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4786-20-3

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4786-20-3 Usage

Chemical Properties

CLEAR LIGHT YELLOW LIQUID

General Description

Neurotoxic properties of crotononitrile have been investigated. Mechanism of the Baylis-Hillman reaction of crotononitrile and benzaldehyde in the presence of 1,4-diazabicyclo[2,2,2]octane (catalyst) has been investigated.

Purification Methods

Separate the mixture by preparative GLC on a column using 5% FFAP on Chromosorb G. [Lewis et al. J Am Chem Soc 108 2818 1986, Beilstein 2 IV 1507.]

Check Digit Verification of cas no

The CAS Registry Mumber 4786-20-3 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 4,7,8 and 6 respectively; the second part has 2 digits, 2 and 0 respectively.
Calculate Digit Verification of CAS Registry Number 4786-20:
(6*4)+(5*7)+(4*8)+(3*6)+(2*2)+(1*0)=113
113 % 10 = 3
So 4786-20-3 is a valid CAS Registry Number.
InChI:InChI=1/C22H16F3N3O2S/c1-13-11-18(27-30-13)20-19(21(29)31-17-9-4-3-5-10-17)14(2)26-28(20)16-8-6-7-15(12-16)22(23,24)25/h3-12H,1-2H3

4786-20-3SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 11, 2017

Revision Date: Aug 11, 2017

1.Identification

1.1 GHS Product identifier

Product name 2-Butenenitrile

1.2 Other means of identification

Product number -
Other names Crotononitrile (pract)

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:4786-20-3 SDS

4786-20-3Synthetic route

trans-2-propenyl bromide
590-15-8

trans-2-propenyl bromide

potassium cyanide
151-50-8

potassium cyanide

crotononitrile
4786-20-3

crotononitrile

Conditions
ConditionsYield
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;
trans-Crotonaldehyde
123-73-9

trans-Crotonaldehyde

crotononitrile
4786-20-3

crotononitrile

Conditions
ConditionsYield
With aluminum oxide; potassium fluoride; hydroxylamine hydrochloride In N,N-dimethyl-formamide at 100℃; for 9h;78%
N2-<(E)-2-Propenyliden>glycinnitril

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

A

pyrrole
109-97-7

pyrrole

B

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

(Z)-2-butenenitrile

C

crotononitrile
4786-20-3

crotononitrile

D

but-3-enenitrile
109-75-1

but-3-enenitrile

Conditions
ConditionsYield
at 650℃; under 0.2 Torr; Product distribution; Irradiation;A 74%
B 7%
C 8%
D 0.7%
trans-2-propenyl bromide
590-15-8

trans-2-propenyl bromide

copper(I) cyanide
544-92-3

copper(I) cyanide

A

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

(Z)-2-butenenitrile

B

crotononitrile
4786-20-3

crotononitrile

Conditions
ConditionsYield
In N,N-dimethyl-formamide at 150℃; Product distribution; Rate constant; other solvent;A 25%
B 62%
(Z)-1-propenyl bromide
590-13-6

(Z)-1-propenyl bromide

copper(I) cyanide
544-92-3

copper(I) cyanide

A

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

(Z)-2-butenenitrile

B

crotononitrile
4786-20-3

crotononitrile

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

4-butannitril

A

pyrrole
109-97-7

pyrrole

B

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

(Z)-2-butenenitrile

C

crotononitrile
4786-20-3

crotononitrile

D

acrylonitrile
107-13-1

acrylonitrile

Conditions
ConditionsYield
at 500 - 700℃; under 0.2 Torr; Product distribution; Irradiation; mol. sieve (3 Angstroem);A 59%
B n/a
C n/a
D 6%
cis-1-(p-fluorophenyl)-4-cyano-3-methylazetidin-2-one

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

A

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

(Z)-2-butenenitrile

B

crotononitrile
4786-20-3

crotononitrile

C

(p-fluorophenyl)iminoacetonitrile
1204614-44-7

(p-fluorophenyl)iminoacetonitrile

D

para-fluorophenyl isocyanate
1195-45-5

para-fluorophenyl isocyanate

Conditions
ConditionsYield
at 720℃; under 0.0015 Torr; regioselective reaction;A n/a
B n/a
C 33%
D n/a
cis-4-cyano-3-methyl-1-(p-tolyl)azetidin-2-one

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

A

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

(Z)-2-butenenitrile

B

crotononitrile
4786-20-3

crotononitrile

C

(p-tolyl)iminoacetonitrile
1204614-43-6

(p-tolyl)iminoacetonitrile

D

p-Tolylisocyanate
622-58-2

p-Tolylisocyanate

Conditions
ConditionsYield
at 720℃; under 0.0015 Torr; regioselective reaction;A n/a
B n/a
C 30%
D n/a
cis-1-(p-chlorophenyl)-4-cyano-3-methylazetidin-2-one

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

A

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

(Z)-2-butenenitrile

B

crotononitrile
4786-20-3

crotononitrile

C

(p-chlorophenyl)iminoacetonitrile
1204614-45-8

(p-chlorophenyl)iminoacetonitrile

D

p-chlorphenylisocyanate
104-12-1

p-chlorphenylisocyanate

Conditions
ConditionsYield
at 720℃; under 0.0015 Torr; regioselective reaction;A n/a
B n/a
C 30%
D n/a
cis-4-cyano-3-methyl-1-(p-methoxyphenyl)azetidin-2-one

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

A

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

(Z)-2-butenenitrile

B

crotononitrile
4786-20-3

crotononitrile

C

(p-methoxyphenyl)iminoacetonitrile
1204614-42-5

(p-methoxyphenyl)iminoacetonitrile

D

4-Methoxyphenyl isocyanate
5416-93-3

4-Methoxyphenyl isocyanate

Conditions
ConditionsYield
at 720℃; under 0.0015 Torr; regioselective reaction;A n/a
B n/a
C 25%
D n/a
oxirane
75-21-8

oxirane

acetonitrile
75-05-8

acetonitrile

crotononitrile
4786-20-3

crotononitrile

Conditions
ConditionsYield
With aluminium oxide catalyst at 315℃;
With silica-alumina at 200℃;
pyridine
110-86-1

pyridine

3-chlorobutyronitrile
53778-71-5

3-chlorobutyronitrile

crotononitrile
4786-20-3

crotononitrile

Conditions
ConditionsYield
beide isom. entstehen;
pyridine
110-86-1

pyridine

β-bromobutyronitrile
20965-20-2

β-bromobutyronitrile

crotononitrile
4786-20-3

crotononitrile

Conditions
ConditionsYield
beide isom. Crotonsaeurenitrile entstehen;
pyridine
110-86-1

pyridine

acetaldehyde
75-07-0

acetaldehyde

cyanoacetic acid
372-09-8

cyanoacetic acid

A

3-methyl glutarimide
25077-26-3

3-methyl glutarimide

B

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

(Z)-2-butenenitrile

C

crotononitrile
4786-20-3

crotononitrile

D

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

(E+Z)-4-cyano-3-methyl-4-hexenenitrile

Conditions
ConditionsYield
erst in der Kaelte, zuletzt bei 60grad;
quinoline
91-22-5

quinoline

3-chlorobutyronitrile
53778-71-5

3-chlorobutyronitrile

A

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

(Z)-2-butenenitrile

B

crotononitrile
4786-20-3

crotononitrile

3-chlorobutyronitrile
53778-71-5

3-chlorobutyronitrile

A

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

(Z)-2-butenenitrile

B

crotononitrile
4786-20-3

crotononitrile

Conditions
ConditionsYield
With quinoline
3-(piperidin-1-yl)butanenitrile
32813-37-9

3-(piperidin-1-yl)butanenitrile

A

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

(Z)-2-butenenitrile

B

crotononitrile
4786-20-3

crotononitrile

Conditions
ConditionsYield
bei langsamer Destillation;
propyl cyanide
109-74-0

propyl cyanide

crotononitrile
4786-20-3

crotononitrile

Conditions
ConditionsYield
With chromium(III) oxide at 615℃; Dehydrierung;
propyl cyanide
109-74-0

propyl cyanide

A

crotononitrile
4786-20-3

crotononitrile

B

but-3-enenitrile
109-75-1

but-3-enenitrile

Conditions
ConditionsYield
With chromium(III) oxide at 580 - 615℃;
4-Chlorobutyronitrile
628-20-6

4-Chlorobutyronitrile

A

but-2-enenitrile
4786-20-3

but-2-enenitrile

B

crotononitrile
4786-20-3

crotononitrile

Conditions
ConditionsYield
β-crotonic acid nitrile (cis-form);
4-Chlorobutyronitrile
628-20-6

4-Chlorobutyronitrile

crotononitrile
4786-20-3

crotononitrile

Conditions
ConditionsYield
bei wiederholter langsamer Destillation; beide isom.Crotonsaeurenitrile entstehen;
2-chlorobutyronitrile
4158-37-6

2-chlorobutyronitrile

A

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

(Z)-2-butenenitrile

B

crotononitrile
4786-20-3

crotononitrile

Conditions
ConditionsYield
With quinoline
2-hydroxybutanenitrile
4476-02-2

2-hydroxybutanenitrile

A

but-2-enenitrile
4786-20-3

but-2-enenitrile

B

crotononitrile
4786-20-3

crotononitrile

Conditions
ConditionsYield
With phosphorus pentaoxide β-crotonic acid nitrile (cis-form);
2-hydroxybutanenitrile
4476-02-2

2-hydroxybutanenitrile

crotononitrile
4786-20-3

crotononitrile

Conditions
ConditionsYield
With phosphoric acid; water at 600℃; under 20 Torr;
(+-)-3-amino-butyronitrile
16750-40-6

(+-)-3-amino-butyronitrile

A

but-2-enenitrile
4786-20-3

but-2-enenitrile

B

crotononitrile
4786-20-3

crotononitrile

Conditions
ConditionsYield
β-crotonic acid nitrile (cis-form);
3-hydroxybutanenitrile
4368-06-3

3-hydroxybutanenitrile

A

but-2-enenitrile
4786-20-3

but-2-enenitrile

B

crotononitrile
4786-20-3

crotononitrile

Conditions
ConditionsYield
With phosphorus pentaoxide β-crotonic acid nitrile (cis-form);
3-hydroxybutanenitrile
4368-06-3

3-hydroxybutanenitrile

A

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

(Z)-2-butenenitrile

B

crotononitrile
4786-20-3

crotononitrile

Conditions
ConditionsYield
With sulfuric acid
With sodium borate at 190℃;
With sodium phosphate at 190℃;
3-hydroxybutanenitrile
4368-06-3

3-hydroxybutanenitrile

crotononitrile
4786-20-3

crotononitrile

Conditions
ConditionsYield
With phosphorus pentaoxide
crotonaldoxime
5314-34-1

crotonaldoxime

crotononitrile
4786-20-3

crotononitrile

Conditions
ConditionsYield
With diethyl ether; acetic anhydride
ethyl crotonate
10544-63-5

ethyl crotonate

A

but-2-enenitrile
4786-20-3

but-2-enenitrile

B

crotononitrile
4786-20-3

crotononitrile

Conditions
ConditionsYield
With aluminum oxide; ammonia at 480 - 500℃; β-crotonic acid nitrile (cis-form);
ethanol
64-17-5

ethanol

crotononitrile
4786-20-3

crotononitrile

3-ethoxy-butyronitrile
33546-80-4

3-ethoxy-butyronitrile

Conditions
ConditionsYield
With tributylphosphine at 50℃; under 2250180 Torr; for 3h; Michael-like addition;99%
morpholine
110-91-8

morpholine

crotononitrile
4786-20-3

crotononitrile

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

3-(morpholin-4-yl)butanenitrile

Conditions
ConditionsYield
[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.
piperidine
110-89-4

piperidine

crotononitrile
4786-20-3

crotononitrile

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

3-(piperidin-1-yl)butanenitrile

Conditions
ConditionsYield
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%
crotononitrile
4786-20-3

crotononitrile

C4H7ClMn
129433-53-0

C4H7ClMn

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

3,4-dimethyl-5-hexenoic acid nitrile

Conditions
ConditionsYield
In tetrahydrofuran at -60℃;96%
crotononitrile
4786-20-3

crotononitrile

4-methylbenzimidazole
4887-83-6

4-methylbenzimidazole

A

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

4-methyl-1H-benzimidazole-1-(3-methyl)propanenitrile

B

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

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

Conditions
ConditionsYield
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
crotononitrile
4786-20-3

crotononitrile

benzyl alcohol
100-51-6

benzyl alcohol

3-(benzyloxy)butanenitrile

3-(benzyloxy)butanenitrile

Conditions
ConditionsYield
With caesium carbonate; copper dichloride In dichloromethane for 12h; Michael Addition; Reflux;96%
crotononitrile
4786-20-3

crotononitrile

1-iodocyclohexane
626-62-0

1-iodocyclohexane

3-cyclohexylbutyronitrile
64198-20-5

3-cyclohexylbutyronitrile

Conditions
ConditionsYield
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%
crotononitrile
4786-20-3

crotononitrile

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

4-(2-pyridinyl)piperidine

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

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

Conditions
ConditionsYield
In methanol; ethanol94%
2-iodohexane
18589-27-0

2-iodohexane

crotononitrile
4786-20-3

crotononitrile

3,4-Dimethyl-octanenitrile

3,4-Dimethyl-octanenitrile

Conditions
ConditionsYield
With borohydride exchange resin; nickel diacetate In methanol at 65℃; for 1h;92%
crotononitrile
4786-20-3

crotononitrile

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

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

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

4-methyl-1H-pyrrole-3-carbonitrile

Conditions
ConditionsYield
With potassium tert-butylate In tetrahydrofuran Heating;92%
crotononitrile
4786-20-3

crotononitrile

β-bromobutyronitrile
20965-20-2

β-bromobutyronitrile

Conditions
ConditionsYield
With 1-oxothiolane; phenyltribromosilane In dichloromethane at 20℃; for 16h; Michael Addition;92%
crotononitrile
4786-20-3

crotononitrile

methyl 2-cyanoacetate
105-34-0

methyl 2-cyanoacetate

3-methyl glutarimide
25077-26-3

3-methyl glutarimide

Conditions
ConditionsYield
With IrH5(P-(i-Pr)3)2; water In tetrahydrofuran at 150℃; for 20h;91%
crotononitrile
4786-20-3

crotononitrile

2-diazopropane
2684-60-8

2-diazopropane

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

4,5,5-Trimethyl-4,5-dihydro-1H-pyrazole-3-carbonitrile

Conditions
ConditionsYield
In diethyl ether from -20 deg C to 0 deg C;90%
4-iodopyridine
15854-87-2

4-iodopyridine

crotononitrile
4786-20-3

crotononitrile

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

(+/-)-3-(pyridin-4-yl)butyronitrile

Conditions
ConditionsYield
With copper(l) iodide; n-butyllithium; Dibutyl sulfide In diethyl ether; hexane at 20℃; for 1h;90%
crotononitrile
4786-20-3

crotononitrile

aniline
62-53-3

aniline

2-Anilinopropyl Cyanide
80935-75-7

2-Anilinopropyl Cyanide

Conditions
ConditionsYield
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%
crotononitrile
4786-20-3

crotononitrile

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

(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

(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
ConditionsYield
With boron trifluoride diethyl etherate at 20℃; for 21h; Inert atmosphere; diastereoselective reaction;89%
crotononitrile
4786-20-3

crotononitrile

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

7-(1-morpholino-1-cyanomethyl)tetrazolo<1,5-a>quinoline

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

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

Conditions
ConditionsYield
With N-benzyl-trimethylammonium hydroxide Ambient temperature;88%
sodium cyanide
773837-37-9

sodium cyanide

crotononitrile
4786-20-3

crotononitrile

4-chlorobenzaldehyde
104-88-1

4-chlorobenzaldehyde

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

4-(4-chlorophenyl)-3-methyl-4-oxobutyronitrile

Conditions
ConditionsYield
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%
crotononitrile
4786-20-3

crotononitrile

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

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

7-(1,3-dicyano-2-methyl-1-morpholinopropyl)-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
ConditionsYield
With N-benzyl-trimethylammonium hydroxide for 3h; Ambient temperature;86%
crotononitrile
4786-20-3

crotononitrile

3-imino-5methylpyrazolidine hydrochloride

3-imino-5methylpyrazolidine hydrochloride

Conditions
ConditionsYield
With hydrogenchloride; hydrazine hydrate In methanol; toluene85%
crotononitrile
4786-20-3

crotononitrile

1,2-propanediene
463-49-0

1,2-propanediene

dimethyl(phenyl)silyllithium
3839-31-4

dimethyl(phenyl)silyllithium

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

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

Conditions
ConditionsYield
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%
C8H11CuSi*LiCN

C8H11CuSi*LiCN

crotononitrile
4786-20-3

crotononitrile

1,2-propanediene
463-49-0

1,2-propanediene

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

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

Conditions
ConditionsYield
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%
crotononitrile
4786-20-3

crotononitrile

ethyl 2-cyanopropionate
1572-99-2

ethyl 2-cyanopropionate

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

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

Conditions
ConditionsYield
With dihydridotetrakis(triphenylphosphine)ruthenium In tetrahydrofuran for 24h; Ambient temperature;82%
crotononitrile
4786-20-3

crotononitrile

phenyl trimethylsiloxane
2996-92-1

phenyl trimethylsiloxane

3-phenyl-butyronitrile
20132-76-7

3-phenyl-butyronitrile

Conditions
ConditionsYield
bis(acetonitrile)(1,5-cyclooctadiene)rhodium(I) tetrafluoroborate In 1,4-dioxane; water at 90℃; for 20h;82%
crotononitrile
4786-20-3

crotononitrile

4-methylbenzimidazole
4887-83-6

4-methylbenzimidazole

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

4-methyl-1H-benzimidazole-1-(3-methyl)propanenitrile

Conditions
ConditionsYield
With benzyltriethylammonium hydroxide Heating;81%
2-bromo-3-picoline
3430-17-9

2-bromo-3-picoline

crotononitrile
4786-20-3

crotononitrile

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

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

Conditions
ConditionsYield
With copper(l) iodide; n-butyllithium; Dibutyl sulfide In diethyl ether; hexane at 20℃; for 1h;81%
1-Iodooctane
629-27-6

1-Iodooctane

crotononitrile
4786-20-3

crotononitrile

3-methylundecanenitrile

3-methylundecanenitrile

Conditions
ConditionsYield
With borohydride exchange resin; nickel diacetate In methanol at 65℃; for 1h;80%
Rh(ClO4)(CO)(PPh3)2
32354-26-0, 36593-52-9

Rh(ClO4)(CO)(PPh3)2

crotononitrile
4786-20-3

crotononitrile

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

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

Conditions
ConditionsYield
In benzene under N2 at 25°C;; filtration; ppt. washed with benzene, dried in vac.; elem. anal.;;80%
crotononitrile
4786-20-3

crotononitrile

crotonamide
625-37-6

crotonamide

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

4786-20-3Relevant articles and documents

C-CN BOND CLEAVAGE UNDER MILD CONDITIONS PROMOTED BY ELECTRON-RICH COBALT COMPLEXES

Ozawa, Fumiyuki,Iri, Kiyoshi,Yamamoto, Akio

, p. 1707 - 1710 (1982)

Electron-rich cobaltate dinitrogen complex, Li(Et2O)3 1, reacts with alkyl and aryl nitrile compounds causing the cleavage of C-CN bond under mild conditions to release hydrocarbons.Catalytic activity of the cobalt complex to isomerize allyl cyanide to crotononitrile is also noted.

Base controlled diverse reactivity of allyl cyanide for synthesis of multi-substituted benzenes

Yadav, Pratik,Shaw, Ranjay,Elagamy, Amr,Kumar, Abhinav,Pratap, Ramendra

, p. 5465 - 5473 (2018)

A base controlled regioselective 1,6-cyanoallylation of suitably functionalized 2H-pyran-2-ones has been demonstrated for the synthesis of various multi-substituted benzenes through a tandem process. We observed that lithium hydroxide provides a major product from α-attack and a minor product from γ-attack of allyl cyanide, while the use of sodium hydride as a base exclusively provides the product by γ-attack of allyl cyanide. We have also performed NMR experiments to understand the mechanistic pathway. The structure of the compound was confirmed by single crystal X-ray analysis.

Relative Donor-Atom Effects on Rates of Isomerization of 3-Butenenitrile Catalyzed by Anions of the Same Basicity

Bordwell, Frederick G.,Hughes, David L.

, p. 619 - 621 (1983)

For base-catalyzed isomerization of 3-butenenitrile in Me2SO solution the order of rate constants for anions of the same basicity is ArS->ArO->RSO2NAr->9-G-Fl- (9-substituted fluorenyl carbanions).The relative rate constants vary somewhat with basicity since the Broensted β values are 0.77, 1.0, 0.82, and ca. 0.8, respectively.

Unusual reactivity of N-tert-butylimines under FVT conditions

Le?niak, Stanis?aw,Pasternak, Beata,Justyna, Katarzyna,Vu, Thien Y.,Huynh, Thi Kieu Xuan,Khayar, Sa?d,Dargelos, Alain,Chrostowska, Anna

, p. 722 - 729 (2013/07/27)

Thermal reactions of N-tert-butyl-(E)-crotonaldimine (1a) and 1,4-di-(tert-butyl)-1,4-diazabuta-1,3-dien (glyoxal-bis-N-tert-butylimine) (1b) under FVT conditions have been studied. It has been found that at 800 °C compound 1a yielded pyrrole and crotonon

CONTROLLED DRUG RELEASE FROM SOLID SUPPORTS

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Page/Page column 31-32, (2011/11/30)

The invention relates to solid supports useful in medical applications that provide controlled release of drugs, such as peptides, nucleic acids and small molecules. The drugs are covalently coupled to the solid support through a linkage that releases the drug or a prodrug through controlled beta elimination.

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