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2025-40-3 Usage

Synthesis Reference(s)

Organic Syntheses, Coll. Vol. 1, p. 451, 1941Synthetic Communications, 26, p. 683, 1996 DOI: 10.1080/00397919608086741

Check Digit Verification of cas no

The CAS Registry Mumber 2025-40-3 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 2,0,2 and 5 respectively; the second part has 2 digits, 4 and 0 respectively.
Calculate Digit Verification of CAS Registry Number 2025-40:
(6*2)+(5*0)+(4*2)+(3*5)+(2*4)+(1*0)=43
43 % 10 = 3
So 2025-40-3 is a valid CAS Registry Number.
InChI:InChI=1/C12H11NO2/c1-2-15-12(14)11(9-13)8-10-6-4-3-5-7-10/h3-8H,2H2,1H3/b11-8-

2025-40-3 Well-known Company Product Price

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  • TCI America

  • (C0448)  Ethyl α-Cyanocinnamate  >98.0%(GC)

  • 2025-40-3

  • 25g

  • 1,490.00CNY

  • Detail

2025-40-3SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 11, 2017

Revision Date: Aug 11, 2017

1.Identification

1.1 GHS Product identifier

Product name Cinnamic acid, .α.-cyano-, ethyl ester

1.2 Other means of identification

Product number -
Other names ETHYL-A-CYANOCINNAMATE

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:2025-40-3 SDS

2025-40-3Synthetic route

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%
benzaldehyde dimethyl acetal
1125-88-8

benzaldehyde dimethyl acetal

ethyl 2-cyanoacetate
105-56-6

ethyl 2-cyanoacetate

ethyl benzylidenecyanoacetate
2025-40-3

ethyl benzylidenecyanoacetate

Conditions
ConditionsYield
With DMAN-SO3H-SiO2-5-5 In water for 10h; Catalytic behavior; Reagent/catalyst; Knoevenagel Condensation;100%
With MS-SO3H(at)MS(at)MS-NH2 In toluene at 80℃; for 0.5h; Reagent/catalyst;100%
With water at 20℃; for 24h; Reagent/catalyst; Knoevenagel Condensation;100%
ethyl 2-cyanoacetate
105-56-6

ethyl 2-cyanoacetate

benzyl alcohol
100-51-6

benzyl alcohol

ethyl benzylidenecyanoacetate
2025-40-3

ethyl benzylidenecyanoacetate

Conditions
ConditionsYield
With dihydrogen peroxide In water; acetonitrile at 80℃; for 6h; Catalytic behavior; Kinetics; Reagent/catalyst; Solvent;99%
Stage #1: benzyl alcohol With oxygen; potassium carbonate In toluene at 89.84℃; for 24.5h; Schlenk technique;
Stage #2: ethyl 2-cyanoacetate In toluene Knoevenagel Condensation; Schlenk technique;
89%
With Ni nanoparticle immobilized-sulfonated imidazolium-based ionic liquid-functionalized magnetic silica nanoparticles; air In water for 1h; Heating;83%
dimethyl 2-benzylidenepropanedioate
6626-84-2

dimethyl 2-benzylidenepropanedioate

ethyl 2-cyanoacetate
105-56-6

ethyl 2-cyanoacetate

ethyl benzylidenecyanoacetate
2025-40-3

ethyl benzylidenecyanoacetate

Conditions
ConditionsYield
With recovered palladium catalyst In ethanol at 20℃; for 18h; Green chemistry;98%
benzaldehyde dimethyl acetal
1125-88-8

benzaldehyde dimethyl acetal

ethyl 2-cyanoacetate
105-56-6

ethyl 2-cyanoacetate

A

ethyl benzylidenecyanoacetate
2025-40-3

ethyl benzylidenecyanoacetate

B

benzaldehyde
100-52-7

benzaldehyde

Conditions
ConditionsYield
With water at 20℃; for 24h; Knoevenagel Condensation;A 8%
B 92%
With MS-SO3H(at)MS; MS(at)MS-NH2 In toluene at 80℃; for 0.5h; Reagent/catalyst;A 67%
B 17%
With tungsten oxide nanocluster supported mesoporous nitrogen-rich carbon In water; toluene at 90℃; for 22h; Catalytic behavior; Inert atmosphere;A 36.9%
B 9.4%
ethyl 2-cyanoacetate
105-56-6

ethyl 2-cyanoacetate

ethyl benzylidenecyanoacetate
2025-40-3

ethyl benzylidenecyanoacetate

Conditions
ConditionsYield
With sodium dodecyl-sulfate In water at 25 - 30℃; for 0.25h;85%
ethanol
64-17-5

ethanol

benzaldehyde
100-52-7

benzaldehyde

methyl 2-cyanoacetate
105-34-0

methyl 2-cyanoacetate

ethyl benzylidenecyanoacetate
2025-40-3

ethyl benzylidenecyanoacetate

Conditions
ConditionsYield
Stage #1: ethanol; benzaldehyde With lipase from porcine pancreas In dimethyl sulfoxide at 37℃; for 0.5h; Knoevenagel condensation/transesterification; Enzymatic reaction;
Stage #2: methyl 2-cyanoacetate In dimethyl sulfoxide at 37℃; for 12h; Kinetics; Knoevenagel condensation/transesterification; Enzymatic reaction;
85%
ethanol
64-17-5

ethanol

benzaldehyde
100-52-7

benzaldehyde

cyanoacetic acid amide
107-91-5

cyanoacetic acid amide

ethyl benzylidenecyanoacetate
2025-40-3

ethyl benzylidenecyanoacetate

Conditions
ConditionsYield
With 1,3,5-trichloro-2,4,6-triazine In neat (no solvent) at 80℃; for 12h; Reagent/catalyst;84%
benzaldehyde dimethyl acetal
1125-88-8

benzaldehyde dimethyl acetal

A

ethyl benzylidenecyanoacetate
2025-40-3

ethyl benzylidenecyanoacetate

B

benzoic acid
65-85-0

benzoic acid

Conditions
ConditionsYield
With poly((divinylbenzene)-sulfonic acid-amine) In water; toluene at 80℃; for 24h; Reagent/catalyst; Schlenk technique; Inert atmosphere;A 23%
B 75%
benzylidene phenylamine
538-51-2

benzylidene phenylamine

ethyl 2-cyanoacetate
105-56-6

ethyl 2-cyanoacetate

ethyl benzylidenecyanoacetate
2025-40-3

ethyl benzylidenecyanoacetate

Conditions
ConditionsYield
With Amberlite IRA-400(OH-) In ethanol for 6h; Heating;70%
solid form;
ethanol
64-17-5

ethanol

2-cyano-3-phenylacrylamide
709-79-5

2-cyano-3-phenylacrylamide

ethyl benzylidenecyanoacetate
2025-40-3

ethyl benzylidenecyanoacetate

Conditions
ConditionsYield
With 1,3,5-trichloro-2,4,6-triazine In acetonitrile at 80℃;68%
ethyl 2-cyanoacetate
105-56-6

ethyl 2-cyanoacetate

benzyl alcohol
100-51-6

benzyl alcohol

A

ethyl benzylidenecyanoacetate
2025-40-3

ethyl benzylidenecyanoacetate

B

benzaldehyde
100-52-7

benzaldehyde

Conditions
ConditionsYield
Stage #1: benzyl alcohol With NH2-MIL-101(Fe); oxygen In acetonitrile at 20℃; under 760.051 Torr; for 40h; Irradiation;
Stage #2: ethyl 2-cyanoacetate In acetonitrile Knoevenagel Condensation;
A 66%
B 5.4%
Stage #1: benzyl alcohol With oxygen; potassium carbonate In toluene at 89.84℃; for 24.5h; Schlenk technique;
Stage #2: ethyl 2-cyanoacetate In toluene Knoevenagel Condensation; Schlenk technique;
A 19%
B 58%
Nitroethane
79-24-3

Nitroethane

benzaldehyde
100-52-7

benzaldehyde

ethyl 2-cyanoacetate
105-56-6

ethyl 2-cyanoacetate

A

C14H16N2O4

C14H16N2O4

B

ethyl benzylidenecyanoacetate
2025-40-3

ethyl benzylidenecyanoacetate

Conditions
ConditionsYield
With N,N-dimethyl-cyclohexanamine; 1,3-bis(3,5-bis(trifluoro-ethyl)phenyl)thiourea In water at 20℃; for 4h;A 64%
B 32%
With 1,3-bis(3,5-bis(trifluoro-ethyl)phenyl)thiourea In water at 20℃; for 2h;A 16%
B 26%
1-(4-(benzylideneamino)phenyl)ethan-1-one
138469-36-0, 138469-40-6, 24296-67-1

1-(4-(benzylideneamino)phenyl)ethan-1-one

ethyl 2-cyanoacetate
105-56-6

ethyl 2-cyanoacetate

ethyl benzylidenecyanoacetate
2025-40-3

ethyl benzylidenecyanoacetate

Conditions
ConditionsYield
With pyridine In benzene for 0.25h; Heating;55%
(E)-N-benzylidenepyridine-2-sulfonamide
721453-65-2

(E)-N-benzylidenepyridine-2-sulfonamide

ethyl 2-cyanoacetate
105-56-6

ethyl 2-cyanoacetate

ethyl benzylidenecyanoacetate
2025-40-3

ethyl benzylidenecyanoacetate

Conditions
ConditionsYield
With C40H33BrN4O2Pd*CHCl3; silver trifluoromethanesulfonate In tetrahydrofuran at 20℃; for 4h; Molecular sieve; Inert atmosphere;55%
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
2-(α-benzylidenamino-benzyl)-2,4-dicyano-3-phenyl-glutaric acid diethyl ester

2-(α-benzylidenamino-benzyl)-2,4-dicyano-3-phenyl-glutaric acid diethyl ester

acetic anhydride
108-24-7

acetic anhydride

A

ethyl benzylidenecyanoacetate
2025-40-3

ethyl benzylidenecyanoacetate

B

benzaldehyde
100-52-7

benzaldehyde

Conditions
ConditionsYield
ethanol
64-17-5

ethanol

2-cyano-3-phenylacrylic acid
1011-92-3

2-cyano-3-phenylacrylic acid

ethyl benzylidenecyanoacetate
2025-40-3

ethyl benzylidenecyanoacetate

Conditions
ConditionsYield
With hydrogenchloride solid form;
With hydrogenchloride
sodium ethanolate
141-52-6

sodium ethanolate

benzaldehyde
100-52-7

benzaldehyde

ethyl 2-cyanoacetate
105-56-6

ethyl 2-cyanoacetate

ethyl benzylidenecyanoacetate
2025-40-3

ethyl benzylidenecyanoacetate

Conditions
ConditionsYield
ethanol
64-17-5

ethanol

diethyl benzalmalonate
5292-53-5

diethyl benzalmalonate

diethylamine
109-89-7

diethylamine

ethyl 2-cyanoacetate
105-56-6

ethyl 2-cyanoacetate

ethyl benzylidenecyanoacetate
2025-40-3

ethyl benzylidenecyanoacetate

Conditions
ConditionsYield
at 20℃; nachfolgend Vakuumdestillation;
diethyl benzalmalonate
5292-53-5

diethyl benzalmalonate

ethyl 2-cyanoacetate
105-56-6

ethyl 2-cyanoacetate

N,N-diethylaniline
91-66-7

N,N-diethylaniline

ethyl benzylidenecyanoacetate
2025-40-3

ethyl benzylidenecyanoacetate

Conditions
ConditionsYield
diethyl benzalmalonate
5292-53-5

diethyl benzalmalonate

ethyl 2-cyanoacetate
105-56-6

ethyl 2-cyanoacetate

ethyl benzylidenecyanoacetate
2025-40-3

ethyl benzylidenecyanoacetate

Conditions
ConditionsYield
With ethanol; diethylamine at 20℃; man destilliert das Reaktionsprodukt im Vakuum;
ethyl 2-cyanoacetate
105-56-6

ethyl 2-cyanoacetate

hydrobenzamide
92-29-5

hydrobenzamide

ethyl benzylidenecyanoacetate
2025-40-3

ethyl benzylidenecyanoacetate

Conditions
ConditionsYield
With benzene in einer Atmosphaere die durch Schwefelsaeure dauernd von dem entstehenden NH3 befreit wird; solid form;
ethyl iodide
75-03-6

ethyl iodide

α-cyano-cinnamate of silver

α-cyano-cinnamate of silver

ethyl benzylidenecyanoacetate
2025-40-3

ethyl benzylidenecyanoacetate

Conditions
ConditionsYield
With ethanol solid form;
liquid form

liquid form

ethyl benzylidenecyanoacetate
2025-40-3

ethyl benzylidenecyanoacetate

Conditions
ConditionsYield
durch Destillation; solid form;
With sodium hydroxide solid form;
With sodium carbonate solid form;
benzaldehyde
100-52-7

benzaldehyde

ethyl 2-cyanoacetate
105-56-6

ethyl 2-cyanoacetate

A

ethyl benzylidenecyanoacetate
2025-40-3

ethyl benzylidenecyanoacetate

B

solid form

solid form

Conditions
ConditionsYield
With piperidine liquid form;
ethanol
64-17-5

ethanol

ethyl 2-cyanoacetate
105-56-6

ethyl 2-cyanoacetate

benzaniline

benzaniline

ethyl benzylidenecyanoacetate
2025-40-3

ethyl benzylidenecyanoacetate

Conditions
ConditionsYield
2-(α-benzylidenamino-benzyl)-2,4-dicyano-3-phenyl-glutaric acid diethyl ester

2-(α-benzylidenamino-benzyl)-2,4-dicyano-3-phenyl-glutaric acid diethyl ester

A

ammonia
7664-41-7

ammonia

B

ethyl benzylidenecyanoacetate
2025-40-3

ethyl benzylidenecyanoacetate

C

benzaldehyde
100-52-7

benzaldehyde

Conditions
ConditionsYield
at 200℃; beim Schmelzen;
C12H12NO2(1-)

C12H12NO2(1-)

ethyl benzylidenecyanoacetate
2025-40-3

ethyl benzylidenecyanoacetate

Conditions
ConditionsYield
With 10-methylacridinium cation In acetonitrile at 25℃; Thermodynamic data;
ethyl benzylidenecyanoacetate
2025-40-3

ethyl benzylidenecyanoacetate

ethyl 2-cyano-3-phenylpropanoate
6731-58-4

ethyl 2-cyano-3-phenylpropanoate

Conditions
ConditionsYield
With Hantzsch ester In tetrahydrofuran at 20℃; for 0.5h; chemoselective reaction;99%
With hydrogen In ethanol at 20℃; under 760.051 Torr; for 1h; chemoselective reaction;98%
With 1-n-butyl-3-methylimidazolium borohydride In water; acetonitrile at 20℃; for 0.666667h; chemoselective reaction;85%
N-cycloheptatrienylidene-4-methyl-aniline
949-68-8

N-cycloheptatrienylidene-4-methyl-aniline

ethyl benzylidenecyanoacetate
2025-40-3

ethyl benzylidenecyanoacetate

ethyl 3-cyano-1,2,3,3a-tetrahydro-2-phenyl-1-p-tolylcyclohepta[b]pyrrole-3-carboxylate

ethyl 3-cyano-1,2,3,3a-tetrahydro-2-phenyl-1-p-tolylcyclohepta[b]pyrrole-3-carboxylate

Conditions
ConditionsYield
With nickel(II) tetrafluoroborate hexahydrate; C43H64N4O4 In dichloromethane at 35℃; for 2h; diastereoselective reaction;99%
6-hydrazino-1,3-dimethyl-1H-pyrimidine-2,4-dione
123506-40-1

6-hydrazino-1,3-dimethyl-1H-pyrimidine-2,4-dione

ethyl benzylidenecyanoacetate
2025-40-3

ethyl benzylidenecyanoacetate

A

1,7-Dihydro-5,7-dimethyl-3-phenyl-4H-pyrazolo<3,4-d>pyrimidin-4,6(5H)-dion
35221-08-0

1,7-Dihydro-5,7-dimethyl-3-phenyl-4H-pyrazolo<3,4-d>pyrimidin-4,6(5H)-dion

B

Benzylmalononitrile
1867-37-4

Benzylmalononitrile

C

malononitrile
109-77-3

malononitrile

Conditions
ConditionsYield
In propan-1-ol for 2h; Heating;A 90%
B 97%
C 90%
benzamidine monohydrochloride
1670-14-0

benzamidine monohydrochloride

ethyl benzylidenecyanoacetate
2025-40-3

ethyl benzylidenecyanoacetate

6-oxo-2,4-diphenyl-1,6-dihydro-pyrimidine-5-carbonitrile
737-54-2

6-oxo-2,4-diphenyl-1,6-dihydro-pyrimidine-5-carbonitrile

Conditions
ConditionsYield
With magnesium oxide In acetonitrile for 0.433333h; Michael addition; Reflux;97%
With bismuth (III) nitrate pentahydrate; triethylamine In acetonitrile for 0.3h; Catalytic behavior; Michael Addition; Reflux;96%
In pyridine Heating;78%
With sodium ethanolate In N,N-dimethyl acetamide for 4h; Reflux;77%
ethyl benzylidenecyanoacetate
2025-40-3

ethyl benzylidenecyanoacetate

thiourea
17356-08-0

thiourea

5-Cyano-4-oxo-6-phenyl-2-thioxohexahydropyrimidine
81585-29-7

5-Cyano-4-oxo-6-phenyl-2-thioxohexahydropyrimidine

Conditions
ConditionsYield
With sodium methylate In methanol at 20℃; for 0.5h;97%
With sodium ethanolate In ethanol at 20℃;
With chromium(III) chloride hexahydrate; potassium hydroxide In water; acetonitrile at 20℃; for 24h;
ethyl benzylidenecyanoacetate
2025-40-3

ethyl benzylidenecyanoacetate

Diethyl 2-bromomalonate
685-87-0

Diethyl 2-bromomalonate

triethyl (2,3-trans)-2-cyano-3-phenylcyclopropane-1,1,2-tricarboxylate

triethyl (2,3-trans)-2-cyano-3-phenylcyclopropane-1,1,2-tricarboxylate

Conditions
ConditionsYield
With triethylamine In N,N-dimethyl-formamide at 20℃; for 10h; Reagent/catalyst; Temperature;97%
In toluene at 20℃; for 3h;
ethyl benzylidenecyanoacetate
2025-40-3

ethyl benzylidenecyanoacetate

2-Pentanone
107-87-9

2-Pentanone

ethyl 2-(3-oxo-3-methyl-1-phenylpentyl)cyanoacetate

ethyl 2-(3-oxo-3-methyl-1-phenylpentyl)cyanoacetate

Conditions
ConditionsYield
With L-proline In methanol at 20℃; for 168h; Michael Addition;96%
ethyl benzylidenecyanoacetate
2025-40-3

ethyl benzylidenecyanoacetate

N-bromoacetamide
79-15-2

N-bromoacetamide

5-cyano-5-ethoxyformacyl-2-methyl-4-phenyl-4,5-dihydrooxazole
1486487-83-5

5-cyano-5-ethoxyformacyl-2-methyl-4-phenyl-4,5-dihydrooxazole

Conditions
ConditionsYield
With potassium phosphate In acetone at 20℃; for 2.5h; Solvent; Reagent/catalyst; Time; Concentration;96%
3-acetyl-4-hydroxy-1-methyl-2(1H)-quinolone
54289-76-8

3-acetyl-4-hydroxy-1-methyl-2(1H)-quinolone

ethyl benzylidenecyanoacetate
2025-40-3

ethyl benzylidenecyanoacetate

2-Amino-6-(4-hydroxy-1-methyl-2-oxo-1,2-dihydro-quinolin-3-yl)-4-phenyl-4H-pyran-3-carboxylic acid ethyl ester
128405-29-8

2-Amino-6-(4-hydroxy-1-methyl-2-oxo-1,2-dihydro-quinolin-3-yl)-4-phenyl-4H-pyran-3-carboxylic acid ethyl ester

Conditions
ConditionsYield
With piperidine In ethanol for 0.166667h; Heating;95%
4-hydroxy-6-methyl-2-pyron
675-10-5

4-hydroxy-6-methyl-2-pyron

ethyl benzylidenecyanoacetate
2025-40-3

ethyl benzylidenecyanoacetate

ethyl 2-amino-5-oxo-4-phenyl-7-methyl-4H,5H-pyrano[3,2-c]pyran-3-carboxylate

ethyl 2-amino-5-oxo-4-phenyl-7-methyl-4H,5H-pyrano[3,2-c]pyran-3-carboxylate

Conditions
ConditionsYield
With N-benzyl-N,N,N-triethylammonium chloride In water at 90℃; for 10h;95%
ethyl benzylidenecyanoacetate
2025-40-3

ethyl benzylidenecyanoacetate

3-phenyl-6-oxo-2,3,4,5,6,7-hexahydrothiazolo<3,2-a>-1,3,5-triazine
78153-30-7

3-phenyl-6-oxo-2,3,4,5,6,7-hexahydrothiazolo<3,2-a>-1,3,5-triazine

(Z)-7-benzylidene-3-phenyl-3,4-dihydro-2H-thiazolo[3,2-a][1,3,5]triazin-6(7H)-one
1334176-95-2

(Z)-7-benzylidene-3-phenyl-3,4-dihydro-2H-thiazolo[3,2-a][1,3,5]triazin-6(7H)-one

Conditions
ConditionsYield
With triethylamine In methanol for 1h; Claisen-Schmidt Condensation; Reflux;95%
ethyl benzylidenecyanoacetate
2025-40-3

ethyl benzylidenecyanoacetate

3β-acetoxy-16-formyl-17-acetamido-androst-5,16-diene
219635-54-8

3β-acetoxy-16-formyl-17-acetamido-androst-5,16-diene

3β-acetoxy-17-acetamido-androst-5,16-dieno-16-formylidenecyanoacetate

3β-acetoxy-17-acetamido-androst-5,16-dieno-16-formylidenecyanoacetate

Conditions
ConditionsYield
With 1-pyrroline In ethanol at 20℃; for 3h; Substitution;94%
diethyl 2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate
1149-23-1

diethyl 2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate

ethyl benzylidenecyanoacetate
2025-40-3

ethyl benzylidenecyanoacetate

A

ethyl 2-cyano-3-phenylpropanoate
6731-58-4

ethyl 2-cyano-3-phenylpropanoate

B

2,6-dimethyl-pyridine-3,5-dicarboxylic acid diethyl ester
1149-24-2

2,6-dimethyl-pyridine-3,5-dicarboxylic acid diethyl ester

Conditions
ConditionsYield
In acetonitrile at 20℃; for 24h; Kinetics; Further Variations:; Temperatures; Reduction; oxidation;A 94%
B n/a
1,3-cylohexanedione
504-02-9

1,3-cylohexanedione

ethyl benzylidenecyanoacetate
2025-40-3

ethyl benzylidenecyanoacetate

2-amino-5,6,7,8-tetrahydro-5-oxo-4-phenyl-4H-benzo--pyran-3-ethylcarboxylate
107752-85-2

2-amino-5,6,7,8-tetrahydro-5-oxo-4-phenyl-4H-benzo--pyran-3-ethylcarboxylate

Conditions
ConditionsYield
With cobalt(II) diacetate tetrahydrate; (R,R)-N,N'-bis(3,5-di-tert-butylsalicylidene)-1,2-cyclohexanediamine In tetrahydrofuran at 20℃; for 24h; Tandem Michael addition - cyclization reaction;94%
In ethylene glycol at 80℃; for 4h;
ethyl benzylidenecyanoacetate
2025-40-3

ethyl benzylidenecyanoacetate

phenylboronic acid
98-80-6

phenylboronic acid

ethyl α-cyano-ββ-diphenylpropionate
25634-96-2

ethyl α-cyano-ββ-diphenylpropionate

Conditions
ConditionsYield
With water In 1,4-dioxane at 60℃; for 6h;94%
ethyl 2,3-butadienoate
14369-81-4

ethyl 2,3-butadienoate

ethyl benzylidenecyanoacetate
2025-40-3

ethyl benzylidenecyanoacetate

(1R,2R)-diethyl 1-cyano-2-phenylcyclopent-3-ene-1,3-dicarboxylate
1239019-85-2

(1R,2R)-diethyl 1-cyano-2-phenylcyclopent-3-ene-1,3-dicarboxylate

Conditions
ConditionsYield
With N-((2S,3S)-1-(diphenylphosphino)-3-methylpentan-2-yl)-3,5-bis(trifluoromethyl)benzamide In toluene at 20℃; for 6h; optical yield given as %ee; enantioselective reaction;93%
ethyl benzylidenecyanoacetate
2025-40-3

ethyl benzylidenecyanoacetate

3-benzylideneazetidine-2,4-dione

3-benzylideneazetidine-2,4-dione

Conditions
ConditionsYield
With tin(II) chloride dihdyrate In 1,4-dioxane at 120℃; for 24h;93%
ethyl benzylidenecyanoacetate
2025-40-3

ethyl benzylidenecyanoacetate

N-(benzothiazol-2-yl)-2-cyanoacetamide
170802-47-8

N-(benzothiazol-2-yl)-2-cyanoacetamide

1-(benzothiazol-2-yl)-6-hydroxy-2-oxo-4-phenyl-1,2-dihydropyridin-3,5-dicarbonitrile

1-(benzothiazol-2-yl)-6-hydroxy-2-oxo-4-phenyl-1,2-dihydropyridin-3,5-dicarbonitrile

Conditions
ConditionsYield
With L-proline In ethanol at 80℃; for 0.333333h; Michael Addition; Sonication;93%
ethyl benzylidenecyanoacetate
2025-40-3

ethyl benzylidenecyanoacetate

3β-benzoyloxy-17-acetamido-16-formylandrosta-5,16-diene
246871-69-2

3β-benzoyloxy-17-acetamido-16-formylandrosta-5,16-diene

3β-benzoyloxy-17-acetamido-androst-5,16-dieno-16-formylidenecyanoacetate

3β-benzoyloxy-17-acetamido-androst-5,16-dieno-16-formylidenecyanoacetate

Conditions
ConditionsYield
With 1-pyrroline In ethanol at 20℃; for 3h; Substitution;92%
ethyl benzylidenecyanoacetate
2025-40-3

ethyl benzylidenecyanoacetate

ethyl 2-cyano-3-phenyloxirane-2-carboxylate
25015-52-5

ethyl 2-cyano-3-phenyloxirane-2-carboxylate

Conditions
ConditionsYield
With calcium hypochlorite In neat (no solvent) at 20℃; for 0.5h; Milling;91%
With pyrene-1,6-dione; oxygen; sodium carbonate; isopropyl alcohol at 20℃; under 760.051 Torr; for 18h; Irradiation; Green chemistry;62%
With Novozym 435; urea hydrogen peroxide adduct In ethyl acetate; N,N-dimethyl-formamide at 50℃; for 3h; Green chemistry;
ethyl benzylidenecyanoacetate
2025-40-3

ethyl benzylidenecyanoacetate

2-hydrazino-3-phenylquinoxaline
1025-22-5

2-hydrazino-3-phenylquinoxaline

(E)-2-(2-(2-benzylidene)hydrazinyl)-3-phenylquinoxaline

(E)-2-(2-(2-benzylidene)hydrazinyl)-3-phenylquinoxaline

Conditions
ConditionsYield
With piperidine In ethanol for 3h; Heating;90.9%
5-benzylidene-2-cyanomethylene-4-oxotetrahydrothiazole
14230-00-3

5-benzylidene-2-cyanomethylene-4-oxotetrahydrothiazole

ethyl benzylidenecyanoacetate
2025-40-3

ethyl benzylidenecyanoacetate

5-amino-2-benzylidene-6-ethoxycarbonyl-7-phenyl-7H-thiazolo<3,2-a>pyrimidin-3-one
129650-67-5

5-amino-2-benzylidene-6-ethoxycarbonyl-7-phenyl-7H-thiazolo<3,2-a>pyrimidin-3-one

Conditions
ConditionsYield
With triethylamine In ethanol for 2h; Heating;90%
ethyl benzylidenecyanoacetate
2025-40-3

ethyl benzylidenecyanoacetate

2,3-naphthalenediol
92-44-4

2,3-naphthalenediol

2,11-Diamino-4,9-diphenyl-4,9-dihydro-1,12-dioxa-triphenylene-3,10-dicarboxylic acid diethyl ester
128405-08-3

2,11-Diamino-4,9-diphenyl-4,9-dihydro-1,12-dioxa-triphenylene-3,10-dicarboxylic acid diethyl ester

Conditions
ConditionsYield
With piperidine In ethanol for 0.5h; Heating;90%
ethyl benzylidenecyanoacetate
2025-40-3

ethyl benzylidenecyanoacetate

phosphonic acid diethyl ester
762-04-9

phosphonic acid diethyl ester

diethyl (2,2-dicyano-1-(5-methylfuran-2-yl)ethyl)phosphonate
22730-58-1

diethyl (2,2-dicyano-1-(5-methylfuran-2-yl)ethyl)phosphonate

Conditions
ConditionsYield
With 3-aminopropylated silica gel at 50℃; for 1h; phospha-Michael addition; Neat (no solvent); optical yield given as %de;90%
With potassium carbonate In ethanol at 20 - 40℃; Addition;84%
With mercapto-functionalized silica-coated nano γ-Fe2O3-pyridine In neat (no solvent) at 70℃; for 3h; Michael Addition; Green chemistry;75%
(i) Na, benzene, (ii) /BRN= 392174/; Multistep reaction;
4-hydroxy[1]benzopyran-2-one
1076-38-6

4-hydroxy[1]benzopyran-2-one

ethyl benzylidenecyanoacetate
2025-40-3

ethyl benzylidenecyanoacetate

ethyl 2-amino-4-phenyl-5-oxo-4,5-dihydropyrano[3,2-c]chromene-3-carboxylate

ethyl 2-amino-4-phenyl-5-oxo-4,5-dihydropyrano[3,2-c]chromene-3-carboxylate

Conditions
ConditionsYield
With N-benzyl-N,N,N-triethylammonium chloride In water at 90℃; for 8h;90%
With tetrabutylammomium bromide In water at 80℃; for 0.25h;90%
With potassium fluoride; Montmorillonite In N,N-dimethyl-formamide at 90℃; for 8h;85%
With piperidine In ethanol for 2h; Condensation; Heating;
With air In ethanol at 20℃; Green chemistry;

2025-40-3Relevant articles and documents

Highly active hybrid mesoporous silica-supported base organocatalysts for C–C bond formation

Erigoni,Hernández-Soto,Rey,Segarra,Díaz

, p. 227 - 236 (2020)

New base hybrid catalysts, based on silyl-derivatives of molecules carrying amino, diamino, pyrrolidine, pyrazolium and imidazolium functionalities have been successfully achieved through post synthetic grafting onto M41S-type support. Different character

H3PW12O40/mpg-C3N4 as an efficient and reusable bifunctional catalyst in one-pot oxidation-Knoevenagel condensation tandem reaction

Wang, Hefang,Wang, Cunyue,Yang, Yongfang,Zhao, Meng,Wang, Yanji

, p. 405 - 417 (2017)

A single-site bifunctional catalyst for the oxidation-Knoevenagel condensation tandem reaction was prepared by the immobilization of phosphotungstic acid (HPW) on mesoporous graphitic carbon nitride (mpg-C3N4) via electrostatic interaction (HPW/mpg-C3N4). The results of Fourier transform infrared spectroscopy (FT-IR), X-ray diffraction (XRD), solid-state 31P nuclear magnetic resonance (solid-state 31P NMR), zeta potentials, X-ray photoelectron spectroscopy (XPS) and thermogravimetric analysis (TGA) demonstrated that HPW was successfully immobilized on the protonated mpg-C3N4 by electrostatic interaction. The acid amounts of the catalysts were determined by NH3 temperature programmed desorption (NH3-TPD). The textural properties and morphology of HPW/mpg-C3N4 were characterized by N2 adsorption-desorption, scanning electron microscopy (SEM) and transmission electron microscopy (TEM). 30% HPW/mpg-C3N4 shows the best catalytic performance in the tandem reaction with 98.4% benzyl alcohol conversion and 96.2% selectivity to benzylidene malononitrile. The excellent catalytic performance of 30% HPW/mpg-C3N4 in the tandem reaction is due to the good catalytic performance of HPW in the oxidation and Knoevenagel condensation, respectively. Furthermore, protonated mpg-C3N4 not only acts as a support to facilitate good dispersion of HPW but also promotes the Knoevenagel condensation reaction effectively. Moreover, the HPW/mpg-C3N4 catalyst could be recycled easily without significant loss of catalytic activity.

Knoevenagel condensation catalysed by new montmorillonitesilylpropylethylenediamine

Subba Rao,Choudary

, p. 1163 - 1166 (1991)

-

Polystyrene Nanometer-Sized Particles Supported Alkaline Imidazolium Ionic Liquids as Reusable and Efficient Catalysts for the Knoevenagel Condensation in Aqueous Phase

Ma, Min,Li, Hansheng,Yang, Wang,Wu, Qin,Shi, Daxin,Zhao, Yun,Feng, Caihong,Jiao, Qingze

, p. 134 - 143 (2018)

Abstract: Polystyrene nanometer-sized particles supported alkaline 1-propyl imidazolium ionic liquids catalysts (nano-PS-CH2-[pIM][B]) were prepared and characterized by FT-IR, SEM, TG/DTA, BET and particle size distribution analysis. The resul

Efficient bifunctional reactivity of K-doped CrO(OH) nanosheets: Exploiting the combined role of Cr(iii) and surface -OH groups in tandem catalysis

Vernekar, Dnyanesh,Ratha, Satyajit,Rode, Chandrashekhar,Jagadeesan, Dinesh

, p. 1154 - 1164 (2019)

This work reports the bifunctional catalytic activity of layered K-doped α-CrO(OH). The combined action of the redox active Cr(iii) and the surface hydroxyl groups was efficiently used to carry out 2-3 oxidation reactions in tandem followed by condensation/coupling reactions in one pot. Oxidation of benzyl alcohol followed by Knoevenagel condensation or coupling reactions forming C-C and C-N linkages in one pot is demonstrated. The catalyst has been characterized using XRD, IR, TGA, CO2-TPD, cyclic voltammetry, XPS and microscopic techniques to gain insight into the nature of active sites. The role of O- and O2- on the CrO(OH) catalyst in the bifunctional activity was studied using analytical techniques. Recyclability and leaching tests confirmed that K-α-CrO(OH) is a stable and environmentally safe catalyst.

Synthesis of cyclopropane-1,1,2,2-tetracarboxylic acid derivatives from aldehydes and CH-acids in the K2CO3/Bun 4NPF6/toluene heterogeneous system

Kryshtal, G. V.,Zhdankina, G. M.,Zlotin, S. G.

, p. 2286 - 2290,5 (2011)

A one-pot method for the synthesis of cyclopropane-1,1,2,2-tetracarboxylic derivatives was developed starting from aldehydes and cyanoacetic and 2-bromomalonic esters under heterogeneous conditions (K2CO 3/PhMe) in the presence of re

Highly active zinc oxide-supported lithium oxide catalyst for solvent-free Knoevenagel condensation

Basude, Manohar,Bhongiri, Yadagiri,Masula, Keshavulu,Pasala, Vijay Kumar,Puppala, Veerasomaiah,Sunkara, Prasad

, (2021/07/09)

Li2O/ZnO catalyst was prepared by wet impregnation method and characterized by XRD, SEM, EDX, FTIR, BET surface area and UV-Vis diffuse reflectance spectroscopy. This study revealed a decrease in average particle size and change in the shape of

Synthesis of lithium/cesium-Zagronas from zagrosian natural asphalt and study of their activity as novel, green, heterogeneous and homogeneous nanocatalysts in the Claisen–Schmidt and Knoevenagel condensations

Soleiman-Beigi, Mohammad,Ghalavand, Saba,Venovel, Hadis Gholami,Kohzadi, Homa

, p. 3267 - 3279 (2021/06/17)

A novel, heterogeneous and homogeneous basic nanocatalysts were synthesized by grafting of lithium and cesium on zagrosian natural asphalt sulfonate (Li/Cs-Zagronas). The activity of these catalysts was examined in the Claisen–Schmidt and Knoevenagel condensations under mild reaction conditions. Li/Cs-Zagronas were characterized by FT-IR spectroscopy, scanning electron microscopy, X-ray diffraction, energy-dispersive spectroscopy, inductively coupled plasma and thermogravimetric analysis techniques. These nanocatalysts were removed by simple filtration and reused several times without any deterioration of activity.

MOFs assembled from C 3symmetric ligands: Structure, iodine capture and role as bifunctional catalysts towards the oxidation-Knoevenagel cascade reaction

Zhang, Ying-Ying,Liu, Qing,Zhang, Lin-Yan,Bao, Yu-Mei,Tan, Jing-Yi,Zhang, Na,Zhang, Jian-Yong,Liu, Zhen-Jiang

, p. 647 - 659 (2021/01/28)

Three new NiII/CoII-metal organic frameworks were self-assembled by the reaction of C3 symmetric 1,3,5-tribenzoic acid (H3BTC) and 2,4,6-tris(4-pyridyl)-1,3,5-triazine (4-TPT) ligands and NiII/CoII salts under solvothermal conditions. Isomorphous MOF1 and MOF2 exhibit a 3D pillar-layer framework based on binuclear M2(OH)(COO)2 units connected by tritopic BTC3- and 4-TPT ligands with a novel (3,5)-connected topology net. MOF3 displays a 3-fold interpenetrated 3D network exhibiting a (3,4)-connected topology net. The porous MOF3 can reversibly take up I2. The activated MOFs contain both Lewis acid (NiII center) and basic (uncoordinated pyridyl or carboxylic groups) sites, and act as bifunctional acid-base catalysts. The catalytic measurements demonstrate that the activated MOF3 exhibits good activities for benzyl alcohol oxidation and the Knoevenagel reaction and can be recycled and reused for at least four cycles without losing its structural integrity and high catalytic activity. Thus, the catalytic properties for the oxidation-Knoevenagel cascade reaction have also been studied.

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