2-hydroxy-3-cyanopyridine
2-chloro-3-pyridinecarbonitrile
Conditions | Yield |
---|---|
With triethylamine; trichlorophosphate at 0 - 5℃; for 8.5h; Reagent/catalyst; Reflux; | 96.6% |
With P,P-dichlorophenylphosphine oxide; phosphorus pentachloride at 160℃; for 5h; | 94.6% |
3-cyanopyridine N-oxide
2-chloro-3-pyridinecarbonitrile
Conditions | Yield |
---|---|
With triethylamine; trichlorophosphate at 20 - 90℃; Temperature; | 96% |
With bis(trichloromethyl) carbonate; N-benzyl-N,N,N-triethylammonium chloride; triethylamine; sodium chloride In 1,2-dichloro-ethane at -10 - 0℃; for 2h; Solvent; Reagent/catalyst; Temperature; | 91.41% |
With oxalyl dichloride; triethylamine In dichloromethane at -70℃; for 0.5h; Inert atmosphere; regioselective reaction; | 90.3% |
With POCl2 for 6h; Heating; | |
With oxalyl dichloride; triethylamine In dichloromethane regioselective reaction; |
2-chloro-3-pyridinecarbonitrile
Conditions | Yield |
---|---|
With N-butylamine; triethylamine; trichlorophosphate In 1,2-dichloro-ethane at 10 - 100℃; for 10.3333h; Solvent; Reagent/catalyst; Temperature; | 93.2% |
2-chloro-3-carbaldehydepyridine
2-chloro-3-pyridinecarbonitrile
Conditions | Yield |
---|---|
With pyridine; ammonium peroxydisulfate; tris(2,2-bipyridine)ruthenium(II) hexafluorophosphate; 4-acetylamino-2,2,6,6-tetramethyl-1-piperidinoxy In acetonitrile at 0.5℃; for 24h; Molecular sieve; Sealed tube; Irradiation; | 74% |
Conditions | Yield |
---|---|
With trichlorophosphate for 3.5h; Heating; | 59% |
With phosphorus pentachloride; trichlorophosphate at 115 - 120℃; |
pyridine-3-carbonitrile
A
2-chloro-3-pyridinecarbonitrile
B
4-chloro-nicotinonitrile
Conditions | Yield |
---|---|
Stage #1: pyridine-3-carbonitrile With 2,2,6,6-tetramethyl-piperidine; n-butyllithium In tetrahydrofuran at -80℃; for 0.75h; Stage #2: With hexachloroethane In tetrahydrofuran at -80℃; for 0.75h; | A 7% B 37% |
Stage #1: pyridine-3-carbonitrile With 2,2,6,6-tetramethyl-piperidine; n-butyllithium In tetrahydrofuran; hexane at -80℃; for 0.75h; Stage #2: With hexachloroethane In tetrahydrofuran; hexane at -80℃; for 0.75h; Further stages.; | A 7% B 37% |
2-chloro-3-carbaldehydepyridine
A
2-chloro-3-pyridinecarbonitrile
B
2-chloronicotinamide
Conditions | Yield |
---|---|
With pyridine; tris(2,2-bipyridine)ruthenium(II) hexafluorophosphate; ammonium peroxydisulfate; 4-acetylamino-2,2,6,6-tetramethyl-1-piperidinoxy; ammonium carbamate In water; acetonitrile at 20℃; for 18h; Irradiation; Sealed tube; | A 30% B n/a |
3-cyanopyridine N-oxide
A
6-chloronicotinonitrile
B
2-chloro-3-pyridinecarbonitrile
C
4-chloro-nicotinonitrile
Conditions | Yield |
---|---|
With trichlorophosphate at 110℃; for 2h; Yield given. Yields of byproduct given; |
nicotinamide N-oxide
A
6-chloronicotinonitrile
B
2-chloro-3-pyridinecarbonitrile
C
4-chloro-nicotinonitrile
Conditions | Yield |
---|---|
With trichlorophosphate for 3.5h; Heating; Yield given. Yields of byproduct given; |
P-toluenesulfonyl cyanide
2-chloro-3-iodopyridine
2-chloro-3-pyridinecarbonitrile
Conditions | Yield |
---|---|
With isopropylmagnesium bromide 1.) THF, -40 deg C, 0.5 h, 2.) THF, -40 to 0 deg C; Yield given. Multistep reaction; |
2-chloro-3-pyridinecarbonitrile
Conditions | Yield |
---|---|
With trichlorophosphate at 100℃; im Rohr; |
2-chloro-3-pyridinecarbonitrile
Conditions | Yield |
---|---|
With phosphorus pentaoxide im Vakuum; | |
With trichlorophosphate at 100℃; im Rohr; |
ricinidine
phosphorus pentachloride
trichlorophosphate
2-chloro-3-pyridinecarbonitrile
Conditions | Yield |
---|---|
at 105℃; im Rohr; |
2-chloro-3-pyridinecarbonitrile
Conditions | Yield |
---|---|
With potassium cyanide; copper(II) sulfate |
2-chloro-3-pyridinecarbonitrile
Conditions | Yield |
---|---|
With phosphorus pentachloride; trichlorophosphate at 105℃; im Rohr; |
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: aqueous H2O2; acetic acid 2: PCl5; POCl3 / 115 - 120 °C View Scheme |
Conditions | Yield |
---|---|
With hydrogenchloride; potassium chromate In water at 0 - 15℃; | 9.77 g |
2-chloro-3-pyridinecarbonitrile
ethyl 2-sulfanylacetate
ethyl 3-aminothieno[2,3-b]pyridine-2-carboxylate
Conditions | Yield |
---|---|
Stage #1: ethyl 2-sulfanylacetate With sodium hydride In dimethyl sulfoxide; mineral oil at 20℃; for 0.25h; Stage #2: 2-chloro-3-pyridinecarbonitrile In dimethyl sulfoxide; mineral oil at 20℃; for 3h; | 100% |
With sodium carbonate In ethanol at 90℃; for 2.5h; | 94% |
With sodium carbonate In ethanol for 4.5h; Heating / reflux; | 93.2% |
Conditions | Yield |
---|---|
With hydrazine In ethanol at 170℃; for 0.166667h; Microwave irradiation; | 100% |
With hydrazine hydrate In ethanol for 12h; Reflux; | 90% |
With hydrazine hydrate In ethanol for 10h; Heating; | 88% |
2-chloro-3-pyridinecarbonitrile
phenylboronic acid
2-phenylpyridine-3-carbonitrile
Conditions | Yield |
---|---|
With palladium on activated charcoal; sodium carbonate; triphenylphosphine In 1,2-dimethoxyethane at 80℃; for 9h; Suzuki-Miyaura coupling; | 100% |
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In toluene for 24h; Suzuki coupling; Heating; | 94% |
With dichloro bis(acetonitrile) palladium(II); C32H25NP2; sodium hydroxide In N,N-dimethyl-formamide at 125℃; for 4h; Suzuki-Miyaura coupling; Inert atmosphere; | 93% |
2-chloro-3-pyridinecarbonitrile
2-hydroxy-3-cyanopyridine
Conditions | Yield |
---|---|
With acetic acid Heating; | 100% |
With acetic acid for 48h; Reflux; | 95% |
With acetic acid for 60h; Reflux; | 70% |
2-chloro-3-pyridinecarbonitrile
(3S)-1-methyl-3-phenylpiperazine
2-[(2S)-4-methyl-2-phenyl-1-piperazinyl]-3-pyridinecarbonitrile
Conditions | Yield |
---|---|
With potassium fluoride In N,N-dimethyl-formamide for 23.5h; Heating / reflux; | 100% |
With potassium fluoride In N,N-dimethyl-formamide for 23.5h; Heating / reflux; | 100% |
With triethylamine In N,N-dimethyl-formamide at 120 - 125℃; for 17h; Product distribution / selectivity; | |
With potassium fluoride In N,N-dimethyl-formamide for 23.5h; Reflux; |
2-chloro-3-pyridinecarbonitrile
pyrid-2-one-3-carbonitrile
Conditions | Yield |
---|---|
With acetic acid for 12h; Reflux; | 100% |
With acetic acid at 0℃; for 24h; | 6.28 g |
Conditions | Yield |
---|---|
With 1,1′-bis(diphenylphosphino)-3,3′-di(tert-butyl)ferrocene; silver fluoride In toluene at 120℃; for 16h; Inert atmosphere; Schlenk technique; | 99% |
With cesium fluoride In dimethyl sulfoxide at 90℃; for 2h; | 69% |
With tetrabutyl phosphonium hydrogen difluoride at 80℃; for 2h; | 88 % Chromat. |
With p-methoxybenzoyl fluoride; 2,3-Dihydro-1,3-diisopropyl-4,5-dimethylimidazol-2-ylidene In N,N-dimethyl-formamide at 25℃; for 16h; Inert atmosphere; | 50 %Spectr. |
With tetramethylammonium fluoride In N,N-dimethyl-formamide at 25℃; for 24h; Sealed tube; | 93 %Spectr. |
2-chloro-3-pyridinecarbonitrile
1-methyl-3-phenylpiperazine
3-cyano-2-(4-methyl-2-phenyl-1-piperazynyl)pyridine
Conditions | Yield |
---|---|
With potassium fluoride In N,N-dimethyl-formamide at 140℃; for 6h; | 99% |
In N,N-dimethyl-formamide at 120 - 125℃; for 18h; Product distribution / selectivity; | 40.9% |
2-chloro-3-pyridinecarbonitrile
[4-[[2-(furan-2-yl)-5-methyl-4-oxazolyl]methoxy]-3-methoxyphenyl]methanol
Conditions | Yield |
---|---|
With sodium hydride In N,N-dimethyl-formamide at 1 - 30℃; for 15h; | 99% |
Conditions | Yield |
---|---|
With potassium phosphate; bis(η3-allyl-μ-chloropalladium(II)); 1,2-bis(diphenylphosphino)-1'-(diisopropylphosphino)-3',4-di-tert-butyl ferrocene In toluene at 115℃; for 20h; Inert atmosphere; | 99% |
2-chloro-3-pyridinecarbonitrile
chloro-trimethyl-silane
2,4-dichloro-6-[(4-fluorophenyl)thio]benzonitrile
Conditions | Yield |
---|---|
Stage #1: 2-chloro-3-pyridinecarbonitrile With 2,2,6,6-tetramethyl-piperidine; n-butyllithium; lithium chloride; magnesium chloride In tetrahydrofuran; hexane at -78℃; Inert atmosphere; Schlenk technique; Stage #2: chloro-trimethyl-silane In tetrahydrofuran; hexane at -78 - 20℃; for 0.25h; Inert atmosphere; Schlenk technique; regioselective reaction; | 99% |
Conditions | Yield |
---|---|
Stage #1: 2-chloro-3-pyridinecarbonitrile; 4-hydroxyphenylacetate With potassium carbonate In dimethyl sulfoxide at 60℃; for 14h; Stage #2: With hydrogenchloride In water; dimethyl sulfoxide | 99% |
2-chloro-3-pyridinecarbonitrile
2-chloronicotinamide
Conditions | Yield |
---|---|
Stage #1: 2-chloro-3-pyridinecarbonitrile With sulfuric acid at 90℃; for 2h; Stage #2: With ammonium hydroxide for 1h; Cooling with ice; | 98% |
With Acetaldehyde oxime; copper(II) oxide In water for 10h; Reflux; | 96% |
With N-ethyl-N-hydroxy-ethanamine; water at 100℃; for 3h; | 95% |
Conditions | Yield |
---|---|
With potassium phosphate; bis(η3-allyl-μ-chloropalladium(II)); 1,2-bis(diphenylphosphino)-1'-(diisopropylphosphino)-3',4-di-tert-butyl ferrocene In toluene at 115℃; for 20h; Inert atmosphere; | 98% |
2-chloro-3-pyridinecarbonitrile
tris(4-methoxyphenyl)bismuth
2-(4-methoxy)phenylpyridine-3-carbonitrile
Conditions | Yield |
---|---|
With tetrakis(triphenylphosphine) palladium(0); caesium carbonate In N,N-dimethyl acetamide at 90℃; for 4h; Inert atmosphere; Schlenk technique; | 98% |
2-chloro-3-pyridinecarbonitrile
thiophenol
2-phenylsulfanylnicotinonitrile
Conditions | Yield |
---|---|
Stage #1: thiophenol With sodium hydride In N,N-dimethyl-formamide; mineral oil at 25℃; for 1h; Inert atmosphere; Stage #2: 2-chloro-3-pyridinecarbonitrile In N,N-dimethyl-formamide; mineral oil at 25℃; for 16h; Inert atmosphere; | 97% |
With water at 100℃; for 2h; | 95% |
With bis(η3-allyl-μ-chloropalladium(II)); 1,1',3,3'-tetrakis(diphenylphosphino)ferrocene; sodium t-butanolate In toluene for 17h; Catalytic behavior; Inert atmosphere; Schlenk technique; Heating; | 95% |
With 1,1'-bis-(diphenylphosphino)ferrocene; bis(η3-allyl-μ-chloropalladium(II)); sodium t-butanolate In toluene at 120℃; for 17h; | 78% |
Conditions | Yield |
---|---|
With potassium carbonate In N,N-dimethyl-formamide at 150℃; for 2h; Inert atmosphere; Green chemistry; | 97% |
Conditions | Yield |
---|---|
With palladium diacetate; potassium carbonate; nixantphos In tetrahydrofuran; water at 20℃; for 6h; Suzuki-Miyaura Coupling; | 97% |
piperazine
2-chloro-3-pyridinecarbonitrile
2-(piperazin-1-yl)nicotinonitrile
Conditions | Yield |
---|---|
In ethanol 1.) ice bath, 2.) room temperature; | 96.1% |
With N-ethyl-N,N-diisopropylamine In DMF (N,N-dimethyl-formamide) for 15h; | 81% |
With sodium hydroxide In ethanol | 72.5% |
3-(5-methyl-2-phenyl-4-oxazolylmethoxy)-5-isoxazolylmethanol
2-chloro-3-pyridinecarbonitrile
Conditions | Yield |
---|---|
With sodium hydride In N,N-dimethyl-formamide at 0 - 30℃; for 1.5h; | 96% |
2-chloro-3-pyridinecarbonitrile
N,N-dimethyl-formamide
2-(N,N-dimethylamine)-3-pyridinecarbonitrile
Conditions | Yield |
---|---|
at 180℃; for 0.416667h; Microwave irradiation; | 96% |
for 22h; Reflux; neat (no solvent); | 73% |
Heating; |
2-chloro-3-pyridinecarbonitrile
(4-(ethoxycarbonyl)phenyl)zinc pivalate
ethyl 4-(3-cyanopyridin-2-yl)benzoate
Conditions | Yield |
---|---|
[1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene](3-chloropyridyl) palladium(II) dichloride In ethyl acetate at 22 - 25℃; for 12h; Product distribution / selectivity; Negishi Coupling Reaction; | 96% |
2-chloro-3-pyridinecarbonitrile
1-mercaptopropan-2-one
2-acetyl-3-aminopyrido[2,3-b]thiophene
Conditions | Yield |
---|---|
With potassium carbonate In water at 90℃; for 2h; Green chemistry; | 96% |
2-chloro-3-pyridinecarbonitrile
rac-3-bromocyclohexene
2-chloro-4-(cyclohex-2-en-1-yl)-3-cyanopyridine
Conditions | Yield |
---|---|
Stage #1: 2-chloro-3-pyridinecarbonitrile With 2,2,6,6-tetramethyl-piperidine; n-butyllithium; copper(I) cyanide di(lithium chloride) In tetrahydrofuran; hexane at -78℃; Inert atmosphere; Schlenk technique; Stage #2: rac-3-bromocyclohexene In tetrahydrofuran; hexane at -78 - 0℃; for 1.16667h; Inert atmosphere; Schlenk technique; regioselective reaction; | 96% |
Stage #1: 2-chloro-3-pyridinecarbonitrile With copper(I) cyanide di(lithium chloride); 2,2,6,6-tetramethylpiperidinyl-lithium In tetrahydrofuran at 0℃; for 0.0111111h; Flow reactor; Inert atmosphere; Stage #2: rac-3-bromocyclohexene In tetrahydrofuran at 0℃; for 1h; Flow reactor; Inert atmosphere; regioselective reaction; | 89% |
Conditions | Yield |
---|---|
With bis(η3-allyl-μ-chloropalladium(II)); 1,1',3,3'-tetrakis(diphenylphosphino)ferrocene; sodium t-butanolate In toluene for 17h; Catalytic behavior; Inert atmosphere; Schlenk technique; Heating; | 96% |
Conditions | Yield |
---|---|
With bis(η3-allyl-μ-chloropalladium(II)); 1,1',3,3'-tetrakis(diphenylphosphino)ferrocene; sodium t-butanolate In toluene for 17h; Catalytic behavior; Inert atmosphere; Schlenk technique; Heating; | 96% |
2-chloro-3-pyridinecarbonitrile
2-(3-bromo-4-hydroxyphenyl)acetic acid
Conditions | Yield |
---|---|
With potassium carbonate In dimethyl sulfoxide at 80℃; for 24h; | 96% |
2-chloro-3-pyridinecarbonitrile
N-butylamine
2-(butylamino)pyridine-3-carbonitrile
Conditions | Yield |
---|---|
In isopropyl alcohol Heating; | 95% |
at 165 - 180℃; for 1h; | 70% |
The 2-Chloro-3-cyanopyridine, with the CAS registry number 6602-54-6, is also known as 3-Cyano-2-chloropyridine.It belongs to the product Pharmaceutical Intermediates. Its EINECS number is 229-550-1. This chemical's molecular formula is C6H3ClN2 and molecular weight is 138.56.What's more,Its systematic name is 2-Chloronicotinonitrile.
Physical properties about 2-Chloro-3-cyanopyridine are:(1)ACD/LogP: 1.168; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 1.17; (4)ACD/LogD (pH 7.4): 1.17; (5)ACD/BCF (pH 5.5): 4.55; (6)ACD/BCF (pH 7.4): 4.55; (7)ACD/KOC (pH 5.5): 102.87; (8)ACD/KOC (pH 7.4): 102.87; (9)#H bond acceptors: 2; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 0; (12)Index of Refraction: 1.566; (13)Molar Refractivity: 33.946 cm3; (14)Molar Volume: 104.13 cm3; (15)Surface Tension: 56.673999786377 dyne/cm; (16)Density: 1.331 g/cm3; (17)Flash Point: 109.591 °C; (18)Enthalpy of Vaporization: 49.516 kJ/mol; (19)Boiling Point: 257.596 °C at 760 mmHg; (20)Vapour Pressure: 0.0140000004321337 mmHg at 25°C.
2-Chloro-3-cyanopyridine may cause damage to health. It is irritating to eyes, respiratory system and skin. In case of contact with eyes, you should rinse immediately with plenty of water and seek medical advice. Whenever you will contact it, please wear suitable protective clothing, gloves and eye/face protection. In case of accident or if you feel unwell seek medical advice immediately .
You can still convert the following datas into molecular structure:
(1)SMILES:N#Cc1cccnc1Cl;
(2)Std. InChI:InChI=1S/C6H3ClN2/c7-6-5(4-8)2-1-3-9-6/h1-3H;
(3)Std. InChIKey:JAUPUQRPBNDMDT-UHFFFAOYSA-N.
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