Crotononitrile supplier | CasNO.4786-20-3

Name
Crotononitrile (pract)
EINECS 225-335-1
CAS No. 4786-20-3
Article Data106
CAS DataBase
Density 0.822 g/cm³
Solubility
Melting Point -51.5ºC
Formula C₄H₅N
Boiling Point 120.5 °C at 760 mmHg
Molecular Weight 67.0904
Flash Point 20 °C
Transport Information UN 2924 3/PG 2
Appearance Clear light yellow liquid
Safety 16-26-36
Risk Codes 11-22-36/37/38-26-16
Molecular Structure
Hazard Symbols F, Xn
Synonyms Crotononitrile(6CI,8CI);1-Cyanopropene;1-Propenyl cyanide;2-Butenenitrile;NSC 165574;b-Methylacrylonitrile;
PSA 23.79000
LogP 1.08608

Synthetic route

: 590-15-8
trans-2-propenyl bromide

: 151-50-8
potassium cyanide

: 4786-20-3
crotononitrile

Conditions

Conditions	Yield
With 18-crown-6 ether; tetrakis(triphenylphosphine) palladium(0) In benzene at 80℃; for 50h; Rate constant; Product distribution;	89%
With potassium hydroxide; (Z)-1-propenyl bromide; hydrogen In water at 45℃; for 4h; Yield given;

: 123-73-9
trans-Crotonaldehyde

: 4786-20-3
crotononitrile

Conditions

Conditions	Yield
With aluminum oxide; potassium fluoride; hydroxylamine hydrochloride In N,N-dimethyl-formamide at 100℃; for 9h;	78%

: N2-<(E)-2-Propenyliden>glycinnitril

A: 109-97-7
pyrrole

B: 1190-76-7
(Z)-2-butenenitrile

C: 4786-20-3
crotononitrile

D: 109-75-1
but-3-enenitrile

Conditions

Conditions	Yield
at 650℃; under 0.2 Torr; Product distribution; Irradiation;	A 74% B 7% C 8% D 0.7%

...Expand

: 590-15-8
trans-2-propenyl bromide

: 544-92-3
copper(I) cyanide

A: 1190-76-7
(Z)-2-butenenitrile

B: 4786-20-3
crotononitrile

Conditions

Conditions	Yield
In N,N-dimethyl-formamide at 150℃; Product distribution; Rate constant; other solvent;	A 25% B 62%

...Expand

: 590-13-6
(Z)-1-propenyl bromide

: 544-92-3
copper(I) cyanide

A: 1190-76-7
(Z)-2-butenenitrile

B: 4786-20-3
crotononitrile

Conditions

Conditions	Yield
In N,N-dimethyl-formamide at 150℃; Product distribution; Rate constant; other solvent;	A 27% B 60%

...Expand

: 4-butannitril

A: 109-97-7
pyrrole

B: 1190-76-7
(Z)-2-butenenitrile

C: 4786-20-3
crotononitrile

D: 107-13-1
acrylonitrile

Conditions

Conditions	Yield
at 500 - 700℃; under 0.2 Torr; Product distribution; Irradiation; mol. sieve (3 Angstroem);	A 59% B n/a C n/a D 6%

...Expand

: cis-1-(p-fluorophenyl)-4-cyano-3-methylazetidin-2-one

A: 1190-76-7
(Z)-2-butenenitrile

B: 4786-20-3
crotononitrile

C: 1204614-44-7
(p-fluorophenyl)iminoacetonitrile

D: 1195-45-5
para-fluorophenyl isocyanate

Conditions

Conditions	Yield
at 720℃; under 0.0015 Torr; regioselective reaction;	A n/a B n/a C 33% D n/a

...Expand

: cis-4-cyano-3-methyl-1-(p-tolyl)azetidin-2-one

A: 1190-76-7
(Z)-2-butenenitrile

B: 4786-20-3
crotononitrile

C: 1204614-43-6
(p-tolyl)iminoacetonitrile

D: 622-58-2
p-Tolylisocyanate

Conditions

Conditions	Yield
at 720℃; under 0.0015 Torr; regioselective reaction;	A n/a B n/a C 30% D n/a

...Expand

: cis-1-(p-chlorophenyl)-4-cyano-3-methylazetidin-2-one

A: 1190-76-7
(Z)-2-butenenitrile

B: 4786-20-3
crotononitrile

C: 1204614-45-8
(p-chlorophenyl)iminoacetonitrile

D: 104-12-1
p-chlorphenylisocyanate

Conditions

Conditions	Yield
at 720℃; under 0.0015 Torr; regioselective reaction;	A n/a B n/a C 30% D n/a

...Expand

: cis-4-cyano-3-methyl-1-(p-methoxyphenyl)azetidin-2-one

A: 1190-76-7
(Z)-2-butenenitrile

B: 4786-20-3
crotononitrile

C: 1204614-42-5
(p-methoxyphenyl)iminoacetonitrile

D: 5416-93-3
4-Methoxyphenyl isocyanate

Conditions

Conditions	Yield
at 720℃; under 0.0015 Torr; regioselective reaction;	A n/a B n/a C 25% D n/a

...Expand

: 75-21-8
oxirane

: 75-05-8
acetonitrile

: 4786-20-3
crotononitrile

Conditions

Conditions	Yield
With aluminium oxide catalyst at 315℃;
With silica-alumina at 200℃;

: 110-86-1
pyridine

: 53778-71-5
3-chlorobutyronitrile

: 4786-20-3
crotononitrile

Conditions

Conditions	Yield
beide isom. entstehen;

: 110-86-1
pyridine

: 20965-20-2
β-bromobutyronitrile

: 4786-20-3
crotononitrile

Conditions

Conditions	Yield
beide isom. Crotonsaeurenitrile entstehen;

: 110-86-1
pyridine

: 75-07-0
acetaldehyde

: 372-09-8
cyanoacetic acid

A: 25077-26-3
3-methyl glutarimide

B: 1190-76-7
(Z)-2-butenenitrile

C: 4786-20-3
crotononitrile

D: 50870-55-8
(E+Z)-4-cyano-3-methyl-4-hexenenitrile

Conditions

Conditions	Yield
erst in der Kaelte, zuletzt bei 60grad;

...Expand

: 91-22-5
quinoline

: 53778-71-5
3-chlorobutyronitrile

A: 1190-76-7
(Z)-2-butenenitrile

B: 4786-20-3
crotononitrile

...Expand

: 53778-71-5
3-chlorobutyronitrile

A: 1190-76-7
(Z)-2-butenenitrile

B: 4786-20-3
crotononitrile

Conditions

Conditions	Yield
With quinoline

: 32813-37-9
3-(piperidin-1-yl)butanenitrile

A: 1190-76-7
(Z)-2-butenenitrile

B: 4786-20-3
crotononitrile

Conditions

Conditions	Yield
bei langsamer Destillation;

: 109-74-0
propyl cyanide

: 4786-20-3
crotononitrile

Conditions

Conditions	Yield
With chromium(III) oxide at 615℃; Dehydrierung;

: 109-74-0
propyl cyanide

A: 4786-20-3
crotononitrile

B: 109-75-1
but-3-enenitrile

Conditions

Conditions	Yield
With chromium(III) oxide at 580 - 615℃;

: 628-20-6
4-Chlorobutyronitrile

A: 4786-20-3
but-2-enenitrile

B: 4786-20-3
crotononitrile

Conditions

Conditions	Yield
β-crotonic acid nitrile (cis-form);

: 628-20-6
4-Chlorobutyronitrile

: 4786-20-3
crotononitrile

Conditions

Conditions	Yield
bei wiederholter langsamer Destillation; beide isom.Crotonsaeurenitrile entstehen;

: 4158-37-6
2-chlorobutyronitrile

A: 1190-76-7
(Z)-2-butenenitrile

B: 4786-20-3
crotononitrile

Conditions

Conditions	Yield
With quinoline

: 4476-02-2
2-hydroxybutanenitrile

A: 4786-20-3
but-2-enenitrile

B: 4786-20-3
crotononitrile

Conditions

Conditions	Yield
With phosphorus pentaoxide β-crotonic acid nitrile (cis-form);

: 4476-02-2
2-hydroxybutanenitrile

: 4786-20-3
crotononitrile

Conditions

Conditions	Yield
With phosphoric acid; water at 600℃; under 20 Torr;

: 16750-40-6
(+-)-3-amino-butyronitrile

A: 4786-20-3
but-2-enenitrile

B: 4786-20-3
crotononitrile

Conditions

Conditions	Yield
β-crotonic acid nitrile (cis-form);

: 4368-06-3
3-hydroxybutanenitrile

A: 4786-20-3
but-2-enenitrile

B: 4786-20-3
crotononitrile

Conditions

Conditions	Yield
With phosphorus pentaoxide β-crotonic acid nitrile (cis-form);

: 4368-06-3
3-hydroxybutanenitrile

A: 1190-76-7
(Z)-2-butenenitrile

B: 4786-20-3
crotononitrile

Conditions

Conditions	Yield
With sulfuric acid
With sodium borate at 190℃;
With sodium phosphate at 190℃;

: 4368-06-3
3-hydroxybutanenitrile

: 4786-20-3
crotononitrile

Conditions

Conditions	Yield
With phosphorus pentaoxide

: 5314-34-1
crotonaldoxime

: 4786-20-3
crotononitrile

Conditions

Conditions	Yield
With diethyl ether; acetic anhydride

: 10544-63-5
ethyl crotonate

A: 4786-20-3
but-2-enenitrile

B: 4786-20-3
crotononitrile

Conditions

Conditions	Yield
With aluminum oxide; ammonia at 480 - 500℃; β-crotonic acid nitrile (cis-form);

: 64-17-5
ethanol

: 4786-20-3
crotononitrile

: 33546-80-4
3-ethoxy-butyronitrile

Conditions

Conditions	Yield
With tributylphosphine at 50℃; under 2250180 Torr; for 3h; Michael-like addition;	99%

: 110-91-8
morpholine

: 4786-20-3
crotononitrile

: 38405-81-1
3-(morpholin-4-yl)butanenitrile

Conditions

Conditions	Yield
[Ni((R)-(S)-Pigiphos)(THF)](ClO4)2 In tetrahydrofuran at 20℃; for 24h;	99%
With [Ni((R)-(S)-Pigiphos)(THF)](ClO4)2 In tetrahydrofuran at 20℃; for 24h;
With [{kp,kc,kp-2,6-(i-Pr2PO)2C6H3}Ni(NCMe)][OSO2CF3]; triethylamine In benzene-d6 at 20℃; for 0.166667h; Michael condensation;	100 %Spectr.

: 110-89-4
piperidine

: 4786-20-3
crotononitrile

: 32813-37-9
3-(piperidin-1-yl)butanenitrile

Conditions

Conditions	Yield
2,6-bis((di-tertbutylphosphino)methyl)pyridine; palladium(II) trifluoroacetate In toluene at 20℃; for 12h; Conversion of starting material;	99%
palladium(II) trifluoroacetate In toluene at 20℃; for 12h; Conversion of starting material;	21%

: 4786-20-3
crotononitrile

: 129433-53-0
C4H7ClMn

: 98096-32-3, 115092-90-5
3,4-dimethyl-5-hexenoic acid nitrile

Conditions

Conditions	Yield
In tetrahydrofuran at -60℃;	96%

: 4786-20-3
crotononitrile

: 4887-83-6
4-methylbenzimidazole

A: 172839-53-1
4-methyl-1H-benzimidazole-1-(3-methyl)propanenitrile

B: 3-(7-Methyl-benzoimidazol-1-yl)-butyronitrile

Conditions

Conditions	Yield
With 1,3,4,6,7,8-hexahydro-2H-pyrimido[1,2-a]pyrimidine In acetonitrile Ambient temperature; Yields of byproduct given. Title compound not separated from byproducts;	A 96% B n/a

...Expand

: 4786-20-3
crotononitrile

: 100-51-6
benzyl alcohol

: 3-(benzyloxy)butanenitrile

Conditions

Conditions	Yield
With caesium carbonate; copper dichloride In dichloromethane for 12h; Michael Addition; Reflux;	96%

: 4786-20-3
crotononitrile

: 626-62-0
1-iodocyclohexane

: 64198-20-5
3-cyclohexylbutyronitrile

Conditions

Conditions	Yield
With indium; N-ethylpiperidine hypophosphite; cetyltrimethylammonim bromide; triethyl borane In 1,4-dioxane; water at 80℃; for 2h;	94%
With borohydride exchange resin; nickel diacetate In methanol at 65℃; for 1h;	93%
With zinc copper In ethanol for 1h; Irradiation;	63%

: 4786-20-3
crotononitrile

: 30532-37-7
4-(2-pyridinyl)piperidine

: 3-[4-(pyridin-2-yl)-piperidin-1-yl)-3-methylpropionitrile

Conditions

Conditions	Yield
In methanol; ethanol	94%

: 18589-27-0
2-iodohexane

: 4786-20-3
crotononitrile

: 3,4-Dimethyl-octanenitrile

Conditions

Conditions	Yield
With borohydride exchange resin; nickel diacetate In methanol at 65℃; for 1h;	92%

: 4786-20-3
crotononitrile

: 87022-42-2
1-(isocyanomethyl)-1H-benzo[d][1,2,3]triazole

: 40167-38-2
4-methyl-1H-pyrrole-3-carbonitrile

Conditions

Conditions	Yield
With potassium tert-butylate In tetrahydrofuran Heating;	92%

: 4786-20-3
crotononitrile

: 20965-20-2
β-bromobutyronitrile

Conditions

Conditions	Yield
With 1-oxothiolane; phenyltribromosilane In dichloromethane at 20℃; for 16h; Michael Addition;	92%

: 4786-20-3
crotononitrile

: 105-34-0
methyl 2-cyanoacetate

: 25077-26-3
3-methyl glutarimide

Conditions

Conditions	Yield
With IrH5(P-(i-Pr)3)2; water In tetrahydrofuran at 150℃; for 20h;	91%

: 4786-20-3
crotononitrile

: 2684-60-8
2-diazopropane

: 86556-95-8
4,5,5-Trimethyl-4,5-dihydro-1H-pyrazole-3-carbonitrile

Conditions

Conditions	Yield
In diethyl ether from -20 deg C to 0 deg C;	90%

: 15854-87-2
4-iodopyridine

: 4786-20-3
crotononitrile

: 79190-37-7
(+/-)-3-(pyridin-4-yl)butyronitrile

Conditions

Conditions	Yield
With copper(l) iodide; n-butyllithium; Dibutyl sulfide In diethyl ether; hexane at 20℃; for 1h;	90%

: 4786-20-3
crotononitrile

: 62-53-3
aniline

: 80935-75-7
2-Anilinopropyl Cyanide

Conditions

Conditions	Yield
1,3-bis[(di-tert-butylphosphino)methyl]benzene; palladium diacetate In toluene at 100℃; for 36h; Conversion of starting material;	90%
With [Ni((R)-(S)-Pigiphos)(THF)](ClO4)2 In tetrahydrofuran at 20℃; for 24h;	65%

: 4786-20-3
crotononitrile

: (3R,4R)-1-benzyl-3,4-bis(benzyloxy)-5-oxo-2-(trifluoromethyl)-pyrrolidin-2-yl acetate

: (3aR,6R,6aS)-4-benzyl-6-(benzyloxy)-2-((E)-prop-1-en-1-yl)-3a-(trifluoromethyl)-6,6a-dihydro-3aH-pyrrolo[2,3-d]oxazol-5(4H)-one

Conditions

Conditions	Yield
With boron trifluoride diethyl etherate at 20℃; for 21h; Inert atmosphere; diastereoselective reaction;	89%

: 4786-20-3
crotononitrile

: 123959-20-6
7-(1-morpholino-1-cyanomethyl)tetrazolo<1,5-a>quinoline

: 123959-21-7
7-(1,3-dicyano-2-methyl-1-morpholinopropyl)tetrazolo<1,5-a>quinoline

Conditions

Conditions	Yield
With N-benzyl-trimethylammonium hydroxide Ambient temperature;	88%

: 773837-37-9
sodium cyanide

: 4786-20-3
crotononitrile

: 104-88-1
4-chlorobenzaldehyde

: 53012-96-7
4-(4-chlorophenyl)-3-methyl-4-oxobutyronitrile

Conditions

Conditions	Yield
Stage #1: sodium cyanide; 4-chlorobenzaldehyde In N,N-dimethyl-formamide at 35 - 38℃; for 2h; Michael Addition; Inert atmosphere; Stage #2: crotononitrile In N,N-dimethyl-formamide at 40℃; for 3.5h; Inert atmosphere;	88%

...Expand

: 4786-20-3
crotononitrile

: 123959-24-0
7-(1-morpholino-1-cyanomethyl)-1,2,4-triazolo<4,3-a>quinoline

: 123959-25-1
7-(1,3-dicyano-2-methyl-1-morpholinopropyl)-1,2,4-triazolo<4,3-a>quinoline

Conditions

Conditions	Yield
With N-benzyl-trimethylammonium hydroxide for 3h; Ambient temperature;	86%

: 4786-20-3
crotononitrile

: 3-imino-5methylpyrazolidine hydrochloride

Conditions

Conditions	Yield
With hydrogenchloride; hydrazine hydrate In methanol; toluene	85%

: 4786-20-3
crotononitrile

: 463-49-0
1,2-propanediene

: 3839-31-4
dimethyl(phenyl)silyllithium

: 374572-22-2
2-(dimethylphenylsilyl)-7-[(dimethylphenylsilyl)methyl]-6-methylocta-1,7-dien-4-one

Conditions

Conditions	Yield
Stage #1: 1,2-propanediene; dimethyl(phenyl)silyllithium With copper(l) cyanide In tetrahydrofuran at -78℃; for 1h; Stage #2: crotononitrile With boron trifluoride diethyl etherate In tetrahydrofuran at -78 - 0℃;	83%

...Expand

: C8H11CuSi*LiCN

: 4786-20-3
crotononitrile

: 463-49-0
1,2-propanediene

: 374572-22-2
2-(dimethylphenylsilyl)-7-[(dimethylphenylsilyl)methyl]-6-methylocta-1,7-dien-4-one

Conditions

Conditions	Yield
Stage #1: C8H11CuSi*LiCN; 1,2-propanediene In tetrahydrofuran at -40℃; for 1h; Stage #2: crotononitrile With boron trifluoride diethyl etherate In tetrahydrofuran at -40 - 0℃; Stage #3: With ammonium chloride In tetrahydrofuran at 0℃; Further stages.;	83%

...Expand

: 4786-20-3
crotononitrile

: 1572-99-2
ethyl 2-cyanopropionate

: ethyl 2,4-dicyano-2,3-dimethylbutanoate

Conditions

Conditions	Yield
With dihydridotetrakis(triphenylphosphine)ruthenium In tetrahydrofuran for 24h; Ambient temperature;	82%

: 4786-20-3
crotononitrile

: 2996-92-1
phenyl trimethylsiloxane

: 20132-76-7
3-phenyl-butyronitrile

Conditions

Conditions	Yield
bis(acetonitrile)(1,5-cyclooctadiene)rhodium(I) tetrafluoroborate In 1,4-dioxane; water at 90℃; for 20h;	82%

: 4786-20-3
crotononitrile

: 4887-83-6
4-methylbenzimidazole

: 172839-53-1
4-methyl-1H-benzimidazole-1-(3-methyl)propanenitrile

Conditions

Conditions	Yield
With benzyltriethylammonium hydroxide Heating;	81%

: 3430-17-9
2-bromo-3-picoline

: 4786-20-3
crotononitrile

: (+/-)-3-(3-methylpyridin-2-yl)-butyronitrile

Conditions

Conditions	Yield
With copper(l) iodide; n-butyllithium; Dibutyl sulfide In diethyl ether; hexane at 20℃; for 1h;	81%

: 629-27-6
1-Iodooctane

: 4786-20-3
crotononitrile

: 3-methylundecanenitrile

Conditions

Conditions	Yield
With borohydride exchange resin; nickel diacetate In methanol at 65℃; for 1h;	80%

: 32354-26-0, 36593-52-9
Rh(ClO4)(CO)(PPh3)2

: 4786-20-3
crotononitrile

: Rh(CH3CHCHCN)(CO)(P(C6H5)3)2(1+)*ClO4(1-)={Rh(CH3CHCHCN)(CO)(P(C6H5)3)2}ClO4

Conditions

Conditions	Yield
In benzene under N2 at 25°C;; filtration; ppt. washed with benzene, dried in vac.; elem. anal.;;	80%

: 4786-20-3
crotononitrile

: 625-37-6
crotonamide

Conditions

Conditions	Yield
With Acetaldehyde oxime; [(eta.(5)-pentamethylcyclopentadienyl)Rh(H2O)3](OTf)2 In water Schlenk technique;	80%

Crotononitrile Chemical Properties

Empirical Formula: C₄H₅N
Molecular Weight: 67.0892
Structure of Crotononitrile (CAS NO.4786-20-3):

Index of Refraction: 1.417
Density: 0.822 g/cm³
Flash Point: 20 °C
Enthalpy of Vaporization: 35.86 kJ/mol
Boiling Point: 120.5 °C at 760 mmHg
Vapour Pressure: 15.2 mmHg at 25 °C
Storage temp: Flammables area
Appearance: Clear light yellow liquid

Crotononitrile Toxicity Data With Reference

1.	orl-rat LD50:501 mg/kg	GISAAA Gigiena i Sanitariya. 37 (4)(1972),10.
2.	orl-mus LD50:396 mg/kg	GISAAA Gigiena i Sanitariya. 37 (4)(1972),10.
3.	ivn-rbt LDLo:60 mg/kg	COREAF Comptes Rendus Hebdomadaires des Seances de l’Academie des Sciences. 153 (1911),895.
4.	orl-gpg LD50:272 mg/kg	GISAAA Gigiena i Sanitariya. 37 (4)(1972),10.
5.	scu-gpg LDLo:230 mg/kg	COREAF Comptes Rendus Hebdomadaires des Seances de l’Academie des Sciences. 153 (1911),895.

Carcinogenicity of Crotononitrile (CAS NO.4786-20-3) hasn't been listed as a carcinogen by NTP, IARC,ACGIH, or CA Prop 65. And its toxicological properties have not been fully investigated.You can see actual entry in RTECS for complete information.

Crotononitrile Consensus Reports

Reported in EPA TSCA Inventory.

Crotononitrile Safety Profile

A poison by ingestion, intravenous, and subcutaneous routes. When heated to decomposition it emits toxic vapors of NO_x and CN⁻.

Hazard Codes: F Harmful Xn
Risk Statements: 11-22-36/37/38-26-16
R11:Highly flammable.
R16:Explosive when mixed with oxidizing substances.
R22:Harmful if swallowed.
R26:Very toxic by inhalation.
R36/37/38:Irritating to eyes, respiratory system and skin.
Safety Statements: 16-26-36
S16:Keep away from sources of ignition.
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
S36:Wear suitable protective clothing.

Crotononitrile Specification

Crotononitrile ,its cas register number is 4786-20-3. It also can be called 2-Butenenitrile ; cis-beta-Methylacrylonitrile ; (E)-2-Butenenitrile ; 2-Butenenitrile, (2E)- and (2E)-But-2-enenitrile . It is hazardous,so the first aid measures and others should be known. Such as: When on the skin: first,should flush skin with plenty of water immediately for at least 15 minutes while removing contaminated clothing. Secondly,Get medical aid. Or in the eyes: Flush eyes with plenty of water for at least 15 minutes, occasionally lifting the upper and lower eyelids. Then get medical aid soon. While ,it's Inhaled: Remove from exposure and move to fresh air immediately.Give artificial respiration while not breathing. When breathing is difficult, give oxygen. And as soon as to get medical aid. Then you have the ingesting of the product : Wash mouth out with water,and get medical aid immediately.Notes to physician: Treat supportively and symptomatically.
In addition, Crotononitrile (CAS NO.4786-20-3) can be stable under normal temperature and pressure conditions.It is not compatible with strong oxidizing agents, and you must not take it with incompatible materials. And also prevent it to broken down into hazardous decomposition products: carbon dioxide, carbon monoxide.

Product Name

Crotononitrile (pract)

Synthetic route

Crotononitrile Chemical Properties

Crotononitrile Toxicity Data With Reference

Crotononitrile Consensus Reports

Crotononitrile Safety Profile

Crotononitrile Specification

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