Product Name

  • Name

    1,4-Dicyanobutane

  • EINECS 203-896-3
  • CAS No. 111-69-3
  • Article Data219
  • CAS DataBase
  • Density 0.945 g/cm3
  • Solubility 90 g/L (20 °C) in water
  • Melting Point 1-3 °C(lit.)
  • Formula C6H8N2
  • Boiling Point 296.1 °C at 760 mmHg
  • Molecular Weight 108.143
  • Flash Point 149 °C
  • Transport Information UN 2205 6.1/PG 3
  • Appearance clear colorless to slightly yellow liquid
  • Safety 26-36-45-39
  • Risk Codes 25-36/37/38-36/38-23/25
  • Molecular Structure Molecular Structure of 111-69-3 (1,4-Dicyanobutane)
  • Hazard Symbols ToxicT
  • Synonyms Adiponitrile(8CI);Adipic acid dinitrile;Adipic acid nitrile;Adipicdinitrile;Hexanedinitrile;Butanedicarbonitrile;NSC 7617;
  • PSA 47.58000
  • LogP 1.59396

Synthetic route

1,4-dibromo-butane
110-52-1

1,4-dibromo-butane

potassium cyanide
151-50-8

potassium cyanide

hexanedinitrile
111-69-3

hexanedinitrile

Conditions
ConditionsYield
With 18-crown-6 ether In acetonitrile for 15h; Heating;96%
With Polysorbate 80 (1) In acetonitrile for 1.5h; Product distribution; Heating; other alkyl halides;70%
With Polysorbate 80 (1) In acetonitrile for 1.5h; Heating;70%
adipamide
628-94-4

adipamide

hexanedinitrile
111-69-3

hexanedinitrile

Conditions
ConditionsYield
With phosphorus pentachloride; toluene-4-sulfonic acid for 2h; Reagent/catalyst; Temperature; Reflux;96%
With di(n-butyl)tin oxide In toluene Heating;84%
With phosphorus pentoxide under 15.0015 - 37.5038 Torr; for 1h; Temperature; Heating;83%
hydrogen cyanide
74-90-8

hydrogen cyanide

2-pentenenitrile
13284-42-9

2-pentenenitrile

4-Pentenenitrile
592-51-8

4-Pentenenitrile

3-pentenenitrile
4635-87-4

3-pentenenitrile

hexanedinitrile
111-69-3

hexanedinitrile

Conditions
ConditionsYield
With zinc(II) chloride at 50℃; for 49 - 53h; Product distribution / selectivity;95%
With zinc(II) chloride at 50℃; for 49 - 53h; Product distribution / selectivity;95%
With iron(II) chloride at 50℃; for 69 - 78h; Product distribution / selectivity;94.4%
1,4-Diiodobutane
628-21-7

1,4-Diiodobutane

para-methylbenzonitrile
104-85-8

para-methylbenzonitrile

hexanedinitrile
111-69-3

hexanedinitrile

Conditions
ConditionsYield
In acetone at 70℃; for 1.83333h; Temperature;94%
1,6-Hexanediamine
124-09-4

1,6-Hexanediamine

hexanedinitrile
111-69-3

hexanedinitrile

Conditions
ConditionsYield
With nickel(II) sulphate; sodium hydroxide; dipotassium peroxodisulfate In dichloromethane for 24h; Ambient temperature;93%
With potassium hydroxide In water; tert-butyl alcohol at 40℃; for 4h; electrolysis at a Ni(OH)2 anode and a steel cathode, current - 2 A, cell voltage - 2.0 V;93%
With tetrabutylammomium bromide; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione In acetonitrile at 20℃; for 0.0833333h; Inert atmosphere; Molecular sieve;86%
hydrogen cyanide
74-90-8

hydrogen cyanide

4-Pentenenitrile
592-51-8

4-Pentenenitrile

3-pentenenitrile
4635-87-4

3-pentenenitrile

hexanedinitrile
111-69-3

hexanedinitrile

Conditions
ConditionsYield
With zinc(II) chloride at 50℃; for 45 - 48h; Product distribution / selectivity;93%
With zinc(II) chloride at 50℃; for 45 - 48h; Product distribution / selectivity;93%
With zinc(II) chloride at 50℃; for 46 - 54h; Product distribution / selectivity;92.5%
acrylonitrile
107-13-1

acrylonitrile

hexanedinitrile
111-69-3

hexanedinitrile

Conditions
ConditionsYield
With water; triphenylphosphine; zinc; diiodobis(triphenylphosphine)cobalt(II) In acetonitrile at 80℃; for 24h;89%
With potassium phosphate; tetraethylammonium phosphate at 20 - 22℃; Product distribution; electrolytic hydrodimerization, var. quaternary ammonium salts, var. electrodes;86.9%
With potassium phosphate; tetraethylammonium phosphate at 20 - 22℃; electrolysis;86.9%
1,4-dicyano-2-butene
1119-85-3

1,4-dicyano-2-butene

hexanedinitrile
111-69-3

hexanedinitrile

Conditions
ConditionsYield
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.
Adipic acid dichloride
111-50-2

Adipic acid dichloride

hexanedinitrile
111-69-3

hexanedinitrile

Conditions
ConditionsYield
With sulfonamide; toluene-4-sulfonic acid In toluene at 120℃; for 3h;85%
Multi-step reaction with 2 steps
1: ammonia
2: phosphorus pentachloride / 150 °C
View Scheme
Adipic acid
124-04-9

Adipic acid

cyanogen chloride
506-77-4

cyanogen chloride

hexanedinitrile
111-69-3

hexanedinitrile

Conditions
ConditionsYield
In sulfolane; iron(III) chloride84%
3-pentenenitrile
4635-87-4

3-pentenenitrile

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

2-hydroxy-2-methylpropanenitrile

hexanedinitrile
111-69-3

hexanedinitrile

Conditions
ConditionsYield
at 70℃; for 3h;82%
at 70℃; for 3h;81%
at 70℃; for 3h;81%
1,4-dibromo-butane
110-52-1

1,4-dibromo-butane

N,N,N',N',N'',N''-Hexamethylguanidiniumcyanid
68897-45-0

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

A

hexanedinitrile
111-69-3

hexanedinitrile

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 78%
B n/a
1,4-dibromo-butane
110-52-1

1,4-dibromo-butane

hexanedinitrile
111-69-3

hexanedinitrile

Conditions
ConditionsYield
With cyanide(1-); <p>-(CH2)3-<sup>+</sup>PBu3</p> In water at 110℃; for 0.5h;74%
3-cyano-propionic acid methyl ester
4107-62-4

3-cyano-propionic acid methyl ester

hexanedinitrile
111-69-3

hexanedinitrile

Conditions
ConditionsYield
Stage #1: 3-cyano-propionic acid methyl ester With potassium hydroxide In methanol at 60℃; for 0.5h; Kolbe coupling;
Stage #2: In acetone at 60℃; Kolbe coupling; Electrochemical reaction;
74%
cyclohexanol
108-93-0

cyclohexanol

hexanedinitrile
111-69-3

hexanedinitrile

Conditions
ConditionsYield
With ammonia In 1,4-dioxane at 150℃; under 4500.45 Torr; for 25h; Temperature; Reagent/catalyst; Solvent;73.2%
Adipic acid
124-04-9

Adipic acid

acetonitrile
75-05-8

acetonitrile

hexanedinitrile
111-69-3

hexanedinitrile

Conditions
ConditionsYield
With bis(acetylacetonate)oxovanadium In tetrachloromethane at 150℃; for 6h; Autoclave;72%
With phosphoric acid at 300℃;
With ammonium phosphate at 300℃;
With sulfuric acid at 300℃;
cyclohexane-1,2-epoxide
286-20-4

cyclohexane-1,2-epoxide

hexanedinitrile
111-69-3

hexanedinitrile

Conditions
ConditionsYield
With ammonia; iodine In water; acetonitrile at 70℃;70%
2-aminocyclohexanol
6850-38-0

2-aminocyclohexanol

hexanedinitrile
111-69-3

hexanedinitrile

Conditions
ConditionsYield
With ammonia; iodine In water at 70℃; for 6h;70%
1,7-Octadiyne
871-84-1

1,7-Octadiyne

hexanedinitrile
111-69-3

hexanedinitrile

Conditions
ConditionsYield
With trimethylsilylazide; silver carbonate In dimethyl sulfoxide at 100℃; for 12h;65%
1,2-diaminocyclohexane
694-83-7

1,2-diaminocyclohexane

hexanedinitrile
111-69-3

hexanedinitrile

Conditions
ConditionsYield
With sodium bromide In methanol at 10℃; electrooxidation (0.3 A, 75 mA/cm2, 5-7 V) 8.4 F/mol;60%
1,6-hexanediol
629-11-8

1,6-hexanediol

hexanedinitrile
111-69-3

hexanedinitrile

Conditions
ConditionsYield
With Iron(III) nitrate nonahydrate; ammonium hydroxide; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical In acetonitrile at 20℃; for 12h;58%
acrylonitrile
107-13-1

acrylonitrile

A

hexanedinitrile
111-69-3

hexanedinitrile

B

propiononitrile
107-12-0

propiononitrile

Conditions
ConditionsYield
With potassium phosphate; C9H20NO3PS3*C5H13N at 20 - 22℃; electrolysis;A 55.1%
B 41%
4-Pentenenitrile
592-51-8

4-Pentenenitrile

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

2-hydroxy-2-methylpropanenitrile

A

3-pentenenitrile
4635-87-4

3-pentenenitrile

B

hexanedinitrile
111-69-3

hexanedinitrile

Conditions
ConditionsYield
With Lewis acid; C70H84O8P2 In tetrahydrofuran at 90℃; for 4h;A 53%
B n/a
4-Pentenenitrile
592-51-8

4-Pentenenitrile

hexanedinitrile
111-69-3

hexanedinitrile

Conditions
ConditionsYield
With bis(acetylacetonate)nickel(II); 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; zinc In toluene for 24h; Inert atmosphere; Sealed tube; Heating; Green chemistry;28%
6-amino-1-hexanol
4048-33-3

6-amino-1-hexanol

A

hexanedinitrile
111-69-3

hexanedinitrile

B

6-hydroxyhexanenitrile
2453-48-7

6-hydroxyhexanenitrile

Conditions
ConditionsYield
With ammonia; iodine In water at 60℃; for 24h;A 24%
B 17%
acrylonitrile
107-13-1

acrylonitrile

A

cis-1,4-dicyano-1-butene
2141-58-4

cis-1,4-dicyano-1-butene

B

trans-1,4-dicyanobut-1-ene
2141-59-5

trans-1,4-dicyanobut-1-ene

C

hexanedinitrile
111-69-3

hexanedinitrile

D

propiononitrile
107-12-0

propiononitrile

Conditions
ConditionsYield
With hydrogen; (η6-1,3,5-cyclooctatriene)(η4-1,5-cyclooctadiene)ruthenium(0) at 150℃; under 19000 Torr; for 3h; Dimerization; hydrogenation;A 20%
B 20%
C 2%
D 19%
3-pentenenitrile
4635-87-4

3-pentenenitrile

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

2-hydroxy-2-methylpropanenitrile

A

4-Pentenenitrile
592-51-8

4-Pentenenitrile

B

hexanedinitrile
111-69-3

hexanedinitrile

Conditions
ConditionsYield
With Lewis acid; bis(1,5-cyclooctadiene)nickel (0); C70H84O8P2 In tetrahydrofuran at 90℃; for 4h; Product distribution / selectivity;A 19%
B n/a
acrylonitrile
107-13-1

acrylonitrile

A

hexanedinitrile
111-69-3

hexanedinitrile

B

propiononitrile
107-12-0

propiononitrile

C

C6H5(2)HN2

C6H5(2)HN2

D

C6H5(2)HN2

C6H5(2)HN2

Conditions
ConditionsYield
With deuterium; (η6-1,3,5-cyclooctatriene)(η4-1,5-cyclooctadiene)ruthenium(0) at 150℃; under 10640 Torr; for 5h; Dimerization; hydrogenation;A 1%
B 15%
C 16%
D 16%
hexanedial
1072-21-5

hexanedial

hexanedinitrile
111-69-3

hexanedinitrile

Conditions
ConditionsYield
With N-(4-sulphonic acid)butylpyridinium hydrogen sulphate; 1-sulfobutyl pyridine bisulfate hydroxylamine salt In acetonitrile at 80℃; under 760.051 Torr; for 1h; Solvent; Temperature; Time;11.34%
hexanedinitrile
111-69-3

hexanedinitrile

palladium
7440-05-3

palladium

tetramethylhexamethylenediamine

tetramethylhexamethylenediamine

Conditions
ConditionsYield
In dimethyl amine100%
RuHCl(H2)(PCy3)2

RuHCl(H2)(PCy3)2

hexanedinitrile
111-69-3

hexanedinitrile

quinoclamine
2797-51-5

quinoclamine

1,6-Hexanediamine
124-09-4

1,6-Hexanediamine

Conditions
ConditionsYield
In N-butylamine100%
hexanedinitrile
111-69-3

hexanedinitrile

adipamide
628-94-4

adipamide

Conditions
ConditionsYield
With [RuH(tBu-PNP(-))(CO)]; water In tert-butyl alcohol at 50℃; for 24h;99%
With water; dihydridotetrakis(triphenylphosphine)ruthenium In 1,2-dimethoxyethane at 120℃; for 24h;91%
With water at 150℃; under 5171.62 - 6205.94 Torr; for 5h; Inert atmosphere; Microwave irradiation;89%
hexanedinitrile
111-69-3

hexanedinitrile

A

5-cyanovaleramide
2304-58-7

5-cyanovaleramide

B

adipamide
628-94-4

adipamide

Conditions
ConditionsYield
With sodium hydroxide; tricyclohexylphosphine; {Rh(OMe)(cod)}2 In isopropyl alcohol at 25℃; for 48h;A 1%
B 99%
With Pseudomonas chlororaphis B23 immobilized on alginate bead at 5℃; pH=7; hydration; Microbiological reaction;A 93%
B 3%
With Acetaldehyde oxime In methanol at 65℃; for 4h;A 46%
B 54%
hexanedinitrile
111-69-3

hexanedinitrile

[Ni2(1,3-diisopropyl-imidazolin-2-ylidene)4(μ-1,5-cyclooctadiene)]

[Ni2(1,3-diisopropyl-imidazolin-2-ylidene)4(μ-1,5-cyclooctadiene)]

[Ni(1,3-di(isopropyl)imidazole-2-ylidene)2(η2-CNC4H8CN)]

[Ni(1,3-di(isopropyl)imidazole-2-ylidene)2(η2-CNC4H8CN)]

Conditions
ConditionsYield
In toluene (N2), Schlenk technique; cyanide was added to a suspn. of complex in toluene, the soln. was stirred for 14 h at room temp.; volatiles were removed in vac.; as oil;99%
hexanedinitrile
111-69-3

hexanedinitrile

5-cyanopentanoic acid
5264-33-5

5-cyanopentanoic acid

Conditions
ConditionsYield
With Bradyrhizobium japonicum strain USDA110 nitrilase bll6402 In phosphate buffer at 30℃; for 24h; pH=7.2;97%
With potassium phosphate buffer; nitrilase from Alcaligenes faecalis ATCC8750 at 30℃; for 53h; pH=7.3;90%
With Arabidopsis thaliana nitrilase In methanol for 19h; pH=8.5;3.92%
With potassium phosphate buffer; diothiothreitol at 30℃; Rhodococcus rhodochrous K22 nitrilase;
With hydrogenchloride 1) microbial hydrolysis by Comamonas testosteroni 5-MGAM-4D, ATCC 55744; pH 7.0 (potassium phosphate buffer), 27 deg C, 86 h; 2) pH 2.5; Yield given. Multistep reaction;
hexanedinitrile
111-69-3

hexanedinitrile

A

hexamethylene imine
111-49-9

hexamethylene imine

B

1,6-Hexanediamine
124-09-4

1,6-Hexanediamine

Conditions
ConditionsYield
With hydrogen; Ni(NO3)2, Cu(NO3)2, Cr(NO3)3, Na2CO3; calcined at 380 deg C for 18 h; pretreatment is given in full text In 1,2,4-Trimethylbenzene; ammonia at 80℃; for 24h; Product distribution / selectivity;A 1.1%
B 97%
With hydrogen; Ni(NO3)2, Cu(NO3)2, Cr(NO3)3, Na2CO3; calcined at 380 deg C for 18 h In 1,2,4-Trimethylbenzene; ammonia at 80℃; for 24h; Product distribution / selectivity;A 1.3%
B 90.1%
With ammonium hydroxide; hydrogen In water; isopropyl alcohol at 130℃; under 41254.1 Torr; for 4h; Autoclave;A 9%
B 90%
With hydrogen; iron catalyst at 140℃; under 233483 Torr;
hexanedinitrile
111-69-3

hexanedinitrile

hexane-1,6-diamine dihydrochloride
6055-52-3

hexane-1,6-diamine dihydrochloride

Conditions
ConditionsYield
With hydrogenchloride; hydrogen In propan-1-ol; water at 60 - 70℃; under 375.038 Torr; for 18h; Flow reactor;97%
Stage #1: hexanedinitrile With ammonium hydroxide; hydrogen In water; isopropyl alcohol at 140℃; under 37503.8 Torr; for 3h; Autoclave;
Stage #2: With hydrogenchloride In methanol
95%
Stage #1: hexanedinitrile With fac-[Mn(1,2-bis(di-n-propylphosphino)ethane)(CO)3(CH3)]; hydrogen In toluene at 100℃; under 37503.8 Torr; for 48h; Autoclave;
Stage #2: With hydrogenchloride In diethyl ether Inert atmosphere;
95%
hexanedinitrile
111-69-3

hexanedinitrile

m-Fluorobenzonitrile
403-54-3

m-Fluorobenzonitrile

2-(3-fluorophenyl)-6,7-dihydro-5H-cyclopentapyrimidin-4-ylamine
1311186-74-9

2-(3-fluorophenyl)-6,7-dihydro-5H-cyclopentapyrimidin-4-ylamine

Conditions
ConditionsYield
With potassium tert-butylate In para-xylene at 120℃; for 4h; Inert atmosphere;96%
hexanedinitrile
111-69-3

hexanedinitrile

((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)4-CN)]
1177406-41-5

[(1,2-bis(diisopropylphosphano)ethane)Ni(η2-N,C-(CH2)4-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;95%
ethanol
64-17-5

ethanol

hexanedinitrile
111-69-3

hexanedinitrile

adipodiimidic acid diethyl ester
1189-48-6

adipodiimidic acid diethyl ester

Conditions
ConditionsYield
With hydrogenchloride In benzene at 15℃;94%
With hydrogenchloride beim anschliessend Feuchtigkeitsausshluss;
With hydrogenchloride In diethyl ether
With hydrogenchloride
hexanedinitrile
111-69-3

hexanedinitrile

phenylboronic acid
98-80-6

phenylboronic acid

1,4-dibenzoylbutane
3375-38-0

1,4-dibenzoylbutane

Conditions
ConditionsYield
With [2,2]bipyridinyl; tris-(dibenzylideneacetone)dipalladium(0); 2,2,2-trifluoroacetic acid ammonia; trifluoroacetic acid In methanol at 90℃; for 48h; Schlenk technique;93%
hexanedinitrile
111-69-3

hexanedinitrile

5-cyanovaleramide
2304-58-7

5-cyanovaleramide

Conditions
ConditionsYield
With water at 150℃; under 5171.62 - 6205.94 Torr; for 1.5h; Inert atmosphere; Microwave irradiation;92%
With hydrogenchloride; diethyl ether at -20℃; Versetzen des Reaktionsprodukts mit 1 Mol Wasser und Behandeln des erhaltenen Hydrochlorids mit wss.Natriumcarbonat-Loesung;
With basic ion exchanger; water at 75℃;
allyl iodid
556-56-9

allyl iodid

hexanedinitrile
111-69-3

hexanedinitrile

(+/-)-1-allyl-2-oxo-1-cyclopentanecarbonitrile
66984-19-8

(+/-)-1-allyl-2-oxo-1-cyclopentanecarbonitrile

Conditions
ConditionsYield
Stage #1: hexanedinitrile Thorpe-Ziegler reaction;
Stage #2: allyl iodid
92%
hexanedinitrile
111-69-3

hexanedinitrile

1,6-Hexanediamine
124-09-4

1,6-Hexanediamine

Conditions
ConditionsYield
With sodium tetrahydroborate; nickel; sodium hydroxide In methanol; water at 30 - 60℃;90%
With hydrogen In ethanol at 75℃; under 1500.15 - 15001.5 Torr; for 3h;80%
With ammonia; hydrogen In toluene at 120℃; under 22502.3 Torr; for 16h; Autoclave;75%
hexanedinitrile
111-69-3

hexanedinitrile

<2,2,5,5-2H4>adiponitrile
136665-53-7

<2,2,5,5-2H4>adiponitrile

Conditions
ConditionsYield
With [carbonylchlorohydrido{bis[2-(diphenylphosphinomethyl)ethyl]amino}ethylamino] ruthenium(II); potassium tert-butylate; water-d2 at 70℃; for 24h; Inert atmosphere;90%
With water-d2; 1,8-diazabicyclo[5.4.0]undec-7-ene In 1,4-dioxane for 24h; Heating;70%
With deuteromethanol; sodium methylate
With water-d2; 1,8-diazabicyclo[5.4.0]undec-7-ene In 1,4-dioxane at 100℃; for 2h;
hexanedinitrile
111-69-3

hexanedinitrile

methylating agent

methylating agent

(+/-)-1-methyl-2-oxo-1-cyclopentanecarbonitrile
66984-18-7

(+/-)-1-methyl-2-oxo-1-cyclopentanecarbonitrile

Conditions
ConditionsYield
Stage #1: hexanedinitrile Thorpe-Ziegler reaction;
Stage #2: methylating agent
90%
4-Cyanochlorobenzene
623-03-0

4-Cyanochlorobenzene

hexanedinitrile
111-69-3

hexanedinitrile

2-(4-chlorophenyl)-6,7-dihydro-5H-cyclopentapyrimidin-4-ylamine
1311186-61-4

2-(4-chlorophenyl)-6,7-dihydro-5H-cyclopentapyrimidin-4-ylamine

Conditions
ConditionsYield
With potassium tert-butylate In para-xylene at 120℃; for 4h; Inert atmosphere;90%
hexanedinitrile
111-69-3

hexanedinitrile

potassium phenyltrifluoborate

potassium phenyltrifluoborate

1,4-dibenzoylbutane
3375-38-0

1,4-dibenzoylbutane

Conditions
ConditionsYield
With [2,2]bipyridinyl; palladium(II) trifluoroacetate; water; trifluoroacetic acid In tetrahydrofuran at 80℃; for 36h; Inert atmosphere; Schlenk technique;90%
With 1,10-Phenanthroline; water; palladium diacetate; trifluoroacetic acid In 2-methyltetrahydrofuran at 80℃; for 48h; Inert atmosphere; Schlenk technique;89%
pyrrolidine
123-75-1

pyrrolidine

hexanedinitrile
111-69-3

hexanedinitrile

1,1'-adipoyldipyrrolidine
92377-34-9

1,1'-adipoyldipyrrolidine

Conditions
ConditionsYield
With water In 1,2-dimethoxyethane at 160℃; for 18h; amidation;89%
hexanedinitrile
111-69-3

hexanedinitrile

Trimethylenediamine
109-76-2

Trimethylenediamine

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

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

Conditions
ConditionsYield
With diphosphorus pentasulfide In toluene at 90℃; for 10h; thio-Pinner's reaction;89%

1,4-Dicyanobutane Chemical Properties

Structure of Adiponitrile (CAS NO.111-69-3):

IUPAC Name: hexanedinitrile 
Empirical Formula: C6H8N2
Molecular Weight: 108.1411 
EINECS: 203-896-3 
Index of Refraction: 1.432
Molar Refractivity: 29.67 cm3
Molar Volume: 114.3 cm3
Polarizability: 11.76×10-24cm3
Surface Tension: 39.9 dyne/cm
Density: 0.945 g/cm3
Flash Point: 149 °C
Enthalpy of Vaporization: 53.58 kJ/mol 
Melting Point: 1-3 °C(lit.)
Boiling Point: 296.1 °C at 760 mmHg
Vapour Pressure: 0.00147 mmHg at 25°C 
Water Solubility: 90 g/L (20 ºC) 
Physical Appearance: clear colorless to slightly yellow liquid
Product Categories: Industrial/Fine Chemicals;Dinitriles & Trinitriles;Dinitriles 
Synonyms of Adiponitrile (CAS NO.111-69-3): 1,4-Dicyanobutane ; Adipic acid dinitrile ; Adipinsaeuredinitril ;
 Hexanedinitrile ; Hexanedioic acid, dinitrile ; Nitrile adipico ; Tetramethylene cyanide ; Tetramethylene dicyanide

1,4-Dicyanobutane Uses

Adiponitrile is an important precursor to the polymer nylon 66.
Almost all adiponitrile is hydrogenated to 1,6-diaminohexane for the production of nylon:
          NC(CH2)4CN + 4 H2 → H2N(CH2)6NH2

1,4-Dicyanobutane Production

  Adiponitrile is made by two different methods.
One method is by the electrohydrodimerization of acrylonitrile. It is converted into hexamethylenediamine (HMDA) that is used to make nylon.
           2CH2=CHCN → NC(CH2)4CN
           NC(CH2)4CN → H2N(CH2)6NH2
In the electrodimerization of acrylonitrile, a two-phase system containing a phase transfer catalyst tetrabutylammonium tosylate is used.

1,4-Dicyanobutane Toxicity Data With Reference

1.    

orl-rat LD50:155 mg/kg

    GISAAA    Gigiena i Sanitariya. 49 (12)(1984),40.
2.    

ihl-rat LC50:1710 mg/m3/4H

    TOXID9    Toxicologist. 1 (1981),76.
3.    

orl-mus LD50:172 mg/kg

    ARTODN    Archives of Toxicology. 57 (1985),88.
4.    

ipr-mus LD50:40 mg/kg

    NTIS**    National Technical Information Service. (Springfield, VA 22161) (Formerly U.S. Clearinghouse for Scientific and Technical Information) AD691-490 .
5.    

orl-rbt LD50:22 mg/kg

    GISAAA    Gigiena i Sanitariya. 49 (12)(1984),40.
6.    

scu-gpg LD50:50 mg/kg

    MELAAD    Medicina del Lavoro. Industrial Medicine. 46 (1955),221.

1,4-Dicyanobutane Consensus Reports

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

1,4-Dicyanobutane Safety Profile

Hazard Codes: ToxicT
Risk Statements: 25-36/37/38-36/38-23/25 
R25 :Toxic if swallowed. 
R36/37/38:Irritating to eyes, respiratory system and skin. 
R36/38:Irritating to eyes and skin. 
R23/25:Toxic by inhalation and if swallowed.
Safety Statements: 26-36-45-39 
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. 
S36:Wear suitable protective clothing. 
S45:In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.) 
S39:Wear eye / face protection.
RIDADR: UN 2205 6.1/PG 3
WGK Germany: 1
RTECS: AV2625000
HazardClass: 6.1
PackingGroup: III
Poison by inhalation, ingestion, subcutaneous, and intraperitoneal routes. The nitrile group will behave as a cyanide when ingested or absorbed in the body. It produces disturbances of the respiration and circulation, irritation of the stomach and intestines, and loss of weight. Its low vapor pressure at room temperature makes exposure to harmful concentrations of its vapors unlikely if handled with reasonable care in well-ventilated areas. Flammable when exposed to heat or flame. When heated to decomposition it emits toxic fumes of CN. Can react with oxidizing materials. To fight fire, use foam, CO2, dry chemical. See also HYDROCYANIC ACID and NITRILES.

1,4-Dicyanobutane Standards and Recommendations

ACGIH TLV: TWA 2 ppm (skin)
NIOSH REL: TWA 18 mg/m3
DOT Classification:  6.1; Label: KEEP AWAY FROM FOOD

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