethyl ester In diethyl ether at 20℃; for 1h; Inert atmosphere;	93%
Stage #1: trimethylsilylacetylene With ethylmagnesium bromide In diethyl ether at 20℃; Reflux; Stage #2: orthocarbonic acid tetraethyl ester In diethyl ether at 20℃; Reflux;	77%
Stage #1: trimethylsilylacetylene With ethylmagnesium bromide In diethyl ether at 20℃; Inert atmosphere; Heating; Stage #2: orthocarbonic acid tetraethyl ester In diethyl ether at 20℃; Inert atmosphere; Reflux;	70%

: 78-09-1
orthocarbonic acid tetraethyl ester

: 61063-11-4
2-Amino-3-nitrobenzoic acid,ethyl ester

: 577957-02-9
ethyl 2-ethoxy-3H-benzimidazole-4-carboxylate

Conditions

Conditions	Yield
With 10% Pd/C; hydrogen; acetic acid In methanol at 20℃; under 760.051 Torr;	93%

: 78-09-1
orthocarbonic acid tetraethyl ester

: 89-62-3
4-methyl-2-nitroaniline

: 71468-10-5
C10H12N2O

Conditions

Conditions	Yield
With 10% Pd/C; hydrogen; acetic acid In methanol at 20℃; under 760.051 Torr;	93%

: 78-09-1
orthocarbonic acid tetraethyl ester

: C30H32N6O5*C2H2O4

: 145040-37-5
candesartan cilexetil

Conditions

Conditions	Yield
Stage #1: C30H32N6O5*C2H2O4 With potassium carbonate In ethyl acetate at 10 - 15℃; pH=6 - 7; Stage #2: orthocarbonic acid tetraethyl ester In acetic acid at 0 - 25℃; for 15h;	92.3%

: 78-09-1
orthocarbonic acid tetraethyl ester

: 136304-78-4
methyl 3-amino-2-[[(2'-cyanobiphenyl-4-yl)methyl]amino]benzoate

: 139481-44-0
methyl 1-[(2'-cyanobiphenyl-4-yl)methyl]-2-ethoxy-benzimidazole-7-carboxylate

Conditions

Conditions	Yield
With acetic acid at 80 - 90℃; for 0.666667h;	91%
With acetic acid at 80℃; for 1h;	86%
With acetic acid at 78 - 82℃; for 1 - 2h; Heating / reflux; Industry scale;	84.8%
With acetic acid In toluene at 20℃; Reflux;

: 78-09-1
orthocarbonic acid tetraethyl ester

: 88-74-4
2-nitro-aniline

: 22219-23-4
2-ethoxy-1H-benzo[d]imidazole

Conditions

Conditions	Yield
With 10% Pd/C; hydrogen; acetic acid In methanol at 20℃; under 760.051 Torr;	91%

: 78-09-1
orthocarbonic acid tetraethyl ester

: C20H16BrN3

: C23H18BrN3O

Conditions

Conditions	Yield
With acetic acid at 80℃; for 4h;	91%

: 50-24-8
prednisolon

: 78-09-1
orthocarbonic acid tetraethyl ester

: 26129-79-3
prednisolone-17,21-diethylorthocarbonate

Conditions

Conditions	Yield
With toluene-4-sulfonic acid In 1,4-dioxane at 22℃; for 17h;	90%

: 850154-78-8
2-cyano-3-methyl-benzenesulfonamide

: 78-09-1
orthocarbonic acid tetraethyl ester

: 937722-17-3
2-cyano-N-diethoxymethylene-3-methyl-benzenesulfonamide

Conditions

Conditions	Yield
at 160℃;	90%

: 78-09-1
orthocarbonic acid tetraethyl ester

: 6393-40-4
4-Amino 3-nitro-benzonitrile

: 952511-49-8
C10H9N3O

Conditions

Conditions	Yield
With 10% Pd/C; hydrogen; acetic acid In methanol at 20℃; under 760.051 Torr;	90%

: 22600-30-2
methyl 5-amino-2-furoate

: 78-09-1
orthocarbonic acid tetraethyl ester

: 110189-96-3
N-(5-methoxycarbonyl-2-furyl)imidocarbonate

Conditions

Conditions	Yield
With trifluoroacetic acid at 80℃; for 24h;	88%

: 78-09-1
orthocarbonic acid tetraethyl ester

: 169270-81-9
methyl 3-amino-2-<<(11-cyano-5-oxo-5H-dibenzocyclohepten-3-yl)methyl>amino>benzoate

: 169270-82-0
methyl 3-<(11-cyano-5-oxo-5H-dibenzocyclohepten-3-yl)methyl>-2-ethoxy-3H-benzimidazole-4-carboxylate

Conditions

Conditions	Yield
With acetic acid at 100℃; for 2h;	88%

: 78-09-1
orthocarbonic acid tetraethyl ester

: 606-18-8
3-nitroanthranilic acid

: 2-ethoxy-1H-benzo[d]imidazole-7-carboxylic acid

Conditions

Conditions	Yield
With 10% Pd/C; hydrogen; acetic acid In methanol at 20℃; under 760.051 Torr;	88%

: 78-09-1
orthocarbonic acid tetraethyl ester

: bicyclo<2.2.1>hept-5-ene-2-endo,3-endo-diamine dihydrochloride

: (3aα,4α,7α,7aα)-2-ethoxy-3a,4,7,7a-tetrahydro-4,7-methano-1H-benzimidazole

Conditions

Conditions	Yield
With sodium acetate In acetic acid	87%

: 78-09-1
orthocarbonic acid tetraethyl ester

: 37466-88-9
2,3-Diaminobenzoic acid,ethyl ester

: 577957-02-9
ethyl 2-ethoxy-3H-benzimidazole-4-carboxylate

Conditions

Conditions	Yield
With acetic acid at 0 - 20℃; for 3h;	87%

: 78-09-1
orthocarbonic acid tetraethyl ester

: 36692-49-6
Methyl 3,4-diaminobenzoate

: methyl 2-ethoxy-1H-benzo[d]imidazole-6-carboxylate

Conditions

Conditions	Yield
With acetic acid at 0 - 20℃; for 4h;	87%

: 7677-24-9
trimethylsilyl cyanide

: 78-09-1
orthocarbonic acid tetraethyl ester

: 68714-37-4
triethoxyacetonitrile

Conditions

Conditions	Yield
tin(IV) chloride for 15h; Ambient temperature;	86%

: 625-72-9
(R)-3-hydroxybutyric acid

: 78-09-1
orthocarbonic acid tetraethyl ester

A: 15890-55-8
β-valerolactone

B: 2,2-dimethoxy-6-methyl-1,3-dioxan-4-one

Conditions

Conditions	Yield
In benzene	A n/a B 86%

...Expand

: 932034-83-8
4-(2-amino-4-methyl-phenylamino)-piperidine-1-carboxylic acid tert-butyl ester

: 78-09-1
orthocarbonic acid tetraethyl ester

: 932035-40-0
4-(2-ethoxy-5-methylbenzoimidazol-1-yl)-piperidine-1-carboxylic acid tert-butyl ester

Conditions

Conditions	Yield
With acetic acid at 20℃; for 4h;	86%

: 78-09-1
orthocarbonic acid tetraethyl ester

: 1258399-19-7
methyl {(3S)-6-[{(3R)-7-[(2-aminophenyl)amino]-2,3-dihydro-1-benzofuran-3-yl}(trifluoroacetyl)amino]-2,3-dihydro-1-benzofuran-3-yl}acetate

: 1258399-22-2
methyl [(3S)-6-{[(3R)-7-(2-ethoxy-1H-benzimidazol-1-yl)-2,3-dihydro-1-benzofuran-3-yl](trifluoroacetyl)amino}-2,3-dihydro-1-benzofuran-3-yl]acetate

Conditions

Conditions	Yield
Stage #1: orthocarbonic acid tetraethyl ester; methyl {(3S)-6-[{(3R)-7-[(2-aminophenyl)amino]-2,3-dihydro-1-benzofuran-3-yl}(trifluoroacetyl)amino]-2,3-dihydro-1-benzofuran-3-yl}acetate With acetic acid at 60℃; for 0.5h; Stage #2: With sodium hydrogencarbonate In water	86%

Tetraethyl orthocarbonate Specification

The Tetraethyl orthocarbonate, with the CAS registry number 78-09-1 and EINECS registry number 201-082-2, has the systematic name of (triethoxymethoxy)ethane. And the molecular formula of this chemical is C₉H₂₀O₄. It is a kind of clear colorless liquid, and belongs to the following product categories: Acetals/Ketals/Ortho Esters; Organic Building Blocks; Oxygen Compounds. What's more, it should be stored in the refrigerator. In addition, it is used in the synthesis of medicine intermediate and cementing compound.

The physical properties of Tetraethyl orthocarbonate are as following: (1)ACD/LogP: 4.68; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 4.68; (4)ACD/LogD (pH 7.4): 4.68; (5)ACD/BCF (pH 5.5): 2122.6; (6)ACD/BCF (pH 7.4): 2122.6; (7)ACD/KOC (pH 5.5): 8374.69; (8)ACD/KOC (pH 7.4): 8374.69; (9)#H bond acceptors: 4; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 8; (12)Polar Surface Area: 36.92 Å²; (13)Index of Refraction: 1.414; (14)Molar Refractivity: 50.69 cm³; (15)Molar Volume: 202.5 cm³; (16)Polarizability: 20.09×10^-24cm³; (17)Surface Tension: 27.5 dyne/cm; (18)Density: 0.948 g/cm³; (19)Flash Point: 52.8 °C; (20)Enthalpy of Vaporization: 37.98 kJ/mol; (21)Boiling Point: 159.5 °C at 760 mmHg; (22)Vapour Pressure: 3.24 mmHg at 25°C.

Uses of Tetraethyl orthocarbonate: It can react with pyrrolidine to produce 1,1'-carbonyl-bis-pyrrolidine. The reaction time is 5 days with heating, and the yield is about 39%.

Tetraethyl orthocarbonate can react with pyrrolidine to produce 1,1'-carbonyl-bis-pyrrolidine

You should be cautious while dealing with this chemical. It is a kind of flammable chemical which irritates eyes, respiratory system and skin. Therefore, you had better take the following instructions: Wear suitable protective clothing, gloves and eye/face protection, and in case of contacting with eyes, rinse immediately with plenty of water and seek medical advice; Keep away from sources of ignition - No smoking.

You can still convert the following datas into molecular structure:
(1)SMILES: O(CC)C(OCC)(OCC)OCC
(2)InChI: InChI=1/C9H20O4/c1-5-10-9(11-6-2,12-7-3)13-8-4/h5-8H2,1-4H3
(3)InChIKey: CWLNAJYDRSIKJS-UHFFFAOYAN

Product Name

Tetraethyl orthocarbonate

Synthetic route

Tetraethyl orthocarbonate Specification

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