Product Name

  • Name

    Ethyl cyanoformate

  • EINECS 210-797-9
  • CAS No. 623-49-4
  • Article Data38
  • CAS DataBase
  • Density 1.084 g/cm3
  • Solubility
  • Melting Point
  • Formula C4H5NO2
  • Boiling Point 115.5 °C at 760 mmHg
  • Molecular Weight 99.0892
  • Flash Point 24.444 °C
  • Transport Information UN 3275
  • Appearance Clear colourless liquid
  • Safety 16-24/25
  • Risk Codes 10-23/24/25
  • Molecular Structure Molecular Structure of 623-49-4 (Ethyl cyanoformate)
  • Hazard Symbols ToxicT
  • Synonyms Formicacid, cyano-, ethyl ester (6CI,7CI,8CI);Cyanocarbonyloxyethane;Cyanoformicacid ethyl ester;Ethoxycarbonyl cyanide;Ethyl carbonocyanidate;Ethylcyanoformate;NSC 65347;
  • PSA 50.09000
  • LogP 0.07308

Synthetic route

ethyl (triphenylphosphoranylidene)acetate
1099-45-2

ethyl (triphenylphosphoranylidene)acetate

A

ethyl cyanoformate
623-49-4

ethyl cyanoformate

B

<(Ethoxycarbonyl)methyl>triphenylphosphoniumnitrat

<(Ethoxycarbonyl)methyl>triphenylphosphoniumnitrat

Conditions
ConditionsYield
With dinitrogen tetraoxide In tetrahydrofuran for 12h;A 73%
B 92%
trimethylsilyl cyanide
7677-24-9

trimethylsilyl cyanide

chloroformic acid ethyl ester
541-41-3

chloroformic acid ethyl ester

ethyl cyanoformate
623-49-4

ethyl cyanoformate

Conditions
ConditionsYield
With dmap for 24h; Ambient temperature;83%
5-acetoxy-3-methoxycarbonyl-5H-1,2-benzodiazepine

5-acetoxy-3-methoxycarbonyl-5H-1,2-benzodiazepine

A

3-indoxyl acetate
608-08-2

3-indoxyl acetate

B

ethyl cyanoformate
623-49-4

ethyl cyanoformate

Conditions
ConditionsYield
In dichloromethane for 0.133333h; Irradiation;A 74%
B n/a
tri-n-butyltin cyanide
2179-92-2

tri-n-butyltin cyanide

chloroformic acid ethyl ester
541-41-3

chloroformic acid ethyl ester

A

ethyl cyanoformate
623-49-4

ethyl cyanoformate

B

tributyltin chloride

tributyltin chloride

Conditions
ConditionsYield
In neat (no solvent) at 70℃; for 2.5h;A 57%
B n/a
...Expand
sodium cyanide
773837-37-9

sodium cyanide

chloroformic acid ethyl ester
541-41-3

chloroformic acid ethyl ester

ethyl cyanoformate
623-49-4

ethyl cyanoformate

Conditions
ConditionsYield
With tetrabutylammomium bromide In dichloromethane; water at 0℃; for 1h;52%
diethyl 1,2,4,5-tetrazine-3,6-dicarboxylate
122747-88-0

diethyl 1,2,4,5-tetrazine-3,6-dicarboxylate

2,2-dimethylpropylidynephosphine
78129-68-7

2,2-dimethylpropylidynephosphine

A

4-tert-Butyl-1-(2,4,5-tri-tert-butyl-[1,3]diphosphol-1-yl)-1H-[1,2,3]azadiphosphole-5-carboxylic acid ethyl ester
122747-90-4

4-tert-Butyl-1-(2,4,5-tri-tert-butyl-[1,3]diphosphol-1-yl)-1H-[1,2,3]azadiphosphole-5-carboxylic acid ethyl ester

B

ethyl cyanoformate
623-49-4

ethyl cyanoformate

C

N2

N2

Conditions
ConditionsYield
In toluene at 110℃; for 24h; sealed tube;A 48%
B n/a
C n/a
...Expand
ethyl 4,4,4-trifluoro-3,3-dihydroxy-2-(hydroxyimino)butanoate

ethyl 4,4,4-trifluoro-3,3-dihydroxy-2-(hydroxyimino)butanoate

ethyl cyanoformate
623-49-4

ethyl cyanoformate

Conditions
ConditionsYield
With acetic anhydride In chloroform for 1h; Reagent/catalyst; Reflux;48%
oct-1-ene
111-66-0

oct-1-ene

3,4-bis(ethoxycarbonyl)-1,2,5-oxadiazole 2-oxide
18417-40-8

3,4-bis(ethoxycarbonyl)-1,2,5-oxadiazole 2-oxide

A

2,5-Dihexyl-tetrahydro-isoxazolo[2,3-b]isoxazole-3a-carboxylic acid ethyl ester
86497-63-4

2,5-Dihexyl-tetrahydro-isoxazolo[2,3-b]isoxazole-3a-carboxylic acid ethyl ester

B

ethyl cyanoformate
623-49-4

ethyl cyanoformate

Conditions
ConditionsYield
In xylene for 24h; Heating;A 38%
B n/a
...Expand
3,4-bis(ethoxycarbonyl)-1,2,5-oxadiazole 2-oxide
18417-40-8

3,4-bis(ethoxycarbonyl)-1,2,5-oxadiazole 2-oxide

anethole
104-46-1

anethole

A

3-(ethoxycarbonyl)-4-methyl-5-(p-methoxyphenyl)isoxazole
51291-35-1

3-(ethoxycarbonyl)-4-methyl-5-(p-methoxyphenyl)isoxazole

B

ethyl cyanoformate
623-49-4

ethyl cyanoformate

Conditions
ConditionsYield
at 150℃; for 24h;A 2%
B 32%
...Expand
ethanol
64-17-5

ethanol

carbon monoxide
201230-82-2

carbon monoxide

phenylsulfonyloxyacetonitrile
10531-13-2

phenylsulfonyloxyacetonitrile

ethyl cyanoformate
623-49-4

ethyl cyanoformate

Conditions
ConditionsYield
With dicobalt octacarbonyl at 80℃; under 30002.4 Torr; for 6h;30%
With dicobalt octacarbonyl at 80℃; under 30002.4 Torr; for 6h; Product distribution; var. temp. pressure and reaction time;
...Expand
2-vinyloxynaphthalene
7309-03-7

2-vinyloxynaphthalene

3,4-bis(ethoxycarbonyl)-1,2,5-oxadiazole 2-oxide
18417-40-8

3,4-bis(ethoxycarbonyl)-1,2,5-oxadiazole 2-oxide

A

2,5-Bis-(naphthalen-2-yloxy)-tetrahydro-isoxazolo[2,3-b]isoxazole-3a-carboxylic acid ethyl ester
86497-62-3

2,5-Bis-(naphthalen-2-yloxy)-tetrahydro-isoxazolo[2,3-b]isoxazole-3a-carboxylic acid ethyl ester

B

ethyl cyanoformate
623-49-4

ethyl cyanoformate

Conditions
ConditionsYield
In xylene for 24h; Heating;A 21%
B n/a
...Expand
diethyl 2-oxo-3-triphenylphosphoranylidenebutanedioate
29393-95-1

diethyl 2-oxo-3-triphenylphosphoranylidenebutanedioate

A

diethyl 2,3-dioxosuccinate
59743-08-7

diethyl 2,3-dioxosuccinate

B

triphenylphosphine oxide-nitric acid complex
18365-29-2

triphenylphosphine oxide-nitric acid complex

C

ethyl cyanoformate
623-49-4

ethyl cyanoformate

Conditions
ConditionsYield
With Nitrogen dioxide In dichloromethane Ambient temperature; Yields of byproduct given;A 20%
B n/a
C n/a
With Nitrogen dioxide In dichloromethane Ambient temperature; Yield given;A 20%
B n/a
C 15%
With Nitrogen dioxide In dichloromethane Ambient temperature; Yields of byproduct given;A n/a
B n/a
C 15%
...Expand
phenylmagnesium bromide

phenylmagnesium bromide

Ethyl oxamate
617-36-7

Ethyl oxamate

A

triphenylmethyl alcohol
76-84-6

triphenylmethyl alcohol

B

biphenyl
92-52-4

biphenyl

C

ethyl cyanoformate
623-49-4

ethyl cyanoformate

...Expand
Ethyl oxamate
617-36-7

Ethyl oxamate

ethyl cyanoformate
623-49-4

ethyl cyanoformate

Conditions
ConditionsYield
With phosphorus pentaoxide
With phosphorus pentachloride der nach der Zugabe von Ligroin gefaellte Niederschlag wird gepresst, getrocknet und destilliert;
With phosphorus pentoxide at 135 - 140℃;
With phosphorus pentoxide
With phosphorus pentoxide Heating;
sodium cyanide
143-33-9

sodium cyanide

chloroformic acid ethyl ester
541-41-3

chloroformic acid ethyl ester

ethyl cyanoformate
623-49-4

ethyl cyanoformate

Conditions
ConditionsYield
With tetrabutylammomium bromide In dichloromethane; water
cyanoformic acid iminoethyl ether

cyanoformic acid iminoethyl ether

ethyl cyanoformate
623-49-4

ethyl cyanoformate

Conditions
ConditionsYield
With hydrogenchloride
isonitrosoacetic acid ester

isonitrosoacetic acid ester

ethyl cyanoformate
623-49-4

ethyl cyanoformate

Conditions
ConditionsYield
With acetic anhydride
hydrogenchloride
7647-01-0

hydrogenchloride

Cyan-imidoameisensaeureethylester
13369-04-5

Cyan-imidoameisensaeureethylester

A

ammonium chloride

ammonium chloride

B

ethyl cyanoformate
623-49-4

ethyl cyanoformate

...Expand
E-ethyl cyano(phenylhydrazono)acetate
27097-85-4

E-ethyl cyano(phenylhydrazono)acetate

A

N-carboethoxyaniline
101-99-5

N-carboethoxyaniline

B

ethyl cyanoformate
623-49-4

ethyl cyanoformate

C

1-phenylcyanamide
622-34-4

1-phenylcyanamide

Conditions
ConditionsYield
at 500℃; under 0.02 Torr; Product distribution;
...Expand
1,4-diaza-bicyclo[2.2.2]octane
280-57-9

1,4-diaza-bicyclo[2.2.2]octane

trimethylsilyl cyanide
7677-24-9

trimethylsilyl cyanide

chloroformic acid ethyl ester
541-41-3

chloroformic acid ethyl ester

ethyl cyanoformate
623-49-4

ethyl cyanoformate

...Expand
water
7732-18-5

water

A

CN(1-)*H2O = CN(H2O)(1-)
68579-77-1

CN(1-)*H2O = CN(H2O)(1-)

B

ethyl cyanoformate
623-49-4

ethyl cyanoformate

Conditions
ConditionsYield
With (CN)2CO2C2H5(1-) In neat (no solvent, gas phase) High Pressure; react. in a pulsed ionization high-pressure mass spectrometer; not isolated, detected by high-pressure mass spectrometry;
sulfur dioxide
7446-09-5

sulfur dioxide

A

isocyanosulfite(1-)

isocyanosulfite(1-)

B

ethyl cyanoformate
623-49-4

ethyl cyanoformate

Conditions
ConditionsYield
With (CN)2CO2C2H5(1-) In neat (no solvent, gas phase) High Pressure; react. in a pulsed ionization high-pressure mass spectrometer; not isolated, detected by high-pressure mass spectrometry;
carbon dioxide
124-38-9

carbon dioxide

A

CN(1-)*CO2

CN(1-)*CO2

B

ethyl cyanoformate
623-49-4

ethyl cyanoformate

Conditions
ConditionsYield
With (CN)2CO2C2H5(1-) In neat (no solvent, gas phase) byproducts: NCCO2(1-); High Pressure; react. following a 50μs, 2000-eV electron beam pulse in a mixt. of (CN)CO2C2H5:CO2:CH4 at a total ion source pressure of 5.0 torr at 55°C in a pulsed ionization high-pressure mass spectrometer; not isolated, detected by high-pressure mass spectrometry;
potassium cyanide

potassium cyanide

chloroformic acid ethyl ester
541-41-3

chloroformic acid ethyl ester

ethyl cyanoformate
623-49-4

ethyl cyanoformate

Conditions
ConditionsYield
With sodium iodide In water at 60 - 70℃; for 24h;
ethyl cyanoformate
623-49-4

ethyl cyanoformate

triethyl 1,3,5-triazine-2,4,6-tricarboxylate
898-22-6

triethyl 1,3,5-triazine-2,4,6-tricarboxylate

Conditions
ConditionsYield
acid100%
With hydrogenchloride for 336h; Inert atmosphere;98%
With hydrogenchloride at 20℃; for 144h;88%
5-phenyl-1,3,4-oxathiazol-2-one
5852-49-3

5-phenyl-1,3,4-oxathiazol-2-one

ethyl cyanoformate
623-49-4

ethyl cyanoformate

ethyl 3-phenyl-1,2,4-thiadiazole-5-carboxylate
50483-79-9

ethyl 3-phenyl-1,2,4-thiadiazole-5-carboxylate

Conditions
ConditionsYield
In para-xylene at 160℃; for 0.166667h; Microwave irradiation;100%
In ethyl acetate at 160℃; for 0.166667h; microwave irradiation;94%
In dodecane
ethyl cyanoformate
623-49-4

ethyl cyanoformate

4-methyl-4-(1-methyl-2,3-dihydro-1H-indol-3-yl)-pentan-2-one
385842-52-4

4-methyl-4-(1-methyl-2,3-dihydro-1H-indol-3-yl)-pentan-2-one

5-methyl-5-(1-methyl-2,3-dihydro-1H-indol-3-yl)-3-oxo-hexanoic acid ethyl ester
385842-53-5

5-methyl-5-(1-methyl-2,3-dihydro-1H-indol-3-yl)-3-oxo-hexanoic acid ethyl ester

Conditions
ConditionsYield
With N,N,N,N,N,N-hexamethylphosphoric triamide; lithium diisopropyl amide In tetrahydrofuran100%
ethyl cyanoformate
623-49-4

ethyl cyanoformate

4-N,N-dimethylphenyl triethylsilyl ketone
461051-92-3

4-N,N-dimethylphenyl triethylsilyl ketone

ethyl-2-cyano-2-(4-N,N-dimethylphenyl)-2-triethylsiloxy acetate

ethyl-2-cyano-2-(4-N,N-dimethylphenyl)-2-triethylsiloxy acetate

Conditions
ConditionsYield
With potassium cyanide; 18-crown-6 ether In toluene at 110℃; for 12h; cyanation/Brook rearrangement/C-acylation;100%
3-methoxy-benzaldehyde
591-31-1

3-methoxy-benzaldehyde

ethyl cyanoformate
623-49-4

ethyl cyanoformate

(2S)-O-ethoxycarbonyl-2-hydroxy-2-(3-methoxyphenyl)-acetonitrile

(2S)-O-ethoxycarbonyl-2-hydroxy-2-(3-methoxyphenyl)-acetonitrile

Conditions
ConditionsYield
With potassium cyanide; 18-crown-6 ether; chiral salen-based titanium In dichloromethane at -40℃; for 24h;100%
With 3,3'-di-naphthalen-2-yl-biphenyl-2,2'-diol; titanium(IV) isopropylate; quinindine; isopropyl alcohol In toluene at -20℃; for 7h; Strecker reaction; Inert atmosphere; optical yield given as %ee; enantioselective reaction;99%
With chiral [(salen)TiO]2 In dichloromethane at -40℃; for 17h;94%
With chiral bimetallic titanium(salen) In dichloromethane at -40℃; for 17h;94%
With potassium cyanide; 18-crown-6 ether; titanium(salen) complex In dichloromethane at -40℃; for 24h;
ortho-anisaldehyde
135-02-4

ortho-anisaldehyde

ethyl cyanoformate
623-49-4

ethyl cyanoformate

(2S)-O-ethoxycarbonyl-2-hydroxy-2-(2-methoxyphenyl)-acetonitrile

(2S)-O-ethoxycarbonyl-2-hydroxy-2-(2-methoxyphenyl)-acetonitrile

Conditions
ConditionsYield
With potassium cyanide; 18-crown-6 ether; chiral salen-based titanium In dichloromethane at -40℃; for 24h;100%
With chiral [(salen)TiO]2 In dichloromethane at -40℃; for 48h;95%
With chiral bimetallic titanium(salen) In dichloromethane at -40℃; for 48h;95%
2-methylphenyl aldehyde
529-20-4

2-methylphenyl aldehyde

ethyl cyanoformate
623-49-4

ethyl cyanoformate

(2S)-O-ethoxycarbonyl-2-hydroxy-2-(2-methylphenyl)-acetonitrile

(2S)-O-ethoxycarbonyl-2-hydroxy-2-(2-methylphenyl)-acetonitrile

Conditions
ConditionsYield
With potassium cyanide; 18-crown-6 ether; chiral salen-based titanium In dichloromethane at -40℃; for 24h;100%
With 2,6-dimethylpyridine; 2C2H5O4S(1-)*C72H104N4O16V2(2+) In dichloromethane at -20℃; for 12h; Inert atmosphere; optical yield given as %ee; enantioselective reaction;97%
With 1H-imidazole; C2H5O4S(1-)*C36H54N2O4V(1+) In dichloromethane at -20℃; for 18h; Inert atmosphere; optical yield given as %ee;96%
With potassium cyanide; 18-crown-6 ether; titanium(salen) complex In dichloromethane at -40℃; for 24h;
4-methyl-benzaldehyde
104-87-0

4-methyl-benzaldehyde

ethyl cyanoformate
623-49-4

ethyl cyanoformate

(2S)-O-ethoxycarbonyl-2-hydroxy-2-(4-methylphenyl)-acetonitrile

(2S)-O-ethoxycarbonyl-2-hydroxy-2-(4-methylphenyl)-acetonitrile

Conditions
ConditionsYield
With potassium cyanide; 18-crown-6 ether; chiral salen-based titanium In dichloromethane at -40℃; for 24h;100%
With 3,3'-di-naphthalen-2-yl-biphenyl-2,2'-diol; titanium(IV) isopropylate; quinindine; isopropyl alcohol In toluene at -20℃; for 5h; Strecker reaction; Inert atmosphere; optical yield given as %ee; enantioselective reaction;97%
With 2,6-dimethylpyridine; 2C2H5O4S(1-)*C72H104N4O16V2(2+) In dichloromethane at -20℃; for 12h; Inert atmosphere; optical yield given as %ee; enantioselective reaction;97%
With 1H-imidazole; C2H5O4S(1-)*C36H54N2O4V(1+) In dichloromethane at -20℃; for 24h; Inert atmosphere; optical yield given as %ee;91%
With potassium cyanide; 18-crown-6 ether; titanium(salen) complex In dichloromethane at -40℃; for 24h;
4-chlorobenzaldehyde
104-88-1

4-chlorobenzaldehyde

ethyl cyanoformate
623-49-4

ethyl cyanoformate

(2S)-O-ethoxycarbonyl-2-hydroxy-2-(4-chlorophenyl)-acetonitrile

(2S)-O-ethoxycarbonyl-2-hydroxy-2-(4-chlorophenyl)-acetonitrile

Conditions
ConditionsYield
With potassium cyanide; 18-crown-6 ether; chiral salen-based titanium In dichloromethane at -40℃; for 24h;100%
With 3,3'-di-naphthalen-2-yl-biphenyl-2,2'-diol; titanium(IV) isopropylate; quinindine; isopropyl alcohol In toluene at -20℃; for 7h; Strecker reaction; Inert atmosphere; optical yield given as %ee; enantioselective reaction;90%
With potassium cyanide; 18-crown-6 ether; titanium(salen) complex In dichloromethane at -40℃; for 24h;
potassium cyanide
151-50-8

potassium cyanide

benzaldehyde
100-52-7

benzaldehyde

ethyl cyanoformate
623-49-4

ethyl cyanoformate

(S)-mandelonitrile ethyl carbonate
6443-66-9

(S)-mandelonitrile ethyl carbonate

Conditions
ConditionsYield
di-μ-oxo-di((R,R)-N,N'-bis((alicylaldehydo)ethylenediamine))dititanium(IV) In dichloromethane at -78 - -40℃; for 24h; Product distribution / selectivity;100%
di-μ-oxo-di((S,S)-N,N'-bis((salicylaldehydo)ethylenediamine))dititanium(IV) In dichloromethane at -40℃; for 19h; Product distribution / selectivity;n/a
...Expand
ethyl cyanoformate
623-49-4

ethyl cyanoformate

potassium cyanoformate

potassium cyanoformate

Conditions
ConditionsYield
With potassium hydroxide In tetrahydrofuran; water at 0 - 20℃; for 12h;100%
ethyl 2-(2-[ethyl(phenyl)amino]phenyl)acetate

ethyl 2-(2-[ethyl(phenyl)amino]phenyl)acetate

ethyl cyanoformate
623-49-4

ethyl cyanoformate

1,2-diethyl 2-(2-[ethyl(phenyl)amino]phenyl)propanedioate

1,2-diethyl 2-(2-[ethyl(phenyl)amino]phenyl)propanedioate

Conditions
ConditionsYield
Stage #1: ethyl 2-(2-[ethyl(phenyl)amino]phenyl)acetate With lithium hexamethyldisilazane In tetrahydrofuran at -78℃; for 1.16667h;
Stage #2: ethyl cyanoformate In tetrahydrofuran at -78 - 20℃; for 17.5h;		100%
potassium cyanide

potassium cyanide

β-naphthaldehyde
66-99-9

β-naphthaldehyde

ethyl cyanoformate
623-49-4

ethyl cyanoformate

2-ethoxycarbonyl (R)-2-hydroxy-2-(2-naphthyl)-acetonitrile

2-ethoxycarbonyl (R)-2-hydroxy-2-(2-naphthyl)-acetonitrile

Conditions
ConditionsYield
With C40H62AlFN3O2(1+)*CF3O3S(1-) In chloroform; 1,2-dichloro-ethane at -50℃; for 72h; Catalytic behavior; Reagent/catalyst; Inert atmosphere; Schlenk technique; enantioselective reaction;100%
With C40H62AlFN3O2(1+)*CF3O3S(1-) In chloroform; 1,2-dichloro-ethane at -50℃; for 24h; Reagent/catalyst; Schlenk technique; Inert atmosphere;99%
...Expand
potassium cyanide

potassium cyanide

3-methoxy-benzaldehyde
591-31-1

3-methoxy-benzaldehyde

ethyl cyanoformate
623-49-4

ethyl cyanoformate

2-ethoxycarbonyl (R)-2-hydroxy-2-(3-methoxyphenyl)-acetonitrile

2-ethoxycarbonyl (R)-2-hydroxy-2-(3-methoxyphenyl)-acetonitrile

Conditions
ConditionsYield
With C40H62AlFN3O2(1+)*CF3O3S(1-) In chloroform; 1,2-dichloro-ethane at -50℃; for 24h; Inert atmosphere; Schlenk technique; enantioselective reaction;100%
With C40H62AlFN3O2(1+)*CF3O3S(1-) In chloroform; 1,2-dichloro-ethane at -50℃; for 24h; Schlenk technique; Inert atmosphere;99%
...Expand
(E)-3-phenylpropenal
14371-10-9

(E)-3-phenylpropenal

potassium cyanide

potassium cyanide

ethyl cyanoformate
623-49-4

ethyl cyanoformate

2-ethoxycarbonyl (R)-2-hydroxy-2-phenyl-but-3-enonitrile

2-ethoxycarbonyl (R)-2-hydroxy-2-phenyl-but-3-enonitrile

Conditions
ConditionsYield
With C40H62AlFN3O2(1+)*CF3O3S(1-) In chloroform; 1,2-dichloro-ethane at -50℃; for 48h; Inert atmosphere; Schlenk technique; enantioselective reaction;100%
With C40H62AlFN3O2(1+)*CF3O3S(1-) In chloroform; 1,2-dichloro-ethane at -50℃; for 72h; Schlenk technique; Inert atmosphere;99%
...Expand
ethyl cyanoformate
623-49-4

ethyl cyanoformate

1H-tetrazole-5-carboxylic acid ethyl ester
55408-10-1

1H-tetrazole-5-carboxylic acid ethyl ester

Conditions
ConditionsYield
With trimethylsilylazide; dibutyltin diacetate In benzene at 30℃; for 60h;99%
With diethylaluminium azide In toluene at 20℃; for 1h;94%
With sodium azide In butanone at 75℃; for 2h;82%
ethyl cyanoformate
623-49-4

ethyl cyanoformate

acetylacetone
123-54-6

acetylacetone

1-amino-2,2-diacetyl-1-(ethoxycarbonyl)ethylene
72373-95-6

1-amino-2,2-diacetyl-1-(ethoxycarbonyl)ethylene

Conditions
ConditionsYield
[Ni{F3CC(O)CHC(O)C6F13}2] In dichloromethane at 20℃; for 24h;99%
With triethylamine; zinc(II) chloride In dichloromethane
benzaldehyde
100-52-7

benzaldehyde

ethyl cyanoformate
623-49-4

ethyl cyanoformate

O-ethoxycarbonyl 2-hydroxy-2-phenylacetonitrile
6443-66-9

O-ethoxycarbonyl 2-hydroxy-2-phenylacetonitrile

Conditions
ConditionsYield
With n-butyllithium In dichloromethane at -20℃; for 3h;99%
With 1-methoxy-2-methyl-1-(trimethylsiloxy)propene at 25℃; for 11h;99%
With dmap In acetonitrile at 20℃; for 8h; Inert atmosphere;99%
(E)-3-phenylpropenal
14371-10-9

(E)-3-phenylpropenal

ethyl cyanoformate
623-49-4

ethyl cyanoformate

<1-Cyan-3-phenyl-2-propenyl>-ethyl-carbonat
100573-40-8

<1-Cyan-3-phenyl-2-propenyl>-ethyl-carbonat

Conditions
ConditionsYield
With 1-methoxy-2-methyl-1-(trimethylsiloxy)propene at 31℃; for 8h;99%
With potassium cyanide; 18-crown-6 ether for 48h; Ambient temperature;90%
(4R,5R)-1-Acetoxy-4-isopropenyl-5-methyl-5-vinylcyclohex-1-ene
149404-74-0

(4R,5R)-1-Acetoxy-4-isopropenyl-5-methyl-5-vinylcyclohex-1-ene

ethyl cyanoformate
623-49-4

ethyl cyanoformate

(1R,4R,5R)-5-Isopropenyl-4-methyl-2-oxo-4-vinyl-cyclohexanecarboxylic acid ethyl ester
202194-28-3

(1R,4R,5R)-5-Isopropenyl-4-methyl-2-oxo-4-vinyl-cyclohexanecarboxylic acid ethyl ester

Conditions
ConditionsYield
With N,N,N,N,N,N-hexamethylphosphoric triamide; methyllithium In tetrahydrofuran; diethyl ether 1.) -78 deg C, 1 h, 2.) -78 deg C, 35 min;99%
dimethyl 2,2-di(but-2-yn-1-yl)malonate
107428-05-7

dimethyl 2,2-di(but-2-yn-1-yl)malonate

ethyl cyanoformate
623-49-4

ethyl cyanoformate

3-ethyl 6,6-dimethyl 1,4-dimethyl-6,7-dihydro-5H-cyclopenta[c]pyridine-3,6,6-tricarboxylate

3-ethyl 6,6-dimethyl 1,4-dimethyl-6,7-dihydro-5H-cyclopenta[c]pyridine-3,6,6-tricarboxylate

Conditions
ConditionsYield
With bis(1,5-cyclooctadiene)rhodium(I) tetrafluoroborate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl In dichloromethane at 20℃; for 3h;99%
ethyl cyanoformate
623-49-4

ethyl cyanoformate

di(2-pentynyl) ether
114764-03-3

di(2-pentynyl) ether

4,7-diethyl-1,3-dihydro-furo[3,4-c]pyridine-6-carboxylic acid ethyl ester

4,7-diethyl-1,3-dihydro-furo[3,4-c]pyridine-6-carboxylic acid ethyl ester

Conditions
ConditionsYield
With bis(1,5-cyclooctadiene)rhodium(I) tetrafluoroborate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl In dichloromethane at 20℃; for 1h;99%
ethyl cyanoformate
623-49-4

ethyl cyanoformate

N,N-bis(2-butynyl)-(4-methylphenyl)sulfonamide
170751-34-5

N,N-bis(2-butynyl)-(4-methylphenyl)sulfonamide

ethyl 4,7-dimethyl-2-p-tosyl-2,3-dihydro-1H-pyrrolo[3,4-c]pyridine-6-carboxylate

ethyl 4,7-dimethyl-2-p-tosyl-2,3-dihydro-1H-pyrrolo[3,4-c]pyridine-6-carboxylate

Conditions
ConditionsYield
With bis(1,5-cyclooctadiene)rhodium(I) tetrafluoroborate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl In dichloromethane at 20℃; for 1h;99%
4-methoxy-benzaldehyde
123-11-5

4-methoxy-benzaldehyde

ethyl cyanoformate
623-49-4

ethyl cyanoformate

(2S)-O-ethoxycarbonyl-2-hydroxy-2-(4-methoxyphenyl)-acetonitrile

(2S)-O-ethoxycarbonyl-2-hydroxy-2-(4-methoxyphenyl)-acetonitrile

Conditions
ConditionsYield
With 3,3'-di-naphthalen-2-yl-biphenyl-2,2'-diol; titanium(IV) isopropylate; quinindine; isopropyl alcohol In toluene at -20℃; for 7h; Strecker reaction; Inert atmosphere; optical yield given as %ee; enantioselective reaction;99%
With potassium cyanide; chiral salen-based titanium In dichloromethane at -40℃; for 24h;98%
With 2,6-dimethylpyridine; 2C2H5O4S(1-)*C72H104N4O16V2(2+) In dichloromethane at -20℃; for 12h; Inert atmosphere; optical yield given as %ee; enantioselective reaction;96%
di-μ-oxo-di((R,R)-N,N'-bis((alicylaldehydo)ethylenediamine))dititanium(IV) In dichloromethane at -84 - -40℃; for 20h; Product distribution / selectivity;92%
With 1H-imidazole; C2H5O4S(1-)*C36H54N2O4V(1+) In dichloromethane at -20℃; for 60h; Inert atmosphere; optical yield given as %ee;90%
2,4-dichlorobenzaldeyhde
874-42-0

2,4-dichlorobenzaldeyhde

ethyl cyanoformate
623-49-4

ethyl cyanoformate

cyano(2,4-dichlorophenyl)methyl ethyl carbonate

cyano(2,4-dichlorophenyl)methyl ethyl carbonate

Conditions
ConditionsYield
With 1-methoxy-2-methyl-1-(trimethylsiloxy)propene at 22℃; for 58h;99%
With 1,3-bis-(2,6-diisopropylphenyl)-imidazol-2-ylidene In tetrahydrofuran at 0 - 20℃; Inert atmosphere;91%
ortho-anisaldehyde
135-02-4

ortho-anisaldehyde

ethyl cyanoformate
623-49-4

ethyl cyanoformate

2-ethoxycarbonyl-2-hydroxy-2-(2-methoxylphenyl)-acetonitrile
408310-12-3

2-ethoxycarbonyl-2-hydroxy-2-(2-methoxylphenyl)-acetonitrile

Conditions
ConditionsYield
With 1-methoxy-2-methyl-1-(trimethylsiloxy)propene at 28℃; for 20h;99%
With 1,3-bis-(2,6-diisopropylphenyl)-imidazol-2-ylidene In tetrahydrofuran at 0 - 20℃; Inert atmosphere;98%
Stage #1: ortho-anisaldehyde With 1-pentyl-3-methylimidazolium bromide at 20℃; for 0.166667h;
Stage #2: ethyl cyanoformate at 20℃; for 2.08333h;		96%
With dmap at 27℃; for 0.75h; Neat (no solvent);94%
With polyacrylonitrile fiber In water at 20℃; for 0.666667h; Catalytic behavior;82%
3-nitro-benzaldehyde
99-61-6

3-nitro-benzaldehyde

ethyl cyanoformate
623-49-4

ethyl cyanoformate

ethoxycarbonyloxy-(3-nitro-phenyl)-acetonitrile

ethoxycarbonyloxy-(3-nitro-phenyl)-acetonitrile

Conditions
ConditionsYield
With 1-methoxy-2-methyl-1-(trimethylsiloxy)propene at 25℃; for 11h;99%
4-methoxy-benzaldehyde
123-11-5

4-methoxy-benzaldehyde

ethyl cyanoformate
623-49-4

ethyl cyanoformate

carbonic acid, cyano(4-methoxyphenyl)methyl ethyl ester
66867-32-1

carbonic acid, cyano(4-methoxyphenyl)methyl ethyl ester

Conditions
ConditionsYield
With 1-methoxy-2-methyl-1-(trimethylsiloxy)propene at 25℃; for 15h;99%
With 3-(diethylamino)propyltrimethoxysilane supported on silica-alumina In toluene at 20℃; for 3h; Inert atmosphere;98%
With dmap at 27℃; for 0.75h; Neat (no solvent);92%
4-chlorobenzaldehyde
104-88-1

4-chlorobenzaldehyde

ethyl cyanoformate
623-49-4

ethyl cyanoformate

cyano(4-chlorophenyl)methyl ethyl carbonate

cyano(4-chlorophenyl)methyl ethyl carbonate

Conditions
ConditionsYield
With 1-methoxy-2-methyl-1-(trimethylsiloxy)propene at 24℃; for 12h;99%
With 3-(diethylamino)propyltrimethoxysilane supported on silica-alumina In toluene at 20℃; for 3h; Inert atmosphere;99%
With 1,3-bis-(2,6-diisopropylphenyl)-imidazol-2-ylidene In tetrahydrofuran at 0 - 20℃; Inert atmosphere;94%
furfural
98-01-1

furfural

ethyl cyanoformate
623-49-4

ethyl cyanoformate

carbonic acid, cyano(2-furyl)methyl ethyl ester
20893-23-6

carbonic acid, cyano(2-furyl)methyl ethyl ester

Conditions
ConditionsYield
With 1-methoxy-2-methyl-1-(trimethylsiloxy)propene at 25℃; for 9h;99%
With dmap In acetonitrile at 20℃; for 8h; Inert atmosphere;97%
With polyacrylonitrile fiber In water at 20℃; for 0.666667h; Catalytic behavior;85%

Ethyl cyanoformate Specification

The IUPAC name of Carbonocyanidic acid,ethyl ester is ethyl cyanoformate . With CAS registry Number 623-49-4, it is also named as NSC 65347 ; Formic acid, cyano-, ethyl ester (8CI) . The product's categories are aliphatics, esters, C2 to C5 and carbonyl compounds. The Carbonocyanidic acid,ethyl ester is clear colourless liquid which is sensitive to moisture. The product must be sealed in the container and keep container tightly closed. Keep container in a well-ventilated place.

The Carbonocyanidic acid,ethyl ester can be used in the preparation of other chemicals. For example: It can react with 4-methyl-5-methylimino-[1,2,4]dithiazolidine-3-thione to get 4-methyl-5-thioxo-4,5-dihydro-[1,2,4]thiadiazole-3-carboxylic acid ethyl ester .

This product is flammable. It is toxic by inhalation, in contact with skin and if swallowed. In addition, it also can cause burns and is irritating to eyes, respiratory system and skin. People should avoid contact with skin and eyes. Keep away from sources of ignition. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. If you want to contact this product, you must wear suitable protective clothing, gloves and eye/face protection. In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.) 

The other characteristics of this product can be summarized as: (1)ACD/LogP: 0.27 ; (2)# of Rule of 5 Violations: 0 ; (3)ACD/LogD (pH 5.5): 0.27 ; (4)ACD/LogD (pH 7.4): 0.27 ; (5)ACD/BCF (pH 5.5): 1 ; (6)ACD/BCF (pH 7.4): 1 ; (7)ACD/KOC (pH 5.5): 33.43 ; (8)ACD/KOC (pH 7.4): 33.43 ; (9)#H bond acceptors: 3 ; (10)#H bond donors: 0 ; (11)#Freely Rotating Bonds: 2 ; (12)Index of Refraction: 1.402 ; (13)Molar Refractivity: 22.26 cm3 ; (14)Molar Volume: 91.4 cm3 ; (15)Polarizability: 8.82×10-24 cm3 ; (16)Surface Tension: 36.2 dyne/cm ; (17)Enthalpy of Vaporization: 35.39 kJ/mol ; (18)Vapour Pressure: 19 mmHg at 25°C ; (19)Rotatable Bond Count: 2 ; (20)Exact Mass: 99.032028 ; (21)MonoIsotopic Mass: 99.032028 ; (22)Topological Polar Surface Area: 50.1 ; (23)Heavy Atom Count: 7.

People can use the following data to convert to the molecule structure. SMILES: N#CC(=O)OCC; InChI: InChI=1/C4H5NO2/c1-2-7-4(6)3-5/h2H2,1H3; InChIKey: MSMGXWFHBSCQFB-UHFFFAOYAN. Carbonocyanidic acid,ethyl ester has many suppliers, such as Nanjing Feihe Pharma Tech Co., Ltd..

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