Conditions | Yield |
---|---|
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% |
Conditions | Yield |
---|---|
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
2-pentenenitrile
4-Pentenenitrile
3-pentenenitrile
hexanedinitrile
Conditions | Yield |
---|---|
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% |
Conditions | Yield |
---|---|
In acetone at 70℃; for 1.83333h; Temperature; | 94% |
Conditions | Yield |
---|---|
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
4-Pentenenitrile
3-pentenenitrile
hexanedinitrile
Conditions | Yield |
---|---|
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% |
Conditions | Yield |
---|---|
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% |
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. |
Conditions | Yield |
---|---|
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 |
Conditions | Yield |
---|---|
In sulfolane; iron(III) chloride | 84% |
Conditions | Yield |
---|---|
at 70℃; for 3h; | 82% |
at 70℃; for 3h; | 81% |
at 70℃; for 3h; | 81% |
1,4-dibromo-butane
N,N,N',N',N'',N''-Hexamethylguanidiniumcyanid
A
hexanedinitrile
B
1,1,2,2,3,3-Hexamethylguanidiniumbromid
Conditions | Yield |
---|---|
In dichloromethane at 20℃; for 2h; | A 78% B n/a |
Conditions | Yield |
---|---|
With cyanide(1-); <p>-(CH2)3-<sup>+</sup>PBu3</p> In water at 110℃; for 0.5h; | 74% |
Conditions | Yield |
---|---|
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% |
Conditions | Yield |
---|---|
With ammonia In 1,4-dioxane at 150℃; under 4500.45 Torr; for 25h; Temperature; Reagent/catalyst; Solvent; | 73.2% |
Conditions | Yield |
---|---|
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℃; |
Conditions | Yield |
---|---|
With ammonia; iodine In water; acetonitrile at 70℃; | 70% |
Conditions | Yield |
---|---|
With ammonia; iodine In water at 70℃; for 6h; | 70% |
Conditions | Yield |
---|---|
With trimethylsilylazide; silver carbonate In dimethyl sulfoxide at 100℃; for 12h; | 65% |
Conditions | Yield |
---|---|
With sodium bromide In methanol at 10℃; electrooxidation (0.3 A, 75 mA/cm2, 5-7 V) 8.4 F/mol; | 60% |
Conditions | Yield |
---|---|
With Iron(III) nitrate nonahydrate; ammonium hydroxide; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical In acetonitrile at 20℃; for 12h; | 58% |
Conditions | Yield |
---|---|
With potassium phosphate; C9H20NO3PS3*C5H13N at 20 - 22℃; electrolysis; | A 55.1% B 41% |
4-Pentenenitrile
2-hydroxy-2-methylpropanenitrile
A
3-pentenenitrile
B
hexanedinitrile
Conditions | Yield |
---|---|
With Lewis acid; C70H84O8P2 In tetrahydrofuran at 90℃; for 4h; | A 53% B n/a |
Conditions | Yield |
---|---|
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% |
Conditions | Yield |
---|---|
With ammonia; iodine In water at 60℃; for 24h; | A 24% B 17% |
acrylonitrile
A
cis-1,4-dicyano-1-butene
B
trans-1,4-dicyanobut-1-ene
C
hexanedinitrile
D
propiononitrile
Conditions | Yield |
---|---|
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
2-hydroxy-2-methylpropanenitrile
A
4-Pentenenitrile
B
hexanedinitrile
Conditions | Yield |
---|---|
With Lewis acid; bis(1,5-cyclooctadiene)nickel (0); C70H84O8P2 In tetrahydrofuran at 90℃; for 4h; Product distribution / selectivity; | A 19% B n/a |
Conditions | Yield |
---|---|
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% |
Conditions | Yield |
---|---|
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% |
Conditions | Yield |
---|---|
In dimethyl amine | 100% |
Conditions | Yield |
---|---|
In N-butylamine | 100% |
Conditions | Yield |
---|---|
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% |
Conditions | Yield |
---|---|
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
Conditions | Yield |
---|---|
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% |
Conditions | Yield |
---|---|
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; |
Conditions | Yield |
---|---|
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; |
Conditions | Yield |
---|---|
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
m-Fluorobenzonitrile
2-(3-fluorophenyl)-6,7-dihydro-5H-cyclopentapyrimidin-4-ylamine
Conditions | Yield |
---|---|
With potassium tert-butylate In para-xylene at 120℃; for 4h; Inert atmosphere; | 96% |
hexanedinitrile
((1,2-bis(diisopropylphosphino)ethane)NiH)2
[(1,2-bis(diisopropylphosphano)ethane)Ni(η2-N,C-(CH2)4-CN)]
Conditions | Yield |
---|---|
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% |
Conditions | Yield |
---|---|
With hydrogenchloride In benzene at 15℃; | 94% |
With hydrogenchloride beim anschliessend Feuchtigkeitsausshluss; | |
With hydrogenchloride In diethyl ether | |
With hydrogenchloride |
Conditions | Yield |
---|---|
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% |
Conditions | Yield |
---|---|
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
hexanedinitrile
(+/-)-1-allyl-2-oxo-1-cyclopentanecarbonitrile
Conditions | Yield |
---|---|
Stage #1: hexanedinitrile Thorpe-Ziegler reaction; Stage #2: allyl iodid | 92% |
Conditions | Yield |
---|---|
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
<2,2,5,5-2H4>adiponitrile
Conditions | Yield |
---|---|
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
(+/-)-1-methyl-2-oxo-1-cyclopentanecarbonitrile
Conditions | Yield |
---|---|
Stage #1: hexanedinitrile Thorpe-Ziegler reaction; Stage #2: methylating agent | 90% |
4-Cyanochlorobenzene
hexanedinitrile
2-(4-chlorophenyl)-6,7-dihydro-5H-cyclopentapyrimidin-4-ylamine
Conditions | Yield |
---|---|
With potassium tert-butylate In para-xylene at 120℃; for 4h; Inert atmosphere; | 90% |
Conditions | Yield |
---|---|
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% |
Conditions | Yield |
---|---|
With water In 1,2-dimethoxyethane at 160℃; for 18h; amidation; | 89% |
Conditions | Yield |
---|---|
With diphosphorus pentasulfide In toluene at 90℃; for 10h; thio-Pinner's reaction; | 89% |
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
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
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. | 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. |
EPA Extremely Hazardous Substances List. Reported in EPA TSCA Inventory. Cyanide and its compounds are on the Community Right-To-Know List.
Hazard Codes: T
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.
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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