Product Name

  • Name

    Ethoxymethylenemalononitrile

  • EINECS 204-597-0
  • CAS No. 123-06-8
  • Article Data46
  • CAS DataBase
  • Density 1.07 g/cm3
  • Solubility insoluble in water
  • Melting Point 64-66 °C(lit.)
  • Formula C6H6N2O
  • Boiling Point 296.1 °C at 760 mmHg
  • Molecular Weight 122.126
  • Flash Point 135.1 °C
  • Transport Information
  • Appearance off white to pale yellow
  • Safety 22-36/37-45-36/37/39-26-36-24/25
  • Risk Codes 22-42/43-23/24/25-43-20/21/22
  • Molecular Structure Molecular Structure of 123-06-8 (Ethoxymethylenemalononitrile)
  • Hazard Symbols HarmfulXn,IrritantXi,ToxicT
  • Synonyms Malononitrile,(ethoxymethylene)- (6CI,7CI,8CI);Propanedinitrile, (ethoxymethylene)- (9CI);(Ethoxymethylene)malonodinitrile;(Ethoxymethylidene)malononitrile;(b-Ethoxymethylene)malononitrile;1,1-Dicyano-2-ethoxyethene;1-Ethoxy-2,2-dicyanoethene;1-Ethoxymethylenemalonitrile;2-Cyano-3-ethoxyacrylonitrile;2-Ethoxy-1,1-ethenedicarbonitrile;NSC 27792;a-Cyano-b-ethoxyacrylonitrile;Propanedinitrile,2-(ethoxymethylene)-;
  • PSA 56.81000
  • LogP 0.95396

Synthetic route

orthoformic acid triethyl ester
122-51-0

orthoformic acid triethyl ester

malononitrile
109-77-3

malononitrile

Ethoxymethylenemalononitrile
123-06-8

Ethoxymethylenemalononitrile

Conditions
ConditionsYield
With acetic anhydride at 110 - 140℃; Reflux;98%
With acetic anhydride at 110 - 140℃;98%
With acetic anhydride at 110 - 140℃;98%
malononitrile
109-77-3

malononitrile

Ethoxymethylenemalononitrile
123-06-8

Ethoxymethylenemalononitrile

Conditions
ConditionsYield
With orthoformic acid triethyl ester at 140℃;
With orthoformic acid triethyl ester at 140℃;
spiro<(2,2-dicyano-3-ethoxy)cyclobutan-1,3'-(1'-acetyl)-2'-oxoindoline>, trans
79343-66-1, 79343-67-2

spiro<(2,2-dicyano-3-ethoxy)cyclobutan-1,3'-(1'-acetyl)-2'-oxoindoline>, trans

ethyl vinyl ether
109-92-2

ethyl vinyl ether

A

2-ethoxy-9-acetyl-2,3-dihydropyran<2,3-b>indole
79343-70-7

2-ethoxy-9-acetyl-2,3-dihydropyran<2,3-b>indole

B

Ethoxymethylenemalononitrile
123-06-8

Ethoxymethylenemalononitrile

Conditions
ConditionsYield
at 100℃; for 40h; sealed tube;A 63%
B 50%
1-(2',3',4',5'-Tetra-O-acetyl-β-D-galactopyranosyl)urea
14059-86-0

1-(2',3',4',5'-Tetra-O-acetyl-β-D-galactopyranosyl)urea

orthoformic acid triethyl ester
122-51-0

orthoformic acid triethyl ester

malononitrile
109-77-3

malononitrile

A

1-(2',3',4',5'-Tetra-O-acetyl-β-D-galactopyranosyl)ureidomethylenemalononitrile
91303-01-4

1-(2',3',4',5'-Tetra-O-acetyl-β-D-galactopyranosyl)ureidomethylenemalononitrile

B

Ethoxymethylenemalononitrile
123-06-8

Ethoxymethylenemalononitrile

Conditions
ConditionsYield
at 70℃; for 12h;A 52%
B n/a
1-(2',3',4',5'-Tetra-O-acetyl-β-D-mannopyranosyl)urea
14241-65-7

1-(2',3',4',5'-Tetra-O-acetyl-β-D-mannopyranosyl)urea

orthoformic acid triethyl ester
122-51-0

orthoformic acid triethyl ester

malononitrile
109-77-3

malononitrile

A

1-(2',3',4',5'-Tetra-O-acetyl-β-D-mannopyranosyl)ureidomethylenemalononitrile
91303-00-3

1-(2',3',4',5'-Tetra-O-acetyl-β-D-mannopyranosyl)ureidomethylenemalononitrile

B

Ethoxymethylenemalononitrile
123-06-8

Ethoxymethylenemalononitrile

Conditions
ConditionsYield
at 60℃; for 2h;A 28%
B n/a
(1SR,3SR)-spiro<(2,2-dicyano-3-ethoxy)cyclobutan-1,3'-(1'-acetyl)-2'-oxoindoline>
79343-66-1, 79343-67-2

(1SR,3SR)-spiro<(2,2-dicyano-3-ethoxy)cyclobutan-1,3'-(1'-acetyl)-2'-oxoindoline>

ethyl vinyl ether
109-92-2

ethyl vinyl ether

A

2-ethoxy-9-acetyl-2,3-dihydropyran<2,3-b>indole
79343-70-7

2-ethoxy-9-acetyl-2,3-dihydropyran<2,3-b>indole

B

Ethoxymethylenemalononitrile
123-06-8

Ethoxymethylenemalononitrile

Conditions
ConditionsYield
at 100℃; for 40h; sealed tube;
sealed tube;
ethyl iodide
75-03-6

ethyl iodide

silver-compound of hydroxymethylene-malonic acid dinitrile

silver-compound of hydroxymethylene-malonic acid dinitrile

Ethoxymethylenemalononitrile
123-06-8

Ethoxymethylenemalononitrile

Conditions
ConditionsYield
With benzene
1-(2',3',4',5'-Tetra-O-acetyl-β-D-mannopyranosyl)urea
14241-65-7

1-(2',3',4',5'-Tetra-O-acetyl-β-D-mannopyranosyl)urea

orthoformic acid triethyl ester
122-51-0

orthoformic acid triethyl ester

malononitrile
109-77-3

malononitrile

A

2-Oxo-4-imino-5-cyano-1-(2',3',4',5'-tetra-O-acetyl-β-D-mannopyranosyl)-1,2,3,4-tetrahydropyrimidine

2-Oxo-4-imino-5-cyano-1-(2',3',4',5'-tetra-O-acetyl-β-D-mannopyranosyl)-1,2,3,4-tetrahydropyrimidine

B

Ethoxymethylenemalononitrile
123-06-8

Ethoxymethylenemalononitrile

Conditions
ConditionsYield
With triethylamine 1) 60 deg C, 2 h; 2) ethanol, reflux, 15 min.;; Yield given. Multistep reaction;
orthoformic acid triethyl ester
122-51-0

orthoformic acid triethyl ester

malononitrile
109-77-3

malononitrile

Ethoxymethylenemalononitrile
123-06-8

Ethoxymethylenemalononitrile

Conditions
ConditionsYield
With acetic anhydride at 110 - 140℃; Reflux;98%
With acetic anhydride at 110 - 140℃;98%
With acetic anhydride at 110 - 140℃;98%
spiro<(2,2-dicyano-3-ethoxy)cyclobutan-1,3'-(1'-acetyl)-2'-oxoindoline>, trans
79343-66-1, 79343-67-2

spiro<(2,2-dicyano-3-ethoxy)cyclobutan-1,3'-(1'-acetyl)-2'-oxoindoline>, trans

ethyl vinyl ether
109-92-2

ethyl vinyl ether

A

2-ethoxy-9-acetyl-2,3-dihydropyran<2,3-b>indole
79343-70-7

2-ethoxy-9-acetyl-2,3-dihydropyran<2,3-b>indole

B

Ethoxymethylenemalononitrile
123-06-8

Ethoxymethylenemalononitrile

Conditions
ConditionsYield
at 100℃; for 40h; sealed tube;A 63%
B 50%
1-(2',3',4',5'-Tetra-O-acetyl-β-D-galactopyranosyl)urea
14059-86-0

1-(2',3',4',5'-Tetra-O-acetyl-β-D-galactopyranosyl)urea

orthoformic acid triethyl ester
122-51-0

orthoformic acid triethyl ester

malononitrile
109-77-3

malononitrile

A

1-(2',3',4',5'-Tetra-O-acetyl-β-D-galactopyranosyl)ureidomethylenemalononitrile
91303-01-4

1-(2',3',4',5'-Tetra-O-acetyl-β-D-galactopyranosyl)ureidomethylenemalononitrile

B

Ethoxymethylenemalononitrile
123-06-8

Ethoxymethylenemalononitrile

Conditions
ConditionsYield
at 70℃; for 12h;A 52%
B n/a
1-(2',3',4',5'-Tetra-O-acetyl-β-D-glucopyranosyl)urea
14059-86-0, 14086-03-4, 14241-65-7, 94345-94-5, 60081-89-2

1-(2',3',4',5'-Tetra-O-acetyl-β-D-glucopyranosyl)urea

orthoformic acid triethyl ester
122-51-0

orthoformic acid triethyl ester

malononitrile
109-77-3

malononitrile

A

1-(2',3',4',5'-Tetra-O-acetyl-β-D-glucopyranosyl)ureidomethylenemalononitrile
91302-99-7

1-(2',3',4',5'-Tetra-O-acetyl-β-D-glucopyranosyl)ureidomethylenemalononitrile

B

Ethoxymethylenemalononitrile
123-06-8

Ethoxymethylenemalononitrile

Conditions
ConditionsYield
for 10h;A 39%
B n/a
1-(2',3',4',5'-Tetra-O-acetyl-β-D-mannopyranosyl)urea
14241-65-7

1-(2',3',4',5'-Tetra-O-acetyl-β-D-mannopyranosyl)urea

orthoformic acid triethyl ester
122-51-0

orthoformic acid triethyl ester

malononitrile
109-77-3

malononitrile

A

1-(2',3',4',5'-Tetra-O-acetyl-β-D-mannopyranosyl)ureidomethylenemalononitrile
91303-00-3

1-(2',3',4',5'-Tetra-O-acetyl-β-D-mannopyranosyl)ureidomethylenemalononitrile

B

Ethoxymethylenemalononitrile
123-06-8

Ethoxymethylenemalononitrile

Conditions
ConditionsYield
at 60℃; for 2h;A 28%
B n/a
acetic anhydride
108-24-7

acetic anhydride

orthoformic acid triethyl ester
122-51-0

orthoformic acid triethyl ester

malononitrile
109-77-3

malononitrile

Ethoxymethylenemalononitrile
123-06-8

Ethoxymethylenemalononitrile

malononitrile
109-77-3

malononitrile

Ethoxymethylenemalononitrile
123-06-8

Ethoxymethylenemalononitrile

Conditions
ConditionsYield
With orthoformic acid triethyl ester at 140℃;
With orthoformic acid triethyl ester at 140℃;
(Diethoxymethyl)triethylammonium-tetrafluoroborat

(Diethoxymethyl)triethylammonium-tetrafluoroborat

malononitrile
109-77-3

malononitrile

Ethoxymethylenemalononitrile
123-06-8

Ethoxymethylenemalononitrile

1-acetyl-3-(dicyanomethylene)-1,3-dihydro-2H-indol-2-one
79343-59-2

1-acetyl-3-(dicyanomethylene)-1,3-dihydro-2H-indol-2-one

ethyl vinyl ether
109-92-2

ethyl vinyl ether

A

2-ethoxy-9-acetyl-2,3-dihydropyran<2,3-b>indole
79343-70-7

2-ethoxy-9-acetyl-2,3-dihydropyran<2,3-b>indole

B

2-ethoxy-4,4-dicyano-9-acetyl-2,3-dihydropyran<2,3-b>indole
79343-71-8

2-ethoxy-4,4-dicyano-9-acetyl-2,3-dihydropyran<2,3-b>indole

(1SR,3SR)-spiro<(2,2-dicyano-3-ethoxy)cyclobutan-1,3'-(1'-acetyl)-2'-oxoindoline>
79343-66-1, 79343-67-2

(1SR,3SR)-spiro<(2,2-dicyano-3-ethoxy)cyclobutan-1,3'-(1'-acetyl)-2'-oxoindoline>

spiro<(2,2-dicyano-3-ethoxy)cyclobutan-1,3'-(1'-acetyl)-2'-oxoindoline>, trans
79343-66-1, 79343-67-2

spiro<(2,2-dicyano-3-ethoxy)cyclobutan-1,3'-(1'-acetyl)-2'-oxoindoline>, trans

E

Ethoxymethylenemalononitrile
123-06-8

Ethoxymethylenemalononitrile

Conditions
ConditionsYield
In acetonitrile Product distribution; with solvent, room temp., or ethylvinylether as solvent, 100 deg C, Paar bomb;
(1SR,3SR)-spiro<(2,2-dicyano-3-ethoxy)cyclobutan-1,3'-(1'-acetyl)-2'-oxoindoline>
79343-66-1, 79343-67-2

(1SR,3SR)-spiro<(2,2-dicyano-3-ethoxy)cyclobutan-1,3'-(1'-acetyl)-2'-oxoindoline>

ethyl vinyl ether
109-92-2

ethyl vinyl ether

A

2-ethoxy-9-acetyl-2,3-dihydropyran<2,3-b>indole
79343-70-7

2-ethoxy-9-acetyl-2,3-dihydropyran<2,3-b>indole

B

Ethoxymethylenemalononitrile
123-06-8

Ethoxymethylenemalononitrile

Conditions
ConditionsYield
at 100℃; for 40h; sealed tube;
sealed tube;
1-(2',3',4',5'-Tetra-O-acetyl-β-D-mannopyranosyl)urea
14241-65-7

1-(2',3',4',5'-Tetra-O-acetyl-β-D-mannopyranosyl)urea

orthoformic acid triethyl ester
122-51-0

orthoformic acid triethyl ester

malononitrile
109-77-3

malononitrile

A

2-Oxo-4-imino-5-cyano-1-(2',3',4',5'-tetra-O-acetyl-β-D-mannopyranosyl)-1,2,3,4-tetrahydropyrimidine

2-Oxo-4-imino-5-cyano-1-(2',3',4',5'-tetra-O-acetyl-β-D-mannopyranosyl)-1,2,3,4-tetrahydropyrimidine

B

Ethoxymethylenemalononitrile
123-06-8

Ethoxymethylenemalononitrile

Conditions
ConditionsYield
With triethylamine 1) 60 deg C, 2 h; 2) ethanol, reflux, 15 min.;; Yield given. Multistep reaction;
ethyl iodide
75-03-6

ethyl iodide

silver-compound of hydroxymethylene-malonic acid dinitrile

silver-compound of hydroxymethylene-malonic acid dinitrile

Ethoxymethylenemalononitrile
123-06-8

Ethoxymethylenemalononitrile

Conditions
ConditionsYield
With benzene
(2-fluorophenyl)hydrazine hydrochloride
2924-15-4

(2-fluorophenyl)hydrazine hydrochloride

Ethoxymethylenemalononitrile
123-06-8

Ethoxymethylenemalononitrile

5-amino-1-(2-fluorophenyl)-1H-pyrazole-4-carbonitrile
135108-48-4

5-amino-1-(2-fluorophenyl)-1H-pyrazole-4-carbonitrile

Conditions
ConditionsYield
With triethylamine In ethanol at 20℃; for 1.5h; Reflux; Inert atmosphere;100%
With triethylamine for 4h;91%
Stage #1: (2-fluorophenyl)hydrazine hydrochloride; Ethoxymethylenemalononitrile With triethylamine In ethanol for 0.666667h;
Stage #2: In diethyl ether; hexane for 16h;
67%
With triethylamine
With sodium acetate In ethanol for 1h; Michael Addition; Reflux;
5-hydrazino-2-chloro-benzamide
896134-44-4

5-hydrazino-2-chloro-benzamide

Ethoxymethylenemalononitrile
123-06-8

Ethoxymethylenemalononitrile

5-(5-amino-4-cyanopyrazol-1-yl)-2-chlorobenzamide

5-(5-amino-4-cyanopyrazol-1-yl)-2-chlorobenzamide

Conditions
ConditionsYield
In ethanol for 18h; Heating / reflux;100%
(2,4-difluorophenyl)hydrazinium chloride
40594-29-4, 51523-79-6

(2,4-difluorophenyl)hydrazinium chloride

Ethoxymethylenemalononitrile
123-06-8

Ethoxymethylenemalononitrile

5-amino-1-(2,4-difluorophenyl)-1H-pyrazole-4-carbonitrile
102996-25-8

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

Conditions
ConditionsYield
With triethylamine In ethanol at 20℃; for 1.5h; Reflux; Inert atmosphere;100%
With sodium acetate; triethylamine In acetic acid at 15 - 60℃; for 3.5h; Large scale reaction;98%
With triethylamine In ethanol for 1h; Heating / reflux;
With triethylamine In ethanol for 1h; Heating / reflux;
o-chlorophenylhydrazine hydrochloride
41052-75-9

o-chlorophenylhydrazine hydrochloride

Ethoxymethylenemalononitrile
123-06-8

Ethoxymethylenemalononitrile

5-amino-1-(2-chlorophenyl)-1H-pyrazole-4-carbonitrile
64096-89-5

5-amino-1-(2-chlorophenyl)-1H-pyrazole-4-carbonitrile

Conditions
ConditionsYield
With triethylamine In ethanol at 20℃; for 1.5h; Reflux; Inert atmosphere;100%
With triethylamine
With sodium acetate In ethanol for 1h; Michael Addition; Reflux;
o-tolylhydrazine hydrochloride
635-26-7

o-tolylhydrazine hydrochloride

Ethoxymethylenemalononitrile
123-06-8

Ethoxymethylenemalononitrile

5-amino-1-o-tolyl-1H-pyrazole-4-carbonitrile
142893-46-7

5-amino-1-o-tolyl-1H-pyrazole-4-carbonitrile

Conditions
ConditionsYield
With triethylamine In ethanol at 20℃; for 1.5h; Reflux; Inert atmosphere;100%
With triethylamine In methanol
C6H6F3N3*ClH
1220512-59-3

C6H6F3N3*ClH

Ethoxymethylenemalononitrile
123-06-8

Ethoxymethylenemalononitrile

5-amino-1-(3-(trifluoromethyl)pyridin-2-yl)-1H-pyrazole-4-carbonitrile
1019010-69-5

5-amino-1-(3-(trifluoromethyl)pyridin-2-yl)-1H-pyrazole-4-carbonitrile

Conditions
ConditionsYield
With triethylamine In ethanol at 20℃; for 1.5h; Reflux; Inert atmosphere;100%
Ethoxymethylenemalononitrile
123-06-8

Ethoxymethylenemalononitrile

(2,5-difluorophenyl)hydrazine hydrochloride

(2,5-difluorophenyl)hydrazine hydrochloride

5-amino-1-(2,5-difluorophenyl)-1H-pyrazole-4-carbonitrile
1220512-60-6

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

Conditions
ConditionsYield
With triethylamine In ethanol at 20℃; for 1.5h; Reflux; Inert atmosphere;100%
propylamine
107-10-8

propylamine

Ethoxymethylenemalononitrile
123-06-8

Ethoxymethylenemalononitrile

2-((propylamino)methylene)malononitrile

2-((propylamino)methylene)malononitrile

Conditions
ConditionsYield
In ethanol at 20℃; for 1h;100%
1-(2,6-difluorophenyl)hydrazine hydrochloride

1-(2,6-difluorophenyl)hydrazine hydrochloride

Ethoxymethylenemalononitrile
123-06-8

Ethoxymethylenemalononitrile

5-amino-1-(2,6-difluorophenyl)-1H-pyrazole-4-carbonitrile
1188285-05-3

5-amino-1-(2,6-difluorophenyl)-1H-pyrazole-4-carbonitrile

Conditions
ConditionsYield
With triethylamine In ethanol at 20 - 75℃; for 1.66667h; Inert atmosphere;99%
With sodium hydroxide In water; acetic acid at 0 - 60℃; for 4.2h; Large scale reaction;71%
With triethylamine In ethanol at 20℃; for 1.66667h; Reflux;
5-amino-2-methylbenzoxazole
72745-76-7

5-amino-2-methylbenzoxazole

Ethoxymethylenemalononitrile
123-06-8

Ethoxymethylenemalononitrile

2-[(2-Methyl-benzooxazol-5-ylamino)-methylene]-malononitrile

2-[(2-Methyl-benzooxazol-5-ylamino)-methylene]-malononitrile

Conditions
ConditionsYield
In ethanol Ambient temperature;98%
2-hydrazino-1,3-thiazole
30216-51-4

2-hydrazino-1,3-thiazole

Ethoxymethylenemalononitrile
123-06-8

Ethoxymethylenemalononitrile

5-amino-1-(1,3-thiazol-2-yl)-1H-pyrazole-4-carbonitrile
650638-01-0

5-amino-1-(1,3-thiazol-2-yl)-1H-pyrazole-4-carbonitrile

Conditions
ConditionsYield
With triethylamine In ethanol for 2h; Heating / reflux;98%
In ethanol for 4h; Heating;
Ethoxymethylenemalononitrile
123-06-8

Ethoxymethylenemalononitrile

3-(4-methylphenyl)-6-hydrazinopyridazine
18772-77-5

3-(4-methylphenyl)-6-hydrazinopyridazine

5-amino-1-(6-p-tolyl-pyridazin-3-yl)-1H-pyrazole-4-carbonitrile
883565-45-5

5-amino-1-(6-p-tolyl-pyridazin-3-yl)-1H-pyrazole-4-carbonitrile

Conditions
ConditionsYield
In ethanol for 2h; Heating;98%
4-(trifluoromethoxy)aniline
461-82-5

4-(trifluoromethoxy)aniline

Ethoxymethylenemalononitrile
123-06-8

Ethoxymethylenemalononitrile

2-[(4-(trifluoromethoxy)phenylamino)methylidene]malononitrile

2-[(4-(trifluoromethoxy)phenylamino)methylidene]malononitrile

Conditions
ConditionsYield
In ethanol at 120℃; for 1h;98%
4-fluorophenylhydrazine
371-14-2

4-fluorophenylhydrazine

Ethoxymethylenemalononitrile
123-06-8

Ethoxymethylenemalononitrile

5-amino-1-(4-fluorophenyl)-1H-pyrazole-4-carbonitrile
51516-70-2

5-amino-1-(4-fluorophenyl)-1H-pyrazole-4-carbonitrile

Conditions
ConditionsYield
In ethanol Reflux;97%
In ethanol at 105℃; for 0.333333h; microwave irradiation;71%
In ethanol for 2h; Reflux;61%
4-fluorophenyhydrazine hydrochloride
823-85-8

4-fluorophenyhydrazine hydrochloride

Ethoxymethylenemalononitrile
123-06-8

Ethoxymethylenemalononitrile

5-amino-1-(4-fluorophenyl)-1H-pyrazole-4-carbonitrile
51516-70-2

5-amino-1-(4-fluorophenyl)-1H-pyrazole-4-carbonitrile

Conditions
ConditionsYield
97%
With sodium ethanolate; sodium hydride In ethanol at 20℃; for 2h; Heating / reflux;86%
With triethylamine In ethanol for 10h; Reflux;66%
Ethoxymethylenemalononitrile
123-06-8

Ethoxymethylenemalononitrile

3-hydrazino-6-(p-methoxyphenyl)pyridazine
18772-76-4

3-hydrazino-6-(p-methoxyphenyl)pyridazine

5-amino-1-[6-(4-methoxyphenyl)pyridazin-3-yl]-1H-pyrazole-4-carbonitrile

5-amino-1-[6-(4-methoxyphenyl)pyridazin-3-yl]-1H-pyrazole-4-carbonitrile

Conditions
ConditionsYield
In ethanol for 2h; Reflux;97%
tert-butylhydrazine
32064-67-8

tert-butylhydrazine

Ethoxymethylenemalononitrile
123-06-8

Ethoxymethylenemalononitrile

5-amino-1-(tert-butyl)-1H-pyrazole-4-carbonitrile
158001-28-6

5-amino-1-(tert-butyl)-1H-pyrazole-4-carbonitrile

Conditions
ConditionsYield
With triethylamine In ethanol at 78℃; for 3h;96.3%
With triethylamine In ethanol at 100℃; for 0.5h; Microwave irradiation;83%
In ethanol at 70℃; for 18h;80%
With sodium methylate In ethanol46 g (87%)
With triethylamine In ethanol at 90℃; Inert atmosphere;
phenylhydrazine
100-63-0

phenylhydrazine

Ethoxymethylenemalononitrile
123-06-8

Ethoxymethylenemalononitrile

5-Amino-4-cyano-1-phenylpyrazole
5334-43-0

5-Amino-4-cyano-1-phenylpyrazole

Conditions
ConditionsYield
In ethanol for 1h; Reflux;96%
In ethanol at 120℃; for 0.75h; Solvent; Temperature; Time; Reagent/catalyst; Sealed tube; Microwave irradiation;95%
With silica gel In N,N-dimethyl acetamide for 0.15h; microwave irradiation;92%
2-acetonylpyridine
6302-02-9

2-acetonylpyridine

Ethoxymethylenemalononitrile
123-06-8

Ethoxymethylenemalononitrile

1-Acetyl-4-imino-4H-quinolizine-3-carbonitrile
123365-98-0

1-Acetyl-4-imino-4H-quinolizine-3-carbonitrile

Conditions
ConditionsYield
With potassium carbonate In dimethyl sulfoxide Ambient temperature;96%
ethyl (1,4-dihydro-5,8-dimethoxy-4-oxoquinolin-2-yl)acetate
109152-07-0

ethyl (1,4-dihydro-5,8-dimethoxy-4-oxoquinolin-2-yl)acetate

Ethoxymethylenemalononitrile
123-06-8

Ethoxymethylenemalononitrile

1-Amino-2-cyano-7,10-dimethoxy-6-oxo-6H-pyrido[1,2-a]quinoline-4-carboxylic acid ethyl ester
109152-18-3

1-Amino-2-cyano-7,10-dimethoxy-6-oxo-6H-pyrido[1,2-a]quinoline-4-carboxylic acid ethyl ester

Conditions
ConditionsYield
at 100℃; for 1h;96%
2-amino-1-benzylideneamino-4-phenyl-1H-imidazole
28734-00-1

2-amino-1-benzylideneamino-4-phenyl-1H-imidazole

Ethoxymethylenemalononitrile
123-06-8

Ethoxymethylenemalononitrile

1-benzylideneamino-6-cyano-5-imino-3-phenyl-1H-imidazo[1,2-a]pyrimidine

1-benzylideneamino-6-cyano-5-imino-3-phenyl-1H-imidazo[1,2-a]pyrimidine

Conditions
ConditionsYield
In acetonitrile for 1h; Heating;96%
tertbutylhydrazine hydrochloride
7400-27-3

tertbutylhydrazine hydrochloride

Ethoxymethylenemalononitrile
123-06-8

Ethoxymethylenemalononitrile

5-amino-1-(tert-butyl)-1H-pyrazole-4-carbonitrile
158001-28-6

5-amino-1-(tert-butyl)-1H-pyrazole-4-carbonitrile

Conditions
ConditionsYield
With triethylamine In ethanol; water at 78℃; for 3h;96%
With triethylamine In ethanol at 78℃; for 3h;96%
With triethylamine In ethanol for 3h; Reflux;95%
3,7-dimethyl-4-(4-nitrophenyl)-2,4-dihydropyrazolo[4',3':5,6]pyrano[2,3-d]pyrimidin-5-ylhydrazine
944478-21-1

3,7-dimethyl-4-(4-nitrophenyl)-2,4-dihydropyrazolo[4',3':5,6]pyrano[2,3-d]pyrimidin-5-ylhydrazine

Ethoxymethylenemalononitrile
123-06-8

Ethoxymethylenemalononitrile

5-amino-1-[3,7-dimethyl-4-(4-nitrophenyl)-2,4-dihydropyrazolo[4',3':5,6]pyrano[2,3-d]pyrimidin-5-yl]-1H-pyrazole-4-carbonitrile

5-amino-1-[3,7-dimethyl-4-(4-nitrophenyl)-2,4-dihydropyrazolo[4',3':5,6]pyrano[2,3-d]pyrimidin-5-yl]-1H-pyrazole-4-carbonitrile

Conditions
ConditionsYield
In ethanol for 2h; Heating;96%
N-cyclopropyl-3-hydrazino-4-methyl-benzamide trifluoroacetic acid salt
836684-56-1

N-cyclopropyl-3-hydrazino-4-methyl-benzamide trifluoroacetic acid salt

Ethoxymethylenemalononitrile
123-06-8

Ethoxymethylenemalononitrile

3-(5-amino-4-cyano-pyrazol-1-yl)-N-cyclopropyl-4-methylbenzamide
836684-78-7

3-(5-amino-4-cyano-pyrazol-1-yl)-N-cyclopropyl-4-methylbenzamide

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine In ethanol at 65℃; for 3h;96%
(x)C2HF3O2*C6H12F2N2

(x)C2HF3O2*C6H12F2N2

Ethoxymethylenemalononitrile
123-06-8

Ethoxymethylenemalononitrile

5-amino-1-(4,4-difluorocyclohexyl)-1H-pyrazol-4-carbonitrile
1082745-53-6

5-amino-1-(4,4-difluorocyclohexyl)-1H-pyrazol-4-carbonitrile

Conditions
ConditionsYield
With triethylamine In ethanol at 50℃; for 2h;96%
C2HF3O2*C6H12F2N2
1214910-81-2

C2HF3O2*C6H12F2N2

Ethoxymethylenemalononitrile
123-06-8

Ethoxymethylenemalononitrile

5-amino-1-(4,4-difluorocyclohexyl)-1H-pyrazol-4-carbonitrile
1082745-53-6

5-amino-1-(4,4-difluorocyclohexyl)-1H-pyrazol-4-carbonitrile

Conditions
ConditionsYield
With triethylamine In ethanol at 50℃; for 2h;96%
With triethylamine In ethanol at 50℃; for 2h;96%
3-hydrazino-6-phenylpyridazine
38956-80-8

3-hydrazino-6-phenylpyridazine

Ethoxymethylenemalononitrile
123-06-8

Ethoxymethylenemalononitrile

5-amino-1-(6-phenyl-pyridazin-3-yl)-1H-pyrazole-4-carbonitrile
1177347-71-5

5-amino-1-(6-phenyl-pyridazin-3-yl)-1H-pyrazole-4-carbonitrile

Conditions
ConditionsYield
In ethanol for 2h; Reflux;96%
In ethanol for 2h; Reflux;84%
Ethoxymethylenemalononitrile
123-06-8

Ethoxymethylenemalononitrile

(1-p-tolyl-1H-pyrazolo[3,4-d]pyrimidin-4-yl)-hydrazine
650628-55-0

(1-p-tolyl-1H-pyrazolo[3,4-d]pyrimidin-4-yl)-hydrazine

5-amino-1-(1-p-tolyl-1H-pyrazolo[3,4-d]pyrimidin-4-yl)-1H-pyrazole-4-carbonitrile

5-amino-1-(1-p-tolyl-1H-pyrazolo[3,4-d]pyrimidin-4-yl)-1H-pyrazole-4-carbonitrile

Conditions
ConditionsYield
In ethanol for 2h; Heating;96%

Ethoxymethylenemalononitrile Chemical Properties

Structure of Ethoxymethylenemalononitrile (CAS NO.123-06-8):

IUPAC Name: 2-(ethoxymethylidene)propanedinitrile 
Empirical Formula: C6H6N2O
Molecular Weight: 122.1246 
EINECS: 204-597-0 
Index of Refraction: 1.461
Molar Refractivity: 31.31 cm3
Molar Volume: 114.1 cm3
Polarizability: 12.41×10-24cm3
Surface Tension: 41.9 dyne/cm
Density: 1.07 g/cm3
Flash Point: 135.1 °C
Enthalpy of Vaporization: 53.59 kJ/mol 
Melting Point: 64-66 °C(lit.)
Boiling Point: 296.1 °C at 760 mmHg
Vapour Pressure: 0.00146 mmHg at 25°C 
Water Solubility: insoluble 
Physical Appearance: Off White to Pale Yellow
Product Categories: Pharmaceutical Intermediates;Aliphatic Compound;Miscellaneous;API intermediates;Various Intermediates;Intermediates;C6 to C7;Cyanides/Nitriles;Nitrogen Compounds

Ethoxymethylenemalononitrile Toxicity Data With Reference

1.    

ipr-mus LD50:50 mg/kg

    NTIS**    National Technical Information Service. (Springfield, VA 22161) (Formerly U.S. Clearinghouse for Scientific and Technical Information) AD277-689 .

Ethoxymethylenemalononitrile Consensus Reports

Reported in EPA TSCA Inventory. Cyanide and its compounds are on the Community Right-To-Know List.

Ethoxymethylenemalononitrile Safety Profile

Poison by intraperitoneal route. When heated to decomposition it emits very toxic fumes of NOx and CN. See also NITRILES.
Hazard Codes: HarmfulXn,IrritantXi,ToxicT
Risk Statements: 22-42/43-23/24/25-43-20/21/22
22:  Harmful if swallowed 
42/43:  May cause sensitization by inhalation and skin contact 
23/24/25:  Toxic by inhalation, in contact with skin and if swallowed 
43:  May cause sensitization by skin contact 
20/21/22:  Harmful by inhalation, in contact with skin and if swallowed 
Safety Statements: 22-36/37-45-36/37/39-26-36-24/25
22:  Do not breathe dust 
36/37:  Wear suitable protective clothing and gloves 
45:  In case of accident or if you feel unwell, seek medical advice immediately (show label where possible) 
36/37/39:  Wear suitable protective clothing, gloves and eye/face protection 
26:  In case of contact with eyes, rinse immediately with plenty of water and seek medical advice 
36:  Wear suitable protective clothing 
24/25:  Avoid contact with skin and eyes 
RIDADR: 3439
WGK Germany: 3
RTECS: OO3850000
F: 21: Sensitive to humidity.
HazardClass: 6.1
PackingGroup: III

Ethoxymethylenemalononitrile Specification

1. First Aid Measures
Ingestion:
Never give anything by mouth to an unconscious person. Get medical aid. Do NOT induce vomiting. If conscious and alert, rinse mouth and drink 2-4 cupfuls of milk or water.
Inhalation:
Get medical aid immediately. Remove from exposure to fresh air immediately. If not breathing, give artificial respiration. If breathing is difficult, give oxygen.
Skin:
Get medical aid immediately. Immediately flush skin with plenty of soap and water for at least 15 minutes while removing contaminated clothing and shoes. Wash clothing before reuse.
Eyes:
Immediately flush eyes with plenty of water for at least 15 minutes, occasionally lifting the upper and lower eyelids. Get medical aid.
2. Handling and Storage
Storage:
Store in a tightly closed container. Store in a cool, dry area away from incompatible substances.
Handling:
Wash thoroughly after handling. Remove contaminated clothing and wash before reuse. Avoid contact with eyes, skin, and clothing. Avoid ingestion and inhalation. Use with adequate ventilation. Use only in a chemical fume hood. Wash clothing before reuse. Do not breathe dust.

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