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Ethyl Cyanoacetate
Cas No: 105-56-6
No Data 100 Gram 100 Metric Ton/Year JINHUA HUAYI CHEMICAL CO., LTD. Contact Supplier
Ethyl cyanoacetate Manufacturer/High quality/Best price/In stock
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Ethyl cyanoacetate
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Factory supply N-Octyl Cyanoacetate
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Good quality Ethyl cyanoacetate//105-56-6
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Ethyl cyanoacetate
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Amadis Chemical offer CAS#105-56-6;CAT#A801268
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105-56-6 Usage

Shipping

UN3276 Nitriles, liquid, toxic, n.o.s., Hazard Class: 6.1; Labels: 6.1-Poisonous materials, Technical Name Required, Potential Inhalation Hazard (Special Provision 5).

Health Hazard

TOXIC; inhalation, ingestion or contact (skin, eyes) with vapors, dusts or substance may cause severe injury, burns or death. Contact with molten substance may cause severe burns to skin and eyes. Reaction with water or moist air will release toxic, corrosive or flammable gases. Reaction with water may generate much heat that will increase the concentration of fumes in the air. Fire will produce irritating, corrosive and/or toxic gases. Runoff from fire control or dilution water may be corrosive and/or toxic and cause pollution.

Fire Hazard

Combustible material: may burn but does not ignite readily. Substance will react with water (some violently) releasing flammable, toxic or corrosive gases and runoff. When heated, vapors may form explosive mixtures with air: indoors, outdoors and sewers explosion hazards. Most vapors are heavier than air. They will spread along ground and collect in low or confined areas (sewers, basements, tanks). Vapors may travel to source of ignition and flash back. Contact with metals may evolve flammable hydrogen gas. Containers may explode when heated or if contaminated with water.

Uses

Reagent used in labelled pyrimidine and purine synthesis. Ethyl cyanoacetate is an ester. It may be used in the synthesis of ethyl glyoxylate.It was used to investigate the Knoevenagel condensation reactions in microreactor using zeolite catalysts obtained by grafting amino groups onto NaX and CsNaX zeolites.

Incompatibilities

Incompatible with oxidizers (chlorates, nitrates, peroxides, permanganates, perchlorates, chlorine, bromine, fluorine, etc.); contact may cause fires or explosions. Keep away from alkaline materials, strong bases, strong acids, oxoacids, epoxides, and reducing agents. Nitriles may polymerize in the presence of metals and some metal compounds. They are incompatible with acids; mixing nitriles with strong oxidizing acids can lead to extremely violent reactions. Nitriles are generally incompatible with other oxidizing agents such as peroxides and epoxides. The combination of bases and nitriles can produce hydrogen cyanide. Nitriles are hydrolyzed in both aqueous acid and base to give carboxylic acids (or salts of carboxylic acids). These reactions generate heat. Peroxides convert nitriles to amides. Nitriles can react vigorously with reducing agents. Acetonitrile and propionitrile are soluble in water, but nitriles higher than propionitrile have low aqueous solubility. They are also insoluble in aqueous acids. Reacts with moisture, water, and steam, forming toxic fumes.

General Description

A colorless liquid. Denser than water. Contact may irritate skin, eyes and mucous membranes. Flash point 210°F. May be toxic by ingestion. Used to make other chemicals.

Air & Water Reactions

Slightly soluble in water.

Hazard

Toxic by ingestion and inhalation.

Reactivity Profile

Ethyl cyanoacetate is both a nitrile and an ester. Esters react with acids to liberate heat along with alcohols and acids. Strong oxidizing acids may cause a vigorous reaction that is sufficiently exothermic to ignite the reaction products. Heat is also generated by the interaction of esters with caustic solutions. Flammable hydrogen is generated by mixing esters with alkali metals and hydrides. Nitriles may polymerize in the presence of metals and some metal compounds. They are incompatible with acids; mixing nitriles with strong oxidizing acids can lead to extremely violent reactions. Nitriles are generally incompatible with other oxidizing agents such as peroxides and epoxides. The combination of bases and nitriles can produce hydrogen cyanide. Nitriles are hydrolyzed in both aqueous acid and base to give carboxylic acids (or salts of carboxylic acids). These reactions generate heat. Peroxides convert nitriles to amides. Nitriles can react vigorously with reducing agents. Acetonitrile and propionitrile are soluble in water, but nitriles higher than propionitrile have low aqueous solubility. They are also insoluble in aqueous acids.

Purification Methods

Shake the ester several times with aqueous 10% Na2CO3, wash it well with water, dry with Na2SO4 and fractionally distil it. [Beilstein 2 IV 1889.]

Preparation

Ethyl cyanoacetate can be prepared by the action of sodium or potassium cyanide on ethyl chloroacetate, and by the action of sodium cyanide on sodium chloroacetate, followed by esterification.

Potential Exposure

A nitrile used to manufacture dyes, pharmaceuticals, and other chemicals.

Chemical Properties

Ethyl cyanoacetate is a colorless to straw colored liquid with a mild pleasant odor

Safety Profile

oison by ingestion. Moderately toxic by intraperitoneal and subcutaneous routes. Combustible when exposed to heat or flame; can react with oxidzing materials. Wdl react with water or steam to produce toxic and flammable vapors. To fight fire, use CO2, dry chemical. When heated to decomposition or on contact with acid or acid fumes it emits highly toxic fumes of CN-. See also NITRILES.

Waste Disposal

Consult with environmental regulatory agencies for guidance on acceptable disposal practices. Generators of waste containing this contaminant (≥100 kg/mo) must conform with EPA regulations governing storage, transportation, treatment, and waste disposal.
InChI:InChI:1S/C5H7NO2/c1-2-8-5(7)3-4-6/h2-3H2,1H3

105-56-6 Well-known Company Product Price

Brand (Code)Product description CAS number Packaging Price Detail
TCI America (C0441)  Ethyl Cyanoacetate  >99.0%(GC) 105-56-6 25g 140.00CNY Detail
TCI America (C0441)  Ethyl Cyanoacetate  >99.0%(GC) 105-56-6 500g 380.00CNY Detail
Alfa Aesar (A11498)  Ethyl cyanoacetate, 98+%    105-56-6 100g 88.0CNY Detail
Alfa Aesar (A11498)  Ethyl cyanoacetate, 98+%    105-56-6 500g 401.0CNY Detail
Alfa Aesar (A11498)  Ethyl cyanoacetate, 98+%    105-56-6 2500g 1042.0CNY Detail

105-56-6SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 10, 2017

Revision Date: Aug 10, 2017

1.Identification

1.1 GHS Product identifier

Product name Ethyl cyanoacetate

1.2 Other means of identification

Product number -
Other names ethyl 2-cyanoacetate

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only. Adhesives and sealant chemicals
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:105-56-6 SDS

105-56-6Synthetic route

3-(ethoxy)propionitrile
2141-62-0

3-(ethoxy)propionitrile

ethyl 2-cyanoacetate
105-56-6

ethyl 2-cyanoacetate

Conditions
ConditionsYield
With N-hydroxyphthalimide; cobalt(II) acetate In acetonitrile at 190℃; under 6750.68 Torr; for 7h;
sodium 3-ethoxy-3-oxoprop-1-en-1-olate

sodium 3-ethoxy-3-oxoprop-1-en-1-olate

ethyl 2-cyanoacetate
105-56-6

ethyl 2-cyanoacetate

Conditions
ConditionsYield
With hydroxylamine hydrochloride In ethanol at 90℃; for 4h; pH=2; pH-value; Reagent/catalyst; Solvent; Temperature; Inert atmosphere;81%
ethanol
64-17-5

ethanol

cyanoacetic acid
372-09-8

cyanoacetic acid

ethyl 2-cyanoacetate
105-56-6

ethyl 2-cyanoacetate

Conditions
ConditionsYield
With sulfuric acid In dichloromethane for 18h; Heating;95%
With sulfuric acid In dichloromethane for 18h; Reflux; Dean-Stark;95%
With sulfuric acid; sulfur trioxide at 20 - 70℃; for 4h; Temperature; Reflux;93.6%
hydrogen cyanide
74-90-8

hydrogen cyanide

chloroacetic acid ethyl ester
105-39-5

chloroacetic acid ethyl ester

ethyl 2-cyanoacetate
105-56-6

ethyl 2-cyanoacetate

Conditions
ConditionsYield
With triethylamine at 15℃; for 4.83333h; Concentration; Reagent/catalyst; Solvent; Temperature; Time;94.2%
sodium cyanide
773837-37-9

sodium cyanide

chloroacetic acid ethyl ester
105-39-5

chloroacetic acid ethyl ester

A

diethyl 2-cyanosuccinate
10359-15-6

diethyl 2-cyanosuccinate

B

triethyl 2-cyano-1,2,3-propanetricarboxylate
20822-61-1

triethyl 2-cyano-1,2,3-propanetricarboxylate

C

ethyl 2-cyanoacetate
105-56-6

ethyl 2-cyanoacetate

Conditions
ConditionsYield
With tetrabutylammomium bromide In dichloromethane; water at 20℃; for 4h;A 10.4%
B 5.4%
C 44%
ethanol
64-17-5

ethanol

cyanoacetic acid amide
107-91-5

cyanoacetic acid amide

ethyl 2-cyanoacetate
105-56-6

ethyl 2-cyanoacetate

Conditions
ConditionsYield
With sulfuric acid for 3h; Time; Reflux;97%
With sulfuric acid for 3h; Reflux;97%
sodium cyanide
773837-37-9

sodium cyanide

hydrogen cyanide
74-90-8

hydrogen cyanide

chloroacetic acid ethyl ester
105-39-5

chloroacetic acid ethyl ester

ethyl 2-cyanoacetate
105-56-6

ethyl 2-cyanoacetate

Conditions
ConditionsYield
With tetrabutylammomium bromide In water; acetonitrile at 55℃; for 2h; Product distribution / selectivity;93.2%
ethanol
64-17-5

ethanol

cyanoacetic acid
372-09-8

cyanoacetic acid

A

ethyl 2-cyanoacetate
105-56-6

ethyl 2-cyanoacetate

B

diethyl malonate
105-53-3

diethyl malonate

Conditions
ConditionsYield
With sulfuric acid In hexane; ethyl acetate at 30 - 62℃; for 5h; Temperature; Solvent; Dean-Stark;A 105.2 g
B 1.8 g
aspartic acid 4-ethyl ester
21860-86-6

aspartic acid 4-ethyl ester

ethyl 2-cyanoacetate
105-56-6

ethyl 2-cyanoacetate

Conditions
ConditionsYield
With trichloroisocyanuric acid; sodium hydroxide In water at 20℃; for 6h; Temperature;85%
acetonitrile
75-05-8

acetonitrile

ethyl 2-cyanoacetate
105-56-6

ethyl 2-cyanoacetate

Conditions
ConditionsYield
With sodium ethanolate; sodium amide; Diethyl carbonate at 140 - 160℃;
With sodium ethanolate; sodium amide; Diethyl carbonate at 140 - 160℃;
With sodium ethanolate; sodium amide; Diethyl carbonate at 140 - 160℃;
ethyl bromide
74-96-4

ethyl bromide

cyanoacetic acid
372-09-8

cyanoacetic acid

ethyl 2-cyanoacetate
105-56-6

ethyl 2-cyanoacetate

Conditions
ConditionsYield
With sodium hydroxide; tetrabutylammomium bromide In water; chlorobenzene
ethyl iodide
75-03-6

ethyl iodide

cyanoacetic acid
372-09-8

cyanoacetic acid

ethyl 2-cyanoacetate
105-56-6

ethyl 2-cyanoacetate

Conditions
ConditionsYield
With caesium carbonate In acetonitrile for 1.5h; Heating;98%
With cesium fluoride In N,N-dimethyl-formamide at 10 - 15℃; for 3h;79 % Chromat.
ethanol
64-17-5

ethanol

malononitrile
109-77-3

malononitrile

A

ethyl 2-cyanoacetate
105-56-6

ethyl 2-cyanoacetate

B

diethyl malonate
105-53-3

diethyl malonate

Conditions
ConditionsYield
With boron trifluoride diethyl etherate for 24h; Heating;A 90%
B 4%
With sulfuric acid at 130 - 135℃;
C11H16N4O2S
78514-93-9

C11H16N4O2S

A

1-isopropenyl-3-methylthio-1H-1,2,4-triazole
99496-77-2

1-isopropenyl-3-methylthio-1H-1,2,4-triazole

B

ethyl 2-cyanoacetate
105-56-6

ethyl 2-cyanoacetate

Conditions
ConditionsYield
In acetic acid at 70℃; for 2h;A 66%
B n/a
ethyl pentacyanocyclopropanecarboxylate
205651-05-4

ethyl pentacyanocyclopropanecarboxylate

ethyl 2-cyanoacetate
105-56-6

ethyl 2-cyanoacetate

Conditions
ConditionsYield
With N,N-Dimethylaniline hydroiodide In ethyl acetate at 50℃; for 0.0833333h; Decomposition;
potassium cyanide
151-50-8

potassium cyanide

chloroacetic acid ethyl ester
105-39-5

chloroacetic acid ethyl ester

A

ethyl 2-cyanoacetate
105-56-6

ethyl 2-cyanoacetate

B

methyl 2-cyanoacetate
105-34-0

methyl 2-cyanoacetate

Conditions
ConditionsYield
With methanol
acetonitrile
75-05-8

acetonitrile

Diethyl carbonate
105-58-8

Diethyl carbonate

ethyl 2-cyanoacetate
105-56-6

ethyl 2-cyanoacetate

Conditions
ConditionsYield
With diethyl ether; sodium amide
benzaldehyde 2-cyano-2-ethoxycarbonylvinylamino(dimethylamino)methylenehydrazone
122604-89-1

benzaldehyde 2-cyano-2-ethoxycarbonylvinylamino(dimethylamino)methylenehydrazone

A

ethyl benzylidenecyanoacetate
2025-40-3

ethyl benzylidenecyanoacetate

B

α,α-bis(3-dimethylamino-1,2,4-triazol-1-yl)toluene
122604-96-0

α,α-bis(3-dimethylamino-1,2,4-triazol-1-yl)toluene

C

ethyl 2-cyanoacetate
105-56-6

ethyl 2-cyanoacetate

Conditions
ConditionsYield
With acetic acid at 80℃; for 0.0833333h; Yield given;A n/a
B 30%
C n/a
With acetic acid at 80℃; for 0.0833333h; Yields of byproduct given;A n/a
B 30%
C n/a
N,N,N',N',N'',N''-Hexamethylguanidiniumcyanid
68897-45-0

N,N,N',N',N'',N''-Hexamethylguanidiniumcyanid

ethyl bromoacetate
105-36-2

ethyl bromoacetate

A

1,1,2,2,3,3-Hexamethylguanidiniumbromid
6926-43-8

1,1,2,2,3,3-Hexamethylguanidiniumbromid

B

ethyl 2-cyanoacetate
105-56-6

ethyl 2-cyanoacetate

Conditions
ConditionsYield
In dichloromethane at 20℃; for 2h;A n/a
B 53%
ethanol
64-17-5

ethanol

malononitrile
109-77-3

malononitrile

ethyl 2-cyanoacetate
105-56-6

ethyl 2-cyanoacetate

Conditions
ConditionsYield
With iron(III) chloride for 1h; Heating;76%
propynoic acid ethyl ester
623-47-2

propynoic acid ethyl ester

A

ethyl (Z)-3-azido-2-propenoate
116270-19-0

ethyl (Z)-3-azido-2-propenoate

B

E-ethyl 3-azidoacrylate
116270-20-3

E-ethyl 3-azidoacrylate

C

ethyl 2-cyanoacetate
105-56-6

ethyl 2-cyanoacetate

D

ethyl (Z)-3-(4-ethoxycarbonyl-1H-1,2,3-triazol-1-yl)propenoate
116270-21-4

ethyl (Z)-3-(4-ethoxycarbonyl-1H-1,2,3-triazol-1-yl)propenoate

Conditions
ConditionsYield
With borax; potassium dihydrogenphosphate; sodium azide In water at 50℃; for 0.5h; ultrasound irradiation; Yield given. Yields of byproduct given;
Cyanothioacetamide
7357-70-2

Cyanothioacetamide

3-bromo-1,1,1-trifluoroacetone
431-35-6

3-bromo-1,1,1-trifluoroacetone

ethanol
64-17-5

ethanol

A

2-[4-(trifluoromethyl)thiazol-2-yl]acetonitrile
329978-21-4

2-[4-(trifluoromethyl)thiazol-2-yl]acetonitrile

B

ethyl 2-cyanoacetate
105-56-6

ethyl 2-cyanoacetate

Conditions
ConditionsYield
for 18h; Heating / reflux;
mer-hydrido[[(ethoxycarbonyl)methyl]cyano](ethyl cyanoacetate)tris(triphenylphosphine)ruthenium(II)
138614-14-9

mer-hydrido[[(ethoxycarbonyl)methyl]cyano](ethyl cyanoacetate)tris(triphenylphosphine)ruthenium(II)

1,2-bis-(diphenylphosphino)ethane
1663-45-2

1,2-bis-(diphenylphosphino)ethane

RuH((C6H5)2PCH2CH2P(C6H5)2)2(NCCHCOOC2H5)*0.5C6H6

RuH((C6H5)2PCH2CH2P(C6H5)2)2(NCCHCOOC2H5)*0.5C6H6

B

ethyl 2-cyanoacetate
105-56-6

ethyl 2-cyanoacetate

Conditions
ConditionsYield
In benzene-d6 room temp., 3 h; NMR monitoring;A 82%
B 60%
2-chloropyrimidine
1722-12-9

2-chloropyrimidine

ethyl 5-oxo-2,5-dihydroisoxazole-4-carboxylate
54535-14-7

ethyl 5-oxo-2,5-dihydroisoxazole-4-carboxylate

A

ethyl 5-oxo-2-(pyrimidin-2-yl)-2,5-dihydroisoxazole-4-carboxylate
100422-78-4

ethyl 5-oxo-2-(pyrimidin-2-yl)-2,5-dihydroisoxazole-4-carboxylate

B

ethyl 2-cyanoacetate
105-56-6

ethyl 2-cyanoacetate

Conditions
ConditionsYield
at 130℃; for 0.25h; Yields of byproduct given;A 62%
B n/a
Ethyl 2-acetyl-5-oxo-2,5-dihydroisoxazole-4-carboxylate
174902-47-7

Ethyl 2-acetyl-5-oxo-2,5-dihydroisoxazole-4-carboxylate

A

ethyl 2-methyloxazole-4-carboxylate
76284-27-0

ethyl 2-methyloxazole-4-carboxylate

B

ethyl 2-cyanoacetate
105-56-6

ethyl 2-cyanoacetate

Conditions
ConditionsYield
at 540℃; under 0.05 Torr; for 1h;A 10%
B 90%
C15H13N3O2
1262279-87-7

C15H13N3O2

A

Benzylidenemalononitrile
2700-22-3

Benzylidenemalononitrile

B

ethyl 2-cyanoacetate
105-56-6

ethyl 2-cyanoacetate

Conditions
ConditionsYield
With palladium 10% on activated carbon In methanol retro-Michael reaction;
potassium cyanide
151-50-8

potassium cyanide

chloroacetic acid ethyl ester
105-39-5

chloroacetic acid ethyl ester

ethyl 2-cyanoacetate
105-56-6

ethyl 2-cyanoacetate

3-(4-Bromo-benzoyl)-4-(4-bromo-phenyl)-1-cyano-4-hydroxy-2,6-diphenyl-cyclohexanecarboxylic acid ethyl ester
135885-92-6

3-(4-Bromo-benzoyl)-4-(4-bromo-phenyl)-1-cyano-4-hydroxy-2,6-diphenyl-cyclohexanecarboxylic acid ethyl ester

A

(E)-1-(4-bromophenyl)-3-phenylprop-2-en-1-one
72758-69-1, 2403-27-2, 22966-23-0

(E)-1-(4-bromophenyl)-3-phenylprop-2-en-1-one

B

ethyl 2-cyanoacetate
105-56-6

ethyl 2-cyanoacetate

Conditions
ConditionsYield
With sodium ethanolate In ethanol Heating;A 86%
B n/a
With sodium ethanolate In ethanol at 50℃; Kinetics; Further Variations:; Temperatures;
3-Benzoyl-2,6-bis-(4-chloro-phenyl)-1-cyano-4-hydroxy-4-phenyl-cyclohexanecarboxylic acid ethyl ester
83624-73-1

3-Benzoyl-2,6-bis-(4-chloro-phenyl)-1-cyano-4-hydroxy-4-phenyl-cyclohexanecarboxylic acid ethyl ester

B

ethyl 2-cyanoacetate
105-56-6

ethyl 2-cyanoacetate

Conditions
ConditionsYield
With sodium ethanolate In ethanol Heating;A 87%
B n/a
With sodium ethanolate In ethanol at 50℃; Kinetics; Further Variations:; Temperatures;
3-Benzoyl-2,6-bis-(4-bromo-phenyl)-1-cyano-4-hydroxy-4-phenyl-cyclohexanecarboxylic acid ethyl ester
135885-91-5

3-Benzoyl-2,6-bis-(4-bromo-phenyl)-1-cyano-4-hydroxy-4-phenyl-cyclohexanecarboxylic acid ethyl ester

A

(2E)-3-(4-bromophenyl)-1-phenylprop-2-en-1-one
22966-09-2

(2E)-3-(4-bromophenyl)-1-phenylprop-2-en-1-one

B

ethyl 2-cyanoacetate
105-56-6

ethyl 2-cyanoacetate

Conditions
ConditionsYield
With sodium ethanolate In ethanol Heating;A 85%
B n/a
With sodium ethanolate In ethanol at 50℃; Kinetics; Further Variations:; Temperatures;
morpholine
110-91-8

morpholine

ethyl 2-cyanoacetate
105-56-6

ethyl 2-cyanoacetate

4-cyanoacetylmorpholine
15029-32-0

4-cyanoacetylmorpholine

Conditions
ConditionsYield
In neat (no solvent) at 20℃; Inert atmosphere;100%
With 1,8-diazabicyclo[5.4.0]undec-7-ene In 2-methyltetrahydrofuran at 40℃; for 4h;87%
at 130℃; for 4h;75%
furfural
98-01-1

furfural

ethyl 2-cyanoacetate
105-56-6

ethyl 2-cyanoacetate

ethyl (E)-2-cyano-3-(2-furyl)-2-propenoate
67449-75-6, 23973-22-0

ethyl (E)-2-cyano-3-(2-furyl)-2-propenoate

Conditions
ConditionsYield
With L-proline for 0.0333333h; Knoevenagel condensation; microwave irradiation;100%
ytterbium(III) perfluorooctanesulfonate In toluene at 80℃; for 3h; Knoevenagel condensation;99%
With polyacrylonitrile fiber modified with triethylenetetramine In water at 50℃; for 1.5h; Knoevenagel condensation;99%
1-phenylmethyl-4-piperidone
3612-20-2

1-phenylmethyl-4-piperidone

ethyl 2-cyanoacetate
105-56-6

ethyl 2-cyanoacetate

ethyl 2-(1-benzylpiperidin-4-ylidene)-2-cyanoacetate
1463-52-1

ethyl 2-(1-benzylpiperidin-4-ylidene)-2-cyanoacetate

Conditions
ConditionsYield
With acetic acid In toluene at 20℃; for 4h; Heating / reflux;100%
With ammonium acetate; acetic acid; benzene Abtrennen des entstehenden H2O;
With triethylamine In dichloromethane at 20℃;
cyclohexanone
108-94-1

cyclohexanone

ethyl 2-cyanoacetate
105-56-6

ethyl 2-cyanoacetate

ethyl 2-cyano-2-cyclohexylideneacetate
6802-76-2

ethyl 2-cyano-2-cyclohexylideneacetate

Conditions
ConditionsYield
With 1,4-diaza-bicyclo[2.2.2]octane In neat liquid at 20℃; for 0.133333h; Knoevenagel Condensation; Green chemistry;100%
With third generation polystyrene supported poly(amidoamine) dendrimer In ethanol at 50℃; for 0.333333h; Knoevenagel condensation;98%
With ammonium acetate; acetic acid In toluene Knoevenagel Condensation; Reflux;97%
2-chloro-benzaldehyde
89-98-5

2-chloro-benzaldehyde

ethyl 2-cyanoacetate
105-56-6

ethyl 2-cyanoacetate

(E)-ethyl 3-(2-chlorophenyl)-2-cyanoacrylate
24393-43-9

(E)-ethyl 3-(2-chlorophenyl)-2-cyanoacrylate

Conditions
ConditionsYield
With IRA-96 anion-exchange resin In ethanol at 25 - 30℃; for 1h; Reagent/catalyst; Knoevenagel Condensation; Sonication; Green chemistry; stereoselective reaction;100%
With polyacrylonitrile fiber functionalized with N,N-dimethyl-1,3-propanediamine In ethanol for 1.5h; Knoevenagel condensation; Reflux;99%
With polystyrene-supported DABCO In methanol at 45℃; for 1.5h; Knoevenagel Condensation; Green chemistry; stereoselective reaction;99%
3-nitro-benzaldehyde
99-61-6

3-nitro-benzaldehyde

ethyl 2-cyanoacetate
105-56-6

ethyl 2-cyanoacetate

(E)-2-cyano-3-(3-nitrophenyl)-2-propenoic acid ethyl ester
18925-00-3, 14394-75-3

(E)-2-cyano-3-(3-nitrophenyl)-2-propenoic acid ethyl ester

Conditions
ConditionsYield
With L-proline for 0.1h; Knoevenagel condensation; microwave irradiation;100%
With third generation polystyrene supported poly(amidoamine) dendrimer In ethanol at 50℃; for 0.333333h; Knoevenagel condensation;100%
With polyacrylonitrile fiber functionalized with N,N-dimethyl-1,3-propanediamine In ethanol for 1.5h; Knoevenagel condensation; Reflux;99%
benzaldehyde
100-52-7

benzaldehyde

ethyl 2-cyanoacetate
105-56-6

ethyl 2-cyanoacetate

ethyl (E)-2-cyano-3-phenyl-2-propenoate
2169-69-9

ethyl (E)-2-cyano-3-phenyl-2-propenoate

Conditions
ConditionsYield
With tetramethyl ammoniumhydroxide at 60℃; for 0.5h; Condensation; Knoevenagel condensation;100%
With L-proline for 0.0833333h; Knoevenagel condensation; microwave irradiation;100%
ytterbium(III) perfluorooctanesulfonate In toluene at 80℃; for 8h; Knoevenagel condensation;100%
benzaldehyde
100-52-7

benzaldehyde

ethyl 2-cyanoacetate
105-56-6

ethyl 2-cyanoacetate

ethyl benzylidenecyanoacetate
2025-40-3

ethyl benzylidenecyanoacetate

Conditions
ConditionsYield
With polymer supported poly(propylene imine)dendrimer In ethanol at 20℃; for 0.0833333h; Knoevenagel Condensation; Green chemistry;100%
With N,N-dimethyl-cyclohexanamine In water at 20℃; Knoevenagel Condensation;100%
With mesoporous hybrid catalyst HYB-75P-25B In ethanol at 59.84℃; for 3.5h; Knoevenagel condensation; Inert atmosphere;99%
4-hydroxy-benzaldehyde
123-08-0

4-hydroxy-benzaldehyde

ethyl 2-cyanoacetate
105-56-6

ethyl 2-cyanoacetate

ethyl (E)-2-cyano-3-(4-hydroxyphenyl)-2-propenoate
6935-44-0, 42205-38-9

ethyl (E)-2-cyano-3-(4-hydroxyphenyl)-2-propenoate

Conditions
ConditionsYield
With third generation polystyrene supported poly(amidoamine) dendrimer In ethanol at 50℃; for 0.25h; Knoevenagel condensation;100%
Ru(+)Cp(NCCHCO2Et)(-)*(PPh3)2 In tetrahydrofuran at 25℃; for 5h; Condensation; Aldol reaction;99%
With polyacrylonitrile fiber functionalized with N,N-dimethyl-1,3-propanediamine In ethanol for 1.5h; Knoevenagel condensation; Reflux;99%
4-methoxy-benzaldehyde
123-11-5

4-methoxy-benzaldehyde

ethyl 2-cyanoacetate
105-56-6

ethyl 2-cyanoacetate

ethyl (2E)-2-cyano-3-(4-methoxyphenyl)acrylate
2017-87-0

ethyl (2E)-2-cyano-3-(4-methoxyphenyl)acrylate

Conditions
ConditionsYield
With diazabicyclo[5.4.0]undec-7-ene-water complex at 20℃; for 0.833333h; Knoevenagel condensation;100%
With ethylenediamine-modified poly(vinyl chloride) at 20℃; for 0.0666667h; Solvent; Knoevenagel Condensation; Green chemistry;100%
With third generation polystyrene supported poly(amidoamine) dendrimer In ethanol at 50℃; for 0.25h; Knoevenagel condensation;99%
4-methoxy-benzaldehyde
123-11-5

4-methoxy-benzaldehyde

ethyl 2-cyanoacetate
105-56-6

ethyl 2-cyanoacetate

ethyl 2-cyano-3-(4-methoxyphenyl)prop-2-enoate
2286-29-5

ethyl 2-cyano-3-(4-methoxyphenyl)prop-2-enoate

Conditions
ConditionsYield
With polymer supported poly(propylene imine)dendrimer In ethanol at 20℃; for 0.0833333h; Knoevenagel Condensation; Green chemistry;100%
In N,N-dimethyl-formamide for 0.166667h; Knoevenagel Condensation;99.4%
With N-aminoethylpiperazine functionalized C60 fullerene In ethanol at 60℃; for 1h; Knoevenagel Condensation;99%
vanillin
121-33-5

vanillin

ethyl 2-cyanoacetate
105-56-6

ethyl 2-cyanoacetate

2-cyano-3-(4-hydroxy-3-methoxyphenyl)acrylic acid ethyl ester
132464-93-8, 13373-29-0

2-cyano-3-(4-hydroxy-3-methoxyphenyl)acrylic acid ethyl ester

Conditions
ConditionsYield
With polymer supported poly(propylene imine)dendrimer In ethanol at 20℃; for 0.166667h; Knoevenagel Condensation; Green chemistry;100%
With ammonium sulphamate for 0.00416667h; Knoevenagel condensation; Microwave irradiation; neat (no solvent);96%
aluminum oxide In ethanol for 1.66667h; Heating;95%
3,4-dimethoxy-benzaldehyde
120-14-9

3,4-dimethoxy-benzaldehyde

ethyl 2-cyanoacetate
105-56-6

ethyl 2-cyanoacetate

ethyl α-cyano-β-(3,4-dimethoxyphenyl)acrylate
2286-55-7

ethyl α-cyano-β-(3,4-dimethoxyphenyl)acrylate

Conditions
ConditionsYield
With piperidine; acetic acid In benzene at 120 - 130℃; for 12h; Heating / reflux;100%
With polymer supported poly(propylene imine)dendrimer In ethanol at 20℃; for 0.166667h; Knoevenagel Condensation; Green chemistry;99%
With ammonium sulphamate for 0.00416667h; Knoevenagel condensation; Microwave irradiation; neat (no solvent);97%
methyl vinyl ketone
78-94-4

methyl vinyl ketone

ethyl 2-cyanoacetate
105-56-6

ethyl 2-cyanoacetate

2-cyano-5-oxo-2-(3-oxobutyl)hexanoic acid ethyl ester

2-cyano-5-oxo-2-(3-oxobutyl)hexanoic acid ethyl ester

Conditions
ConditionsYield
With triphenylphosphine In acetonitrile at 23℃; for 0.133333h;100%
With N-ethyl-N,N-diisopropylamine; 2,6-(NMe2)2PhPd(1+)*BF4(1-) In dichloromethane at 20℃; Product distribution; Kinetics; Further Variations:; Catalysts; double Michael reaction;100%
With [2,6-bis(4',4'-dimethyl-2'-oxazolinyl)phenyl](acetonitrile)nickel(II) tetrafluoroborate; N-ethyl-N,N-diisopropylamine In dichloromethane at 0℃; for 1h; Michael addition;100%
cyclopentanone
120-92-3

cyclopentanone

ethyl 2-cyanoacetate
105-56-6

ethyl 2-cyanoacetate

ethyl 2-cyano-2-cyclopentylideneacetate
5407-83-0

ethyl 2-cyano-2-cyclopentylideneacetate

Conditions
ConditionsYield
piperidine at 23℃; under 750.06 Torr; for 2h; Knoevenagel condensation;100%
With morpholine; bis(acetylacetonate)oxovanadium at 40℃; for 1h; Reagent/catalyst; Temperature; Time; Knoevenagel Condensation;99%
With ammonium acetate; acetic acid In toluene Knoevenagel Condensation; Reflux;93%
ethyl 2-cyanoacetate
105-56-6

ethyl 2-cyanoacetate

ortho-anisaldehyde
135-02-4

ortho-anisaldehyde

(E)-2-cyano-3-(2-methoxyphenyl)-2-propenoic acid ethyl ester
14533-89-2

(E)-2-cyano-3-(2-methoxyphenyl)-2-propenoic acid ethyl ester

Conditions
ConditionsYield
With L-proline for 0.0666667h; Knoevenagel condensation; microwave irradiation;100%
With polyacrylonitrile fiber modified with triethylenetetramine In water at 50℃; for 1.5h; Knoevenagel condensation;99%
calcined Mg-Al-layered double hydroxide-supported iPr2-amide In N,N-dimethyl-formamide at 20℃; for 0.25h; Knoevenagel condensation;98%
ethyl 2-cyanoacetate
105-56-6

ethyl 2-cyanoacetate

4-dimethylamino-benzaldehyde
100-10-7

4-dimethylamino-benzaldehyde

ethyl (E)-2-cyano-3-[4-(dimethylamino)phenyl]prop-2-enoate
1886-52-8, 74897-86-2, 14394-77-5

ethyl (E)-2-cyano-3-[4-(dimethylamino)phenyl]prop-2-enoate

Conditions
ConditionsYield
With third generation polystyrene supported poly(amidoamine) dendrimer In ethanol at 50℃; for 0.25h; Knoevenagel condensation;100%
With diazabicyclo[5.4.0]undec-7-ene-water complex at 20℃; for 1h; Knoevenagel condensation;100%
With polyacrylonitrile fiber functionalized with N,N-dimethyl-1,3-propanediamine In ethanol for 1.5h; Knoevenagel condensation; Reflux;99%
ethyl 2-cyanoacetate
105-56-6

ethyl 2-cyanoacetate

cyanoacetic acid amide
107-91-5

cyanoacetic acid amide

Conditions
ConditionsYield
With ammonia100%
With ammonia In tetrahydrofuran; water at 20℃; for 2h;93%
With ammonium hydroxide In tetrahydrofuran at 20℃; for 24h;91%
4-methyl-benzaldehyde
104-87-0

4-methyl-benzaldehyde

ethyl 2-cyanoacetate
105-56-6

ethyl 2-cyanoacetate

ethyl (E)-2-cyano-3-p-tolylacrylate
2017-88-1

ethyl (E)-2-cyano-3-p-tolylacrylate

Conditions
ConditionsYield
With L-proline for 0.0833333h; Knoevenagel condensation; microwave irradiation;100%
With 1,4-diaza-bicyclo[2.2.2]octane In neat liquid at 20℃; for 0.0166667h; Knoevenagel Condensation; Green chemistry;100%
With ASCPEI In ethanol at 43℃; for 3h; Knoevenagel condensation;99%
vanillin
121-33-5

vanillin

ethyl 2-cyanoacetate
105-56-6

ethyl 2-cyanoacetate

ethyl (E)-2-cyano-3-(3-methoxy 4-hydroxyphenyl)-2-propenoate
132464-93-8

ethyl (E)-2-cyano-3-(3-methoxy 4-hydroxyphenyl)-2-propenoate

Conditions
ConditionsYield
With third generation polystyrene supported poly(amidoamine) dendrimer In ethanol at 50℃; for 0.333333h; Knoevenagel condensation;100%
With aluminum oxide; potassium oxide at 23℃; for 3h; Knoevenagel condensation;97%
With dimethyl 3-methyl-9-oxo-7-(3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-heptadecafluorodecyl)-2,4-di(pyridin-2-yl)-3,7-diazabicyclo-[3.3.1]nonane-1,5-dicarboxylate In water at 40℃; for 2h; Knoevenagel Condensation;96%
3,4-dimethoxy-benzaldehyde
120-14-9

3,4-dimethoxy-benzaldehyde

ethyl 2-cyanoacetate
105-56-6

ethyl 2-cyanoacetate

ethyl (E)-2-cyano-3-(3,4-dimethoxyphenyl)-2-propenoate
24393-47-3

ethyl (E)-2-cyano-3-(3,4-dimethoxyphenyl)-2-propenoate

Conditions
ConditionsYield
With third generation polystyrene supported poly(amidoamine) dendrimer In ethanol at 50℃; for 0.333333h; Knoevenagel condensation;100%
With ASCPEI In ethanol at 43℃; for 2h; Knoevenagel condensation;98%
With ammonium acetate for 0.25h; Knoevenagel condensation; microwave irradiation;94%
isopropylamine
75-31-0

isopropylamine

ethyl 2-cyanoacetate
105-56-6

ethyl 2-cyanoacetate

2-cyano-N-isopropylacetamide
52573-74-7

2-cyano-N-isopropylacetamide

Conditions
ConditionsYield
for 18h;100%
With sodium hydroxide
(E)-3-phenylpropenal
14371-10-9

(E)-3-phenylpropenal

ethyl 2-cyanoacetate
105-56-6

ethyl 2-cyanoacetate

(2E,4E)-2-cyano-5-phenyl-2,4-pentadienoic acid ethyl ester
41109-95-9

(2E,4E)-2-cyano-5-phenyl-2,4-pentadienoic acid ethyl ester

Conditions
ConditionsYield
With 1,4-diaza-bicyclo[2.2.2]octane In neat liquid at 20℃; for 0.25h; Knoevenagel Condensation; Green chemistry;100%
With zinc(II) chloride at 100℃; for 1.5h;92%
With 1-methyl-piperazine at 25 - 30℃; for 0.166667h; Knoevenagel condensation;91%
ethyl 2-cyanoacetate
105-56-6

ethyl 2-cyanoacetate

Cyclopropylamine
765-30-0

Cyclopropylamine

2-cyano-N-cyclopropylacetamide
15029-37-5

2-cyano-N-cyclopropylacetamide

Conditions
ConditionsYield
at 45℃; for 1.5h;100%
at 38℃; for 2.33333h;91%
In ethanol at 20℃;82%
4-fluorobenzaldehyde
459-57-4

4-fluorobenzaldehyde

ethyl 2-cyanoacetate
105-56-6

ethyl 2-cyanoacetate

ethyl (E)-2-cyano-3-(4-fluorophenyl)-2-propenoate
18861-57-9, 50737-52-5

ethyl (E)-2-cyano-3-(4-fluorophenyl)-2-propenoate

Conditions
ConditionsYield
With 1-(3-silica-supported propyl)-3-[(3-{[1-(3-silica-supported propyl)-4,5-dihydro-1H-imidazol-3-ium-3-yl]methyl}-2,4,6-trimethylphenyl)methyl]-4,5-dihydro-1H-imidazol-3-ium chloride at 130℃; for 2h; Knoevenagel condensation;100%
With polyacrylonitrile fiber functionalized with N,N-dimethyl-1,3-propanediamine In ethanol for 1.5h; Knoevenagel condensation; Reflux;99%
With N-(propylcarbamoyl)sulfamic acid bonded on silica at 100℃; for 0.25h;97%
4-chlorobenzaldehyde
104-88-1

4-chlorobenzaldehyde

ethyl 2-cyanoacetate
105-56-6

ethyl 2-cyanoacetate

ethyl (E)-3-(4-chlorophenyl)-2-cyanoacrylate
2169-68-8

ethyl (E)-3-(4-chlorophenyl)-2-cyanoacrylate

Conditions
ConditionsYield
With L-proline for 0.0333333h; Knoevenagel condensation; microwave irradiation;100%
With IRA-96 anion-exchange resin In ethanol at 25 - 30℃; for 1h; Reagent/catalyst; Knoevenagel Condensation; Sonication; Green chemistry; stereoselective reaction;100%
With ammonium acetate; acetic acid for 0.0111111h; Knoevenagel condensation; Irradiation;99%
2-aminoacetophenone
551-93-9

2-aminoacetophenone

ethyl 2-cyanoacetate
105-56-6

ethyl 2-cyanoacetate

1,2-dihydro-2-oxo-4-methylquinoline-3-carbonitrile
28448-12-6

1,2-dihydro-2-oxo-4-methylquinoline-3-carbonitrile

Conditions
ConditionsYield
With ammonium acetate for 1h; Heating;100%
cerium(III) chloride for 0.1h; microwave irradiation;86%
With ammonium acetate at 220℃; for 0.25h;78%
4-nitrobenzaldehdye
555-16-8

4-nitrobenzaldehdye

ethyl 2-cyanoacetate
105-56-6

ethyl 2-cyanoacetate

(E)-ethyl 2-cyano-3-(4-nitrophenyl)acrylate
2017-89-2

(E)-ethyl 2-cyano-3-(4-nitrophenyl)acrylate

Conditions
ConditionsYield
With L-proline for 0.1h; Knoevenagel condensation; microwave irradiation;100%
With third generation polystyrene supported poly(amidoamine) dendrimer In ethanol at 50℃; for 0.333333h; Knoevenagel condensation;100%
With 1,4-diaza-bicyclo[2.2.2]octane In neat liquid at 20℃; for 0.0333333h; Knoevenagel Condensation; Green chemistry;100%
4-nitrobenzaldehdye
555-16-8

4-nitrobenzaldehdye

ethyl 2-cyanoacetate
105-56-6

ethyl 2-cyanoacetate

ethyl (Z)-2-cyano-3-(4-nitrophenyl)propenoate
96238-12-9

ethyl (Z)-2-cyano-3-(4-nitrophenyl)propenoate

Conditions
ConditionsYield
hydrotalcite structure integrating fluoride ions In acetonitrile at 60℃; for 1.5h; Conversion of starting material; Knoevenagel Condensation;100%
With PEG-600 at 20℃; for 0.25h; Knoevenagel condensation;95%
With lipase lipoprotein from Aspergillus niger In dimethyl sulfoxide at 35℃; for 48h; Knoevenagel Condensation; Green chemistry; Enzymatic reaction;94%
3,4,5-trimethoxy-benzaldehyde
86-81-7

3,4,5-trimethoxy-benzaldehyde

ethyl 2-cyanoacetate
105-56-6

ethyl 2-cyanoacetate

2-cyano-3-(3,4,5-trimethoxyphenyl)acrylic acid ethyl ester
2601-03-8

2-cyano-3-(3,4,5-trimethoxyphenyl)acrylic acid ethyl ester

Conditions
ConditionsYield
With ytterbium(III) triflate at 80 - 85℃; Knoevenagel condensation; neat (no solvent);100%
With recovered palladium catalyst In ethanol at 20℃; for 18h; Knoevenagel Condensation; Green chemistry;97%
With montmorillonitesilylpropylidenediamine In toluene Ambient temperature;96%
With piperidine In ethanol at 20℃;
In ethanol at 20℃; Knoevenagel Condensation; Sonication;

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The Knoevenagel condensation with chlorine substituted benzaldehyde is difficult because of deactivation of aldehyde group. In this work we have shown that the activity of mesoporous cellular foams (MCF and Nb/MCF), modified with 3-aminopropyl-trimethoxysilane (AP) as a source of basicity, can b...detailed

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