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40497-11-8

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40497-11-8 Usage

Synthesis

The preparation method of Ethyl 2,3-dicyanopropionate is to add potassium cyanide solution and ethyl cyanoacetate into the reaction flask, use dimethyl sulfoxide as solvent, slowly add formaldehyde solution to the solution, and maintain the reaction temperature at 5 ℃ After the addition, the reaction was continued at 20°C for 15h, then the reaction solution was added to ice water, the organic layer was separated, the aqueous layer was extracted with a solvent, the organic layers were mixed, dried and desolubilized to obtain the product. Reaction equation: HCHO+KCN+CNCH2COOC2H5→CNCH2—CHCNCOOC2H5

Chemical Properties

Brown Oil

Uses

Different sources of media describe the Uses of 40497-11-8 differently. You can refer to the following data:
1. An intermediate for insecticide.
2. An intermediate for insecticide

Check Digit Verification of cas no

The CAS Registry Mumber 40497-11-8 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 4,0,4,9 and 7 respectively; the second part has 2 digits, 1 and 1 respectively.
Calculate Digit Verification of CAS Registry Number 40497-11:
(7*4)+(6*0)+(5*4)+(4*9)+(3*7)+(2*1)+(1*1)=108
108 % 10 = 8
So 40497-11-8 is a valid CAS Registry Number.
InChI:InChI=1/C7H8N2O2/c1-2-11-7(10)6(5-9)3-4-8/h6H,2-3H2,1H3

40497-11-8SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 19, 2017

Revision Date: Aug 19, 2017

1.Identification

1.1 GHS Product identifier

Product name Ethyl 2,3-dicyanopropanoate

1.2 Other means of identification

Product number -
Other names Ethyl 2,3-Dicyanopropionate

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:40497-11-8 SDS

40497-11-8Synthetic route

sodium cyanide
773837-37-9

sodium cyanide

formaldehyd
50-00-0

formaldehyd

ethyl 2-cyanoacetate
105-56-6

ethyl 2-cyanoacetate

ethyl 2,3-dicyanopropanoate
40497-11-8

ethyl 2,3-dicyanopropanoate

Conditions
ConditionsYield
Stage #1: sodium cyanide; formaldehyd In N,N-dimethyl-formamide for 2h; Reflux;
Stage #2: ethyl 2-cyanoacetate In N,N-dimethyl-formamide at 28 - 30℃; for 4h; Temperature;
98.5%
With 2-amino-3-hydroxypyridine; 2-Amino-2-methylpropane-1,3-diol; diethyl malonate In dimethyl sulfoxide at 20℃; for 20h; Temperature; Reagent/catalyst;97.2%
Stage #1: sodium cyanide; formaldehyd In ethanol at 5 - 10℃; for 4h;
Stage #2: With hydrogenchloride In ethanol at 5 - 10℃;
Stage #3: ethyl 2-cyanoacetate With ethanol; sodium at 5 - 30℃; for 10h; Product distribution / selectivity;
75.2%
In ethanol; dichloromethane for 0.666667h; Reflux;63%
With tetrabutylammomium bromide In dichloromethane; water at 10 - 90℃; Reagent/catalyst; Solvent;81.21 g
sodium cyanide
773837-37-9

sodium cyanide

ethyl 2-cyanoacrylate
7085-85-0

ethyl 2-cyanoacrylate

ethyl 2,3-dicyanopropanoate
40497-11-8

ethyl 2,3-dicyanopropanoate

Conditions
ConditionsYield
Stage #1: sodium cyanide In isopropyl alcohol at 30℃; for 4h;
Stage #2: ethyl-2-cyanoacrilate With methanesulfonic acid In isopropyl alcohol at 20 - 25℃; for 6h; Solvent; Reagent/catalyst; Temperature;
86%
Stage #1: sodium cyanide; ethyl-2-cyanoacrilate With methanesulfonic acid In isopropyl alcohol at 20 - 25℃; for 6h;
Stage #2: With hydrogenchloride In isopropyl alcohol at 10℃; Product distribution / selectivity;
trimethylsilyl cyanide
7677-24-9

trimethylsilyl cyanide

ethyl (E)-3-[(4-methylphenyl)sulfonyl]-2-propenoate
117659-25-3

ethyl (E)-3-[(4-methylphenyl)sulfonyl]-2-propenoate

ethyl 2,3-dicyanopropanoate
40497-11-8

ethyl 2,3-dicyanopropanoate

Conditions
ConditionsYield
With tetrabutyl ammonium fluoride In tetrahydrofuran; acetonitrile at 20℃; for 2h; Michael Addition; Inert atmosphere;83%
formaldehyd
50-00-0

formaldehyd

potassium cyanide
151-50-8

potassium cyanide

ethyl 2-cyanoacetate
105-56-6

ethyl 2-cyanoacetate

ethyl 2,3-dicyanopropanoate
40497-11-8

ethyl 2,3-dicyanopropanoate

Conditions
ConditionsYield
With water In dimethyl sulfoxide at 20℃; for 15h;80%
In ethanol
glycolonitrile
107-16-4

glycolonitrile

ethyl 2-cyanoacetate
105-56-6

ethyl 2-cyanoacetate

ethyl 2,3-dicyanopropanoate
40497-11-8

ethyl 2,3-dicyanopropanoate

Conditions
ConditionsYield
Stage #1: ethyl 2-cyanoacetate With sodium ethanolate In ethanol for 0.5h;
Stage #2: glycolonitrile In ethanol at 5 - 30℃; for 8h;
Stage #3: In ethanol; water at 5 - 10℃; pH=4.45;
79.6%
Stage #1: ethyl 2-cyanoacetate With sodium ethanolate; sodium In ethanol for 0.5h;
Stage #2: glycolonitrile In ethanol at 5 - 30℃; for 8h;
79.6%
With potassium carbonate In N,N-dimethyl-formamide at 15 - 25℃; Product distribution / selectivity;77%
With sodium ethanolate In ethanol for 1h; Heating;
Stage #1: ethyl 2-cyanoacetate With ethanol; sodium for 0.5h;
Stage #2: glycolonitrile In ethanol at 5 - 30℃; for 8h;
ethyl 2-cyanoacetate
105-56-6

ethyl 2-cyanoacetate

ethyl 2,3-dicyanopropanoate
40497-11-8

ethyl 2,3-dicyanopropanoate

Conditions
ConditionsYield
With paraformaldehyde In ethanol; water77%
ethanol
64-17-5

ethanol

sodium cyanoacetic acid ethyl ester
18852-51-2

sodium cyanoacetic acid ethyl ester

glycolonitrile
107-16-4

glycolonitrile

ethyl 2,3-dicyanopropanoate
40497-11-8

ethyl 2,3-dicyanopropanoate

Conditions
ConditionsYield
in kaltem Alkohol;
sodium cyanoacetic acid ethyl ester
18852-51-2

sodium cyanoacetic acid ethyl ester

glycolonitrile
107-16-4

glycolonitrile

ethyl 2,3-dicyanopropanoate
40497-11-8

ethyl 2,3-dicyanopropanoate

Conditions
ConditionsYield
With ethanol
diethyl sulfate
64-67-5

diethyl sulfate

carbon dioxide
124-38-9

carbon dioxide

tetraethylammoniumcyanide
13435-20-6

tetraethylammoniumcyanide

acrylonitrile
107-13-1

acrylonitrile

ethyl 2,3-dicyanopropanoate
40497-11-8

ethyl 2,3-dicyanopropanoate

Conditions
ConditionsYield
(i), (ii) /BRN= 605310/, (iii) /BRN= 1209714/; Multistep reaction;
potassium cyanide
151-50-8

potassium cyanide

Ethyl 2-bromopropionate
535-11-5, 41978-69-2

Ethyl 2-bromopropionate

A

ethyl 2,3-dicyanopropanoate
40497-11-8

ethyl 2,3-dicyanopropanoate

B

α-cyano-propionic acid ester

α-cyano-propionic acid ester

Conditions
ConditionsYield
With ethanol
ethanedinitrile
460-19-5

ethanedinitrile

ethyl 2-cyanoacetate
105-56-6

ethyl 2-cyanoacetate

ethyl 2,3-dicyanopropanoate
40497-11-8

ethyl 2,3-dicyanopropanoate

Conditions
ConditionsYield
Stage #1: ethanedinitrile; ethyl 2-cyanoacetate With potassium carbonate In DMF (N,N-dimethyl-formamide); water at 30℃; for 1.5h;
Stage #2: at 20℃;
ethyl acrylate
140-88-5

ethyl acrylate

ethyl 2,3-dicyanopropanoate
40497-11-8

ethyl 2,3-dicyanopropanoate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: iodine / dichloromethane / 48 h / 20 °C / Inert atmosphere
1.2: 3 h / 0 °C / Inert atmosphere
2.1: tetrabutyl ammonium fluoride / acetonitrile; tetrahydrofuran / 2 h / 20 °C / Inert atmosphere
View Scheme
diethyl malonate
105-53-3

diethyl malonate

ethyl 2,3-dicyanopropanoate
40497-11-8

ethyl 2,3-dicyanopropanoate

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: methanol / 3 h / 10 °C
1.2: 1 h / 0 °C
1.3: 1 h / 0 - 10 °C
2.1: ammonia / toluene / 2 h / 80 °C / 750.08 Torr / Inert atmosphere; Autoclave
3.1: 1,4-diaza-bicyclo[2.2.2]octane; phosgene / 5 h / 100 °C
View Scheme
ethyl 2-amido-3-cyanopropionate

ethyl 2-amido-3-cyanopropionate

ethyl 2,3-dicyanopropanoate
40497-11-8

ethyl 2,3-dicyanopropanoate

Conditions
ConditionsYield
With 1,4-diaza-bicyclo[2.2.2]octane; phosgene at 100℃; for 5h; Concentration;134.5 g
ethyl 2,3-dicyanopropanoate
40497-11-8

ethyl 2,3-dicyanopropanoate

2,6-dichloro-4-(trifluoromethyl)aniline
24279-39-8

2,6-dichloro-4-(trifluoromethyl)aniline

5-amino-3-cyano-1-(2,6-dichloro-4-trifluoromethylphenyl)pyrazole
120068-79-3

5-amino-3-cyano-1-(2,6-dichloro-4-trifluoromethylphenyl)pyrazole

Conditions
ConditionsYield
Stage #1: 2,6-dichloro-4-(trifluoromethyl)aniline With nitrosylsulfuric acid; acetic acid at 5 - 50℃; for 11h; Large scale;
Stage #2: ethyl 2,3-dicyanopropanoate In water at 10 - 30℃; for 20h; Large scale;
95%
Stage #1: 2,6-dichloro-4-(trifluoromethyl)aniline With nitrosylsulfuric acid; sulfuric acid In hexane at 10 - 30℃;
Stage #2: ethyl 2,3-dicyanopropanoate In hexane at 0 - 30℃; for 6h; Solvent;
95.2%
Stage #1: 2,6-dichloro-4-(trifluoromethyl)aniline With hydrogenchloride; sulfuric acid In water; toluene at 30 - 40℃; for 1.5h; Green chemistry;
Stage #2: With sodium nitrite In water; toluene at 15 - 20℃; for 1h; Green chemistry;
Stage #3: ethyl 2,3-dicyanopropanoate In water; toluene at 10 - 25℃; for 12h; Temperature; Green chemistry;
90%
ethyl 2,3-dicyanopropanoate
40497-11-8

ethyl 2,3-dicyanopropanoate

4-chloro-aniline
106-47-8

4-chloro-aniline

5-amino-1-(4-chlorophenyl)-1H-pyrazole-3-carbonitrile

5-amino-1-(4-chlorophenyl)-1H-pyrazole-3-carbonitrile

Conditions
ConditionsYield
Stage #1: 4-chloro-aniline With hydrogenchloride; sodium nitrite In ethanol; water for 0.5h; Cooling with ice;
Stage #2: ethyl 2,3-dicyanopropanoate With ammonium hydroxide In ethanol; water at 20℃; for 4h; pH=9 - 10;
93.6%
Stage #1: 4-chloro-aniline With hydrogenchloride; sodium nitrite at -5℃;
Stage #2: ethyl 2,3-dicyanopropanoate at 20℃;
Stage #3: With ammonia In dichloromethane; water at 20℃;
Stage #1: 4-chloro-aniline With hydrogenchloride; sodium nitrite at -5℃;
Stage #2: ethyl 2,3-dicyanopropanoate at 20℃;
Stage #3: With ammonium hydroxide In dichloromethane at 20℃;
ethyl 2,3-dicyanopropanoate
40497-11-8

ethyl 2,3-dicyanopropanoate

2,6-dichloro-4-trifluoromethylaniline-13C

2,6-dichloro-4-trifluoromethylaniline-13C

5-amino-3-cyano-1-(2,6-dichloro-4-trifluoromethyl)pyrazole-13C6

5-amino-3-cyano-1-(2,6-dichloro-4-trifluoromethyl)pyrazole-13C6

Conditions
ConditionsYield
Stage #1: 2,6-dichloro-4-trifluoromethylaniline-13C With sulfuric acid; acetic acid; sodium nitrite at 55℃; for 0.75h; Cooling;
Stage #2: ethyl 2,3-dicyanopropanoate With acetic acid at 10℃; for 0.25h;
91.4%
ethyl 2,3-dicyanopropanoate
40497-11-8

ethyl 2,3-dicyanopropanoate

2,3-dicyanopropionamide
98024-59-0

2,3-dicyanopropionamide

Conditions
ConditionsYield
With ammonium hydroxide at 0℃; for 4h;85%
ethyl 2,3-dicyanopropanoate
40497-11-8

ethyl 2,3-dicyanopropanoate

4-phenoxyphenylboronic acid
51067-38-0

4-phenoxyphenylboronic acid

ethyl 2,5-bis(4-phenoxyphenyl)-1H-pyrrole-3-carboxylate

ethyl 2,5-bis(4-phenoxyphenyl)-1H-pyrrole-3-carboxylate

Conditions
ConditionsYield
With [2,2]bipyridinyl; palladium(II) trifluoroacetate; 2,2,2-trifluoroacetic acid ammonia; trifluoroacetic acid In tetrahydrofuran; water at 80℃; for 48h; Schlenk technique;83%
ethyl 2,3-dicyanopropanoate
40497-11-8

ethyl 2,3-dicyanopropanoate

2,4-Difluor-benzoldiazonium-chlorid
90802-25-8

2,4-Difluor-benzoldiazonium-chlorid

5-amino-1-(2,4-difluorophenyl)-3-cyano-1H-pyrazole

5-amino-1-(2,4-difluorophenyl)-3-cyano-1H-pyrazole

Conditions
ConditionsYield
for 2h;81%
Stage #1: ethyl 2,3-dicyanopropanoate; 2,4-Difluor-benzoldiazonium-chlorid for 2h;
Stage #2: With ammonium hydroxide at 20℃; for 2h; pH=9 - 10;
58.8%
ethyl 2,3-dicyanopropanoate
40497-11-8

ethyl 2,3-dicyanopropanoate

4-bromo-aniline
106-40-1

4-bromo-aniline

5-amino-1-(4-bromophenyl)-3-cyano-1H-pyrazole

5-amino-1-(4-bromophenyl)-3-cyano-1H-pyrazole

Conditions
ConditionsYield
Stage #1: 4-bromo-aniline With hydrogenchloride; sodium nitrite In ethanol; water for 0.5h; Cooling with ice;
Stage #2: ethyl 2,3-dicyanopropanoate In ethanol; water at 20℃; for 4h; pH=9 - 10;
80.3%
Stage #1: 4-bromo-aniline With hydrogenchloride; sodium nitrite at -5℃;
Stage #2: ethyl 2,3-dicyanopropanoate at 20℃;
Stage #3: With ammonia In dichloromethane; water at 20℃;
Stage #1: 4-bromo-aniline With hydrogenchloride; sodium nitrite at -5℃;
Stage #2: ethyl 2,3-dicyanopropanoate at 20℃;
Stage #3: With ammonium hydroxide In dichloromethane at 20℃;
ethyl 2,3-dicyanopropanoate
40497-11-8

ethyl 2,3-dicyanopropanoate

p-chlorobenzenediazonium chloride
2028-74-2

p-chlorobenzenediazonium chloride

5-amino-1-(4-chlorophenyl)-1H-pyrazole-3-carbonitrile

5-amino-1-(4-chlorophenyl)-1H-pyrazole-3-carbonitrile

Conditions
ConditionsYield
for 2h;79.6%
Stage #1: ethyl 2,3-dicyanopropanoate; p-chlorobenzenediazonium chloride for 2h;
Stage #2: With ammonium hydroxide at 20℃; for 2h; pH=9 - 10;
72.6%
ethyl 2,3-dicyanopropanoate
40497-11-8

ethyl 2,3-dicyanopropanoate

benzene diazonium chloride
100-34-5

benzene diazonium chloride

5-amino-1-phenyl-1H-pyrazole-3-carbonitrile

5-amino-1-phenyl-1H-pyrazole-3-carbonitrile

Conditions
ConditionsYield
for 2h;78.8%
Stage #1: ethyl 2,3-dicyanopropanoate; benzene diazonium chloride for 2h;
Stage #2: With ammonium hydroxide at 20℃; for 2h; pH=9 - 10;
66.8%
ethyl 2,3-dicyanopropanoate
40497-11-8

ethyl 2,3-dicyanopropanoate

p-toluidine
106-49-0

p-toluidine

5-amino-1-(4-methylphenyl)-3-cyano-1H-pyrazole

5-amino-1-(4-methylphenyl)-3-cyano-1H-pyrazole

Conditions
ConditionsYield
Stage #1: p-toluidine With hydrogenchloride; sodium nitrite In ethanol; water for 0.5h; Cooling with ice;
Stage #2: ethyl 2,3-dicyanopropanoate With ammonium hydroxide In ethanol; water at 20℃; for 4h; pH=9 - 10;
78.2%
Stage #1: p-toluidine With hydrogenchloride; sodium nitrite In ethanol; water for 0.5h; Cooling with ice;
Stage #2: ethyl 2,3-dicyanopropanoate With ammonia In ethanol; water at 20℃; for 4h; pH=9 - 10;
60.5%
Stage #1: p-toluidine With hydrogenchloride; sodium nitrite at -5℃;
Stage #2: ethyl 2,3-dicyanopropanoate at 20℃;
Stage #3: With ammonia In dichloromethane; water at 20℃;
Stage #1: p-toluidine With hydrogenchloride; sodium nitrite at -5℃;
Stage #2: ethyl 2,3-dicyanopropanoate at 20℃;
Stage #3: With ammonium hydroxide In dichloromethane at 20℃;
ethyl 2,3-dicyanopropanoate
40497-11-8

ethyl 2,3-dicyanopropanoate

2-fluorobenzenediazonium chloride
53559-92-5

2-fluorobenzenediazonium chloride

5-amino-1-(2-fluorophenyl)-3-cyano-1H-pyrazole

5-amino-1-(2-fluorophenyl)-3-cyano-1H-pyrazole

Conditions
ConditionsYield
for 2h;78%
Stage #1: ethyl 2,3-dicyanopropanoate; 2-fluorobenzenediazonium chloride for 2h;
Stage #2: With ammonium hydroxide at 20℃; for 2h; pH=9 - 10;
67.3%
ethyl 2,3-dicyanopropanoate
40497-11-8

ethyl 2,3-dicyanopropanoate

4-(trifluoromethoxy)aniline
461-82-5

4-(trifluoromethoxy)aniline

5-amino-1-(4-trifluoromethoxyphenyl)-3-cyano-1H-pyrazole

5-amino-1-(4-trifluoromethoxyphenyl)-3-cyano-1H-pyrazole

Conditions
ConditionsYield
Stage #1: 4-(trifluoromethoxy)aniline With hydrogenchloride; sodium nitrite In ethanol; water for 0.5h; Cooling with ice;
Stage #2: ethyl 2,3-dicyanopropanoate With ammonia In ethanol; water at 20℃; for 4h; pH=9 - 10;
77.4%
Stage #1: 4-(trifluoromethoxy)aniline With hydrogenchloride; sodium nitrite at -5℃;
Stage #2: ethyl 2,3-dicyanopropanoate at 20℃;
Stage #3: With ammonium hydroxide In dichloromethane at 20℃;
ethyl 2,3-dicyanopropanoate
40497-11-8

ethyl 2,3-dicyanopropanoate

ethyl 2-(aminomethyl)-4-aminobutyrate dihydrochloride

ethyl 2-(aminomethyl)-4-aminobutyrate dihydrochloride

Conditions
ConditionsYield
With hydrogenchloride; hydrogen; platinum(IV) oxide In methanol under 2585.7 Torr; for 2h;77%
ethyl 2,3-dicyanopropanoate
40497-11-8

ethyl 2,3-dicyanopropanoate

1-amino-3-methylbenzene
108-44-1

1-amino-3-methylbenzene

5-amino-1-(3-methylphenyl)-3-cyano-1H-pyrazole

5-amino-1-(3-methylphenyl)-3-cyano-1H-pyrazole

Conditions
ConditionsYield
Stage #1: 1-amino-3-methylbenzene With hydrogenchloride; sodium nitrite In ethanol; water for 0.5h; Cooling with ice;
Stage #2: ethyl 2,3-dicyanopropanoate With ammonia In ethanol; water at 20℃; for 4h; pH=9 - 10;
76.2%
Stage #1: 1-amino-3-methylbenzene With hydrogenchloride; sodium nitrite at -5℃;
Stage #2: ethyl 2,3-dicyanopropanoate at 20℃;
Stage #3: With ammonium hydroxide In dichloromethane at 20℃;
ethyl 2,3-dicyanopropanoate
40497-11-8

ethyl 2,3-dicyanopropanoate

p-methylbenzenediazonium chloride
2028-84-4

p-methylbenzenediazonium chloride

5-amino-1-(4-methylphenyl)-3-cyano-1H-pyrazole

5-amino-1-(4-methylphenyl)-3-cyano-1H-pyrazole

Conditions
ConditionsYield
for 2h;75.8%
ethyl 2,3-dicyanopropanoate
40497-11-8

ethyl 2,3-dicyanopropanoate

3,4-dichlorobenzenediazonium chloride
50379-99-2

3,4-dichlorobenzenediazonium chloride

5-amino-1-(3,4-dichlorophenyl)-3-cyano-1H-pyrazole

5-amino-1-(3,4-dichlorophenyl)-3-cyano-1H-pyrazole

Conditions
ConditionsYield
for 2h;75.3%
ethyl 2,3-dicyanopropanoate
40497-11-8

ethyl 2,3-dicyanopropanoate

(4-bromophenyl)diazonium chloride
2028-85-5

(4-bromophenyl)diazonium chloride

5-amino-1-(4-bromophenyl)-3-cyano-1H-pyrazole

5-amino-1-(4-bromophenyl)-3-cyano-1H-pyrazole

Conditions
ConditionsYield
Stage #1: ethyl 2,3-dicyanopropanoate; (4-bromophenyl)diazonium chloride for 2h;
Stage #2: With ammonium hydroxide at 20℃; for 2h; pH=9 - 10;
75.2%
ethyl 2,3-dicyanopropanoate
40497-11-8

ethyl 2,3-dicyanopropanoate

C7H2Cl2F3N2(1+)*Cl(1-)

C7H2Cl2F3N2(1+)*Cl(1-)

5-amino-3-cyano-1-(2,6-dichloro-4-trifluoromethylphenyl)pyrazole
120068-79-3

5-amino-3-cyano-1-(2,6-dichloro-4-trifluoromethylphenyl)pyrazole

Conditions
ConditionsYield
for 2h;74.7%
Stage #1: ethyl 2,3-dicyanopropanoate; C7H2Cl2F3N2(1+)*Cl(1-) for 2h;
Stage #2: With ammonium hydroxide at 20℃; for 2h; pH=9 - 10;
48.8%
ethyl 2,3-dicyanopropanoate
40497-11-8

ethyl 2,3-dicyanopropanoate

2,6-Difluoro-benzenediazonium; chloride

2,6-Difluoro-benzenediazonium; chloride

5-amino-1-(2,3,4-trifluorophenyl)-3-cyano-1H-pyrazole

5-amino-1-(2,3,4-trifluorophenyl)-3-cyano-1H-pyrazole

Conditions
ConditionsYield
Stage #1: ethyl 2,3-dicyanopropanoate; 2,6-Difluoro-benzenediazonium; chloride for 2h;
Stage #2: With ammonium hydroxide at 20℃; for 2h; pH=9 - 10;
73.8%
2,6-dibromo-4-(trifluoromethoxy)aniline
88149-49-9

2,6-dibromo-4-(trifluoromethoxy)aniline

ethyl 2,3-dicyanopropanoate
40497-11-8

ethyl 2,3-dicyanopropanoate

5-amino-1-[2,6-dibromo-4-(trifluoromethoxy)phenyl]-1H-pyrazole-3-carbonitrile

5-amino-1-[2,6-dibromo-4-(trifluoromethoxy)phenyl]-1H-pyrazole-3-carbonitrile

Conditions
ConditionsYield
Stage #1: 2,6-dibromo-4-(trifluoromethoxy)aniline With sulfuric acid; acetic acid; sodium nitrite In water at 0 - 55℃; for 1h;
Stage #2: ethyl 2,3-dicyanopropanoate With acetic acid In water at 5 - 20℃; for 2h;
73%
ethyl 2,3-dicyanopropanoate
40497-11-8

ethyl 2,3-dicyanopropanoate

ethyl 2,3-dicarbamoylpropionate

ethyl 2,3-dicarbamoylpropionate

Conditions
ConditionsYield
Stage #1: ethyl 2,3-dicyanopropanoate With acetamide; acetic acid at 50℃; under 760.051 Torr; for 0.5h;
Stage #2: With tetrakis(acetonitrile)palladium(II) tetrafluoroborate at 50℃; under 2 Torr; for 2h;
72%
4-trifluoromethylphenylamine
455-14-1

4-trifluoromethylphenylamine

ethyl 2,3-dicyanopropanoate
40497-11-8

ethyl 2,3-dicyanopropanoate

5-amino-1-(4-trifluoromethylphenyl)-3-cyano-1H-pyrazole

5-amino-1-(4-trifluoromethylphenyl)-3-cyano-1H-pyrazole

Conditions
ConditionsYield
Stage #1: 4-trifluoromethylphenylamine With hydrogenchloride; sodium nitrite In ethanol; water for 0.5h; Cooling with ice;
Stage #2: ethyl 2,3-dicyanopropanoate With ammonia In ethanol; water at 20℃; for 4h; pH=9 - 10;
70.4%
Stage #1: 4-trifluoromethylphenylamine With hydrogenchloride; sodium nitrite In ethanol; water for 0.5h; Cooling with ice;
Stage #2: ethyl 2,3-dicyanopropanoate With ammonium hydroxide In ethanol; water at 20℃; for 4h; pH=9 - 10;
58.9%
Stage #1: 4-trifluoromethylphenylamine With hydrogenchloride; sodium nitrite at -5℃;
Stage #2: ethyl 2,3-dicyanopropanoate at 20℃;
Stage #3: With ammonia In dichloromethane; water at 20℃;
Stage #1: 4-trifluoromethylphenylamine With hydrogenchloride; sodium nitrite at -5℃;
Stage #2: ethyl 2,3-dicyanopropanoate at 20℃;
Stage #3: With ammonium hydroxide In dichloromethane at 20℃;
ethyl 2,3-dicyanopropanoate
40497-11-8

ethyl 2,3-dicyanopropanoate

3-trifluoromethylaniline
98-16-8

3-trifluoromethylaniline

5-amino-1-(3-trifluoromethylphenyl)-3-cyano-1H-pyrazole

5-amino-1-(3-trifluoromethylphenyl)-3-cyano-1H-pyrazole

Conditions
ConditionsYield
Stage #1: 3-trifluoromethylaniline With hydrogenchloride; sodium nitrite In ethanol; water for 0.5h; Cooling with ice;
Stage #2: ethyl 2,3-dicyanopropanoate With ammonia In ethanol; water at 20℃; for 4h; pH=9 - 10;
70.4%
ethyl 2,3-dicyanopropanoate
40497-11-8

ethyl 2,3-dicyanopropanoate

p-trifluorobenzene diazonium chloride
25102-84-5

p-trifluorobenzene diazonium chloride

5-amino-1-(4-trifluoromethylphenyl)-3-cyano-1H-pyrazole

5-amino-1-(4-trifluoromethylphenyl)-3-cyano-1H-pyrazole

Conditions
ConditionsYield
for 2h;70.4%

40497-11-8Relevant articles and documents

Intermediates Formed in the Reactions of Organocuprates with α,β-Unsaturated Nitriles

Putau, Aliaksei,Brand, Harald,Koszinowski, Konrad

, p. 12868 - 12876 (2016)

Conjugate additions of organocuprates are of outstanding importance for organic synthesis. To improve our mechanistic understanding of these reactions, we have used electrospray ionization mass spectrometry for the identification of the ionic intermediates formed upon the treatment of LiCuR2?LiCN (R=Me, Bu, Ph) with a series of α,β-unsaturated nitriles. Acrylonitrile, the weakest Michael acceptor included, did not afford any detectable intermediates. Fumaronitrile (FN) yielded adducts of the type Lin?1CunR2n(FN)n?, n=1–3. When subjected to fragmentation in the gas phase, these adducts were not converted into the conjugate addition products, but re-dissociated into the reactants. In contrast, the reaction with 1,1-dicyanoethylene furnished the products of the conjugate addition without any observable intermediates. Tri- and tetracyanoethylene proved to be quite reactive as well. The presence of several cyano groups in these substrates opened up reaction pathways different from simple conjugate additions, however, and led to dimerization and substitution reactions. Moreover, the gas-phase fragmentation behavior of the species formed from these substrates indicated the occurrence of single-electron transfer processes. Additional quantum-chemical calculations provided insight into the structures and stabilities of the observed intermediates and their consecutive reactions.

Preparation method of ethyl 2,3-dicyanopropionate

-

Paragraph 0019-0026, (2021/02/20)

The invention discloses a preparation method of ethyl 2,3-dicyanopropionate. The preparation method comprises the steps of adding a liquid sodium cyanide aqueous solution into a reaction tank, conducting concentrating and dehydrating, and then adding dichloromethane to separate water; conducting cooling after the reaction is qualified, adding ethyl cyanoacetate, paraformaldehyde and a catalyst, keeping the temperature for reaction until the reaction is finished, starting to add hydrochloric acid for acidification, and conducting standing for layering to obtain a dichloromethane organic layer;and washing the organic layer with water, removing dichloromethane to obtain a crude product, and performing vacuum distillation to obtain a finished product. According to the method, dichloromethaneis directly used as a reaction solvent, and a small amount of catalyst is added, so that the reaction period is short, the solvent is easy to recover, and the used liquid sodium cyanide is safer to store and use compared with solid sodium cyanide.

Production process of ethyl 2,3-dicyanopropionate

-

Paragraph 0028-0083, (2020/09/30)

The invention provides a production process of ethyl 2,3-dicyanopropionate. The production process comprises the following steps: S1, premixing of raw materials: adding ethyl cyanoacetate, dimethyl sulfoxide and diethyl malonate into a reaction kettle, and carrying out mixing and stirring to form a premixture; S2, a synthetic reaction: adding sodium cyanide and paraformaldehyde into the reaction kettle, and carrying out a constant-temperature reaction for 15-20 h under stirring and mixing conditions to form a reaction mixed solution; S3, addition of acid; step S4, extraction; S5, reduced-pressure distillation and recovery; and S6, rectification: removing a small amount of front fraction impurities to obtain a red oily target product, namely ethyl 2,3-dicyanopropionate. The raw materials ofthe process are composed of, in parts by weight, 100 parts of ethyl cyanoacetate, 100-150 parts of dimethyl sulfoxide, 60-100 parts of sodium cyanide, 50-80 parts of paraformaldehyde, and 20-30 partsof diethyl malonate. The production process of ethyl 2,3-dicyanopropionate in the invention provides has the advantages of high safety, high product yield and few byproducts.

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