6162-76-1

Basic information

• Product Name: cyanoacetaldehyde
• Synonyms: cyanoacetaldehyde;3-Oxopropanenitrile;3-Oxopropiononitrile;2-(naphthalen-2-yloxy)-N-(pyridin-4-yl)acetaMide;Propanenitrile, 3-oxo-(9CI)
• CAS NO: 6162-76-1
• Molecular Formula: C₃H₃NO
• Molecular Weight: 69.06
• Mol File: 6162-76-1.mol
• Article Data: 15

Chemical Properties

• Boiling Point: 560°C at 760 mmHg
• Flash Point: 292.5°C
• Appearance: /
• Density: 1.275g/cm³
• Vapor Pressure: 1.42E-12mmHg at 25°C
• Refractive Index: 1.682
• PKA: 10.58±0.10(Predicted)
• CAS DataBase Reference: cyanoacetaldehyde(CAS DataBase Reference)
• NIST Chemistry Reference: cyanoacetaldehyde(6162-76-1)
• EPA Substance Registry System: cyanoacetaldehyde(6162-76-1)

Safety Data

• Hazardous Substances Data: 6162-76-1(Hazardous Substances Data)

Usage

General Description

Cyanoacetaldehyde is a chemical compound with the chemical formula C3H3NO. It is a highly reactive, colorless liquid with a strong odor. It is used in organic synthesis as a versatile building block for the formation of various organic compounds, such as pharmaceuticals, agrochemicals, and dyes. Cyanoacetaldehyde is also a precursor to the production of other important chemicals, such as cyanoacetamide, which is used in the synthesis of anti-inflammatory drugs. It is a potentially hazardous chemical and should be handled with care, as it can be harmful if inhaled, ingested, or in contact with skin or eyes.

InChI:InChI=1/C17H14N2O2/c20-17(19-15-7-9-18-10-8-15)12-21-16-6-5-13-3-1-2-4-14(13)11-16/h1-11H,12H2,(H,18,19,20)

Synthetic route

ISOXAZOLE (288-14-2) → cyanoacetaldehyde (6162-76-1)

Conditions	Yield
With sodium methylate
With potassium ethoxide In ethanol
With sodium ethanolate In ethanol at 0 - 8℃; for 0.5h; Ring cleavage;
at -258.16℃; Wavelength; Time; Inert atmosphere; UV-irradiation;

iodoacetic anhydride (55782-51-9) + silver(I) cyanide (506-64-9) → cyanoacetaldehyde (6162-76-1)

trans-1,4-dicyano-2-butene (18715-38-3) → cyanoacetaldehyde (6162-76-1)

Conditions	Yield
With dimethylsulfide; oxygen; ozone multistep reaction, ozonolyse of olefins; other olefin;
With dimethylsulfide; oxygen; ozone MeOH, CH2Cl2, 1) -40 deg C, 2) -40 deg C to RT; Yield given. Multistep reaction;

ethyl 3-(N-tert-butylamino)propenoate (131297-23-9) → cyanoacetaldehyde (6162-76-1) + 3-hydroxylacrylic nitrile (25078-62-0)

Conditions	Yield
at 400 - 600℃; under 1E-05 - 0.0001 Torr;

2,2-dimethyl-5-<(tert-butylamino)methylene>-1,3-dioxane-4,6-dione (118060-67-6) → cyanoacetaldehyde (6162-76-1) + (Z)-3-hydroxypropenenitrile (69277-49-2) + (E)-3-hydroxypropenenitrile (69245-11-0) + acetone (67-64-1)

Conditions	Yield
at 550℃; under 1E-05 - 0.0001 Torr; Further byproducts given;
at 550℃; under 1E-05 - 0.0001 Torr; other 5-<(alkylamino)methylene>-2,2-dimethyl-1,3-dioxane-4,6-diones;

but-3-enenitrile (109-75-1) → cyanoacetaldehyde (6162-76-1)

Conditions	Yield
With dimethylsulfide; oxygen; ozone CH2Cl2, 1) -40 deg C, 2) -40 deg C to RT; Yield given. Multistep reaction;

acetonitrile (75-05-8) + formic acid ethyl ester (109-94-4) → cyanoacetaldehyde (6162-76-1)

Conditions	Yield
With sodium hydride In diethyl ether; ethanol Ambient temperature; overnight;
With sodium hydride In ethanol; toluene at 20℃; for 25h; Cooling with ice;
With sodium In ethanol Reflux;

ISOXAZOLE (288-14-2) + OH-ions → cyanoacetaldehyde (6162-76-1)

Conditions	Yield
at 25℃; Rate constant;

3-Hydroxypropionitrile (109-78-4) → cyanoacetaldehyde (6162-76-1) + cyanoacetic acid (372-09-8) + HCN

Conditions	Yield
In sulfuric acid anodic oxidation at Pt or PbO2; Yield given. Yields of byproduct given;

3,3-bis(ethyloxy)propanenitrile (2032-34-0) → cyanoacetaldehyde (6162-76-1)

Conditions	Yield
With trifluoroacetic acid In chloroform; water for 15h;
With water; trifluoroacetic acid at 5 - 10℃; for 6h; Inert atmosphere;
With water; trifluoroacetic acid In chloroform at 20℃;

3-Hydroxypropionitrile (109-78-4) → cyanoacetaldehyde (6162-76-1) + cyanoacetic acid (372-09-8)

Conditions	Yield
With [2,2]bipyridinyl; osmium (III) chloride; dihydrogen peroxide In acetonitrile at 70℃; for 4h; Product distribution; Further Variations:; Reagents; Temperatures; Solvents;

5-amino-2,2,6,6-tetramethyl-4-hepten-3-one → t-Butyl radical (1605-73-8) + cyanoacetaldehyde (6162-76-1)

Conditions	Yield
at 350℃; Product distribution; Further Variations:; Temperatures;

carbon monoxide (201230-82-2) + acetonitrile (75-05-8) → cyanoacetaldehyde (6162-76-1)

Conditions	Yield
With tert.-butylhydroperoxide; iron(III) chloride at 120℃; under 3800.26 - 7600.51 Torr; for 10h;

Methyl formate (107-31-3) + acetonitrile (75-05-8) → cyanoacetaldehyde (6162-76-1)

Conditions	Yield
With potassium 2-methylbutan-2-olate In tetrahydrofuran; toluene at 0 - 20℃; for 78h;

cyanoacetaldehyde (6162-76-1) + ethylhydrazine carboxylate (4114-31-2) → N'-[2-Cyano-eth-(E)-ylidene]-hydrazinecarboxylic acid ethyl ester

Conditions	Yield
In methanol; dichloromethane for 4h; Heating;	95%

cyanoacetaldehyde (6162-76-1) + (2,4-dinitro-phenyl)-hydrazine (119-26-6) → 3-(2,4-dinitro-phenylhydrazono)-propionitrile (90323-50-5)

Conditions	Yield
In methanol; dichloromethane for 6h; Heating;	93%

cyanoacetaldehyde (6162-76-1) + ethyl 5-acetamido-2-amino-4-ethoxybenzoate (1222172-51-1) → ethyl 2-[(2-cyanovinyl)amino]-4-ethoxy-5-acetylamidobenzoate (1222172-52-2)

Conditions	Yield
In ethyl acetate at 20℃; for 12h;	92%

hydrazinecarboxylic acid methyl ester (6294-89-9) + cyanoacetaldehyde (6162-76-1) → N'-[2-Cyano-eth-(E)-ylidene]-hydrazinecarboxylic acid methyl ester

Conditions	Yield
In methanol; dichloromethane for 24h; Heating;	90%

cyanoacetaldehyde (6162-76-1) + methyl 5-acetamido-2-amino-4-ethoxybenzoate (1222172-49-7) → methyl 5-acetamido-2-[(2-cyanovinyl)amino]-4-ethoxybenzoate (1222172-50-0)

Conditions	Yield
In ethyl acetate at 20℃; for 12h;	90%

cyanoacetaldehyde (6162-76-1) + phenylmagnesium bromide (100-58-3) → 3-hydroxy-3-phenylpropanenitrile (73627-97-1, 121617-17-2, 132203-26-0, 17190-29-3)

Conditions	Yield
In tetrahydrofuran at 20℃; for 0.208333h; Grignard reaction; Inert atmosphere; chemoselective reaction;	85%

Nicotinic acid hydrazide (553-53-7) + cyanoacetaldehyde (6162-76-1) → Nicotinic acid [2-cyano-eth-(E)-ylidene]-hydrazide

Conditions	Yield
In methanol; dichloromethane for 24h; Heating;	84%

cyanoacetaldehyde (6162-76-1) + 4-chlorobenzoic acid hydrazide (536-40-3) → 4-Chloro-benzoic acid [2-cyano-eth-(E)-ylidene]-hydrazide

Conditions	Yield
In methanol; dichloromethane for 24h; Heating;	80%

cyanoacetaldehyde (6162-76-1) + 6-chloro-2-(4-fluoroindolin-2-yl)pyridin-3-ol (1426942-85-9) → C16H11ClFN3O (1446249-05-3)

Conditions	Yield
With methanesulfonic acid In tetrahydrofuran at 40℃;	76%

cyanoacetaldehyde (6162-76-1) + 2-amino-benzenethiol (137-07-5) → 2-cyanomethylbenzothiazole (56278-50-3)

Conditions	Yield
With acetic acid Reflux;	75%

cyanoacetaldehyde (6162-76-1) + C11H15N3O3 (1222172-56-6) → 2-[(2-Cyanovinyl)amino]-4-ethoxy-5-acetylamido benzoylamide (1222172-57-7)

Conditions	Yield
trifluoroacetic acid In ethyl acetate	68%

cyanoacetaldehyde (6162-76-1) + N,N-dimethyl-formamide dimethyl acetal (4637-24-5) → α-cyano-β-dimethylaminoacrolein (149139-41-3)

Conditions	Yield
In methanol; dichloromethane for 1h; Ambient temperature;	65%

cyanoacetaldehyde (6162-76-1) + acetic acid 5-amino-4-iodo-2-methyl-phenyl ester (719299-02-2) → Acetic acid 5-((E)-2-cyano-vinylamino)-4-iodo-2-methyl-phenyl ester (719298-94-9)

Conditions	Yield
In chloroform; water; ethyl acetate for 7h;	65%

2-hydroxyethylhydrazine (109-84-2) + cyanoacetaldehyde (6162-76-1) → 5-amino-1-(2-hydroxyethyl)-1H-pyrazole (73616-27-0)

Conditions	Yield
In methanol; dichloromethane for 4h; Heating;	60%

cyanoacetaldehyde (6162-76-1) → sodium 2,4-dicyano-1,3-butadiene-1-olate

Conditions	Yield
With sodium; phenol In methanol; ethanol; dichloromethane at 50℃; for 1h;	60%

cyanoacetaldehyde (6162-76-1) + m,p-dichloroaniline (95-76-1) → β-(3,4-dichlorophenyl)aminoacrylonitrile

Conditions	Yield
In methanol; dichloromethane at 40℃; for 2h;	60%

cyanoacetaldehyde (6162-76-1) + 4-chlorobenzaldehyde (104-88-1) + 4-Oxo-1-phenyl-4,5,6,7-tetrahydrobenopyrazole (14823-31-5) → C23H15ClN4O

Conditions	Yield
With ammonium acetate In neat (no solvent) at 110℃; Microwave irradiation;	50%

cyanoacetaldehyde (6162-76-1) + p-toluidine (106-49-0) → β-(4-methylphenyl)aminoacrylonitrile

Conditions	Yield
In methanol; dichloromethane at 40℃; for 2h;	33%

cyanoacetaldehyde (6162-76-1) + aniline (62-53-3) → β-phenylaminoacrylonitrile (4818-39-7)

Conditions	Yield
In methanol; dichloromethane at 40℃; for 2h;	30%

cyanoacetaldehyde (6162-76-1) + 2-fluoro-4-chloroaniline (57946-56-2) → β-(4-chloro-2-fluorophenyl)aminoacrylonitrile

Conditions	Yield
In methanol; dichloromethane at 40℃; for 2h;	28%

cyanoacetaldehyde (6162-76-1) + 3-trifluoromethylaniline (98-16-8) → β-(3-trifluoromethylphenyl)aminoacrylonitrile

Conditions	Yield
In methanol; dichloromethane at 40℃; for 2h;	20%

cyanoacetaldehyde (6162-76-1) + 4-nitrobenzenediazonium tetrafluoroborate (456-27-9) → 2-(4-nitro-phenylhydrazono)-3-oxo-propionitrile

cyanoacetaldehyde (6162-76-1) + aniline (62-53-3) → 3,3-dianilino-propionitrile

Conditions	Yield
at 300 - 320℃; Anilin im Ueberschuss;
at 300 - 320℃;

cyanoacetaldehyde (6162-76-1) + 4-nitrophenylhydrazone (100-16-3) → 3-(4-nitro-phenylhydrazono)-propionitrile (25112-06-5)

cyanoacetaldehyde (6162-76-1) → Dicyano-2,4-hydroxy-3-butanal (60278-74-2)

Conditions	Yield
With potassium hydroxide In water at 19.5℃; Rate constant; pH 6 - 12;

cyanoacetaldehyde (6162-76-1) + semicarbazide hydrochloride (563-41-7) → 5-aminopyrazole-1-carboxamide (77668-01-0)

Conditions	Yield
In water for 5h;	2.4 g

Upstream product

• 288-14-2 ISOXAZOLE 
• 55782-51-9 iodoacetic anhydride 
• 506-64-9 silver(I) cyanide 
• 18715-38-3 trans-1,4-dicyano-2-butene 
• 131297-23-9 ethyl 3-(N-tert-butylamino)propenoate 
• 118060-67-6 2,2-dimethyl-5-<(tert-butylamino)methylene>-1,3-dioxane-4,6-dione 
• 109-75-1 but-3-enenitrile 
• 75-05-8 acetonitrile 
• 109-94-4 formic acid ethyl ester 
• 109-78-4 3-Hydroxypropionitrile 
• 2032-34-0 3,3-bis(ethyloxy)propanenitrile 
• 107-31-3 Methyl formate 
• 201230-82-2 carbon monoxide 

Downstream Products

• 25112-06-5 3-(4-nitro-phenylhydrazono)-propionitrile 
• 57597-62-3 3,3-dimethoxypropionitrile 
• 372-09-8 cyanoacetic acid 
• 73627-97-1 3-hydroxy-3-phenylpropanenitrile 
• 3528-58-3 5-Amino-1-ethylpyrazole 
• 1192-21-8 5-Amino-1-methylpyrazole 
• 3528-51-6 1-benzyl-1H-pyrazol-5-amine 
• 3702-09-8 1-cyclopentyl-1H-pyrazol-5-amine 
• 1222172-50-0 methyl 5-acetamido-2-[(2-cyanovinyl)amino]-4-ethoxybenzoate 
• 1222172-57-7 2-[(2-Cyanovinyl)amino]-4-ethoxy-5-acetylamido benzoylamide 
• 1225387-53-0 3⁽⁵⁾-aminopyrazole 
• 35146-02-2 3,3-diethoxypropenenitrile 
• 1820-80-0 3-aminopyrazole 
• 1021175-71-2 diethyl 2-(2-cyanovinylamino)malonate 

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