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110-61-2

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110-61-2 Usage

General Description

1,4-Butanedinitrile, also known as succinonitrile, is a chemical compound with the formula C4H4N2. It is a colorless, water-soluble liquid that is commonly used as an intermediate in organic synthesis. 1,4-Butanedinitrile is primarily used in the production of acrylic and acrylonitrile fibers, as well as in the manufacture of pharmaceuticals, agrochemicals, and plasticizers. It is also utilized as a solvent for various chemical processes and as a raw material for the synthesis of heterocyclic compounds. Additionally, 1,4-Butanedinitrile has potential applications in electrochemistry and as a component in ionic liquids due to its high conductivity. Overall, this chemical compound plays a significant role in various industrial processes and has diverse potential applications in different fields.

Check Digit Verification of cas no

The CAS Registry Mumber 110-61-2 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 1,1 and 0 respectively; the second part has 2 digits, 6 and 1 respectively.
Calculate Digit Verification of CAS Registry Number 110-61:
(5*1)+(4*1)+(3*0)+(2*6)+(1*1)=22
22 % 10 = 2
So 110-61-2 is a valid CAS Registry Number.
InChI:InChI=1/C4H4N2/c1-4(2-5)3-6/h4H,1H3

110-61-2 Well-known Company Product Price

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  • Alfa Aesar

  • (L05037)  Succinonitrile, 98%   

  • 110-61-2

  • 100g

  • 373.0CNY

  • Detail
  • Alfa Aesar

  • (L05037)  Succinonitrile, 98%   

  • 110-61-2

  • 500g

  • 1259.0CNY

  • Detail

110-61-2SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 10, 2017

Revision Date: Aug 10, 2017

1.Identification

1.1 GHS Product identifier

Product name Succinonitrile

1.2 Other means of identification

Product number -
Other names Butanedinitrile

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:110-61-2 SDS

110-61-2Synthetic 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%

110-61-2Relevant articles and documents

Photochemical Production of Ethane from an Iridium Methyl Complex

Pitman, Catherine L.,Miller, Alexander J. M.

, p. 1906 - 1914 (2017)

An iridium methyl complex, [Cp?Ir(bpy)(CH3)]+, was prepared by electrophilic methylation of Cp?Ir(bpy) with CH3I and characterized electrochemically, photophysically, crystallographically, and computationally. Irradiation of the MLCT transition of [Cp?Ir(bpy)(CH3)]+ in the presence of CH3I in acetonitrile produces ethane, methane, propionitrile, and succinonitrile. A series of mechanistic studies indicates that C-C bond formation is mediated by free methyl radicals produced through monometallic photochemical homolysis of the Ir-CH3 bond.

Reactions in water: Alkyl nitrile coupling reactions using Fenton's reagent

Keller, Christopher L.,Dalessandro, James D.,Hotz, Richard P.,Pinhas, Allan R.

, p. 3616 - 3618 (2008)

(Chemical Equation Presented) The coupling reaction of water-soluble alkyl nitriles using Fenton's reagent (Fe(II) and H2O2) is described. The best metal for the reaction is iron(II), and the greatest yields are obtained when the concentration of the metal is kept low. Hydrogen-atom abstraction is selective, preferentially producing the radical α to the nitrile. In order to increase the production of dinitrile, in situ reduction of iron(III) to iron(II), using a variety of reducing agents, was investigated.

Combined preparation method of 2-cyano-3-chloro-5-trifluoromethylpyridine and succinonitrile

-

Paragraph 0024-0036, (2021/02/24)

The invention discloses a combined preparation method of 2-cyano-3-chloro-5-trifluoromethylpyridine and succinonitrile, and belongs to the field of organic chemistry. The method comprises the following steps: taking 2-fluoro-3-chloro-5-trifluoromethylpyridine and dichloroethane as raw materials, reacting in a potassium cyanide/sodium solution under the action of a phase transfer catalyst to obtaina mixed solution of 2-cyano-3-chloro-5-trifluoromethylpyridine and succinonitrile, layering, washing with water, and rectifying to obtain the 2-cyano-3-chloro-5-trifluoromethylpyridine with the content of more than 99% and the succinonitrile with the content of more than 99.9%. According to the method, the yield is high, the wastewater treatment is simple, byproducts are fully utilized, the yieldof the 2-cyano-3-chloro-5-trifluoromethylpyridine can reach 93%, and the yield of the succinonitrile can reach 95%.

Copper(II)-Photocatalyzed N-H Alkylation with Alkanes

Donabauer, Karsten,K?nig, Burkhard,Narobe, Rok,Yakubov, Shahboz,Zheng, Yi-Wen

, p. 8582 - 8589 (2020/09/23)

We report a practical method for the alkylation of N-H bonds with alkanes using a photoinduced copper(II) peroxide catalytic system. Upon light irradiation, the peroxide serves as a hydrogen atom transfer reagent to activate stable C(sp3)-H bonds for the reaction with a broad range of nitrogen nucleophiles. The method enables the chemoselective alkylation of amides and is utilized for the late-stage functionalization of N-H bond containing pharmaceuticals with good to excellent yields. The mechanism of the reaction was preliminarily investigated by radical trapping experiments and spectroscopic methods.

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