Conditions | Yield |
---|---|
With tetrabutyl ammonium fluoride In tetrahydrofuran; acetonitrile at 20℃; for 20h; Michael Addition; Inert atmosphere; | 98% |
Conditions | Yield |
---|---|
Stage #1: 2-hydroxy-2-methylpropanenitrile With lithium hydroxide monohydrate In tetrahydrofuran at 50℃; for 1h; Stage #2: 3-Chloropropionitrile In tetrahydrofuran | 98% |
Conditions | Yield |
---|---|
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% |
Conditions | Yield |
---|---|
at 600℃; under 20 Torr; for 0.0333333h; | A 87% B 90% |
Conditions | Yield |
---|---|
With hydrogen sulfide | 90% |
With hydrogen at 20℃; under 750.075 Torr; for 0.0833333h; Inert atmosphere; Neat (no solvent); | 96 %Chromat. |
Conditions | Yield |
---|---|
With Cp*2Sm(THF)2 In toluene for 15h; Product distribution; Ambient temperature; other reagent; | 89% |
With sodium hydroxide |
1,2-dichloro-ethane
2-fluoro-3-chloro-5-(trifluoromethyl)pyridine
A
butanedinitrile
B
3-chloro-2-cyano-5-(trifluoromethyl)pyridine
Conditions | Yield |
---|---|
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
ethylene dibromide
A
butanedinitrile
B
1,1,2,2,3,3-Hexamethylguanidiniumbromid
Conditions | Yield |
---|---|
In dichloromethane at 20℃; for 2h; | A 85% B n/a |
Conditions | Yield |
---|---|
With lead acetate In dichloromethane for 12h; Reflux; | 85% |
With sieve-supported lead catalyst at 200℃; under 2250.23 Torr; for 0.3h; |
Conditions | Yield |
---|---|
With HCl·DMPU; hydroxylamine hydrochloride In acetonitrile at 60℃; | 84% |
Conditions | Yield |
---|---|
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. |
Conditions | Yield |
---|---|
With copper(l) chloride In cyclohexane at 55 - 135℃; under 75.0075 Torr; for 16.1667h; Temperature; Pressure; | 82% |
Conditions | Yield |
---|---|
In ethanol; water for 24h; Reflux; | 72% |
1,2:5,6-diepoxycyclooctane
butanedinitrile
Conditions | Yield |
---|---|
With ammonia; iodine In water; acetonitrile at 70℃; | 71% |
Conditions | Yield |
---|---|
With ammonia; silicon monophosphate In water at 420℃; for 5h; Product distribution / selectivity; | 70% |
Conditions | Yield |
---|---|
In ethanol; water for 24h; Reflux; | 69% |
trifluoroacetic acid
1,2-Dicyanoethylene
A
butanedinitrile
B
1,2,3,4-tetracyanobutane
C
2-(trifluoromethyl)succinonitrile
Conditions | Yield |
---|---|
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
A
butanedinitrile
B
1,2,3,4-tetracyanobutane
C
2-(trifluoromethyl)succinonitrile
Conditions | Yield |
---|---|
With sodium hydroxide In water; acetonitrile; trifluoroacetic acid at 50℃; | A 7% B 8% C 65% |
Conditions | Yield |
---|---|
With rongalite In water for 3h; Heating; | 49% |
With diethyl ether; copper at 140℃; Hydrogenation.unter Druck; |
Conditions | Yield |
---|---|
With ammonia; oxygen; Catalyst I at 560℃; Product distribution / selectivity; | 36% |
With ammonia; oxygen; Catalyst A at 560℃; Product distribution / selectivity; | 31% |
Conditions | Yield |
---|---|
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 |
Conditions | Yield |
---|---|
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
toluene
A
butanedinitrile
B
3-methylbenzyl cyanide
C
(4-methylphenyl)acetonitrile
D
1,1'-(1,2-ethanediyl)bisbenzene
E
dihydrocinnamonitrile
F
2-tolylmethylnitrile
Conditions | Yield |
---|---|
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
chloroacetonitrile
toluene
A
butanedinitrile
B
benzyl chloride
C
1,1'-(1,2-ethanediyl)bisbenzene
Conditions | Yield |
---|---|
In acetonitrile at 80℃; for 168h; Product distribution; | A 1.2% B 5.7% C 3.6% |
2-cyanoaziridine
A
butanedinitrile
B
(E/Z)-3-aminoprop-2-enenitrile
C
iminodiacetonitrile
Conditions | Yield |
---|---|
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
chloroacetonitrile
toluene
A
butanedinitrile
B
1,1'-(1,2-ethanediyl)bisbenzene
C
dihydrocinnamonitrile
Conditions | Yield |
---|---|
In acetonitrile at 60℃; for 24h; Product distribution; | A 0.2% B 1% C 3.4% |
chloroacetonitrile
methoxybenzene
A
butanedinitrile
B
3-methoxyphenylacetonitrile
C
2-methoxy-benzeneacetonitrile
D
p-methoxybenzylnitrile
Conditions | Yield |
---|---|
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
benzene
A
butanedinitrile
B
phenylacetonitrile
Conditions | Yield |
---|---|
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
chloroacetonitrile
A
butanedinitrile
B
3-fluorophenylacetonitrile
C
2-fluorophenyl acetonitrile
D
4-fluorophenylacetonitrile
Conditions | Yield |
---|---|
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; |
Conditions | Yield |
---|---|
With zinc(II) chloride In chlorobenzene for 133h; Condensation; Heating; | 100% |
Conditions | Yield |
---|---|
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
3-cyanopropanoic acid
Conditions | Yield |
---|---|
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
ethanol
succinodiimidic acid diethyl ester; dihydrochloride
Conditions | Yield |
---|---|
With hydrogenchloride In benzene at 0 - 5℃; for 1.5h; | 98% |
butanedinitrile
formic acid ethyl ester
(E,Z)-2-formylsuccinonitrile potassium salt
Conditions | Yield |
---|---|
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
Trimethylenediamine
1,2-bis(1,4,5,6-tetrahydropyrimidin-2-yl)ethane
Conditions | Yield |
---|---|
With Lawessons reagent In toluene at 90℃; for 10h; thio-Pinner's reaction; | 98% |
butanedinitrile
ethylenediamine
1,2-bis(4,5-dihydro-1H-imidazol-2-yl)ethane
Conditions | Yield |
---|---|
With diphosphorus pentasulfide In toluene at 90℃; for 10h; thio-Pinner's reaction; | 97% |
butanedinitrile
((1,2-bis(diisopropylphosphino)ethane)NiH)2
[(1,2-bis(diisopropylphosphano)ethane)Ni(η2-N,C-(CH2)2-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; | 96% |
butanedinitrile
1,3-diaminopropane mono-p-toluenesulfonate
C24H30N4O4S2
Conditions | Yield |
---|---|
at 140℃; for 0.5h; | 95% |
butanedinitrile
Conditions | Yield |
---|---|
With manganese(IV) oxide; sulfuric acid; chlorine; sodium chloride In chlorobenzene Heating; | 95% |
Conditions | Yield |
---|---|
With i-Amyl alcohol; sodium hydride In toluene; mineral oil at 20℃; | 95% |
Conditions | Yield |
---|---|
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% |
Conditions | Yield |
---|---|
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% |
Conditions | Yield |
---|---|
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% |
Conditions | Yield |
---|---|
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% |
Conditions | Yield |
---|---|
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% |
Conditions | Yield |
---|---|
With [2,2]bipyridinyl; palladium(II) acetylacetonate; toluene-4-sulfonic acid In water; toluene at 80℃; for 24h; Schlenk technique; | 92% |
Conditions | Yield |
---|---|
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
1-(3,3,3-trifluoropropynyl)-1-prop-2-ynyloxy-cyclohexane
Conditions | Yield |
---|---|
With CoCl2(phen); zinc dibromide; zinc In 1,2-dichloro-ethane at 80℃; for 24h; Glovebox; regioselective reaction; | 92% |
Conditions | Yield |
---|---|
With potassium tert-butylate In toluene; tert-butyl alcohol at 0 - 20℃; for 4h; | 91.2% |
Conditions | Yield |
---|---|
With water; dihydridotetrakis(triphenylphosphine)ruthenium In 1,2-dimethoxyethane at 160℃; for 24h; | 91% |
butanedinitrile
<2,2,3,3-(2)H4>succinonitrile
Conditions | Yield |
---|---|
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
bis(2,2'-bipyridine)carbonatoruthenium(II)
trifluorormethanesulfonic acid
Conditions | Yield |
---|---|
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% |
Conditions | Yield |
---|---|
Stage #1: adamantane With nitric acid at 15 - 20℃; Ritter Amidation; Stage #2: butanedinitrile at 25℃; for 2h; | 90% |
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(110-61-2) is produced by the addition of hydrogen cyanide to acrylonitrile.
CH2=CHCN + HCN → NCCH2CH2CN
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. |
Cyanide and its compounds are on the Community Right-To-Know List. Reported in EPA TSCA Inventory.
Hazard Codes: Xn
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.
ACGIH TLV: CL 5 mg(CN)/m3 (skin)
NIOSH REL: (Nitriles) TWA 20 mg/m3
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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