Product Name

  • Name

    Ethyl N-cyanoethanimideate

  • EINECS
  • CAS No. 1558-82-3
  • Article Data12
  • CAS DataBase
  • Density 0.943 g/cm3
  • Solubility
  • Melting Point 78-81 °C(Solv: ethyl ether (60-29-7))
  • Formula C5H8N2O
  • Boiling Point 133.2 °C at 760 mmHg
  • Molecular Weight 112.131
  • Flash Point 34.358 °C
  • Transport Information
  • Appearance
  • Safety
  • Risk Codes
  • Molecular Structure Molecular Structure of 1558-82-3 (Ethyl N-cyanoethanimideate)
  • Hazard Symbols
  • Synonyms N-Cyanoethanimidic acid ethyl ester;
  • PSA 45.38000
  • LogP 0.92238

Synthetic route

CYANAMID
420-04-2

CYANAMID

ethyl acetimidate hydrochloride
2208-07-3

ethyl acetimidate hydrochloride

ethyl N‐cyanoethanimidate
1558-82-3

ethyl N‐cyanoethanimidate

Conditions
ConditionsYield
With disodium hydrogenphosphate In water at 40℃; for 4h;95.3%
With disodium hydrogenphosphate
CYANAMID
420-04-2

CYANAMID

Triethyl orthoacetate
78-39-7

Triethyl orthoacetate

ethyl N‐cyanoethanimidate
1558-82-3

ethyl N‐cyanoethanimidate

Conditions
ConditionsYield
With acetic acid for 6h; Reflux;78%
With acetic anhydride58%
With acetic anhydride at 100 - 140℃;30%
With acetic anhydride at 135 - 150℃;
In acetonitrile at 20℃; for 39h; Reflux;
CYANAMID
420-04-2

CYANAMID

ethyl acetate
141-78-6

ethyl acetate

ethyl N‐cyanoethanimidate
1558-82-3

ethyl N‐cyanoethanimidate

Conditions
ConditionsYield
With acetic acid for 6h; Reflux;78%
ethyl N‐cyanoethanimidate
1558-82-3

ethyl N‐cyanoethanimidate

1-(6-chloropyridin-3-yl)-N-methylmethanamine
120739-62-0

1-(6-chloropyridin-3-yl)-N-methylmethanamine

acetamiprid

acetamiprid

Conditions
ConditionsYield
at 75℃; for 9h; Industrial scale;96%
ethyl 2-cyanoacetate
105-56-6

ethyl 2-cyanoacetate

ethyl N‐cyanoethanimidate
1558-82-3

ethyl N‐cyanoethanimidate

ethyl 2-cyano-3-(cyanoamino)crotonate sodium salt

ethyl 2-cyano-3-(cyanoamino)crotonate sodium salt

Conditions
ConditionsYield
With sodium In ethanol Ambient temperature;87%
ethyl N‐cyanoethanimidate
1558-82-3

ethyl N‐cyanoethanimidate

3-hydrazinylpropanenitrile
353-07-1

3-hydrazinylpropanenitrile

C6H9N5
1072106-44-5

C6H9N5

Conditions
ConditionsYield
In methanol for 20h; Reflux;86%
phosphorohydrazidic acid diethyl ester
56183-69-8

phosphorohydrazidic acid diethyl ester

ethyl N‐cyanoethanimidate
1558-82-3

ethyl N‐cyanoethanimidate

5-amino-3-methyl[1,2,4]triazol-1-ylphosphonic acid diethyl ester

5-amino-3-methyl[1,2,4]triazol-1-ylphosphonic acid diethyl ester

Conditions
ConditionsYield
With toluene-4-sulfonic acid Reflux;81%
1,2-diamino-benzene
95-54-5

1,2-diamino-benzene

ethyl N‐cyanoethanimidate
1558-82-3

ethyl N‐cyanoethanimidate

2-Methyl-1H-benzimidazole
615-15-6

2-Methyl-1H-benzimidazole

Conditions
ConditionsYield
In methanol for 10h; Reflux;79%
1H-benzimidazol-2-amine
934-32-7

1H-benzimidazol-2-amine

ethyl N‐cyanoethanimidate
1558-82-3

ethyl N‐cyanoethanimidate

4-Amino-2-methylbenzimidazole<1,2-a><1,3,5>triazine
76278-99-4

4-Amino-2-methylbenzimidazole<1,2-a><1,3,5>triazine

Conditions
ConditionsYield
In 1,2-dimethoxyethane Heating;73%
4,5-dimethyl-1,2-phenylenediamine
3171-45-7

4,5-dimethyl-1,2-phenylenediamine

ethyl N‐cyanoethanimidate
1558-82-3

ethyl N‐cyanoethanimidate

2,5,6-trimethylbenzimidazole
3363-56-2

2,5,6-trimethylbenzimidazole

Conditions
ConditionsYield
In methanol for 10h; Reflux;69%
monohydrazido thiophosphoric acid diphenylester
53144-23-3

monohydrazido thiophosphoric acid diphenylester

ethyl N‐cyanoethanimidate
1558-82-3

ethyl N‐cyanoethanimidate

5-amino-3-methyl[1,2,4]triazol-1-ylthiophosphonic acid diphenyl ester

5-amino-3-methyl[1,2,4]triazol-1-ylthiophosphonic acid diphenyl ester

Conditions
ConditionsYield
With toluene-4-sulfonic acid Reflux;68%
S,S-tetramethylenesulfoximide
50578-18-2

S,S-tetramethylenesulfoximide

ethyl N‐cyanoethanimidate
1558-82-3

ethyl N‐cyanoethanimidate

C7H11N3OS
114113-46-1

C7H11N3OS

Conditions
ConditionsYield
at 80℃; for 18h;65%
ethyl N‐cyanoethanimidate
1558-82-3

ethyl N‐cyanoethanimidate

3-hydrazinylpropanenitrile
353-07-1

3-hydrazinylpropanenitrile

C6H9N5
1072106-47-8

C6H9N5

Conditions
ConditionsYield
In toluene for 48h; Reflux;64%
1-Methyl-5-(4-methylphenyl)-1λ4,4-thiazin-3-amin-1-oxid
102423-32-5

1-Methyl-5-(4-methylphenyl)-1λ4,4-thiazin-3-amin-1-oxid

ethyl N‐cyanoethanimidate
1558-82-3

ethyl N‐cyanoethanimidate

N-Cyan-N'-(1-methyl-5-p-tolyl-1λ4,4-thiazin-3-yl)acetamidin-S-oxid
107325-92-8

N-Cyan-N'-(1-methyl-5-p-tolyl-1λ4,4-thiazin-3-yl)acetamidin-S-oxid

Conditions
ConditionsYield
at 150℃; for 0.25h;61%
5-aminotetrazole
4418-61-5

5-aminotetrazole

ethyl N‐cyanoethanimidate
1558-82-3

ethyl N‐cyanoethanimidate

4-Azido-6-methyl-[1,3,5]triazin-2-ylamine

4-Azido-6-methyl-[1,3,5]triazin-2-ylamine

Conditions
ConditionsYield
With triethylamine In pyridine for 264h; Ambient temperature;60%
S-benzyl-S-ethyl-sulfodiimide
30223-23-5

S-benzyl-S-ethyl-sulfodiimide

ethyl N‐cyanoethanimidate
1558-82-3

ethyl N‐cyanoethanimidate

N1-(Benzylethylimino-λ6-sulfanyliden)-N2-cyanacetamidin
111268-17-8

N1-(Benzylethylimino-λ6-sulfanyliden)-N2-cyanacetamidin

Conditions
ConditionsYield
at 60℃;57%
1-Methyl-5-phenyl-1λ4,4-thiazin-3-amin-1-oxid
102423-30-3

1-Methyl-5-phenyl-1λ4,4-thiazin-3-amin-1-oxid

ethyl N‐cyanoethanimidate
1558-82-3

ethyl N‐cyanoethanimidate

N-Cyan-N'-(1-methyl-5-phenyl-1λ4,4-thiazin-3-yl)acetamidin-S-oxid
107325-91-7

N-Cyan-N'-(1-methyl-5-phenyl-1λ4,4-thiazin-3-yl)acetamidin-S-oxid

Conditions
ConditionsYield
at 150℃; for 0.25h;57%
Methyl thioglycolate
2365-48-2

Methyl thioglycolate

ethyl N‐cyanoethanimidate
1558-82-3

ethyl N‐cyanoethanimidate

4-amino-2-methyl-thiazole-5-carboxylic acid methyl ester

4-amino-2-methyl-thiazole-5-carboxylic acid methyl ester

Conditions
ConditionsYield
With sodium hydride In tetrahydrofuran at 20℃; for 12h; Condensation;57%
4-amino-1H-imidazole
4919-03-3

4-amino-1H-imidazole

ethyl N‐cyanoethanimidate
1558-82-3

ethyl N‐cyanoethanimidate

N-cyano-N'-(imidazol-4-yl)acetamidine
145837-48-5

N-cyano-N'-(imidazol-4-yl)acetamidine

Conditions
ConditionsYield
In 1,4-dioxane54%
tetrahydrothiophene-S,S-diimine
53245-06-0

tetrahydrothiophene-S,S-diimine

ethyl N‐cyanoethanimidate
1558-82-3

ethyl N‐cyanoethanimidate

N2-Cyan-N1-(tetrahydro-1-imino-λ6-thiophen-1-yliden)acetamidin
111268-15-6

N2-Cyan-N1-(tetrahydro-1-imino-λ6-thiophen-1-yliden)acetamidin

Conditions
ConditionsYield
at 60℃;54%
ethyl 2-sulfanylacetate
623-51-8

ethyl 2-sulfanylacetate

ethyl N‐cyanoethanimidate
1558-82-3

ethyl N‐cyanoethanimidate

4-amino-2-methyl-thiazole-5-carboxylic acid ethyl ester

4-amino-2-methyl-thiazole-5-carboxylic acid ethyl ester

Conditions
ConditionsYield
With sodium hydride In tetrahydrofuran at 20℃; for 12h; Condensation;53%
dimethylsulfoximine
1520-31-6

dimethylsulfoximine

ethyl N‐cyanoethanimidate
1558-82-3

ethyl N‐cyanoethanimidate

C5H9N3OS
114113-54-1

C5H9N3OS

Conditions
ConditionsYield
at 80℃; for 18h;50%
dimethylsulfoxonium methylide
70775-39-2, 5367-24-8

dimethylsulfoxonium methylide

ethyl N‐cyanoethanimidate
1558-82-3

ethyl N‐cyanoethanimidate

<2-(Dimethyloxo-λ6-sulfanyliden)-1-methylethyliden>cyanamid
102423-28-9

<2-(Dimethyloxo-λ6-sulfanyliden)-1-methylethyliden>cyanamid

Conditions
ConditionsYield
In dimethyl sulfoxide for 24h; Ambient temperature;46%
S-benzyl-S-methyl-sulfodiimine
30223-22-4

S-benzyl-S-methyl-sulfodiimine

ethyl N‐cyanoethanimidate
1558-82-3

ethyl N‐cyanoethanimidate

N1-(Benzyliminomethyl-λ6-sulfanyliden)-N2-cyanacetamidin
111268-16-7

N1-(Benzyliminomethyl-λ6-sulfanyliden)-N2-cyanacetamidin

Conditions
ConditionsYield
at 60℃;43%
(7S,8S)-8-Amino-7-hydroxy-6,6-dimethyl-5-oxo-5,6,7,8-tetrahydro-naphthalene-2-carbonitrile

(7S,8S)-8-Amino-7-hydroxy-6,6-dimethyl-5-oxo-5,6,7,8-tetrahydro-naphthalene-2-carbonitrile

ethyl N‐cyanoethanimidate
1558-82-3

ethyl N‐cyanoethanimidate

trans-4-<(N-cyanoacetimidoyl)amino>-2,2-dimethyl-3-hydroxy-1-oxo-1,2,3,4-tetrahydronaphthalene-6-carbonitrile

trans-4-<(N-cyanoacetimidoyl)amino>-2,2-dimethyl-3-hydroxy-1-oxo-1,2,3,4-tetrahydronaphthalene-6-carbonitrile

Conditions
ConditionsYield
at 100℃;40%
(2-methoxyethyl)hydrazine
3044-15-3

(2-methoxyethyl)hydrazine

ethyl N‐cyanoethanimidate
1558-82-3

ethyl N‐cyanoethanimidate

C6H12N4O

C6H12N4O

Conditions
ConditionsYield
With triethylamine In ethanol at 0 - 20℃; for 18h;39%
5-amino-2-(cyclopropanecarbonylamino)-N-(cyclopropylmethyl)-4,5,6,7-tetrahydrobenzothiophene-3-carboxamide hydrochloride

5-amino-2-(cyclopropanecarbonylamino)-N-(cyclopropylmethyl)-4,5,6,7-tetrahydrobenzothiophene-3-carboxamide hydrochloride

ethyl N‐cyanoethanimidate
1558-82-3

ethyl N‐cyanoethanimidate

5-[[N-cyano-C-methyl-carbonimidoyl]amino]-2-(cyclopropanecarbonylamino)-N-(cyclopropylmethyl)-4,5,6,7-tetrahydrobenzothiophene-3-carboxamide

5-[[N-cyano-C-methyl-carbonimidoyl]amino]-2-(cyclopropanecarbonylamino)-N-(cyclopropylmethyl)-4,5,6,7-tetrahydrobenzothiophene-3-carboxamide

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine In ethanol at 100℃; for 4h; Microwave irradiation;37%
S,S-dibenzylsulphurdi-imide
30223-27-9

S,S-dibenzylsulphurdi-imide

ethyl N‐cyanoethanimidate
1558-82-3

ethyl N‐cyanoethanimidate

N2-Cyan-N1-(dibenzylimino-λ6-sulfanyliden)acetamidin
111268-18-9

N2-Cyan-N1-(dibenzylimino-λ6-sulfanyliden)acetamidin

Conditions
ConditionsYield
at 60℃;19%
2-Isopropyl-1-methyl-1H-imidazol-4-ylamine

2-Isopropyl-1-methyl-1H-imidazol-4-ylamine

ethyl N‐cyanoethanimidate
1558-82-3

ethyl N‐cyanoethanimidate

N-cyano-N'-(2-isopropyl-1-methylimidazol-4-yl)acetamidine
145837-47-4

N-cyano-N'-(2-isopropyl-1-methylimidazol-4-yl)acetamidine

Conditions
ConditionsYield
In 1,4-dioxane for 1h;16%

Ethyl N-cyanoethanimideate Specification

The Ethanimidic acid,N-cyano-, ethyl ester, with CAS registry number 1558-82-3, has the systematic name of ethyl (1Z)-N-cyanoethanimidoate. And its IUPAC name is ethyl N-cyanoethanimidate. And the chemical formula of this chemical is C5H8N2O.

Physical properties of Ethanimidic acid,N-cyano-, ethyl ester: (1)ACD/LogP: 1.15; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 1; (4)ACD/LogD (pH 7.4): 1; (5)ACD/BCF (pH 5.5): 3; (6)ACD/BCF (pH 7.4): 3; (7)ACD/KOC (pH 5.5): 70; (8)ACD/KOC (pH 7.4): 70; (9)#H bond acceptors: 3; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 2; (12)Polar Surface Area: 45.38 Å2; (13)Index of Refraction: 1.444; (14)Molar Refractivity: 31.572 cm3; (15)Molar Volume: 118.908 cm3; (16)Polarizability: 12.516×10-24cm3; (17)Surface Tension: 30.068 dyne/cm; (18)Enthalpy of Vaporization: 37.071 kJ/mol; (19)Vapour Pressure: 8.561 mmHg at 25°C.

Uses of Ethanimidic acid,N-cyano-, ethyl ester: it can be used to produce 2,5-dimethyl-2H-[1,2,4]triazol-3-ylamine. This reaction will need solvent ethanol. The yield is about 75%.

You can still convert the following datas into molecular structure:
(1)SMILES: C\C(=N\C#N)OCC
(2)InChI: InChI=1/C5H8N2O/c1-3-8-5(2)7-4-6/h3H2,1-2H3/b7-5-
(3)InChIKey: PLVWUINOWYHRAA-ALCCZGGFBL
(4)Std. InChI: InChI=1S/C5H8N2O/c1-3-8-5(2)7-4-6/h3H2,1-2H3/b7-5-
(5)Std. InChIKey: PLVWUINOWYHRAA-ALCCZGGFSA-N

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