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78-09-1

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78-09-1 Usage

Chemical Properties

clear colorless liquid

Uses

Tetraethyl Orthocarbonate is used in the synthesis of chemokine receptor-5 inhibitors against HIV-1, benzobisoxazoles and in the preparation of organic semiconductors. It is also employed in the synthesis of 2,7-dimethylene-1,4,6,9-tetraoxaspiro[4,4]nonane and in the synthesis of cross linked poly(orthocarbonate)s used as organic solvent absorbent.

Purification Methods

Likely impurities are hydrolysis products. Shake the orthocarbonate with brine (saturated NaCl, dilute with a little Et2O if amount of material is small) and dry (MgSO4). The organic layer is filtered off and evaporated, and the residue is distilled through a helices packed fractionating column with a total reflux partial take-off head. All distillations can be done at atmospheric pressure in an inert atmosphere (e.g. N2). [Roberts & McMahon Org Synth Coll Vol IV 457 1963, Connolly & Dyson J Chem Soc 828 1937, Tieckelmann & Post J Org Chem 13 266 1948, for review see Kantlehner et al. Justus Liebigs Ann Chem 507 207 1982, Beilstein 3 IV 6.]

Check Digit Verification of cas no

The CAS Registry Mumber 78-09-1 includes 5 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 2 digits, 7 and 8 respectively; the second part has 2 digits, 0 and 9 respectively.
Calculate Digit Verification of CAS Registry Number 78-09:
(4*7)+(3*8)+(2*0)+(1*9)=61
61 % 10 = 1
So 78-09-1 is a valid CAS Registry Number.
InChI:InChI=1/C9H20O4/c1-5-10-9(11-6-2,12-7-3)13-8-4/h5-8H2,1-4H3

78-09-1 Well-known Company Product Price

  • Brand
  • (Code)Product description
  • CAS number
  • Packaging
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  • Detail
  • Alfa Aesar

  • (A17835)  Tetraethyl orthocarbonate, 98+%   

  • 78-09-1

  • 5g

  • 281.0CNY

  • Detail
  • Alfa Aesar

  • (A17835)  Tetraethyl orthocarbonate, 98+%   

  • 78-09-1

  • 25g

  • 1131.0CNY

  • Detail
  • Alfa Aesar

  • (A17835)  Tetraethyl orthocarbonate, 98+%   

  • 78-09-1

  • 100g

  • 3849.0CNY

  • Detail
  • Aldrich

  • (163627)  Tetraethylorthocarbonate  97%

  • 78-09-1

  • 163627-5G

  • 280.80CNY

  • Detail
  • Aldrich

  • (163627)  Tetraethylorthocarbonate  97%

  • 78-09-1

  • 163627-25G

  • 1,017.90CNY

  • Detail

78-09-1SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 12, 2017

Revision Date: Aug 12, 2017

1.Identification

1.1 GHS Product identifier

Product name Tetraethyl orthocarbonate

1.2 Other means of identification

Product number -
Other names Tetraethoxymethane

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:78-09-1 SDS

78-09-1Synthetic route

ethanol
64-17-5

ethanol

chloropicrin
76-06-2

chloropicrin

orthocarbonic acid tetraethyl ester
78-09-1

orthocarbonic acid tetraethyl ester

Conditions
ConditionsYield
With sodium ethanolate at 65 - 70℃; for 3h; Temperature; Large scale;91%
With sodium Darst.;
ethyl 2,2,2-trichloroacetimidate
23213-96-9

ethyl 2,2,2-trichloroacetimidate

sodium methylate
124-41-4

sodium methylate

orthocarbonic acid tetraethyl ester
78-09-1

orthocarbonic acid tetraethyl ester

Conditions
ConditionsYield
In ethanol for 1h; Heating;85%
sodium ethanolate
141-52-6

sodium ethanolate

trichloroacetonitrile
545-06-2

trichloroacetonitrile

orthocarbonic acid tetraethyl ester
78-09-1

orthocarbonic acid tetraethyl ester

Conditions
ConditionsYield
In ethanol for 3.5h; Heating / reflux;83%
In ethanol Heating;
tetrachloromethane
56-23-5

tetrachloromethane

ethanol
64-17-5

ethanol

sodium ethanolate
141-52-6

sodium ethanolate

orthocarbonic acid tetraethyl ester
78-09-1

orthocarbonic acid tetraethyl ester

Conditions
ConditionsYield
at 80 - 95℃; for 5h; Temperature;83%
ethanol
64-17-5

ethanol

triethoxyacetonitrile
68714-37-4

triethoxyacetonitrile

orthocarbonic acid tetraethyl ester
78-09-1

orthocarbonic acid tetraethyl ester

Conditions
ConditionsYield
With toluene-4-sulfonic acid Heating;71%
triethoxyacetonitrile
68714-37-4

triethoxyacetonitrile

sodium ethanolate
141-52-6

sodium ethanolate

A

orthocarbonic acid tetraethyl ester
78-09-1

orthocarbonic acid tetraethyl ester

B

Triethylmethylorthocarbonat
81759-13-9

Triethylmethylorthocarbonat

C

Trimethylethylorthocarbonat
81759-14-0

Trimethylethylorthocarbonat

Conditions
ConditionsYield
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%
carbon disulfide
75-15-0

carbon disulfide

ethanol
64-17-5

ethanol

orthocarbonic acid tetraethyl ester
78-09-1

orthocarbonic acid tetraethyl ester

Conditions
ConditionsYield
With silver trifluoroacetate; triethylamine for 5h; Ambient temperature;61%
Yield given. Multistep reaction;
triethoxyacetonitrile
68714-37-4

triethoxyacetonitrile

N-butylamine
109-73-9

N-butylamine

A

orthocarbonic acid tetraethyl ester
78-09-1

orthocarbonic acid tetraethyl ester

B

Diethyl(butylimido)carbonat
81759-28-6

Diethyl(butylimido)carbonat

C

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

1,3-Dibutyl-2-ethylisoharnstoff

Conditions
ConditionsYield
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%
chloropicrin
76-06-2

chloropicrin

sodium ethanolate
141-52-6

sodium ethanolate

orthocarbonic acid tetraethyl ester
78-09-1

orthocarbonic acid tetraethyl ester

Conditions
ConditionsYield
In ethanol at 57 - 64℃; for 2h; Heating / reflux; Industry scale;58.3%
triethoxyacetonitrile
68714-37-4

triethoxyacetonitrile

sodium methylate
124-41-4

sodium methylate

A

orthocarbonic acid tetraethyl ester
78-09-1

orthocarbonic acid tetraethyl ester

B

Triethylmethylorthocarbonat
81759-13-9

Triethylmethylorthocarbonat

C

Trimethylethylorthocarbonat
81759-14-0

Trimethylethylorthocarbonat

Conditions
ConditionsYield
In methanol at 60℃; Title compound not separated from byproducts;A 8 % Chromat.
B 58%
C 2 % Chromat.
3,3-diethoxypentane
36749-09-4

3,3-diethoxypentane

A

orthocarbonic acid tetraethyl ester
78-09-1

orthocarbonic acid tetraethyl ester

B

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

3-chloro-benzoic acid ethyl ester

C

Ethyl propionate
105-37-3

Ethyl propionate

D

Diethyl carbonate
105-58-8

Diethyl carbonate

Conditions
ConditionsYield
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%
triethoxyacetonitrile
68714-37-4

triethoxyacetonitrile

benzylamine
100-46-9

benzylamine

A

orthocarbonic acid tetraethyl ester
78-09-1

orthocarbonic acid tetraethyl ester

B

Diethyl(benzylimido)carbonat
6263-03-2

Diethyl(benzylimido)carbonat

C

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

1,3-Dibenzyl-2-ethylisoharnstoff

Conditions
ConditionsYield
at 120℃;A n/a
B 45%
C 14%
at 120℃; Heating;A n/a
B 45%
C 14%
Triethyl orthopropionate
115-80-0

Triethyl orthopropionate

A

orthocarbonic acid tetraethyl ester
78-09-1

orthocarbonic acid tetraethyl ester

B

Diethyl carbonate
105-58-8

Diethyl carbonate

Conditions
ConditionsYield
With 3-chloro-benzenecarboperoxoic acid In dichloromethane at 15 - 30℃; for 0.5h;A 25%
B 45%
sodium methylate
124-41-4

sodium methylate

trichloroacetonitrile
545-06-2

trichloroacetonitrile

A

orthocarbonic acid tetraethyl ester
78-09-1

orthocarbonic acid tetraethyl ester

B

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

ethyl 2,2,2-trichloroacetimidate

C

triethoxyacetonitrile
68714-37-4

triethoxyacetonitrile

D

Ethyl-triethoxyacetimidat
77388-04-6

Ethyl-triethoxyacetimidat

Conditions
ConditionsYield
In n-heptane at 94℃; for 2h;A n/a
B n/a
C n/a
D 5.5%
tetrachloromethane
56-23-5

tetrachloromethane

sodium ethanolate
141-52-6

sodium ethanolate

A

orthocarbonic acid tetraethyl ester
78-09-1

orthocarbonic acid tetraethyl ester

B

orthoformic acid triethyl ester
122-51-0

orthoformic acid triethyl ester

diethyl ether
60-29-7

diethyl ether

carbon tetrabromide
558-13-4

carbon tetrabromide

sodium ethanolate
141-52-6

sodium ethanolate

orthocarbonic acid tetraethyl ester
78-09-1

orthocarbonic acid tetraethyl ester

carbon tetrabromide
558-13-4

carbon tetrabromide

sodium ethanolate
141-52-6

sodium ethanolate

orthocarbonic acid tetraethyl ester
78-09-1

orthocarbonic acid tetraethyl ester

Conditions
ConditionsYield
With diethyl ether
trichloro-methanesulfenic acid ethyl ester
13029-05-5

trichloro-methanesulfenic acid ethyl ester

sodium ethanolate
141-52-6

sodium ethanolate

orthocarbonic acid tetraethyl ester
78-09-1

orthocarbonic acid tetraethyl ester

diethyl ether
60-29-7

diethyl ether

ethanol
64-17-5

ethanol

sodium ethanolate
141-52-6

sodium ethanolate

chlorothio-trichloro-methane
594-42-3

chlorothio-trichloro-methane

orthocarbonic acid tetraethyl ester
78-09-1

orthocarbonic acid tetraethyl ester

Conditions
ConditionsYield
bei Einw.;
sodium ethanolate
141-52-6

sodium ethanolate

chlorothio-trichloro-methane
594-42-3

chlorothio-trichloro-methane

orthocarbonic acid tetraethyl ester
78-09-1

orthocarbonic acid tetraethyl ester

Conditions
ConditionsYield
With diethyl ether
carbon disulfide
75-15-0

carbon disulfide

orthocarbonic acid tetraethyl ester
78-09-1

orthocarbonic acid tetraethyl ester

ethanol
64-17-5

ethanol

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

N-(di-ethoxymethylene)-benzamide

orthocarbonic acid tetraethyl ester
78-09-1

orthocarbonic acid tetraethyl ester

ethanol
64-17-5

ethanol

phenyl cyanate
1122-85-6

phenyl cyanate

orthocarbonic acid tetraethyl ester
78-09-1

orthocarbonic acid tetraethyl ester

Conditions
ConditionsYield
With hydrogenchloride
ethanol
64-17-5

ethanol

dichlorodiphenoxymethane
4885-03-4

dichlorodiphenoxymethane

orthocarbonic acid tetraethyl ester
78-09-1

orthocarbonic acid tetraethyl ester

Conditions
ConditionsYield
With pyridine Ambient temperature;
Acetyl cyanide
631-57-2

Acetyl cyanide

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

N,N-Dimethyl-orthocarbamidsaeure-triethylester

A

N,N-dimethyl acetamide
127-19-5

N,N-dimethyl acetamide

B

orthocarbonic acid tetraethyl ester
78-09-1

orthocarbonic acid tetraethyl ester

C

triethoxyacetonitrile
68714-37-4

triethoxyacetonitrile

D

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

2,2-diethoxy-2-dimethylaminoacetonitrile

Conditions
ConditionsYield
In diethyl ether for 5h; Ambient temperature; Yield given;
In diethyl ether for 5h; Ambient temperature;
sodium methylate
124-41-4

sodium methylate

triethoxycarbenium tetrafluoroborate

triethoxycarbenium tetrafluoroborate

A

tetramethoxymethane
1850-14-2

tetramethoxymethane

B

orthocarbonic acid tetraethyl ester
78-09-1

orthocarbonic acid tetraethyl ester

C

Triethylmethylorthocarbonat
81759-13-9

Triethylmethylorthocarbonat

D

Trimethylethylorthocarbonat
81759-14-0

Trimethylethylorthocarbonat

E

Diethyldimethylorthocarbonat

Diethyldimethylorthocarbonat

Conditions
ConditionsYield
In methanol for 12h; Product distribution; Ambient temperature; also with other sodium-alcoholates;
methyl 2-(trifluoroacetamido)acrylate
58137-35-2

methyl 2-(trifluoroacetamido)acrylate

ketene diethyl acetal
2678-54-8

ketene diethyl acetal

A

C12H16F3NO5

C12H16F3NO5

B

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

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

C

ethyl 2-ethoxypropionate
7737-40-8

ethyl 2-ethoxypropionate

D

orthocarbonic acid tetraethyl ester
78-09-1

orthocarbonic acid tetraethyl ester

Conditions
ConditionsYield
In chloroform-d1 at 25℃; Product distribution; Michael-Dieckmann type reaction;
orthocarbonic acid tetraethyl ester
78-09-1

orthocarbonic acid tetraethyl ester

aniline
62-53-3

aniline

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

N,N',N''-triphenylguanidine

Conditions
ConditionsYield
at 160 - 170℃; for 10h;98%
at 120℃; for 3h; Product distribution; other times and temperatures;21%
at 160℃;
4,5-dicyano-1H-imidazole
1122-28-7

4,5-dicyano-1H-imidazole

orthocarbonic acid tetraethyl ester
78-09-1

orthocarbonic acid tetraethyl ester

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

1-ethyl-4,5-dicyanoimidazole

Conditions
ConditionsYield
1) 0.5 h, 100 deg C 2) 2 h, 150 deg C;96%
orthocarbonic acid tetraethyl ester
78-09-1

orthocarbonic acid tetraethyl ester

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

2-nitro-5-(trifluoromethyl)aniline

C10H9F3N2O
1060705-50-1

C10H9F3N2O

Conditions
ConditionsYield
With 10% Pd/C; hydrogen; acetic acid In methanol at 20℃; under 760.051 Torr;96%
orthocarbonic acid tetraethyl ester
78-09-1

orthocarbonic acid tetraethyl ester

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

1,2-diamino-benzene

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

2-ethoxy-1H-benzo[d]imidazole

Conditions
ConditionsYield
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%
orthocarbonic acid tetraethyl ester
78-09-1

orthocarbonic acid tetraethyl ester

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

4,5-dimethyl-2-nitrobenzenamine

C11H14N2O

C11H14N2O

Conditions
ConditionsYield
With 10% Pd/C; hydrogen; acetic acid In methanol at 20℃; under 760.051 Torr;94%
orthocarbonic acid tetraethyl ester
78-09-1

orthocarbonic acid tetraethyl ester

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

5-fluoro-2-nitroaniline

C9H9FN2O
1060705-58-9

C9H9FN2O

Conditions
ConditionsYield
With 10% Pd/C; hydrogen; acetic acid In methanol at 20℃; under 760.051 Torr;94%
orthocarbonic acid tetraethyl ester
78-09-1

orthocarbonic acid tetraethyl ester

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

candesartan cilexetil
145040-37-5

candesartan cilexetil

Conditions
ConditionsYield
With acetic acid In ethyl acetate at 30℃; Temperature;93.9%
With acetic acid In toluene at 60℃; for 2h;81%
orthocarbonic acid tetraethyl ester
78-09-1

orthocarbonic acid tetraethyl ester

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

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

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

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

Conditions
ConditionsYield
at 20℃; for 17h;93.4%
orthocarbonic acid tetraethyl ester
78-09-1

orthocarbonic acid tetraethyl ester

trimethylsilylacetylene
1066-54-2

trimethylsilylacetylene

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

trimethyl(3,3,3-triethoxyprop-1-yn-1-yl)silane

Conditions
ConditionsYield
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%
orthocarbonic acid tetraethyl ester
78-09-1

orthocarbonic acid tetraethyl ester

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

2-Amino-3-nitrobenzoic acid,ethyl ester

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

ethyl 2-ethoxy-3H-benzimidazole-4-carboxylate

Conditions
ConditionsYield
With 10% Pd/C; hydrogen; acetic acid In methanol at 20℃; under 760.051 Torr;93%
orthocarbonic acid tetraethyl ester
78-09-1

orthocarbonic acid tetraethyl ester

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

4-methyl-2-nitroaniline

C10H12N2O
71468-10-5

C10H12N2O

Conditions
ConditionsYield
With 10% Pd/C; hydrogen; acetic acid In methanol at 20℃; under 760.051 Torr;93%
orthocarbonic acid tetraethyl ester
78-09-1

orthocarbonic acid tetraethyl ester

C30H32N6O5*C2H2O4

C30H32N6O5*C2H2O4

candesartan cilexetil
145040-37-5

candesartan cilexetil

Conditions
ConditionsYield
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%
orthocarbonic acid tetraethyl ester
78-09-1

orthocarbonic acid tetraethyl ester

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

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

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

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

Conditions
ConditionsYield
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;
orthocarbonic acid tetraethyl ester
78-09-1

orthocarbonic acid tetraethyl ester

2-nitro-aniline
88-74-4

2-nitro-aniline

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

2-ethoxy-1H-benzo[d]imidazole

Conditions
ConditionsYield
With 10% Pd/C; hydrogen; acetic acid In methanol at 20℃; under 760.051 Torr;91%
orthocarbonic acid tetraethyl ester
78-09-1

orthocarbonic acid tetraethyl ester

C20H16BrN3

C20H16BrN3

C23H18BrN3O

C23H18BrN3O

Conditions
ConditionsYield
With acetic acid at 80℃; for 4h;91%
prednisolon
50-24-8

prednisolon

orthocarbonic acid tetraethyl ester
78-09-1

orthocarbonic acid tetraethyl ester

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

prednisolone-17,21-diethylorthocarbonate

Conditions
ConditionsYield
With toluene-4-sulfonic acid In 1,4-dioxane at 22℃; for 17h;90%
2-cyano-3-methyl-benzenesulfonamide
850154-78-8

2-cyano-3-methyl-benzenesulfonamide

orthocarbonic acid tetraethyl ester
78-09-1

orthocarbonic acid tetraethyl ester

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

2-cyano-N-diethoxymethylene-3-methyl-benzenesulfonamide

Conditions
ConditionsYield
at 160℃;90%
orthocarbonic acid tetraethyl ester
78-09-1

orthocarbonic acid tetraethyl ester

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

4-Amino 3-nitro-benzonitrile

C10H9N3O
952511-49-8

C10H9N3O

Conditions
ConditionsYield
With 10% Pd/C; hydrogen; acetic acid In methanol at 20℃; under 760.051 Torr;90%
methyl 5-amino-2-furoate
22600-30-2

methyl 5-amino-2-furoate

orthocarbonic acid tetraethyl ester
78-09-1

orthocarbonic acid tetraethyl ester

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

N-(5-methoxycarbonyl-2-furyl)imidocarbonate

Conditions
ConditionsYield
With trifluoroacetic acid at 80℃; for 24h;88%
orthocarbonic acid tetraethyl ester
78-09-1

orthocarbonic acid tetraethyl ester

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

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

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

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

Conditions
ConditionsYield
With acetic acid at 100℃; for 2h;88%
orthocarbonic acid tetraethyl ester
78-09-1

orthocarbonic acid tetraethyl ester

3-nitroanthranilic acid
606-18-8

3-nitroanthranilic acid

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

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

Conditions
ConditionsYield
With 10% Pd/C; hydrogen; acetic acid In methanol at 20℃; under 760.051 Torr;88%
orthocarbonic acid tetraethyl ester
78-09-1

orthocarbonic acid tetraethyl ester

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

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

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

Conditions
ConditionsYield
With sodium acetate In acetic acid87%
orthocarbonic acid tetraethyl ester
78-09-1

orthocarbonic acid tetraethyl ester

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

2,3-Diaminobenzoic acid,ethyl ester

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

ethyl 2-ethoxy-3H-benzimidazole-4-carboxylate

Conditions
ConditionsYield
With acetic acid at 0 - 20℃; for 3h;87%
orthocarbonic acid tetraethyl ester
78-09-1

orthocarbonic acid tetraethyl ester

Methyl 3,4-diaminobenzoate
36692-49-6

Methyl 3,4-diaminobenzoate

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

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

Conditions
ConditionsYield
With acetic acid at 0 - 20℃; for 4h;87%
trimethylsilyl cyanide
7677-24-9

trimethylsilyl cyanide

orthocarbonic acid tetraethyl ester
78-09-1

orthocarbonic acid tetraethyl ester

triethoxyacetonitrile
68714-37-4

triethoxyacetonitrile

Conditions
ConditionsYield
tin(IV) chloride for 15h; Ambient temperature;86%
(R)-3-hydroxybutyric acid
625-72-9

(R)-3-hydroxybutyric acid

orthocarbonic acid tetraethyl ester
78-09-1

orthocarbonic acid tetraethyl ester

A

β-valerolactone
15890-55-8

β-valerolactone

B

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

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

Conditions
ConditionsYield
In benzeneA n/a
B 86%
4-(2-amino-4-methyl-phenylamino)-piperidine-1-carboxylic acid tert-butyl ester
932034-83-8

4-(2-amino-4-methyl-phenylamino)-piperidine-1-carboxylic acid tert-butyl ester

orthocarbonic acid tetraethyl ester
78-09-1

orthocarbonic acid tetraethyl ester

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

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

Conditions
ConditionsYield
With acetic acid at 20℃; for 4h;86%
orthocarbonic acid tetraethyl ester
78-09-1

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
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

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
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
ConditionsYield
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%

78-09-1Relevant articles and documents

Method for efficiently rectifying and producing tetraethyl orthocarbonate

-

Paragraph 0023-0028; 0029-0034; 0035-0040; 0041-0046, (2018/04/02)

The invention relates to the field of refining chemicals and specifically relates to a method for efficiently rectifying and producing tetraethyl orthocarbonate. According to the method, a low-polarity inert solvent is used for treating tetraethyl orthocarbonate, so that the extracting function is achieved, less water can be co-boiled and brought away in a rectifying process and the product is prevented from degrading in the rectifying process; the solid alkali is added, so that the pH value of the rectifying system is increased and the product is prevented from continuously degrading under the effect of pH value decreasing in the rectifying process; the technical measure is adopted for acquiring the efficiently rectified and stably produced high-purity tetraethyl orthocarbonate. Comparedwith the present technology, the method provided by the invention has the characteristics of high efficiency, stability, and the like, the high-purity product can be continuously rectified and separated and the purity of the product can reach up to 99.5% or above.

Mechanistic study of the ring-size modulation in Michael-Dieckmann type reactions of 2-acylaminoacrylates with ketene diethyl acetal

Avenoza, Alberto,Busto, Jesus H.,Canal, Noelia,Garcia, Jose I.,Jimenez-Oses, Gonzalo,Peregrina, Jesus M.,Perez-Fernandez, Marta

, p. 224 - 229 (2008/02/02)

An unexpected modulation of the chemoselectivity in the Michael-Dieckmann type reactions of 2-acylaminoacrylates with ketene diethyl acetal is observed, depending on the nature of the acylamino group. Experimental and theoretical studies are presented to offer insights into the origin of this substituent effect in terms of a polar stepwise mechanism. The Royal Society of Chemistry and the Centre National de la Recherche Scientifique.

CRYSTAL AND PROCESS FOR PRODUCING THE SAME

-

Page 18, (2010/02/06)

A process for producing crystals of 2-ethoxy-1-[[2'-(1H-tetrazol-5-yl)biphenyl-4-yl]methyl]-1H-benzimdazole-7-carboxylic acid (compound (I)), characterized by dissolving or suspending the compound (I) or a salt thereof in a solvent comprising an aprotic polar solvent and crystallizing it. By the process, the contaminants which are contained in the compound (I) or its salt and are difficult to remove, such as tin compounds, analogues of the compound (I), and a residual organic solvent, can be easily removed. Crystals of the compound (I) can be efficiently and easily mass-produced in high yield on an industrial scale.

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