α-phenylsulfonylpyridine-2-acetonitrile
pyridine-2-acetonitrile
Conditions | Yield |
---|---|
With zinc In ethanol; acetic acid for 1h; Ambient temperature; | 94% |
Conditions | Yield |
---|---|
With potassium hexamethylsilazane In toluene at 0 - 20℃; | 87% |
sodium cyanide
2-chloromethylpyridine hydrochloride
pyridine-2-acetonitrile
Conditions | Yield |
---|---|
In dimethyl sulfoxide for 2.5h; Heating; | 84% |
In dimethyl sulfoxide at 40℃; for 2.5h; | 84% |
Conditions | Yield |
---|---|
With (dimethoxy)methylsilane; copper diacetate; 1,2-bis-(dicyclohexylphosphino)ethane In tetrahydrofuran at 20℃; for 12h; Sealed tube; | 81% |
With 1,2-dichloro-ethane; sodium chloride; trichlorophosphate |
Conditions | Yield |
---|---|
Stage #1: acetonitrile With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.75h; Metallation; Stage #2: 2-bromo-pyridine In tetrahydrofuran; hexane at -78 - 20℃; for 2.5h; Alkylation; | 69% |
2-bromo-pyridine
4-isoxazoleboronic acid pinacol ester
pyridine-2-acetonitrile
Conditions | Yield |
---|---|
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium fluoride; water In dimethyl sulfoxide at 130℃; for 16h; Domino Suzuki coupling and fragmentation reaction; Inert atmosphere; | 65% |
pyridine N-oxide
A
pyridine
B
2-Pyridone
C
pyridine-2-acetonitrile
D
[2,2]bipyridinyl
E
pyrrole
Conditions | Yield |
---|---|
at 750 - 850℃; under 0.001 - 0.01 Torr; Product distribution; Mechanism; | A 31% B 4% C 6% D 7% E n/a |
Conditions | Yield |
---|---|
With sodium hexamethyldisilazane In tetrahydrofuran; toluene at 0 - 20℃; | 15% |
potassium cyanide
2-chloromethylpyridine hydrochloride
pyridine-2-acetonitrile
Conditions | Yield |
---|---|
With ethanol; potassium iodide |
2-bromo-pyridine
acetonitrile
A
2-aminopyridine
B
pyridine-2-acetonitrile
Conditions | Yield |
---|---|
With ammonia In diethyl ether for 0.25h; Irradiation; | A 16 % Chromat. B 75 % Chromat. |
Conditions | Yield |
---|---|
With TEA; trichloroisocyanuric acid In dichloromethane at 15℃; for 1h; |
pyridine-2-acetonitrile
Conditions | Yield |
---|---|
With alkali hydroxide In not given from react. of acidic soln. with alkali hydroxide;; | |
With alkali hydroxide In not given from react. of acidic soln. with alkali hydroxide;; |
2-(Bromomethyl)pyridine
pyridine-2-acetonitrile
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: water 2: neat (no solvent) 3: perchloric acid 4: alkali hydroxide / not given View Scheme |
pyridine-2-acetonitrile
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: perchloric acid 2: alkali hydroxide / not given View Scheme |
pyridine-2-acetonitrile
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: neat (no solvent) 2: perchloric acid 3: alkali hydroxide / not given View Scheme |
pyridine
acetonitrile
A
pyridine-2-acetonitrile
B
3-pyridinylacetonitrile
Conditions | Yield |
---|---|
With water for 1h; Irradiation; Overall yield = 1.1 %; |
2‐(pyridin‐2‐yl)acetaldehyde
pyridine-2-acetonitrile
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: ammonia / water / 20 °C / Green chemistry 2: iodine / water / 20 °C / Green chemistry 3: ammonia / water / 20 °C / Green chemistry View Scheme |
C7H8N2
pyridine-2-acetonitrile
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: iodine / water / 20 °C / Green chemistry 2: ammonia / water / 20 °C / Green chemistry View Scheme |
pyridine-2-acetonitrile
Conditions | Yield |
---|---|
With ammonia In water at 20℃; Green chemistry; |
A
pyridine-2-acetonitrile
B
1H-3-amino-4-(pyridine-2-yl)-pyrazole
Conditions | Yield |
---|---|
With hydrazine hydrate; acetic acid for 12h; |
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: thionyl chloride / 3 h / 60 °C 2: dimethyl sulfoxide / 2.5 h / Heating View Scheme |
2-bromo-5-cyanopyridine
pyridine-2-acetonitrile
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1.1: sodium hydride / mineral oil; dimethyl sulfoxide / 2 h / 20 °C 1.2: 3 h / 120 °C 2.1: toluene-4-sulfonic acid / toluene / 6 h / Reflux View Scheme |
pyridine-2-acetonitrile
Conditions | Yield |
---|---|
With toluene-4-sulfonic acid In toluene for 6h; Reflux; | 1.2 g |
sodium cyanide
2-(bromomethyl)pyridine hydrobromide
pyridine-2-acetonitrile
Conditions | Yield |
---|---|
Stage #1: 2-(bromomethyl)pyridine hydrobromide With sodium hydrogencarbonate In water Stage #2: sodium cyanide In ethanol at 75℃; for 24h; |
pyridine-2-acetonitrile
N-hydroxy-2-(2-pyridinyl)ethanimidamide
Conditions | Yield |
---|---|
With hydroxylamine hydrochloride; sodium In methanol | 100% |
With hydroxylamine hydrochloride; sodium In methanol | 100% |
With hydroxylamine hydrochloride; triethylamine In methanol at 20℃; |
Conditions | Yield |
---|---|
With sodium ethanolate In ethanol for 0.133333h; Microwave irradiation; | 100% |
With sodium ethanolate; sodium In ethanol; dichloromethane |
Conditions | Yield |
---|---|
With sodium hydride In diethyl ether; dimethyl sulfoxide; mineral oil at 15 - 20℃; for 25h; Inert atmosphere; | 100% |
Stage #1: pyridine-2-acetonitrile With lithium diisopropyl amide In tetrahydrofuran at -78℃; for 0.666667h; Stage #2: 1,5-dibromo-pentane In tetrahydrofuran at -78 - 20℃; for 10h; | 88% |
With sodium hydride In diethyl ether; dimethyl sulfoxide; mineral oil at 15 - 20℃; for 25h; Inert atmosphere; | 74% |
In water; dimethyl sulfoxide; ethyl acetate; isopropyl alcohol | 72% |
1,4-dibromo-butane
pyridine-2-acetonitrile
1-(pyridin-2-yl)cyclopentanecarbonitrile
Conditions | Yield |
---|---|
With sodium hydride In diethyl ether; dimethyl sulfoxide; mineral oil at 15 - 20℃; for 25h; Inert atmosphere; | 100% |
Stage #1: pyridine-2-acetonitrile With lithium diisopropyl amide In tetrahydrofuran at -78℃; for 0.666667h; Stage #2: 1,4-dibromo-butane In tetrahydrofuran at -78 - 20℃; for 10h; | 96% |
Stage #1: pyridine-2-acetonitrile With sodium hydride In N,N-dimethyl-formamide for 0.5h; Cooling with ice; Stage #2: 1,4-dibromo-butane In N,N-dimethyl-formamide at 20℃; for 2h; | 86.2% |
With sodium hydride In diethyl ether; dimethyl sulfoxide at 0 - 20℃; for 4.5h; | 82% |
Conditions | Yield |
---|---|
With hydrogenchloride In methanol; water at 70 - 72℃; for 5h; Solvent; Reagent/catalyst; Temperature; Mannich Aminomethylation; | 99.1% |
pyridine-2-acetonitrile
methyl (Z)-2-benzoylamino-3-dimethylaminopropenoate
3-benzoylamino-1-cyano-4H-pyrido[1,2-a]pyridin-4-one
Conditions | Yield |
---|---|
With acetic acid for 4h; Heating; | 99% |
pyridine-2-acetonitrile
4,5-dimethyl-1,2-phenylenediamine
5,6-Dimethyl-2-pyridin-2-ylmethyl-1H-benzoimidazole
Conditions | Yield |
---|---|
With PPA; Polyphosphoric acid (PPA) at 170 - 180℃; for 5h; | 99% |
Conditions | Yield |
---|---|
Stage #1: 3-aminopyrazole With hydrogenchloride; sodium nitrite In water at 0 - 5℃; for 0.5h; Stage #2: pyridine-2-acetonitrile With sodium acetate In water at 0 - 5℃; for 0.5h; | 99% |
Conditions | Yield |
---|---|
Stage #1: carbon dioxide; (2-fluorophenyl)acetylene With ethyl bromide; caesium carbonate; silver(l) oxide In N,N-dimethyl-formamide at 50℃; for 12h; Schlenk technique; Stage #2: pyridine-2-acetonitrile In N,N-dimethyl-formamide at 100℃; for 4h; Inert atmosphere; | 99% |
Conditions | Yield |
---|---|
With C30H29BrMnNO2P2; caesium carbonate In toluene at 135℃; for 18h; Inert atmosphere; Sealed tube; Green chemistry; chemoselective reaction; | 99% |
pyridine-2-acetonitrile
salicylaldehyde
3-(pyridine-2-yl)-2H-chromen-2-one
Conditions | Yield |
---|---|
With sodium hydroxide In water at 90℃; for 3h; pH 12.4; | 98% |
With sodium hydroxide; water at 90℃; for 3.5h; | 92% |
With piperidine Inert atmosphere; | 71% |
Multi-step reaction with 2 steps 1: piperidine / ethanol / 20 h / 20 °C / Cooling with ice 2: hydrogenchloride; water / ethanol / 10 h / Reflux View Scheme |
Conditions | Yield |
---|---|
Stage #1: carbon dioxide; 2-chlorophenylacetylene With ethyl bromide; caesium carbonate; silver(l) oxide In N,N-dimethyl-formamide at 50℃; for 12h; Schlenk technique; Stage #2: pyridine-2-acetonitrile In N,N-dimethyl-formamide at 100℃; for 4h; Inert atmosphere; | 98% |
Conditions | Yield |
---|---|
Stage #1: carbon dioxide; 1-ethynyl-3-methoxybenzene With ethyl bromide; caesium carbonate; silver(l) oxide In N,N-dimethyl-formamide at 50℃; for 12h; Schlenk technique; Stage #2: pyridine-2-acetonitrile In N,N-dimethyl-formamide at 100℃; for 4h; Inert atmosphere; | 98% |
pyridine-2-acetonitrile
pentanal
(E)-2-Pyridin-2-yl-hept-2-enenitrile
Conditions | Yield |
---|---|
With piperidine; acetic acid In benzene for 3h; Heating; | 97% |
pyridine-2-acetonitrile
hexachlorobenzene
1,2,3,4-tetrachloro-10-cyanopyrido<1,2-a>indole
Conditions | Yield |
---|---|
With potassium carbonate In N,N-dimethyl-formamide for 3h; | 97% |
pyridine-2-acetonitrile
isobutyraldehyde
4-methyl-2-(2-pirydyl)-2-pentenenitrile
Conditions | Yield |
---|---|
With piperidine; acetic acid In benzene for 3h; Heating; | 97% |
Conditions | Yield |
---|---|
Stage #1: 3-amino-4-pyrazolecarboxylic acid ethyl ester With hydrogenchloride; sodium nitrite In water at 0 - 5℃; Stage #2: pyridine-2-acetonitrile With sodium acetate In water at 0 - 5℃; | 97% |
pyridine-2-acetonitrile
Conditions | Yield |
---|---|
With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) at 20℃; for 6h; Inert atmosphere; Irradiation; | 97% |
With N-Bromosuccinimide In tetrachloromethane | 18.6 g (94%) |
With N-Bromosuccinimide In tetrachloromethane | 18.6 g (94%) |
With N-Bromosuccinimide In tetrachloromethane | 18.6 g (94%) |
Conditions | Yield |
---|---|
Stage #1: carbon dioxide; phenylacetylene With ethyl bromide; caesium carbonate; silver(l) oxide In N,N-dimethyl-formamide at 50℃; for 12h; Schlenk technique; Stage #2: pyridine-2-acetonitrile In N,N-dimethyl-formamide at 100℃; for 4h; Catalytic behavior; Solvent; Reagent/catalyst; Inert atmosphere; | 97% |
Conditions | Yield |
---|---|
With lithium hexamethyldisilazane In tetrahydrofuran at 60℃; under 760.051 Torr; for 6h; Inert atmosphere; Sealed tube; | 97% |
Conditions | Yield |
---|---|
With potassium tert-butylate; palladium diacetate; nixantphos In 1,4-dioxane at 60℃; for 10h; Inert atmosphere; Sealed tube; | 97% |
Conditions | Yield |
---|---|
With potassium tert-butylate; palladium diacetate; nixantphos In 1,4-dioxane at 60℃; for 10h; Inert atmosphere; Sealed tube; | 97% |
pyridine-2-acetonitrile
Methyl (Z)-2-<(benzyloxycarbonyl)amino>-3-dimethylaminopropenoate
3-(benzyloxycarbonyl)amino-1-cyano-4H-pyrido[1,2-a]pyridin-4-one
Conditions | Yield |
---|---|
In acetic acid for 2h; Heating; | 96% |
With acetic acid for 4h; Reflux; | 87% |
Conditions | Yield |
---|---|
With lithium tert-butoxide In N,N-dimethyl-formamide at 20℃; for 0.5h; Inert atmosphere; regioselective reaction; | 96% |
Conditions | Yield |
---|---|
With [carbonylchlorohydrido{bis[2-(diphenylphosphinomethyl)ethyl]amino}ethylamino] ruthenium(II); potassium tert-butylate In toluene at 135℃; for 4h; Inert atmosphere; | 96% |
pyridine-2-acetonitrile
Conditions | Yield |
---|---|
With 1,8-diazabicyclo[5.4.0]undec-7-ene In dimethyl sulfoxide at 21℃; for 12h; | 96% |
Conditions | Yield |
---|---|
Stage #1: carbon dioxide; 4-n-methylphenylacetylene With ethyl bromide; caesium carbonate; silver(l) oxide In N,N-dimethyl-formamide at 50℃; for 12h; Schlenk technique; Stage #2: pyridine-2-acetonitrile In N,N-dimethyl-formamide at 100℃; for 4h; Inert atmosphere; | 96% |
Conditions | Yield |
---|---|
Stage #1: Cyclopropylacetylene; carbon dioxide With ethyl bromide; caesium carbonate; silver(l) oxide In N,N-dimethyl-formamide at 50℃; for 12h; Schlenk technique; Stage #2: pyridine-2-acetonitrile In N,N-dimethyl-formamide at 100℃; for 4h; Inert atmosphere; | 96% |
pyridine-2-acetonitrile
2-iodophenyl isothiocyanate
Conditions | Yield |
---|---|
With sodium hydride In dimethyl sulfoxide at 20℃; Temperature; Inert atmosphere; | 96% |
pyridine-2-acetonitrile
tert-butylisonitrile
4-chlorobenzaldehyde
Conditions | Yield |
---|---|
With 1-butyl-3-methylimidazolium chloride In neat (no solvent) at 20℃; for 0.666667h; Catalytic behavior; Solvent; Temperature; Time; | 96% |
The 2-Pyridylacetonitrile, with the CAS registry number 2739-97-1 and EINECS registry number 220-364-6, has the systematic name of pyridin-2-ylacetonitrile. It belongs to the following product categories: Miscellaneous; Pyridines; Pyridine; C7 and C8; Heterocyclic Building Blocks. And the molecular formula of this chemical is C7H6N2.
The physical properties of 2-Pyridylacetonitrile are as following: (1)ACD/LogP: -0.04; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): -0.05; (4)ACD/LogD (pH 7.4): -0.04; (5)ACD/BCF (pH 5.5): 1; (6)ACD/BCF (pH 7.4): 1; (7)ACD/KOC (pH 5.5): 22.45; (8)ACD/KOC (pH 7.4): 22.57; (9)#H bond acceptors: 2; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 1; (12)Polar Surface Area: 36.68 Å2; (13)Index of Refraction: 1.533; (14)Molar Refractivity: 33.8 cm3; (15)Molar Volume: 108.8 cm3; (16)Polarizability: 13.4×10-24cm3; (17)Surface Tension: 47.8 dyne/cm; (18)Density: 1.085 g/cm3; (19)Flash Point: 93.9 °C; (20)Enthalpy of Vaporization: 46.87 kJ/mol; (21)Boiling Point: 232.1 °C at 760 mmHg; (22)Vapour Pressure: 0.0602 mmHg at 25°C.
Uses of 2-Pyridylacetonitrile: It can react with ethoxymethylene-malonic acid diethyl ester to produce 1-cyano-4-oxo-4H-quinolizin-3-carboxylic acid ethyl ester. This reaction will need reagent sodium ethoxide, and the solvent ethanol. The reaction time is 45 minutes with temperature of 25°C, and the yield is about 55%
You should be cautious while dealing with this chemical. It irritates eyes, respiratory system and skin. Therefore, you had better take the following instructions: Wear suitable protective clothing, and in case of contacting with eyes, rinse immediately with plenty of water and seek medical advice.
You can still convert the following datas into molecular structure:
(1)SMILES: N#CCc1ncccc1
(2)InChI: InChI=1/C7H6N2/c8-5-4-7-3-1-2-6-9-7/h1-3,6H,4H2
(3)InChIKey: UKVQBONVSSLJBB-UHFFFAOYAP
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