Ethyl 2,3-dicyanopropionate supplier

Name
Ethyl 2,3-dicyanopropionate
EINECS
CAS No. 40497-11-8
Article Data21
CAS DataBase
Density 1.129 g/cm³
Solubility
Melting Point
Formula C₇H₈N₂O₂
Boiling Point 338.17 °C at 760 mmHg
Molecular Weight 152.153
Flash Point 147.474 °C
Transport Information
Appearance Brown oil
Safety
Risk Codes
Molecular Structure
Hazard Symbols
Synonyms Propionicacid, 2,3-dicyano-, ethyl ester (6CI);2,3-Dicyanopropanoic acid ethyl ester;2,3-Dicyanopropionic acid ethyl ester;Ethyl 2,3-dicyanopropanoate;
PSA 73.88000
LogP 0.60296

Synthetic route

: 773837-37-9
sodium cyanide

: 50-00-0
formaldehyd

: 105-56-6
ethyl 2-cyanoacetate

: 40497-11-8
ethyl 2,3-dicyanopropanoate

Conditions

Conditions	Yield
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

...Expand

: 773837-37-9
sodium cyanide

: 7085-85-0
ethyl 2-cyanoacrylate

: 40497-11-8
ethyl 2,3-dicyanopropanoate

Conditions

Conditions	Yield
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;

: 7677-24-9
trimethylsilyl cyanide

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

: 40497-11-8
ethyl 2,3-dicyanopropanoate

Conditions

Conditions	Yield
With tetrabutyl ammonium fluoride In tetrahydrofuran; acetonitrile at 20℃; for 2h; Michael Addition; Inert atmosphere;	83%

: 50-00-0
formaldehyd

: 151-50-8
potassium cyanide

: 105-56-6
ethyl 2-cyanoacetate

: 40497-11-8
ethyl 2,3-dicyanopropanoate

Conditions

Conditions	Yield
With water In dimethyl sulfoxide at 20℃; for 15h;	80%
In ethanol

...Expand

: 107-16-4
glycolonitrile

: 105-56-6
ethyl 2-cyanoacetate

: 40497-11-8
ethyl 2,3-dicyanopropanoate

Conditions

Conditions	Yield
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;

: 105-56-6
ethyl 2-cyanoacetate

: 40497-11-8
ethyl 2,3-dicyanopropanoate

Conditions

Conditions	Yield
With paraformaldehyde In ethanol; water	77%

: 64-17-5
ethanol

: 18852-51-2
sodium cyanoacetic acid ethyl ester

: 107-16-4
glycolonitrile

: 40497-11-8
ethyl 2,3-dicyanopropanoate

Conditions

Conditions	Yield
in kaltem Alkohol;

...Expand

: 18852-51-2
sodium cyanoacetic acid ethyl ester

: 107-16-4
glycolonitrile

: 40497-11-8
ethyl 2,3-dicyanopropanoate

Conditions

Conditions	Yield
With ethanol

: 64-67-5
diethyl sulfate

: 124-38-9
carbon dioxide

: 13435-20-6
tetraethylammoniumcyanide

: 107-13-1
acrylonitrile

: 40497-11-8
ethyl 2,3-dicyanopropanoate

Conditions

Conditions	Yield
(i), (ii) /BRN= 605310/, (iii) /BRN= 1209714/; Multistep reaction;

...Expand

: 151-50-8
potassium cyanide

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

A: 40497-11-8
ethyl 2,3-dicyanopropanoate

B α-cyano-propionic acid ester: α-cyano-propionic acid ester

Conditions

Conditions	Yield
With ethanol

...Expand

: 460-19-5
ethanedinitrile

: 105-56-6
ethyl 2-cyanoacetate

: 40497-11-8
ethyl 2,3-dicyanopropanoate

Conditions

Conditions	Yield
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℃;

: 140-88-5
ethyl acrylate

: 40497-11-8
ethyl 2,3-dicyanopropanoate

Conditions

Conditions	Yield
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

: 105-53-3
diethyl malonate

: 40497-11-8
ethyl 2,3-dicyanopropanoate

Conditions

Conditions	Yield
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

: 40497-11-8
ethyl 2,3-dicyanopropanoate

Conditions

Conditions	Yield
With 1,4-diaza-bicyclo[2.2.2]octane; phosgene at 100℃; for 5h; Concentration;	134.5 g

: 40497-11-8
ethyl 2,3-dicyanopropanoate

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

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

Conditions

Conditions	Yield
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%

: 40497-11-8
ethyl 2,3-dicyanopropanoate

: 106-47-8
4-chloro-aniline

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

Conditions

Conditions	Yield
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℃;

: 40497-11-8
ethyl 2,3-dicyanopropanoate

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

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

Conditions

Conditions	Yield
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%

: 40497-11-8
ethyl 2,3-dicyanopropanoate

: 98024-59-0
2,3-dicyanopropionamide

Conditions

Conditions	Yield
With ammonium hydroxide at 0℃; for 4h;	85%

: 40497-11-8
ethyl 2,3-dicyanopropanoate

: 51067-38-0
4-phenoxyphenylboronic acid

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

Conditions

Conditions	Yield
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%

: 40497-11-8
ethyl 2,3-dicyanopropanoate

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

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

Conditions

Conditions	Yield
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%

: 40497-11-8
ethyl 2,3-dicyanopropanoate

: 106-40-1
4-bromo-aniline

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

Conditions

Conditions	Yield
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℃;

: 40497-11-8
ethyl 2,3-dicyanopropanoate

: 2028-74-2
p-chlorobenzenediazonium chloride

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

Conditions

Conditions	Yield
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%

: 40497-11-8
ethyl 2,3-dicyanopropanoate

: 100-34-5
benzene diazonium chloride

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

Conditions

Conditions	Yield
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%

: 40497-11-8
ethyl 2,3-dicyanopropanoate

: 106-49-0
p-toluidine

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

Conditions

Conditions	Yield
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℃;

: 40497-11-8
ethyl 2,3-dicyanopropanoate

: 53559-92-5
2-fluorobenzenediazonium chloride

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

Conditions

Conditions	Yield
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%

: 40497-11-8
ethyl 2,3-dicyanopropanoate

: 461-82-5
4-(trifluoromethoxy)aniline

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

Conditions

Conditions	Yield
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℃;

: 40497-11-8
ethyl 2,3-dicyanopropanoate

: ethyl 2-(aminomethyl)-4-aminobutyrate dihydrochloride

Conditions

Conditions	Yield
With hydrogenchloride; hydrogen; platinum(IV) oxide In methanol under 2585.7 Torr; for 2h;	77%

: 40497-11-8
ethyl 2,3-dicyanopropanoate

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

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

Conditions

Conditions	Yield
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℃;

: 40497-11-8
ethyl 2,3-dicyanopropanoate

: 2028-84-4
p-methylbenzenediazonium chloride

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

Conditions

Conditions	Yield
for 2h;	75.8%

: 40497-11-8
ethyl 2,3-dicyanopropanoate

: 50379-99-2
3,4-dichlorobenzenediazonium chloride

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

Conditions

Conditions	Yield
for 2h;	75.3%

: 40497-11-8
ethyl 2,3-dicyanopropanoate

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

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

Conditions

Conditions	Yield
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%

: 40497-11-8
ethyl 2,3-dicyanopropanoate

: C7H2Cl2F3N2(1+)*Cl(1-)

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

Conditions

Conditions	Yield
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%

: 40497-11-8
ethyl 2,3-dicyanopropanoate

: 2,6-Difluoro-benzenediazonium; chloride

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

Conditions

Conditions	Yield
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%

: 88149-49-9
2,6-dibromo-4-(trifluoromethoxy)aniline

: 40497-11-8
ethyl 2,3-dicyanopropanoate

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

Conditions

Conditions	Yield
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%

: 40497-11-8
ethyl 2,3-dicyanopropanoate

: ethyl 2,3-dicarbamoylpropionate

Conditions

Conditions	Yield
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%

: 455-14-1
4-trifluoromethylphenylamine

: 40497-11-8
ethyl 2,3-dicyanopropanoate

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

Conditions

Conditions	Yield
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℃;

: 40497-11-8
ethyl 2,3-dicyanopropanoate

: 98-16-8
3-trifluoromethylaniline

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

Conditions

Conditions	Yield
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%

: 40497-11-8
ethyl 2,3-dicyanopropanoate

: 25102-84-5
p-trifluorobenzene diazonium chloride

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

Conditions

Conditions	Yield
for 2h;	70.4%

Ethyl 2,3-dicyanopropionate Specification

The CAS register number of Ethyl 2,3-dicyanopropionate is 40497-11-8. It also can be called as Propanoic acid,2,3-dicyano-, ethyl ester and the systematic name about this chemical is ethyl 2,3-dicyanopropanoate. The molecular formula about this chemical is C₇H₈N₂O₂and the molecular weight is 152.15. It belongs to the following product categories which include All Aliphatics; Aliphatics and so on. This chemical can be used as an intermediate for insecticide.

Physical properties about Ethyl 2,3-dicyanopropionate are: (1)ACD/LogP: -0.11; (2)#H bond acceptors: 4; (3)#Freely Rotating Bonds: 4; (4)Polar Surface Area: 73.88Å²; (5)Index of Refraction: 1.448; (6)Molar Refractivity: 36.04 cm³; (7)Molar Volume: 134.708 cm³; (8)Polarizability: 14.287x10^-24cm³; (9)Surface Tension: 45.236 dyne/cm; (10)Flash Point: 147.474 °C; (11)Enthalpy of Vaporization: 58.15 kJ/mol; (12)Boiling Point: 338.17 °C at 760 mmHg.

You can still convert the following datas into molecular structure:
(1)SMILES: N#CCC(C#N)C(=O)OCC
(2)InChI: InChI=1/C7H8N2O2/c1-2-11-7(10)6(5-9)3-4-8/h6H,2-3H2,1H3
(3)InChIKey: NPZOLWMDTPEVEI-UHFFFAOYAF
(4)Std. InChI: InChI=1S/C7H8N2O2/c1-2-11-7(10)6(5-9)3-4-8/h6H,2-3H2,1H3
(5)Std. InChIKey: NPZOLWMDTPEVEI-UHFFFAOYSA-N

Product Name

Ethyl 2,3-dicyanopropionate

Synthetic route

Ethyl 2,3-dicyanopropionate Specification

Related Products

Hot Products