6602-54-6

Basic information

• Product Name: 2-Chloro-3-cyanopyridine
• Synonyms: 2-CHLOROPYRIDINE-3-CARBONITRILE;2-CHLORONICOTINITRILE;2-CHLORONICOTINONITRILE;RARECHEM AH CK 0066;2-Chloro-3-cyanopyridine 97%;2-Chloronicotinonitrile (2-Chloro-3-cyano pyridine);2-CHLORONICOTINONITRILE ( CNN );2-CHLORO-3-CYANO PYRIDINE 2-CHLORONICOTINONITRILE
• CAS NO: 6602-54-6
• Molecular Formula: C₆H₃ClN₂
• Molecular Weight: 138.55
• EINECS: 229-550-1
• Product Categories: Pyridine;Pyridines, Pyrimidines, Purines and Pteredines;Halides;Pyridines;Heterocyclic Compounds;Chloropyridines;Halopyridines;pyridine series;Amines;Aromatics;Heterocycles;cyanide| alkyl chloride
• Mol File: 6602-54-6.mol

Chemical Properties

• Melting Point: 104-107 °C(lit.)
• Boiling Point: 112°C 1mm
• Flash Point: 112°C/1mm
• Appearance: White to off-white/Crystalline Powder or Flakes
• Density: 1.3185 (rough estimate)
• Vapor Pressure: 0.0144mmHg at 25°C
• Refractive Index: 1.4877 (estimate)
• Storage Temp.: 2-8°C
• PKA: -2.17±0.10(Predicted)
• BRN: 115772
• CAS DataBase Reference: 2-Chloro-3-cyanopyridine(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Chloro-3-cyanopyridine(6602-54-6)
• EPA Substance Registry System: 2-Chloro-3-cyanopyridine(6602-54-6)

Safety Data

• Hazard Codes: Xn,T,Xi
• Statements: 20/21/22-36/37/38
• Safety Statements: 26-36-36/37/39
• RIDADR: UN 3439 6.1/PG 3
• WGK Germany: 3
• HazardClass: 6.1
• PackingGroup: III
• Hazardous Substances Data: 6602-54-6(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
2-Chloro-3-cyanopyridine is used as a key intermediate for the synthesis of various pharmaceuticals, agrochemicals, and other specialty chemicals. Its chemical properties allow it to participate in a wide array of reactions, such as nucleophilic substitution, electrophilic aromatic substitution, and cross-coupling reactions, making it a valuable building block in the development of complex molecular structures.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 2-Chloro-3-cyanopyridine is utilized as a starting material for the synthesis of novel drug candidates with potential therapeutic applications. Its unique structural features enable the creation of diverse chemical entities that can target specific biological receptors or enzymes, contributing to the discovery of new medicines for various diseases.
Used in Agrochemical Industry:
2-Chloro-3-cyanopyridine also finds application in the agrochemical industry, where it is employed in the synthesis of new pesticides, herbicides, and insecticides. Its reactivity and structural diversity allow for the development of innovative compounds that can effectively control pests and diseases in agriculture, ensuring increased crop yield and food security.
Used in Chemical Research:
In the field of chemical research, 2-Chloro-3-cyanopyridine serves as a valuable compound for exploring new reaction mechanisms, understanding structure-activity relationships, and developing new synthetic methodologies. Its unique properties make it an attractive candidate for studying various aspects of organic chemistry, including reaction kinetics, stereochemistry, and catalysis.

InChI:InChI=1/C6H3ClN2/c7-6-5(4-8)2-1-3-9-6/h1-3H

Synthetic route

2-hydroxy-3-cyanopyridine (20577-27-9) → 2-chloro-3-pyridinecarbonitrile (6602-54-6)

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 (14906-64-0) → 2-chloro-3-pyridinecarbonitrile (6602-54-6)

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;

N-oxonicotinamide → 2-chloro-3-pyridinecarbonitrile (6602-54-6)

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 (36404-88-3) → 2-chloro-3-pyridinecarbonitrile (6602-54-6)

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%

nicotinamide N-oxide (1986-81-8) → 2-chloro-3-pyridinecarbonitrile (6602-54-6)

Conditions	Yield
With trichlorophosphate for 3.5h; Heating;	59%
With phosphorus pentachloride; trichlorophosphate at 115 - 120℃;

pyridine-3-carbonitrile (100-54-9) → 2-chloro-3-pyridinecarbonitrile (6602-54-6) + 4-chloro-nicotinonitrile (89284-61-7)

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 (36404-88-3) → 2-chloro-3-pyridinecarbonitrile (6602-54-6) + 2-chloronicotinamide (10366-35-5)

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 (14906-64-0) → 6-chloronicotinonitrile (33252-28-7) + 2-chloro-3-pyridinecarbonitrile (6602-54-6) + 4-chloro-nicotinonitrile (89284-61-7)

Conditions	Yield
With trichlorophosphate at 110℃; for 2h; Yield given. Yields of byproduct given;

nicotinamide N-oxide (1986-81-8) → 6-chloronicotinonitrile (33252-28-7) + 2-chloro-3-pyridinecarbonitrile (6602-54-6) + 4-chloro-nicotinonitrile (89284-61-7)

Conditions	Yield
With trichlorophosphate for 3.5h; Heating; Yield given. Yields of byproduct given;

P-toluenesulfonyl cyanide (19158-51-1) + 2-chloro-3-iodopyridine (78607-36-0) → 2-chloro-3-pyridinecarbonitrile (6602-54-6)

Conditions	Yield
With isopropylmagnesium bromide 1.) THF, -40 deg C, 0.5 h, 2.) THF, -40 to 0 deg C; Yield given. Multistep reaction;

1-methyl-pyridone-(2)-carboxylic acid-(3)-amide → 2-chloro-3-pyridinecarbonitrile (6602-54-6)

Conditions	Yield
With trichlorophosphate at 100℃; im Rohr;

2-chloro-pyridine-carboxylic acid-(3)-amide → 2-chloro-3-pyridinecarbonitrile (6602-54-6)

Conditions	Yield
With phosphorus pentaoxide im Vakuum;
With trichlorophosphate at 100℃; im Rohr;

ricinidine (767-88-4) + phosphorus pentachloride (10026-13-8, 874483-75-7) + trichlorophosphate (10025-87-3, 12599-09-6, 63736-95-8) → 2-chloro-3-pyridinecarbonitrile (6602-54-6)

Conditions	Yield
at 105℃; im Rohr;

diazotized 3-amino-2-chloro-pyridine → 2-chloro-3-pyridinecarbonitrile (6602-54-6)

Conditions	Yield
With potassium cyanide; copper(II) sulfate

ricinidine → 2-chloro-3-pyridinecarbonitrile (6602-54-6)

Conditions	Yield
With phosphorus pentachloride; trichlorophosphate at 105℃; im Rohr;

nicotinamide (98-92-0) → 2-chloro-3-pyridinecarbonitrile (6602-54-6)

Conditions	Yield
Multi-step reaction with 2 steps 1: aqueous H2O2; acetic acid 2: PCl5; POCl3 / 115 - 120 °C View Scheme

pyridine-3-carbonitrile (100-54-9) → 2-chloro-3-pyridinecarbonitrile (6602-54-6)

Conditions	Yield
With hydrogenchloride; potassium chromate In water at 0 - 15℃;	9.77 g

2-chloro-3-pyridinecarbonitrile (6602-54-6) + ethyl 2-sulfanylacetate (623-51-8) → ethyl 3-aminothieno[2,3-b]pyridine-2-carboxylate (52505-46-1)

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%

2-chloro-3-pyridinecarbonitrile (6602-54-6) → 1H-pyrazolo[3,4-b]pyridin-3-amine (6752-16-5)

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 (6602-54-6) + phenylboronic acid (98-80-6) → 2-phenylpyridine-3-carbonitrile (39065-49-1)

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 (6602-54-6) → 2-hydroxy-3-cyanopyridine (20577-27-9)

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 (6602-54-6) + (3S)-1-methyl-3-phenylpiperazine (931115-08-1) → 2-[(2S)-4-methyl-2-phenyl-1-piperazinyl]-3-pyridinecarbonitrile (931115-11-6)

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 (6602-54-6) → pyrid-2-one-3-carbonitrile (20577-27-9)

Conditions	Yield
With acetic acid for 12h; Reflux;	100%
With acetic acid at 0℃; for 24h;	6.28 g

2-chloro-3-pyridinecarbonitrile (6602-54-6) → 3-cyano-2-fluoropyridine (3939-13-7)

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 (6602-54-6) + 1-methyl-3-phenylpiperazine (5271-27-2) → 3-cyano-2-(4-methyl-2-phenyl-1-piperazynyl)pyridine (61337-88-0)

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 (6602-54-6) + [4-[[2-(furan-2-yl)-5-methyl-4-oxazolyl]methoxy]-3-methoxyphenyl]methanol (250603-01-1) → 3-cyano-2-[4-[[2-(furan-2-yl)-5-methyl-4-oxazolyl]methoxy]-3-methoxybenzyloxy]pyridine

Conditions	Yield
With sodium hydride In N,N-dimethyl-formamide at 1 - 30℃; for 15h;	99%

2-chloro-3-pyridinecarbonitrile (6602-54-6) + phenol (108-95-2) → 3-cyanopyridine-2-phenyl ether (14178-15-5)

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 (6602-54-6) + chloro-trimethyl-silane (75-77-4) → 2,4-dichloro-6-[(4-fluorophenyl)thio]benzonitrile (1644384-53-1)

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%

2-chloro-3-pyridinecarbonitrile (6602-54-6) + 4-hydroxyphenylacetate (156-38-7) → 2-(4-((3-cyanopyridin-2-yl)oxy)phenyl)acetic acid hydrochloride

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 (6602-54-6) → 2-chloronicotinamide (10366-35-5)

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%

2-chloro-3-pyridinecarbonitrile (6602-54-6) + O-methylresorcine (150-19-6) → 3-cyano-2-(3-methoxyphenoxy)pyridine

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 (6602-54-6) + tris(4-methoxyphenyl)bismuth (33397-21-6) → 2-(4-methoxy)phenylpyridine-3-carbonitrile (1246461-85-7)

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 (6602-54-6) + thiophenol (108-98-5) → 2-phenylsulfanylnicotinonitrile (35620-68-9)

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%

1H-imidazole (288-32-4) + 2-chloro-3-pyridinecarbonitrile (6602-54-6) → C9H6N4

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 150℃; for 2h; Inert atmosphere; Green chemistry;	97%

2-chloro-3-pyridinecarbonitrile (6602-54-6) + 4-tert-butylphenylboronic acid (123324-71-0) → C16H16N2

Conditions	Yield
With palladium diacetate; potassium carbonate; nixantphos In tetrahydrofuran; water at 20℃; for 6h; Suzuki-Miyaura Coupling;	97%

piperazine (110-85-0) + 2-chloro-3-pyridinecarbonitrile (6602-54-6) → 2-(piperazin-1-yl)nicotinonitrile (84951-44-0)

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 (342024-34-4) + 2-chloro-3-pyridinecarbonitrile (6602-54-6) → 2-[[3-[(5-methyl-2-phenyl-4-oxazolyl)methoxy]-5-isoxazolyl]methoxy]nicotinonitrile

Conditions	Yield
With sodium hydride In N,N-dimethyl-formamide at 0 - 30℃; for 1.5h;	96%

2-chloro-3-pyridinecarbonitrile (6602-54-6) + N,N-dimethyl-formamide (68-12-2, 33513-42-7) → 2-(N,N-dimethylamine)-3-pyridinecarbonitrile (60138-76-3)

Conditions	Yield
at 180℃; for 0.416667h; Microwave irradiation;	96%
for 22h; Reflux; neat (no solvent);	73%
Heating;

2-chloro-3-pyridinecarbonitrile (6602-54-6) + (4-(ethoxycarbonyl)phenyl)zinc pivalate (1344727-27-0) → ethyl 4-(3-cyanopyridin-2-yl)benzoate (1208081-99-5)

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 (6602-54-6) + 1-mercaptopropan-2-one (24653-75-6) → 2-acetyl-3-aminopyrido[2,3-b]thiophene (52505-41-6)

Conditions	Yield
With potassium carbonate In water at 90℃; for 2h; Green chemistry;	96%

2-chloro-3-pyridinecarbonitrile (6602-54-6) + rac-3-bromocyclohexene (1521-51-3) → 2-chloro-4-(cyclohex-2-en-1-yl)-3-cyanopyridine (1644384-68-8)

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%

2-chloro-3-pyridinecarbonitrile (6602-54-6) + p-Chlorothiophenol (106-54-7) → 2-((4-chlorophenyl)thio)nicotinonitrile

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 (6602-54-6) + 4-Fluorothiophenol (371-42-6) → 2-((4-fluorophenyl)thio)nicotinonitrile

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 (6602-54-6) + 2-(3-bromo-4-hydroxyphenyl)acetic acid (38692-80-7) → 2-(3-bromo-4-((3-cyanopyridin-2-yl)oxy)phenyl)acetic acid

Conditions	Yield
With potassium carbonate In dimethyl sulfoxide at 80℃; for 24h;	96%

2-chloro-3-pyridinecarbonitrile (6602-54-6) + N-butylamine (109-73-9) → 2-(butylamino)pyridine-3-carbonitrile (74611-50-0)

Conditions	Yield
In isopropyl alcohol Heating;	95%
at 165 - 180℃; for 1h;	70%

Upstream product

• 1986-81-8 nicotinamide N-oxide 
• 14906-64-0 3-cyanopyridine N-oxide 
• 19158-51-1 P-toluenesulfonyl cyanide 
• 78607-36-0 2-chloro-3-iodopyridine 
• 767-88-4 ricinidine 
• 10026-13-8 phosphorus pentachloride 
• 10025-87-3 trichlorophosphate 
• 100-54-9 pyridine-3-carbonitrile 
• 98-92-0 nicotinamide 
• 20577-27-9 2-hydroxy-3-cyanopyridine 
• 36404-88-3 2-chloro-3-carbaldehydepyridine 

Downstream Products

• 10366-35-5 2-chloronicotinamide 
• 609-71-2 2-hydroxy-3-carboxypyridine 
• 7254-34-4 2-methoxy-3-cyanopyridine 
• 7145-28-0 2-methoxy-3-pyridinecarboxamide 
• 55557-48-7 3-Amino-2-carboxamidothieno<2,3-b>pyridine 
• 73161-38-3 1-methyl-2,2-dioxo-1,2-dihydro-2λ⁶-pyrido[2,3-c][1,2]thiazin-4-ylamine 
• 52505-46-1 ethyl 3-aminothieno[2,3-b]pyridine-2-carboxylate 
• 84951-44-0 2-(piperazin-1-yl)nicotinonitrile 
• 74611-49-7 2-propylamino-3-pyridinecarbonitrile 
• 55676-21-6 3-acetyl-2-chloropyridine 
• 60559-93-5 2-((S)-3-tert-Butyl-2-phenyl-oxazolidin-5-ylmethoxy)-nicotinonitrile 
• 152061-89-7 2-propylthio-3-pyridinecarbonitrile 
• 75424-69-0 2-Octyloxy-nicotinonitrile 
• 152061-90-0 2-butylthio-3-pyridinecarbonitrile 

Relevant articles and documents

Preparation method of 2- novel chloronicotinic acid (by machine translation)

The method disclosed by the invention 2 - comprises the following steps: reacting the obtained :1) product with trichlorooxygen phosphorus, in the presence of 1) an acid, to give 2 - the product of 2 - the present invention ;2) in the following steps: reacting the obtained product with phosphorus oxychloride, in 2 - the presence of a ;3) base with 2) phosphorus oxychloride in the presence of a base, 2 - 2 . (by machine translation)

Environment-friendly preparation method of 2-chloro-3-cyanopyridine

The invention discloses an environment-friendly preparation method of 2-chloro-3-cyanopyridine. The method comprises the steps of dissolving 3-cyanopyridine N-oxide as a raw material into a certain amount of an organic solvent, adding an additive, organic alkali and a phase transfer catalyst to form a raw material system, controlling to form a proper temperature, dissolving bis(trichloromethyl)carbonate in a certain amount of the organic solvent to obtain a mixture, slowly dropwise adding the mixture into the raw material system for reaction, and after the reaction is finished, carrying out simple treatment, so as to obtain 2-chloro-3-cyanopyridine. The preparation method is simple, the reaction period is short, a phosphorus-containing reagent is replaced with an environment-friendly chlorination reagent, and heavy metals are not adopted; and compared with the prior art, the method has the advantages that the environmental pollution is low, the operation is safe, the cost is low, and the preparation method is suitable for industrial production. The method is applied to the environment-friendly chlorination reaction of 3-cyanopyridine N-oxide and is not limited to the preparation of2-chloro-3-cyanopyridine.

Visible-light-driven catalytic oxidation of aldehydes and alcohols to nitriles by 4-acetamido-tempo using ammonium carbamate as a nitrogen source

A mild and efficient route to prepare nitriles from aldehydes by combining photoredox catalysis with oxoammonium cations is reported. The reaction is performed using ammonium carbamate as the nitrogen source. The practicality of the method is increased by the extension of the dual catalytic system to one-pot two-step conversion of alcohols to nitriles.

2-chloro-3-cyanopyridine preparation process

The invention provides a 2-chloro-3-cyanopyridine preparation process which includes the steps: dissolving N-oxynicotinamide in an organic solvent; dripping phosphorus oxychloride at the temperature of 15+/-5 DEG C; dripping organic alkali at the temperature of 10+/-5 DEG C after dripping; keeping the temperature of 10+/-5 DEG C to stir mixture for 30+/-10 minutes after dripping; heating the mixture to reach the temperature of 35+/-10 DEG C, and keeping the temperature for 1+/-0.5 hour; heating the mixture to reach the temperature of 55+/-5 DEG C, and keeping the temperature for 1+/-0.5 hour;heating the mixture to reach the temperature of 95-100 DEG C, and keeping the temperature for 4+/-1 hours to obtain chloride reaction solution after temperature keeping; performing reduced pressure distillation on the chloride reaction solution until flow out of visible liquid is omitted; adding water, controlling the temperature to reach 65+/-5 DEG C, and stirring mixture for 2+/-0.5 hour; cooling the mixture to reach the temperature of 20+/-5 DEG C, stirring the mixture for 30+/-10 minutes, and filtering the mixture to obtain a wet 2-chlorine-3-cyanopyridine product. According to the process, two mixed organic alkali substances serve as catalysts, and the yield of 2-chlorine-3-cyanopyridine is improved to some extent.

Combining Oxoammonium Cation Mediated Oxidation and Photoredox Catalysis for the Conversion of Aldehydes into Nitriles

A method to oxidize aromatic aldehydes to nitriles has been developed. It involves a dual catalytic system of 4-acetamido-TEMPO and visible-light photoredox catalysis. The reaction is performed using ammonium persulfate as both the terminal oxidant and nitrogen source.

A halogenated nitrogen-containing unsaturated cyclic hydrocarbon preparation method

The invention discloses a halogenated nitrogen-containing unsaturated cyclic hydrocarbon of the preparation method, the steps of: (1) the nitrogen-containing unsaturated cyclic hydrocarbon dissolved in hydrochloric acid or hydrobromic acid, addition of an oxidizing agent, the reaction system halogenated reaction, in the reaction process timing sampling detection, when detecting the target product quality of a halide accounted for is a reaction system in the total of the organic matter of 70% - 95% when, added to the reaction system in the terminator to terminate reaction, to obtain containing nitrogen-containing unsaturated cyclic hydrocarbon feed; (2) to the liquid mixed into the organic solvent extraction, extraction to obtain the organic phase, the organic phase temperature is reduced to make the solid precipitation or distilling the organic solvent to obtain a liquid product to be deducted, the resulting solid or liquid product is halogenated nitrogen-containing unsaturated cyclic hydrocarbon. The method solves the problem of the nitrogen-containing unsaturated cyclic hydrocarbon over [...] reaction problems.

A continuous reaction to produce 2-chloro-3-cyano pyridine method

The invention belongs to the field of organic synthesis, and particularly relates to a method for producing 2-chloro-3-cyanopyridine. The method is implemented by taking nicotinonitrile-1-oxide, phosphorus oxychloride and triethylamine as raw materials through the steps that the three raw materials are simultaneously continuously dropwise added into a first reactor, and the reaction temperature is controlled at minus 10-40 DEG C; and a reaction liquid in the first reactor continuously enters subsequent reactors connected in series to react at a reaction temperature of 80-100 DEG C, 1-2 hours later, the reaction liquid is distilled for recovering phosphorus oxychloride, and the phosphorus oxychloride is subjected to hydraulic analysis, so that 2-chloro-3-cyanopyridine is obtained. The method is implemented by adopting a continuous reaction thought, and reaction conditions in the related reactors are smooth, so that the implementation of automation control is facilitated, therefore, the method has the advantages of safe process, high production efficiency, stable product quality, and the like.

Application of 1,1-ADEQUATE, HMBC, and Density Functional Theory to Determine Regioselectivity in the Halogenation of Pyridine N-Oxides

The 1,1-ADEQUATE spectrum clearly shows specific two-bond proton to carbon correlations to unequivocally distinguish the major and minor regioisomers of ortho-halogenated pyridines and to aid in assignment of the corresponding proton and carbon chemical shifts. M06-2X/6-31+G(d,p) free energies of the regioisomeric intermediates arising from deprotonation correctly predict the experimentally observed preference and thus can be used to tune the substituent pattern to yield a desired regiochemical outcome.

PhPOCl2as a potent catalyst for chlorination reaction of phenols with PCl5

Phenols are easily converted to the corresponding aryl chlorides by using phosphorus pentachloride (PCl5) and a catalytic amount of phenylphosphonic dichloride (PhPOCl2), which is a new efficient method for synthesis of aryl chloride in good yields.

Highly Regioselective Halogenation of Pyridine N -Oxide: Practical Access to 2-Halo-Substituted Pyridines

A highly efficient and regioselective halogenation reaction of unsymmetrical pyridine N-oxide under mild conditions is described. The methodology provides a practical access to various 2-halo-substituted pyridines, which are pharmaceutically important intermediates.