• Name

  1,4-DICYANO-2-BUTENE

• EINECS 242-519-7
• CAS No. 1119-85-3
• Article Data13
• CAS DataBase
• Density 0.983 g/cm³
• Solubility very soluble in water
• Melting Point 77.5 - 78.2ºC
• Formula C6H6 N2
• Boiling Point 289.6 °C at 760 mmHg
• Molecular Weight 106.127
• Flash Point 146.2 °C
• Transport Information
• Appearance Tan to brown crystals
• Safety Poison by intravenous route. When heated to decomposition it emits toxic fumes of NO_x and CN⁻. See also NITRILES.
• Risk Codes R20/21
• Molecular Structure
• Hazard Symbols Xn
• Synonyms b-Hydromucononitrile (6CI);1,4-Dicyano-2-butene; NSC 11685
• PSA 47.58000
• LogP 1.36996

Synthetic route

764-41-0

1,4-dichloro-2-butene

143-33-9

sodium cyanide

1119-85-3

1,4-dicyano-2-butene

Conditions

Conditions	Yield
With hydrogenchloride; copper; copper(l) chloride; sodium chloride

13269-52-8

trans-3-Hexene

109-75-1

but-3-enenitrile

A

4786-20-3

crotononitrile

B

74-85-1

ethene

C

1119-85-3

1,4-dicyano-2-butene

Conditions

Conditions	Yield
aluminum oxide; rhenium(VII) oxide on aluminum oxide; tetraethyltin; tetramethylstannane for 24h; Product distribution; Ambient temperature; heterogeneous self-metathesis, co-metathesis;

...Expand

109-75-1

but-3-enenitrile

A

74-85-1

ethene

B

1119-85-3

1,4-dicyano-2-butene

Conditions

Conditions	Yield
With 1,1,3,3-tetramethyl-1,3-disiletane; tungsten(IV) chloride In benzene at 60℃; under 0.001 Torr; for 10h; other temperature; metathesis of allyl cyanide;
aluminum oxide; rhenium(VII) oxide on aluminum oxide; tetraethyltin; tetramethylstannane for 24h; Product distribution; Ambient temperature; heterogeneous metathesis;
With 1,1,3,3-tetramethyl-1,3-disiletane; tungsten(IV) chloride In benzene at 60℃; under 0.01 Torr; for 10h; Yield given;

109-75-1

but-3-enenitrile

1119-85-3

1,4-dicyano-2-butene

Conditions

Conditions	Yield
1,1,3,3-tetramethyl-1,3-disiletane; tungsten(VI) chloride In benzene at 60℃; for 10h;	83 % Turnov.

107-13-1

acrylonitrile

A

1119-85-3

1,4-dicyano-2-butene

B

13042-02-9

2-hexenedinitrile

C

1572-52-7

2,4-dicyano-1-butene

D

68334-52-1

4,7-Bis-<2-cyan-aethyl>-4,7-dicyan-decen-(5)-disaeure-dinitril

Conditions

Conditions	Yield
With isopropyl diphenylphosphinite; isopropyl alcohol In toluene at 60℃; Rate constant; Equilibrium constant; Thermodynamic data; other phosphinite catalysts; activation parameters (EA, ΔS(act., 298 K); kinetics and mechanism of the phosphinite-catalyzed dimerization of acrylonitrile;

...Expand

930-22-3

epoxybutene

74-90-8

hydrogen cyanide

copper (I)-chloride

copper (I)-chloride

1119-85-3

1,4-dicyano-2-butene

...Expand

13019-22-2

9-Decen-1-ol

109-75-1

but-3-enenitrile

A

(E)-12-Hydroxy-dodec-3-enenitrile

B

1119-85-3

1,4-dicyano-2-butene

Conditions

Conditions	Yield
With ruthenium In dichloromethane for 2h; Heating; Title compound not separated from byproducts;

...Expand

17084-13-8

potassium hexafluorophosphate

58298-10-5

[Re2Cl4(μ-bis(diphenylphosphino)methane)2]

1119-85-3

1,4-dicyano-2-butene

294213-46-0

Re2Cl3((C6H5)2PCH2P(C6H5)2)2(NCC4H6NC)2(1+)*PF6(1-)=Re2Cl3(P(C6H5)2CH2P(C6H5)2)2(NCC4H6CN)2PF6

Conditions

Conditions	Yield
In acetone mixt. of Re-complex, KPF6 and ligand in acetone was stirred at room temp. for 2 h under N2; vol. was reduced by vac. evaporator, filtered, filtrate was treated with Et2O, stirred for 30 min, extracted into CH2Cl2, vol. of extract was reduced, Et2O was added; elem. anal.;	91%

...Expand

1119-85-3

1,4-dicyano-2-butene

111-69-3

hexanedinitrile

Conditions

Conditions	Yield
With formic acid In methanol; water at 100℃; for 12h; Green chemistry; chemoselective reaction;	88%
With hydrogen; (o-OC6H4CH3)3PRuCl(PPh3)2 at 130℃; under 3620.04 Torr; for 20h;	78 % Chromat.
With hydrogen; (o-OC6H4CH3)3PRuCl(PPh3)2 at 130℃; under 3620.04 Torr; for 20h; Product distribution;	78 % Chromat.

16029-98-4

trimethylsilyl iodide

1119-85-3

1,4-dicyano-2-butene

2-trimethylsilyl-2-hexenedinitrile

Conditions

Conditions	Yield
With triethylamine at 120℃; for 0.0333333h;	39%

98-01-1

furfural

1119-85-3

1,4-dicyano-2-butene

41520-36-9

2,5-difurfurylidene-hex-3-enedinitrile

Conditions

Conditions	Yield
With ethanol; sodium ethanolate

110-80-5

2-ethoxy-ethanol

1119-85-3

1,4-dicyano-2-butene

3-(2-ethoxy-ethoxy)-hexanediyldiamine

Conditions

Conditions	Yield
With sodium hydroxide; cobalt at 120℃; under 397174 - 441305 Torr; Hydrogenation;

74-90-8

hydrogen cyanide

1119-85-3

1,4-dicyano-2-butene

5238-65-3

butane-1,2,4-tricarbonitrile

Conditions

Conditions	Yield
With pyridine; potassium cyanide at 80℃;

1119-85-3

1,4-dicyano-2-butene

55911-96-1

hexane-1,3,6-triyltriamine

Conditions

Conditions	Yield
With ammonia; water; hydrogen; cobalt

1119-85-3

1,4-dicyano-2-butene

3-methoxy-hexanediyldiamine

Conditions

Conditions	Yield
With methanol; sodium hydroxide; cobalt at 120℃; under 397174 - 441305 Torr; Hydrogenation;

1119-85-3

1,4-dicyano-2-butene

5867-88-9

trans,trans-mucononitrile

1119-85-3

1,4-dicyano-2-butene

117121-99-0

Dihydromuconsaeure-nitril-amidooxim

Conditions

Conditions	Yield
With hydroxylamine In butan-1-ol

1119-85-3

1,4-dicyano-2-butene

36700-30-8

meso-β,β'-Dibromadipodinitril

Conditions

Conditions	Yield
With bromine

1119-85-3

1,4-dicyano-2-butene

18804-98-3

1,4-Dicyan-2,3-bis-(difluoramino)-butan

Conditions

Conditions	Yield
With tetrafluorohydrazine In tetrachloromethane

1119-85-3

1,4-dicyano-2-butene

107-13-1

acrylonitrile

68334-52-1

4,7-Bis-<2-cyan-aethyl>-4,7-dicyan-decen-(5)-disaeure-dinitril

Conditions

Conditions	Yield
With N-benzyl-trimethylammonium hydroxide In tert-butyl alcohol

1119-85-3

1,4-dicyano-2-butene

1666-13-3

diphenyl diselenide

142271-25-8

3-Fluoro-4-phenylselanyl-hexanedinitrile

Conditions

Conditions	Yield
With xenon difluoride 1) CH2Cl2, -20 deg C, 10 min; Yield given. Multistep reaction;

1119-85-3

1,4-dicyano-2-butene

142271-30-5

3-fluoro-1-buten-1,4-dinitrile

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 1) XeF2 / 1) CH2Cl2, -20 deg C, 10 min 2: 88 percent / H2O2 View Scheme

1119-85-3

1,4-dicyano-2-butene

1188-35-8

3-ethoxycarbonylhexane-1,6-dioic acid diethyl ester

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: potassium cyanide; pyridine / 80 °C 2: sulfuric acid / 135 °C View Scheme

1119-85-3

1,4-dicyano-2-butene

923-42-2

butane-1,2,4-tricarboxylic acid

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: potassium cyanide; pyridine / 80 °C 2: aqueous hydrochloric acid / 140 °C View Scheme

1119-85-3

1,4-dicyano-2-butene

95-92-1

oxalic acid diethyl ester

147299-51-2, 76344-73-5

diethyl 3,6-dicyano-2,7-hydroxyocta-2,4,6-trienedioate

Conditions

Conditions	Yield
Stage #1: oxalic acid diethyl ester With ethanol; sodium ethanolate at 0℃; for 0.5h; Stage #2: 1,4-dicyano-2-butene at 20℃;	11.9 g

3-HEXENEDINITRILE Chemical Properties

3-HEXENEDINITRILE Toxicity Data With Reference

3-HEXENEDINITRILE Consensus Reports

3-HEXENEDINITRILE Safety Profile