Product Name

  • Name

    1,4-Butanedinitrile

  • EINECS 203-783-9
  • CAS No. 110-61-2
  • Article Data79
  • CAS DataBase
  • Density 0.984 g/cm3
  • Solubility Slightly soluble in water
  • Melting Point 50-54 °C(lit.)
  • Formula C4H4N2
  • Boiling Point 268.5 °C at 760 mmHg
  • Molecular Weight 80.0892
  • Flash Point 141.1 °C
  • Transport Information
  • Appearance almost white to brown crystalline solid
  • Safety 26-36/37-45-36/37/39-22
  • Risk Codes 22-36/37/38-36/38-20/21/22
  • Molecular Structure Molecular Structure of 110-61-2 (1,4-Butanedinitrile)
  • Hazard Symbols HarmfulXn
  • Synonyms Deprelin;Dician;Dinile;Disuxyl;Ethane, 1,2-dicyano-;Ethylene cyanide;Ethylene dicyanide;Evanex;NSC 4852;Succinic acid dinitrile;Succinic acidnitrile;Succinic dinitrile;Succinil;Succinodinitrile;Suxil;sym-Dicyanoethane;Succinonitrile(8CI);1,2-Dicyanoethane;1,2-Ethanedicarbonitrile;1,4-Butanedinitrile;
  • PSA 47.58000
  • LogP 0.81376

Synthetic route

trimethylsilyl cyanide
7677-24-9

trimethylsilyl cyanide

butanedinitrile
110-61-2

butanedinitrile

Conditions
ConditionsYield
With tetrabutyl ammonium fluoride In tetrahydrofuran; acetonitrile at 20℃; for 20h; Michael Addition; Inert atmosphere;98%
3-Chloropropionitrile
542-76-7

3-Chloropropionitrile

2-hydroxy-2-methylpropanenitrile
75-86-5

2-hydroxy-2-methylpropanenitrile

butanedinitrile
110-61-2

butanedinitrile

Conditions
ConditionsYield
Stage #1: 2-hydroxy-2-methylpropanenitrile With lithium hydroxide monohydrate In tetrahydrofuran at 50℃; for 1h;
Stage #2: 3-Chloropropionitrile In tetrahydrofuran
98%
WH2(η-cyclopentadienyl)2

WH2(η-cyclopentadienyl)2

1,2-Dicyanoethylene
764-42-1

1,2-Dicyanoethylene

A

butanedinitrile
110-61-2

butanedinitrile

B

(C5H5)2W(CNCHCHCN)

(C5H5)2W(CNCHCHCN)

Conditions
ConditionsYield
In toluene Irradiation (UV/VIS); (Ar); addn. of fumaronitrile to soln. of W-compd. in toluene portionwise, irradn. (500 W Hg-lamp, >550 nm, 62 h), pptn.; decantation of supernatant, washing (toluene), drying in vac.; elem. anal., detn. of isomeric ratio of CNCH=CHCN ligand fumaronitrile/maleonitrile 3:2 by (1)H-NMR spectroscopy;A 92%
B 38%
(phenylselenenyl)acetonitrile
33695-47-5

(phenylselenenyl)acetonitrile

A

butanedinitrile
110-61-2

butanedinitrile

B

diphenyl diselenide
1666-13-3

diphenyl diselenide

Conditions
ConditionsYield
at 600℃; under 20 Torr; for 0.0333333h;A 87%
B 90%
butenedinitrile
764-42-1

butenedinitrile

butanedinitrile
110-61-2

butanedinitrile

Conditions
ConditionsYield
With hydrogen sulfide90%
With hydrogen at 20℃; under 750.075 Torr; for 0.0833333h; Inert atmosphere; Neat (no solvent);96 %Chromat.
acrylonitrile
107-13-1

acrylonitrile

2-hydroxy-2-methylpropanenitrile
75-86-5

2-hydroxy-2-methylpropanenitrile

butanedinitrile
110-61-2

butanedinitrile

Conditions
ConditionsYield
With Cp*2Sm(THF)2 In toluene for 15h; Product distribution; Ambient temperature; other reagent;89%
With sodium hydroxide
potassium cyanide

potassium cyanide

1,2-dichloro-ethane
107-06-2

1,2-dichloro-ethane

2-fluoro-3-chloro-5-(trifluoromethyl)pyridine
72537-17-8

2-fluoro-3-chloro-5-(trifluoromethyl)pyridine

A

butanedinitrile
110-61-2

butanedinitrile

B

3-chloro-2-cyano-5-(trifluoromethyl)pyridine
80194-70-3

3-chloro-2-cyano-5-(trifluoromethyl)pyridine

Conditions
ConditionsYield
With dmap In water at 75 - 78℃; for 12h; Reagent/catalyst; Temperature;A 81.8%
B 86.7%
N,N,N',N',N'',N''-Hexamethylguanidiniumcyanid
68897-45-0

N,N,N',N',N'',N''-Hexamethylguanidiniumcyanid

ethylene dibromide
106-93-4

ethylene dibromide

A

butanedinitrile
110-61-2

butanedinitrile

B

1,1,2,2,3,3-Hexamethylguanidiniumbromid
6926-43-8

1,1,2,2,3,3-Hexamethylguanidiniumbromid

Conditions
ConditionsYield
In dichloromethane at 20℃; for 2h;A 85%
B n/a
butanediamide
110-14-5

butanediamide

butanedinitrile
110-61-2

butanedinitrile

Conditions
ConditionsYield
With lead acetate In dichloromethane for 12h; Reflux;85%
With sieve-supported lead catalyst at 200℃; under 2250.23 Torr; for 0.3h;
4-oxobutanenitrile
3515-93-3

4-oxobutanenitrile

butanedinitrile
110-61-2

butanedinitrile

Conditions
ConditionsYield
With HCl·DMPU; hydroxylamine hydrochloride In acetonitrile at 60℃;84%
1,4-diaminobutane
110-60-1

1,4-diaminobutane

butanedinitrile
110-61-2

butanedinitrile

Conditions
ConditionsYield
With ammonium hydroxide; oxygen In tert-Amyl alcohol at 110℃; under 2250.23 Torr; for 15h; Autoclave; Green chemistry;82%
With [Ru(p-cymene)(pzH-NP)(Cl)]Cl; potassium tert-butylate In toluene at 70℃; for 24h; Schlenk technique; Inert atmosphere;58 %Chromat.
2-cyanoacetyl bromide
105041-08-5

2-cyanoacetyl bromide

4-nitrobenzonitrile
619-72-7

4-nitrobenzonitrile

butanedinitrile
110-61-2

butanedinitrile

Conditions
ConditionsYield
With copper(l) chloride In cyclohexane at 55 - 135℃; under 75.0075 Torr; for 16.1667h; Temperature; Pressure;82%
sodium cyanide
773837-37-9

sodium cyanide

ethylene dibromide
106-93-4

ethylene dibromide

butanedinitrile
110-61-2

butanedinitrile

Conditions
ConditionsYield
In ethanol; water for 24h; Reflux;72%
1,2:5,6-diepoxycyclooctane
286-75-9, 19740-81-9, 57378-35-5

1,2:5,6-diepoxycyclooctane

butanedinitrile
110-61-2

butanedinitrile

Conditions
ConditionsYield
With ammonia; iodine In water; acetonitrile at 70℃;71%
succinic acid
110-15-6

succinic acid

butanedinitrile
110-61-2

butanedinitrile

Conditions
ConditionsYield
With ammonia; silicon monophosphate In water at 420℃; for 5h; Product distribution / selectivity;70%
potassium cyanide

potassium cyanide

1,2-dichloro-ethane
107-06-2

1,2-dichloro-ethane

butanedinitrile
110-61-2

butanedinitrile

Conditions
ConditionsYield
In ethanol; water for 24h; Reflux;69%
trifluoroacetic acid
76-05-1

trifluoroacetic acid

1,2-Dicyanoethylene
764-42-1

1,2-Dicyanoethylene

A

butanedinitrile
110-61-2

butanedinitrile

B

1,2,3,4-tetracyanobutane
90220-86-3

1,2,3,4-tetracyanobutane

C

2-(trifluoromethyl)succinonitrile
127085-57-8

2-(trifluoromethyl)succinonitrile

Conditions
ConditionsYield
With sodium hydroxide In water; acetonitrile at 50℃; Product distribution; Mechanism; other temperatures, various electrode distances;A 7%
B 8%
C 65%
With sodium hydroxide In water; acetonitrile at 50℃; Mechanism; Product distribution; electrolytical trifluoromethylation, Pt electrodes, variation of temperature and cell dimensions;A 7%
B 8%
C 65%
With sodium hydroxide In water; acetonitrile at 50℃; electrolytical trifluoromethylation, Pt electrodes, undivided cell;A 7%
B 8%
C 65%
With sodium hydroxide In water; acetonitrile at 50℃;A 7%
B 8%
C 65%
1,2-Dicyanoethylene
764-42-1

1,2-Dicyanoethylene

A

butanedinitrile
110-61-2

butanedinitrile

B

1,2,3,4-tetracyanobutane
90220-86-3

1,2,3,4-tetracyanobutane

C

2-(trifluoromethyl)succinonitrile
127085-57-8

2-(trifluoromethyl)succinonitrile

Conditions
ConditionsYield
With sodium hydroxide In water; acetonitrile; trifluoroacetic acid at 50℃;A 7%
B 8%
C 65%
1,2-Dicyanoethylene
764-42-1

1,2-Dicyanoethylene

butanedinitrile
110-61-2

butanedinitrile

Conditions
ConditionsYield
With rongalite In water for 3h; Heating;49%
With diethyl ether; copper at 140℃; Hydrogenation.unter Druck;
buta-1,3-diene
106-99-0

buta-1,3-diene

butanedinitrile
110-61-2

butanedinitrile

Conditions
ConditionsYield
With ammonia; oxygen; Catalyst I at 560℃; Product distribution / selectivity;36%
With ammonia; oxygen; Catalyst A at 560℃; Product distribution / selectivity;31%
N-Ethylidenasparaginsaeuredinitril

N-Ethylidenasparaginsaeuredinitril

A

4-aminopyridine
504-24-5

4-aminopyridine

B

butanedinitrile
110-61-2

butanedinitrile

C

2-Eth-(E)-ylideneamino-acrylonitrile

2-Eth-(E)-ylideneamino-acrylonitrile

D

(Z)-2-Methyl-3-azahex-4-endinitril

(Z)-2-Methyl-3-azahex-4-endinitril

E

(E)-2-Methyl-3-azahex-4-endinitril

(E)-2-Methyl-3-azahex-4-endinitril

Conditions
ConditionsYield
With 4 A molecular sieve at 500℃; under 0.1 Torr; Product distribution; flash vaccum pyrolysis;A 26.1%
B n/a
C n/a
D n/a
E n/a
N-Ethylidenasparaginsaeuredinitril

N-Ethylidenasparaginsaeuredinitril

A

4-aminopyridine
504-24-5

4-aminopyridine

B

butanedinitrile
110-61-2

butanedinitrile

C

(Z)-2-Methyl-3-azahex-4-endinitril

(Z)-2-Methyl-3-azahex-4-endinitril

D

(E)-2-Methyl-3-azahex-4-endinitril

(E)-2-Methyl-3-azahex-4-endinitril

Conditions
ConditionsYield
With 4 A molecular sieve at 500℃; under 0.1 Torr; Yield given. Further byproducts given. Yields of byproduct given. Title compound not separated from byproducts;A 26.1%
B n/a
C n/a
D n/a
chloroacetonitrile
107-14-2

chloroacetonitrile

toluene
108-88-3

toluene

A

butanedinitrile
110-61-2

butanedinitrile

B

3-methylbenzyl cyanide
2947-60-6

3-methylbenzyl cyanide

C

(4-methylphenyl)acetonitrile
2947-61-7

(4-methylphenyl)acetonitrile

D

1,1'-(1,2-ethanediyl)bisbenzene
103-29-7

1,1'-(1,2-ethanediyl)bisbenzene

E

dihydrocinnamonitrile
645-59-0

dihydrocinnamonitrile

F

2-tolylmethylnitrile
22364-68-7

2-tolylmethylnitrile

Conditions
ConditionsYield
In acetonitrile Product distribution; Mechanism; Irradiation; different concentration ratios;A 0.7%
B n/a
C n/a
D 2.1%
E 6.4%
F n/a
In acetonitrile for 22h; Kinetics; Product distribution; Mechanism; Irradiation;A 0.7%
B n/a
C n/a
D 2.1%
E 6.4%
F n/a
OO-tert-butyl O-isopropyl monoperoxycarbonate
2372-21-6

OO-tert-butyl O-isopropyl monoperoxycarbonate

chloroacetonitrile
107-14-2

chloroacetonitrile

toluene
108-88-3

toluene

A

butanedinitrile
110-61-2

butanedinitrile

B

benzyl chloride
100-44-7

benzyl chloride

C

1,1'-(1,2-ethanediyl)bisbenzene
103-29-7

1,1'-(1,2-ethanediyl)bisbenzene

Conditions
ConditionsYield
In acetonitrile at 80℃; for 168h; Product distribution;A 1.2%
B 5.7%
C 3.6%
2-cyanoaziridine
33898-53-2

2-cyanoaziridine

A

butanedinitrile
110-61-2

butanedinitrile

B

(E/Z)-3-aminoprop-2-enenitrile
19866-98-9

(E/Z)-3-aminoprop-2-enenitrile

C

iminodiacetonitrile
628-87-5

iminodiacetonitrile

Conditions
ConditionsYield
With quartz at 630℃; under 0.1 Torr; Product distribution; flash vaccum pyrolysis;A 3%
B 4.8%
C 2%
With quartz at 630℃; under 0.1 Torr;A 3%
B 4.8%
C 2%
di-n-propyl peroxydicarbonate
16066-38-9

di-n-propyl peroxydicarbonate

chloroacetonitrile
107-14-2

chloroacetonitrile

toluene
108-88-3

toluene

A

butanedinitrile
110-61-2

butanedinitrile

B

1,1'-(1,2-ethanediyl)bisbenzene
103-29-7

1,1'-(1,2-ethanediyl)bisbenzene

C

dihydrocinnamonitrile
645-59-0

dihydrocinnamonitrile

Conditions
ConditionsYield
In acetonitrile at 60℃; for 24h; Product distribution;A 0.2%
B 1%
C 3.4%
chloroacetonitrile
107-14-2

chloroacetonitrile

methoxybenzene
100-66-3

methoxybenzene

A

butanedinitrile
110-61-2

butanedinitrile

B

3-methoxyphenylacetonitrile
19924-43-7

3-methoxyphenylacetonitrile

C

2-methoxy-benzeneacetonitrile
7035-03-2

2-methoxy-benzeneacetonitrile

D

p-methoxybenzylnitrile
104-47-2

p-methoxybenzylnitrile

Conditions
ConditionsYield
In acetonitrile Product distribution; Mechanism; Irradiation; different concentration ratios;A 2.3%
B n/a
C n/a
D n/a
In acetonitrile for 22h; Kinetics; Product distribution; Mechanism; Irradiation;A 2.3%
B n/a
C n/a
D n/a
chloroacetonitrile
107-14-2

chloroacetonitrile

benzene
71-43-2

benzene

A

butanedinitrile
110-61-2

butanedinitrile

B

phenylacetonitrile
140-29-4

phenylacetonitrile

Conditions
ConditionsYield
In acetonitrile for 22h; Irradiation;A 0.5%
B 1.9%
In acetonitrile Product distribution; Mechanism; Irradiation; different times of photolysis; different concentration ratios;A 0.5%
B 1.9%
fluorobenzene
462-06-6

fluorobenzene

chloroacetonitrile
107-14-2

chloroacetonitrile

A

butanedinitrile
110-61-2

butanedinitrile

B

3-fluorophenylacetonitrile
501-00-8

3-fluorophenylacetonitrile

C

2-fluorophenyl acetonitrile
326-62-5

2-fluorophenyl acetonitrile

D

4-fluorophenylacetonitrile
459-22-3

4-fluorophenylacetonitrile

Conditions
ConditionsYield
In acetonitrile Product distribution; Mechanism; Irradiation; different concentration ratios;A 0.5%
B n/a
C n/a
D n/a
In acetonitrile for 22h; Kinetics; Product distribution; Mechanism; Irradiation;
butanedinitrile
110-61-2

butanedinitrile

C18H19NO
252959-29-8

C18H19NO

C40H36N2O2

C40H36N2O2

Conditions
ConditionsYield
With zinc(II) chloride In chlorobenzene for 133h; Condensation; Heating;100%
butanedinitrile
110-61-2

butanedinitrile

butanediamide
110-14-5

butanediamide

Conditions
ConditionsYield
With manganese(IV) oxide; water In isopropyl alcohol at 100℃; under 5171.62 Torr; for 0.5h;99%
With aluminum oxide; methanesulfonic acid at 120℃; for 0.25h;85%
Stage #1: butanedinitrile With acetamide; acetic acid at 50℃; under 760.051 Torr; for 0.5h;
Stage #2: With tetrakis(acetonitrile)palladium(II) tetrafluoroborate at 50℃; under 1 - 3 Torr; for 2h;
61%
butanedinitrile
110-61-2

butanedinitrile

3-cyanopropanoic acid
16051-87-9

3-cyanopropanoic acid

Conditions
ConditionsYield
enzyme from Synechocystis sp. PCC 6803 In phosphate buffer at 30℃; for 12h;99%
With Bradyrhizobium japonicum strain USDA110 nitrilase bll6402 In phosphate buffer at 30℃; for 24h; pH=7.2;97%
With water; nitrile hydratase SP361 at 30℃; for 71h; in potassium phosphate buffer (pH = 7);65%
butanedinitrile
110-61-2

butanedinitrile

ethanol
64-17-5

ethanol

succinodiimidic acid diethyl ester; dihydrochloride
52426-61-6

succinodiimidic acid diethyl ester; dihydrochloride

Conditions
ConditionsYield
With hydrogenchloride In benzene at 0 - 5℃; for 1.5h;98%
butanedinitrile
110-61-2

butanedinitrile

formic acid ethyl ester
109-94-4

formic acid ethyl ester

(E,Z)-2-formylsuccinonitrile potassium salt
89283-73-8

(E,Z)-2-formylsuccinonitrile potassium salt

Conditions
ConditionsYield
With potassium tert-butylate In toluene; tert-butyl alcohol at 20℃; for 2h; Cooling with ice;98%
With potassium tert-butylate In toluene; tert-butyl alcohol at 5℃; for 6h;96%
With potassium tert-butylate In toluene; tert-butyl alcohol at 3 - 10℃; for 2.5h;
butanedinitrile
110-61-2

butanedinitrile

Trimethylenediamine
109-76-2

Trimethylenediamine

1,2-bis(1,4,5,6-tetrahydropyrimidin-2-yl)ethane
78706-92-0

1,2-bis(1,4,5,6-tetrahydropyrimidin-2-yl)ethane

Conditions
ConditionsYield
With Lawessons reagent In toluene at 90℃; for 10h; thio-Pinner's reaction;98%
butanedinitrile
110-61-2

butanedinitrile

ethylenediamine
107-15-3

ethylenediamine

1,2-bis(4,5-dihydro-1H-imidazol-2-yl)ethane
29957-52-6

1,2-bis(4,5-dihydro-1H-imidazol-2-yl)ethane

Conditions
ConditionsYield
With diphosphorus pentasulfide In toluene at 90℃; for 10h; thio-Pinner's reaction;97%
butanedinitrile
110-61-2

butanedinitrile

((1,2-bis(diisopropylphosphino)ethane)NiH)2
130777-67-2

((1,2-bis(diisopropylphosphino)ethane)NiH)2

[(1,2-bis(diisopropylphosphano)ethane)Ni(η2-N,C-(CH2)2-CN)]
1177406-40-4

[(1,2-bis(diisopropylphosphano)ethane)Ni(η2-N,C-(CH2)2-CN)]

Conditions
ConditionsYield
In tetrahydrofuran byproducts: H2; under Ar, in glove box; ((dippe)NiH)2 dissolved in dry THF at room temp., 2 equiv. of dinitrile added, mixt. stirred for 15 min; evapd. under vac., residue dried under vac. for 6 h;96%
butanedinitrile
110-61-2

butanedinitrile

1,3-diaminopropane mono-p-toluenesulfonate
59543-92-9

1,3-diaminopropane mono-p-toluenesulfonate

C24H30N4O4S2
78707-11-6

C24H30N4O4S2

Conditions
ConditionsYield
at 140℃; for 0.5h;95%
butanedinitrile
110-61-2

butanedinitrile

dichlorosuccinonitrile

dichlorosuccinonitrile

Conditions
ConditionsYield
With manganese(IV) oxide; sulfuric acid; chlorine; sodium chloride In chlorobenzene Heating;95%
butanedinitrile
110-61-2

butanedinitrile

ethyl acetate
141-78-6

ethyl acetate

sodium 3,4-dicyanobut-2-en-2-olate
1510825-77-0

sodium 3,4-dicyanobut-2-en-2-olate

Conditions
ConditionsYield
With i-Amyl alcohol; sodium hydride In toluene; mineral oil at 20℃;95%
butanedinitrile
110-61-2

butanedinitrile

putrescine dihydrochloride
333-93-7

putrescine dihydrochloride

Conditions
ConditionsYield
Stage #1: butanedinitrile With cobalt pivalate; 1,1,3,3-Tetramethyldisiloxane; tert-butylisonitrile at 80℃; for 24h;
Stage #2: With hydrogenchloride In diethyl ether at 20℃; for 0.5h;
95%
butanedinitrile
110-61-2

butanedinitrile

C6H4BF4*K(1+)

C6H4BF4*K(1+)

2,5-bis(4-fluorophenyl)-1H-pyrrole

2,5-bis(4-fluorophenyl)-1H-pyrrole

Conditions
ConditionsYield
With [2,2]bipyridinyl; ammonium trifluoroacetate; palladium(II) trifluoroacetate; trifluoroacetic acid In tetrahydrofuran; water at 80℃; for 30h; Solvent; Reagent/catalyst; Inert atmosphere;93.6%
butanedinitrile
110-61-2

butanedinitrile

4-fluoroboronic acid
1765-93-1

4-fluoroboronic acid

2,5-bis(4-fluorophenyl)-1H-pyrrole

2,5-bis(4-fluorophenyl)-1H-pyrrole

Conditions
ConditionsYield
With [2,2]bipyridinyl; palladium(II) trifluoroacetate; 2,2,2-trifluoroacetic acid ammonia; trifluoroacetic acid In tetrahydrofuran; water at 80℃; for 48h; Schlenk technique;93%
butanedinitrile
110-61-2

butanedinitrile

potassium phenyltrifluoroborate

potassium phenyltrifluoroborate

2,5-diphenyl-1H-pyrrole
838-40-4

2,5-diphenyl-1H-pyrrole

Conditions
ConditionsYield
With [2,2]bipyridinyl; ammonium trifluoroacetate; palladium(II) trifluoroacetate; trifluoroacetic acid In tetrahydrofuran; water at 70℃; for 40h; Solvent; Reagent/catalyst; Inert atmosphere;92.7%
butanedinitrile
110-61-2

butanedinitrile

A

2-pyrrolidinon
616-45-5

2-pyrrolidinon

B

acrylobutyronitril

acrylobutyronitril

C

1,4-diaminobutane
110-60-1

1,4-diaminobutane

Conditions
ConditionsYield
With rubidium hydroxide; hydrogen; ethylenediamine; RaNi catalyst doped with Fe and Cr, slurry in water In water at 80℃; under 525053 Torr; Product distribution / selectivity;A 3%
B 1%
C 92%
With cesium hydroxide; hydrogen; ethylenediamine; RaNi catalyst doped with Fe and Cr, slurry in water In water at 80℃; under 525053 Torr; Product distribution / selectivity;A 3%
B 5%
C 90%
With sodium hydroxide; hydrogen; ethylenediamine; RaNi catalyst doped with Fe and Cr, slurry in water In water at 80℃; under 525053 Torr; Product distribution / selectivity;A 4%
B 5%
C 85%
butanedinitrile
110-61-2

butanedinitrile

phenylboronic acid
98-80-6

phenylboronic acid

4-oxo-4-phenylbutanenitrile
5343-98-6

4-oxo-4-phenylbutanenitrile

Conditions
ConditionsYield
With [2,2]bipyridinyl; palladium(II) acetylacetonate; toluene-4-sulfonic acid In water; toluene at 80℃; for 24h; Schlenk technique;92%
butanedinitrile
110-61-2

butanedinitrile

phenylboronic acid
98-80-6

phenylboronic acid

2,5-diphenyl-1H-pyrrole
838-40-4

2,5-diphenyl-1H-pyrrole

Conditions
ConditionsYield
With [2,2]bipyridinyl; palladium(II) trifluoroacetate; 2,2,2-trifluoroacetic acid ammonia; trifluoroacetic acid In tetrahydrofuran; water at 80℃; for 48h; Reagent/catalyst; Solvent; Schlenk technique;92%
butanedinitrile
110-61-2

butanedinitrile

1-(3,3,3-trifluoropropynyl)-1-prop-2-ynyloxy-cyclohexane
1225289-40-6

1-(3,3,3-trifluoropropynyl)-1-prop-2-ynyloxy-cyclohexane

C28H30F6N2O2

C28H30F6N2O2

Conditions
ConditionsYield
With CoCl2(phen); zinc dibromide; zinc In 1,2-dichloro-ethane at 80℃; for 24h; Glovebox; regioselective reaction;92%
butanedinitrile
110-61-2

butanedinitrile

formic acid ethyl ester
109-94-4

formic acid ethyl ester

formyl succinonitrile potassium salt

formyl succinonitrile potassium salt

Conditions
ConditionsYield
With potassium tert-butylate In toluene; tert-butyl alcohol at 0 - 20℃; for 4h;91.2%
pyrrolidine
123-75-1

pyrrolidine

butanedinitrile
110-61-2

butanedinitrile

1,4-dipyrrolidinyl-1,4-dioxobutane
63958-62-3

1,4-dipyrrolidinyl-1,4-dioxobutane

Conditions
ConditionsYield
With water; dihydridotetrakis(triphenylphosphine)ruthenium In 1,2-dimethoxyethane at 160℃; for 24h;91%
butanedinitrile
110-61-2

butanedinitrile

<2,2,3,3-(2)H4>succinonitrile
23923-29-7

<2,2,3,3-(2)H4>succinonitrile

Conditions
ConditionsYield
With [carbonylchlorohydrido{bis[2-(diphenylphosphinomethyl)ethyl]amino}ethylamino] ruthenium(II); potassium tert-butylate; water-d2 at 70℃; for 24h; Inert atmosphere;91%
With water-d2 for 96h; Heating;85%
With water-d2; 1,8-diazabicyclo[5.4.0]undec-7-ene In 1,4-dioxane for 24h; Heating;75%
With 1,2-diazabicyclo[5.4.0]undec-7-ene; water-d2 In 1,4-dioxane for 49h; Heating;57%
With potassium deuteroxide; water-d2 for 4h; Ambient temperature;
butanedinitrile
110-61-2

butanedinitrile

ammonium hexafluorophosphate

ammonium hexafluorophosphate

bis(2,2'-bipyridine)carbonatoruthenium(II)
59460-48-9

bis(2,2'-bipyridine)carbonatoruthenium(II)

trifluorormethanesulfonic acid
1493-13-6

trifluorormethanesulfonic acid

bis(2,2'-bipyridine)bis(succinonitrile)ruthenium(II) hexafluorophosphate

bis(2,2'-bipyridine)bis(succinonitrile)ruthenium(II) hexafluorophosphate

Conditions
ConditionsYield
In methanol; water byproducts: CO2; soln. of Ru compd. (0.230 mmol) in dry MeOH stirred at room temp. for 30min under Ar, triflic acid added, mixt. stirred for 3 h, succinonitrile (0.750 mmol) added, mixt. refluxed overnight, concd., aq. satd. soln. o f NH4PF6 added; ppt. filtered off, washed with Et2O, dried under vac.; elem. anal.;90%
butanedinitrile
110-61-2

butanedinitrile

adamantane

adamantane

N-(adamantan-1-yl)butanediamide

N-(adamantan-1-yl)butanediamide

Conditions
ConditionsYield
Stage #1: adamantane With nitric acid at 15 - 20℃; Ritter Amidation;
Stage #2: butanedinitrile at 25℃; for 2h;
90%

Succinonitrile Chemical Properties

Molecular Formula: C4H4N2
Molar mass: 80.088 g/mol
Density: 0.984 g/cm3
Flash Point: 141.1 °C
Index of Refraction: 1.415
Melting point: 50-54 °C(lit.)
storage temp: 2-8°C
Water solubility: slightly soluble
Boiling Point: 268.5 °C at 760 mmHg
Vapour Pressure: 0.00767 mmHg at 25°C
Solubility: methanol: 0.1 g/mL, clear,colorless
Appearance: almost white to brown crystalline solid
Structure of Succinonitrile (CAS NO.110-61-2):
                                     
Product Categories of Succinonitrile (CAS NO.110-61-2): Dinitriles & Trinitriles
Synonyms of Succinonitrile (CAS NO.110-61-2): 1,2-Dicyanoethane 1,4-Butanedinitrile ; Butanedinitrile ; Deprelin ; Disuxyl ; Ethane, 1,2-dicyano- ; Ethylene cyanide ; Succinic acid dinitrile ; Succinic acid nitrile ; Succinodinitrile ; Succinonitrile ; Sukcinonitril ; s-Dicyanoethane .

Succinonitrile Production

Succinonitrile(110-61-2) is produced by the addition of hydrogen cyanide to acrylonitrile.
CH2=CHCN + HCN → NCCH2CH2CN

Succinonitrile Toxicity Data With Reference

dog LDLo subcutaneous 150mg/kg (150mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD
GASTROINTESTINAL: NAUSEA OR VOMITING
Archives Internationales de Pharmacodynamie et de Therapie. Vol. 3, Pg. 77, 1897.
frog LDLo subcutaneous 1gm/kg (1000mg/kg)   Archives Internationales de Pharmacodynamie et de Therapie. Vol. 3, Pg. 77, 1897.
mouse LD50 intraperitoneal 63110ug/kg (63.11mg/kg) KIDNEY, URETER, AND BLADDER: OTHER CHANGES IN URINE COMPOSITION Biochemical Pharmacology. Vol. 27, Pg. 1135, 1978.
mouse LD50 oral 129mg/kg (129mg/kg)   Archives of Toxicology. Vol. 57, Pg. 88, 1985.
pigeon LDLo subcutaneous 2200mg/kg (2200mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD
GASTROINTESTINAL: NAUSEA OR VOMITING
Archives Internationales de Pharmacodynamie et de Therapie. Vol. 3, Pg. 77, 1897.
rabbit LDLo subcutaneous 36mg/kg (36mg/kg) PERIPHERAL NERVE AND SENSATION: SPASTIC PARALYSIS WITH OR WITHOUT SENSORY CHANGE Archives Internationales de Pharmacodynamie et de Therapie. Vol. 3, Pg. 77, 1897.
rat LCLo inhalation 730mg/m3/4H (730mg/m3) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)
BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD
LUNGS, THORAX, OR RESPIRATION: ACUTE PULMONARY EDEMA
National Technical Information Service. Vol. OTS0570875,
rat LD50 oral 450mg/kg (450mg/kg)   "Patty's Industrial Hygiene and Toxicology," 3rd rev. ed., Clayton, G.D., and F.E. Clayton, eds., New York, John Wiley & Sons, Inc., 1978-82. Vol. 3 originally pub. in 1979; pub. as 2n rev. ed. in 1985.Vol. 2C, Pg. 4879, 1982.

Succinonitrile Consensus Reports

 Cyanide and its compounds are on the Community Right-To-Know List. Reported in EPA TSCA Inventory.

Succinonitrile Safety Profile

Hazard Codes: HarmfulXn
Risk Statements: 22-36/37/38-36/38-20/21/22
R22:Harmful if swallowed. 
R36/37/38:Irritating to eyes, respiratory system and skin. 
R36/38:Irritating to eyes and skin. 
R20/21/22:Harmful by inhalation, in contact with skin and if swallowed.
Safety Statements: 26-36/37-45-36/37/39-22
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. 
S36/37:Wear suitable protective clothing and gloves. 
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection. 
S22:Do not breathe dust.
RIDADR: 3276
WGK Germany: 3
RTECS: WN3850000
HazardClass: 6.1
PackingGroup: III
HS Code: 29051900
HS Code: 29269095
Poison by ingestion, intraperitoneal, and subcutaneous routes. An experimental teratogen. Combustible when exposed to heat or flame. Decomposes exothermically above 195°C. Can react with oxidizing materials. To fight fire, use alcohol foam, CO2, dry chemical. When heated to decomposition, or on contact with acid or acid fumes, it emits highly toxic fumes of NOx and CN. See also NITRILES.

Succinonitrile Standards and Recommendations

ACGIH TLV: CL 5 mg(CN)/m3 (skin)
NIOSH REL: (Nitriles) TWA 20 mg/m3

Succinonitrile Specification

 Succinonitrile (CAS NO.110-61-2) is hazardous,so the first aid measures and others should be known .Such as:
Skin: Get medical aid. Should flush skin with plenty of water immediatelyfor at least 15 minutes while removing contaminated clothing and shoes.
Eyes: Flush eyes with plenty of water for at least 15 minutes, occasionally lifting the upper and lower eyelids.Then get medical aid soon. 
Inhalation: 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.
Ingestion: Wash mouth out with water,and get medical aid immediately.
Notes to Physician: Treat supportively and symptomatically.
Chemical Stability: Stable under normal pressures and temperatures.   
Incompatibilities with Other Materials: Strong reducing agents, strong bases, strong acids,strong oxidizing agents.
Conditions to Avoid: Incompatible materials,moisture.
Hazardous Decomposition Products: Nitrogen,oxides of phosphorus, hydrogen iodide, oxides of nitrogen, carbon dioxide, carbon monoxide.
 

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