3-Oxobutanenitrile supplier

Name
3-Oxobutanenitrile
EINECS 219-590-8
CAS No. 2469-99-0
Article Data64
CAS DataBase
Density 0.976g/cm³
Solubility Slightly soluble in water.
Melting Point
Formula C₄H₅NO
Boiling Point 123.5°C at 760 mmHg
Molecular Weight 83.0898
Flash Point 28.5°C
Transport Information
Appearance
Safety
Risk Codes
Molecular Structure
Hazard Symbols
Synonyms Acetoacetonitrile(7CI,8CI);3-Oxobutanenitrile;3-Oxobutyronitrile;Acetylacetonitrile;Cyanoacetone;a-Cyanoacetone;
PSA 40.86000
LogP 0.48908

Synthetic route

: 4433-76-5
2-methyl-3-oxobutanamide

: 2469-99-0
Cyanoaceton

Conditions

Conditions	Yield
at 300℃; for 1h; Temperature;	89%

: 141-78-6
ethyl acetate

: 75-05-8
acetonitrile

: 2469-99-0
Cyanoaceton

Conditions

Conditions	Yield
With n-butyllithium; diisopropylamine In tetrahydrofuran; hexane at -78 - 20℃; for 2h; Reagent/catalyst; Inert atmosphere;	87%
With sodium amide; benzene
With sodium

: 79-20-9
acetic acid methyl ester

: 75-05-8
acetonitrile

: 2469-99-0
Cyanoaceton

Conditions

Conditions	Yield
With n-butyllithium; diisopropylamine In tetrahydrofuran; hexane at -78 - 20℃; for 2h; Reagent/catalyst; Inert atmosphere;	85%
With potassium 2-methylbutan-2-olate In tetrahydrofuran; toluene at 0 - 20℃; Inert atmosphere;	81%
With potassium tert-butylate In tetrahydrofuran at 20℃;
With potassium 2-methylbutan-2-olate In tetrahydrofuran; toluene at 0 - 20℃; for 78h;

: 81056-48-6
3-Amino-3-butennitril

: 2469-99-0
Cyanoaceton

Conditions

Conditions	Yield
With hydrogenchloride; water In water at 80℃; for 2h;	76%
With hydrogenchloride 1.) 15 min, 2.) O(CH2CH3)2, 3 d; Yield given. Multistep reaction;

: 24068-54-0
3-acetyl-5-methylisoxazole

: 2469-99-0
Cyanoaceton

Conditions

Conditions	Yield
With methanol; sodium for 5h; Heating;	75%
With sodium methylate In methanol at 20℃;

: 5765-44-6
5-methylisoxazole

: 78191-00-1
N-Methoxy-N-methylacetamide

A: 2469-99-0
Cyanoaceton

B: 115706-49-5
3,5-dioxohexanenitrile

Conditions

Conditions	Yield
With lithium diisopropyl amide In tetrahydrofuran at 0℃; for 1.25h;	A 7% B 73%

...Expand

: 201230-82-2
carbon monoxide

: 107-14-2
chloroacetonitrile

: 74-88-4
methyl iodide

: 2469-99-0
Cyanoaceton

Conditions

Conditions	Yield
With sodium hydroxide; iron pentacarbonyl; tetra(n-butyl)ammonium hydrogensulfate In dichloromethane at 10℃; under 10 Torr;	65%

...Expand

: 1118-61-2
3-Aminocrotononitrile

: 2469-99-0
Cyanoaceton

Conditions

Conditions	Yield
With hydrogenchloride In water at 80℃; for 3h;	53%
With hydrogenchloride
With hydrogenchloride In diethyl ether at 0℃;

: 870-64-4
2-aminocrotononitrile

: 2469-99-0
Cyanoaceton

Conditions

Conditions	Yield
With hydrogenchloride In water at 80℃; for 3h; Inert atmosphere;	49%
With hydrogenchloride; water at 80℃; for 3h;	48%

: 1118-60-1
3-iminobutyronitrile

: 2469-99-0
Cyanoaceton

Conditions

Conditions	Yield
With hydrogenchloride; water at 80℃; for 3h;	48%

: 5765-44-6
5-methylisoxazole

: 141-52-6
sodium ethanolate

: 2469-99-0
Cyanoaceton

: 5765-44-6
5-methylisoxazole

: 2469-99-0
Cyanoaceton

Conditions

Conditions	Yield
In gas at 530℃; under 0.1 Torr; for 2.77778E-05h; Rate constant; Thermodynamic data; Kinetics; mechanism; Arrhenius parameters: log A, Ea; different temp., pressures, and times;
With sodium ethanolate
With potassium hydroxide

: 313048-10-1
but-2-ynal oxime

: 141-52-6
sodium ethanolate

: 2469-99-0
Cyanoaceton

: 1118-61-2
3-Aminocrotononitrile

: 144-62-7
oxalic acid

: 2469-99-0
Cyanoaceton

Conditions

Conditions	Yield
at 0 - 20℃; Geschwindigkeit des Uebergangs;

: 1118-61-2
3-Aminocrotononitrile

: 64-19-7
acetic acid

: 2469-99-0
Cyanoaceton

Conditions

Conditions	Yield
at 0 - 20℃; Geschwindigkeit des Uebergangs;

: 625-60-5
ethyl thioacetate

: 75-05-8
acetonitrile

: 2469-99-0
Cyanoaceton

Conditions

Conditions	Yield
With sodium

: 88511-40-4
α-Cyan-acetessigsaeure

: 2469-99-0
Cyanoaceton

Conditions

Conditions	Yield
In water

: 1116-98-9
cyanoacetic acid tert-butyl ester

: 75-36-5
acetyl chloride

: 2469-99-0
Cyanoaceton

Conditions

Conditions	Yield
(i) benzene, (ii) TsOH; Multistep reaction;

: 107-12-0
propiononitrile

: 109-94-4
formic acid ethyl ester

: 2469-99-0
Cyanoaceton

Conditions

Conditions	Yield
With sodium hydride In diethyl ether; ethanol Ambient temperature; overnight;

: 5765-44-6
5-methylisoxazole

aqueous KOH: aqueous KOH

: 2469-99-0
Cyanoaceton

Conditions

Conditions	Yield
at 25.5℃; Rate constant; sowie bei 37.1grad und 41.75grad;

: 5765-44-6
5-methylisoxazole

diluted KOH-solution: diluted KOH-solution

: 2469-99-0
Cyanoaceton

: 625-60-5
ethyl thioacetate

: 75-05-8
acetonitrile

sodium: sodium

: 2469-99-0
Cyanoaceton

...Expand

: 1118-61-2
3-Aminocrotononitrile

: 7664-93-9
sulfuric acid

: 2469-99-0
Cyanoaceton

Conditions

Conditions	Yield
at 0 - 20℃; Geschwindigkeit des Uebergangs;

: 3075-23-8
S-ethyl acetothioacetate

: 75-05-8
acetonitrile

sodium: sodium

: 2469-99-0
Cyanoaceton

...Expand

: 313048-10-1
but-2-ynal oxime

strong NaOH-solution: strong NaOH-solution

: 2469-99-0
Cyanoaceton

: 7647-01-0
hydrogenchloride

: 1118-61-2
3-Aminocrotononitrile

A: 2469-99-0
Cyanoaceton

B: 7664-41-7
ammonia

Conditions

Conditions	Yield
stable form;

...Expand

: 7647-01-0
hydrogenchloride

: 27036-88-0
N-(2-cyano-1-methyl-vinyl)-benzamide

A: 2469-99-0
Cyanoaceton

B: 7664-41-7
ammonia

C: 65-85-0
benzoic acid

...Expand

: potassium cyanide

: 78-95-5
chloroacetone

: 2469-99-0
Cyanoaceton

Conditions

Conditions	Yield
In N,N-dimethyl-formamide for 0.166667h; Heating;

: 59-63-2
isocarboxazid

A: 2469-99-0
Cyanoaceton

B: N-(benzylamino)isocyanate

Conditions

Conditions	Yield
Heating; neat (no solvent);

: 2469-99-0
Cyanoaceton

: 122-51-0
orthoformic acid triethyl ester

: 105224-25-7
2-(ethoxymethylene)-3-oxobutane-nitrile

Conditions

Conditions	Yield
With acetic anhydride for 2h; Reflux; Inert atmosphere;	100%
for 5h; Heating;
With acetic anhydride
With acetic anhydride at 95 - 115℃; for 1h;

: 2469-99-0
Cyanoaceton

: 371-14-2
4-fluorophenylhydrazine

: 76606-39-8
1‐(4‐fluorophenyl)‐3‐methyl‐1H‐pyrazol‐5‐amine

Conditions

Conditions	Yield
With acetic acid In ethanol Reflux;	100%

: 2469-99-0
Cyanoaceton

: 24214-73-1
cyclohexylhydrazine hydrochloride

: 56547-82-1
1-cyclohexyl-3-methyl-1H-pyrazol-5-amine

Conditions

Conditions	Yield
In ethanol for 18h; Reflux;	99.2%
With acetic acid In ethanol for 6h; Reflux;	40%
In ethanol Reflux;

: 120-72-9
indole

: 2469-99-0
Cyanoaceton

: 1346266-72-5
2-(1H-indol-3-yl)-3-oxobutanenitrile

Conditions

Conditions	Yield
With tert.-butylhydroperoxide; cerium(III) acetate; 2,3,6-trimethyl-beta-cyclodextrin In water at 100℃; for 10h;	93%

: 6342-56-9
Pyruvic aldehyde dimethyl acetal

: 2469-99-0
Cyanoaceton

: 936919-14-1
2-acetyl-4,4-dimethoxy-3-methylbut-2-enenitrile

Conditions

Conditions	Yield
With ammonium acetate; acetic acid In toluene at 80 - 85℃; for 2h;	91%

: 2469-99-0
Cyanoaceton

: 84-58-2
2,3-dicyano-5,6-dichloro-p-benzoquinone

: 1476782-12-3
5-methylfuran-2,3,4-tricarbonitrile

Conditions

Conditions	Yield
In acetonitrile at 20℃; Inert atmosphere;	91%
In ethyl acetate at 25℃;	77%

: 2469-99-0
Cyanoaceton

: 1147550-11-5
ammonium thiocyanate

: (E)-3-amino-2-thiocyanatobut-2-enenitrile

Conditions

Conditions	Yield
With fluorescein free acid In acetonitrile at 20℃; UV-irradiation;	91%
With fluorescein In acetonitrile at 20℃; for 6h; Irradiation;	91%

: 2469-99-0
Cyanoaceton

: 100-52-7
benzaldehyde

: 104919-31-5
3-oxo-2-[1-phenylmeth-(E)-ylidene]butyronitrile

Conditions

Conditions	Yield
With L-proline In ethanol at 20℃; for 24h; Knoevenagel condensation;	90%

: 1022094-45-6
1-(β,β-difluorovinyl)4-phenylbenzene

: 2469-99-0
Cyanoaceton

: 5-([1,1'-biphenyl]-4-yl)-2-methylfuran-3-carbonitrile

Conditions

Conditions	Yield
With copper(l) iodide; caesium carbonate In dimethyl sulfoxide at 120℃; Inert atmosphere;	90%

: 36075-44-2
quinazolin-4-ylhydrazine

: 2469-99-0
Cyanoaceton

: 1206693-96-0
3-methyl-1-(quinazolin-4-yl)-1H-pyrazol-5-amine

Conditions

Conditions	Yield
In ethanol at 60℃; for 18h;	89%
In ethanol at 60℃; for 18h;	89%

: 2469-99-0
Cyanoaceton

: C18H22O2

: (R)-6-(tert-butyl)-2-methyl-4-(o-tolyl)-4H-chromene-3-carbonitrile

Conditions

Conditions	Yield
Stage #1: Cyanoaceton; C18H22O2 With C44H45O4P In chloroform at 0℃; for 72h; Stage #2: With toluene-4-sulfonic acid In chloroform for 4h; Reflux; enantioselective reaction;	89%

: 2469-99-0
Cyanoaceton

: 99-61-6
3-nitro-benzaldehyde

: 2-(3-nitrobenzylidene)-3-oxobutanenitrile

Conditions

Conditions	Yield
With D-Prolin In methanol; ethanol at 20℃; for 48h; Knoevenagel Condensation;	88.1%

: 2469-99-0
Cyanoaceton

: 64-17-5
ethanol

: 38046-53-6, 123689-94-1, 123689-96-3
(3S)-2-ethyl-3-hydroxybutyronitrile

Conditions

Conditions	Yield
In water for 48h; Ambient temperature; bakers' yeast, in solution of D-glucose;	88%

: 2469-99-0
Cyanoaceton

: 1576-35-8
toluene-4-sulfonic acid hydrazide

: C11H13N3O2S

Conditions

Conditions	Yield
In methanol for 2h; Solvent; Reflux;	88%

: 2469-99-0
Cyanoaceton

: 80-17-1
benzenesufonyl hydrazide

: 93-91-4
1-phenylbutan-1,3-dione

Conditions

Conditions	Yield
With 1,10-Phenanthroline; water; palladium diacetate In N,N-dimethyl-formamide at 100℃; under 760.051 Torr; for 6h;	87%

: 2469-99-0
Cyanoaceton

: 98-53-3
4-tercbutyl-cyclohexanone

: 1-{2-amino-6-(tert-butyl)-4,5,6,7-tetrahydrobenzo[b]thiophen-3-yl}ethanone

Conditions

Conditions	Yield
With piperidine; octasulfur In methanol at 55 - 65℃; for 24h; Gewald Aminoheterocycles Synthesis;	86%
With piperidine; sulfur at 55 - 65℃; for 24h; Gewald Aminoheterocycles Synthesis;

: 88-21-1
2-amino-1-benzenesulfonic acid

: 2469-99-0
Cyanoaceton

: sodium 2-(2-(1-cyano-2-oxopropylidene)hydrazinyl)benzenesulfonate

Conditions

Conditions	Yield
Stage #1: 2-amino-1-benzenesulfonic acid With hydrogenchloride; sodium hydroxide; sodium nitrite In water at 0 - 5℃; for 1h; Stage #2: Cyanoaceton With sodium acetate; sodium hydroxide In ethanol; water at 0℃; Japp-Klingemann Hydrazone Synthesis;	86%

: 2469-99-0
Cyanoaceton

: 67515-50-8
3-methyl-1-phenylpenta-3,4-dien-2-one

: 6-hydroxy-2,4,5-trimethylbiphenyl-3-carbonitrile

Conditions

Conditions	Yield
With caesium carbonate In acetonitrile at 80℃; for 4h;	85%

: 2469-99-0
Cyanoaceton

: C18H22O3

: (R)-6-(tert-butyl)-4-(2-methoxyphenyl)-2-methyl-4H-chromene-3-carbonitrile

Conditions

Conditions	Yield
Stage #1: Cyanoaceton; C18H22O3 With C44H45O4P In chloroform at 0℃; for 72h; Stage #2: With toluene-4-sulfonic acid In chloroform for 4h; Reflux; enantioselective reaction;	85%

: 2469-99-0
Cyanoaceton

: 123-11-5
4-methoxy-benzaldehyde

: 2-(4-methoxybenzylidene)-3-oxobutanenitrile

Conditions

Conditions	Yield
With D-Prolin In methanol; ethanol at 20℃; for 48h; Knoevenagel Condensation;	84.6%

: 2469-99-0
Cyanoaceton

: 4637-24-5
N,N-dimethyl-formamide dimethyl acetal

: 885121-98-2
(E/Z)-2-((dimethylamino)methylene)-3-oxobutanenitrile

Conditions

Conditions	Yield
at 25 - 80℃; for 1.5h;	84%
In tetrahydrofuran at 20℃; for 16h; Inert atmosphere;	80%

: 2469-99-0
Cyanoaceton

: C15H16O4

: C17H17NO3

Conditions

Conditions	Yield
With C33H28F5N3O2; potassium carbonate In toluene at 0℃; for 48h; enantioselective reaction;	83%

: 2469-99-0
Cyanoaceton

: 104-88-1
4-chlorobenzaldehyde

: 2-(4-chlorobenzylidene)-3-oxobutanenitrile

Conditions

Conditions	Yield
With D-Prolin In methanol; ethanol at 20℃; for 48h; Knoevenagel Condensation;	82.3%

: 2469-99-0
Cyanoaceton

: 15330-50-4
4-hydrazinylisoquinoline

: 1452183-81-1
1-(isoquinolin-4-yl)-3-methyl-1H-pyrazol-5-amine

Conditions

Conditions	Yield
In ethanol at 80℃; for 3h;	81%
Stage #1: Cyanoaceton; 4-hydrazinylisoquinoline In ethanol at 80℃; for 3h; Stage #2: With sodium hydroxide In ethanol; water at 80℃; for 1h;	81%

: 2469-99-0
Cyanoaceton

: 28321-09-7
1-chloro-4-(2,2-difluorovinyl)benzene

: 5-(4-chlorophenyl)-2-methylfuran-3-carbonitrile

Conditions

Conditions	Yield
With copper(l) iodide; caesium carbonate In dimethyl sulfoxide at 120℃; Inert atmosphere;	81%

: 75-15-0
carbon disulfide

: 2469-99-0
Cyanoaceton

: 96-11-7
1,2,3-tribromopropane

: 889100-80-5
2-(4-(bromomethyl)-1,3-dithiolan-2-ylidene)-3-oxobutanenitrile

Conditions

Conditions	Yield
Stage #1: carbon disulfide; Cyanoaceton With potassium carbonate In N,N-dimethyl-formamide at 20℃; Stage #2: 1,2,3-tribromopropane In N,N-dimethyl-formamide at 0 - 20℃; Further stages.;	80%

...Expand

3-Oxobutanenitrile Specification

The 3-Oxobutanenitrile with the cas number 2469-99-0 is also called a-Cyanoacetone. Its EINECS registry number is 219-590-8. The molecular formula of this chemical is C₄H₅NO. This chemical is a kind of organics. It should be stored in dry and cool environment.

Properties Computed from Structure: (1)XLogP3-AA -0.2 ; (2)H-Bond Donor: 0; (3)H-Bond Acceptor: 2; (4)Rotatable Bond Count: 1; (5)Tautomer Count: 3; (6)Exact Mass: 83.037114; (7)MonoIsotopic Mass: 83.037114; (8)Topological Polar Surface Area: 40.9; (9)Heavy Atom Count: 6; (10)Formal Charge: 0; (11)Complexity: 97.4; (12)Isotope Atom Count: 0; (13)Defined Atom StereoCenter Count: 0; (14)Undefined Atom StereoCenter Count: 0; (15)Defined Bond StereoCenter Count: 0; (16)Undefined Bond StereoCenter Count: 0; (17)Covalently-Bonded Unit Count: 1.

You can still convert the following datas into molecular structure:
(1)SMILES: N#CCC(=O)C
(2)InChI: InChI=1/C4H5NO/c1-4(6)2-3-5/h2H2,1H3

Product Name

3-Oxobutanenitrile

Synthetic route

3-Oxobutanenitrile Specification

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