109-09-1

Basic information

• Product Name: 2-Chloropyridine
• Synonyms: 2-Chloropyridine ,99%;2-Pyridinyl chloride;2-Chloro Pyridine (2CP);NSC 4649;2- chlorinepyridine;2-Chloropyridi;2-chloro-pyridin;o-Chloropyridine
• CAS NO: 109-09-1
• Molecular Formula: C₅H₄ClN
• Molecular Weight: 113.54
• EINECS: 203-646-3
• Product Categories: Chloropyridines;Halopyridines;C5Heterocyclic Building Blocks;Halogenated Heterocycles;Heterocyclic Building Blocks;Pyridines;Amines;Aromatics;Bases & Related Reagents;Mutagenesis Research Chemicals;Nucleotides;API Intermediate;Pharmaceutical Intermediates;Pyridines, Pyrimidines, Purines and Pteredines;Pyridines derivates
• Mol File: 109-09-1.mol
• Article Data: 82

Chemical Properties

• Melting Point: -46 °C
• Boiling Point: 168 °C
• Flash Point: 149 °F
• Appearance: Clear colorless to light yellow/Liquid
• Density: 1.209
• Vapor Pressure: 1.7 mm Hg ( 20 °C)
• Refractive Index: n20/D 1.532(lit.)
• Storage Temp.: Refrigerator
• Solubility: 27g/l
• PKA: 0.49(at 25℃)
• Water Solubility: 27 g/L (20 ºC)
• BRN: 105788
• CAS DataBase Reference: 2-Chloropyridine(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Chloropyridine(109-09-1)
• EPA Substance Registry System: 2-Chloropyridine(109-09-1)

Safety Data

• Hazard Codes: T
• Statements: 23/24/25-36/37/38
• Safety Statements: 26-36/37/39-45-28A-27
• RIDADR: UN 2822 6.1/PG 2
• WGK Germany: 3
• RTECS: US5950000
• TSCA: Yes
• HazardClass: 6.1
• PackingGroup: II
• Hazardous Substances Data: 109-09-1(Hazardous Substances Data)

Usage

Chemical Properties

Clear colourless to light yellow liquid

Uses

Different sources of media describe the Uses of 109-09-1 differently. You can refer to the following data:
1. 2-Chloropyridine (2-CPY) has been identified as a trace organic chemical in process streams, wastewater and even drinking water. Furthermore, it appears to be formed as a secondary pollutant during t he decomposition of specific insecticides.
2. 2- Chloropyridine is used as an intermediate chemical in the production of various pyrithione, for use in cosmetics, personal care products and pharmaceutical products.

Synthesis Reference(s)

Synthetic Communications, 19, p. 897, 1989 DOI: 10.1080/00397918908051009Synthesis, p. 337, 1990

General Description

A colorless oily liquid. Toxic by ingestion and/or skin absorption. Used to make other chemicals.

Air & Water Reactions

Slightly soluble in water and denser than water.

Hazard

Toxic by ingestion.

Fire Hazard

Combustible material: may burn but does not ignite readily. When heated, vapors may form explosive mixtures with air: indoors, outdoors and sewers explosion hazards. Contact with metals may evolve flammable hydrogen gas. Containers may explode when heated. Runoff may pollute waterways. Substance may be transported in a molten form.

Safety Profile

Poison by ingestion, inhalation, skin contact, and intraperitoneal routes. Combustible when exposed to heat or flame. Can react with oxidizing materials. When heated to decomposition it emits very toxic fumes of Cl-, NOx, and phosgene.

Purification Methods

Dry 2-chloropyridine with NaOH for several days, then distil it from CaO under reduced pressure. [Beilstein 20/5 V 402.]

InChI:InChI=1/C5H4ClN/c6-5-3-1-2-4-7-5/h1-4H

Synthetic route

2-hydroxypyridin (142-08-5) → 2-chloropyridine (109-09-1)

Conditions	Yield
With P,P-dichlorophenylphosphine oxide; phosphorus pentachloride at 160℃; for 5h;	96.5%
With pyridine; trichlorophosphate at 180℃; under 150.015 - 900.09 Torr; for 2h; Neat (no solvent);	90%
With dmap; thionyl chloride; bis(trichloromethyl) carbonate for 4h; Reflux; Green chemistry;	89%
With N-chloro-succinimide; triphenylphosphine In 1,4-dioxane for 4h; Chlorination; substitution; Heating;	43%
With trichloroacetonitrile; triphenylphosphine In toluene for 4h; Reflux;	100 %Chromat.

2-chloropyridine N-oxide hydrochloride (20295-64-1) → 2-chloropyridine (109-09-1)

Conditions	Yield
With titanium In tetrahydrofuran for 0.25h; Ambient temperature;	96%

2-aminopyridine (504-29-0) → 2-chloropyridine (109-09-1)

Conditions	Yield
With hydrogenchloride; dinitrogen trioxide; tetrabutyl-ammonium chloride In dichloromethane for 2h; Ambient temperature;	95%
With tert-Butyl thionitrate; copper dichloride In acetonitrile at 25℃; for 0.025h; Product distribution; Mechanism; other copper(II) halide, other reagent;	64 % Chromat.
With hydrogenchloride; sodium nitrite
With tert-Butyl thionitrate; copper dichloride In acetonitrile at 25℃; for 0.025h;	64 % Chromat.

2-chloropyridine-N-oxide (2402-95-1) → 2-chloropyridine (109-09-1)

Conditions	Yield
With cerium(III) chloride heptahydrate; zinc In methanol at 20℃; for 0.5h;	95%
With hydrogen; triethyl phosphite In isopropyl alcohol at 100℃; under 4500.45 Torr; for 18h; Glovebox; chemoselective reaction;	90%
With polymethylhydrosiloxane; palladium on activated charcoal In ethanol at 20℃;	87%

2-bromo-pyridine (109-04-6) → 2-chloropyridine (109-09-1)

Conditions	Yield
With trans-bis(glycinato)copper(II) monohydrate; tetramethlyammonium chloride In ethanol at 100℃; for 12h; Finkelstein Reaction; Schlenk technique; Inert atmosphere;	92%
With copper(I) oxide; tetramethlyammonium chloride; L-proline In ethanol at 110℃; for 20h; Inert atmosphere;	93 %Chromat.

pyridine N-oxide (694-59-7) → 2-chloropyridine (109-09-1)

Conditions	Yield
With oxalyl dichloride; triethylamine In dichloromethane at 5℃; for 1h; Temperature;	91.2%
With triethylamine; trichlorophosphate In dichloromethane at 40℃; for 1h;	90%
With diisopropylamine; trichloromethyl chloroformate In dichloromethane at -40 - 20℃;

Pyridin-Palladium(II)-chlorid-Komplex → 2-chloropyridine (109-09-1)

Conditions	Yield
With chlorine In pyridine at 0 - 5℃; for 1h;	90%

pyridine (110-86-1) → 2-chloropyridine (109-09-1)

Conditions	Yield
With Fluoroacetic acid In dichloromethane at 25 - 60℃; under 675.068 Torr; for 5.5h; Temperature; Pressure;	82.1%
With chlorine at 220℃; Product distribution / selectivity; UV-irradiation;	29.7%
With sulfuryl dichloride at 350℃; Leiten durch Glasrohr;
With hydrogenchloride; sodium hypochlorite In water at 20 - 60℃; for 2h; Temperature; Reagent/catalyst;

2,2'-dipyridyldisulphide (2127-03-9) → 2-chloropyridine (109-09-1)

Conditions	Yield
With chlorine In chloroform; water; acetic acid at 15 - 17℃; for 0.5h;	82%

C19H14N2O2 (93845-11-5) → 2-chloropyridine (109-09-1) + benzophenone (119-61-9) + hexachloroethane (67-72-1) + benzophenone azine (983-79-9)

Conditions	Yield
With tetrachloromethane Ambient temperature; Irradiation; Yields of byproduct given;	A 80% B n/a C n/a D n/a

2,2'-dipyridyldisulphide (2127-03-9) → 2-chloropyridine (109-09-1) + pyridine-2-sulfonyl chloride (66715-65-9)

Conditions	Yield
With 1,3-dichloro-5,5-dimethylhydantoin; acetic acid In dichloromethane; water at 0 - 20℃; Inert atmosphere;	A 20% B 78%

2,6-dichloropyridine N-oxide (2587-00-0) → 2-chloropyridine (109-09-1) + 2,6-dichloropyridine (2402-78-0)

Conditions	Yield
With copper(l) iodide; zinc In ethanol at 55 - 60℃; for 3h;	A n/a B 75%

pyridine (110-86-1) + acetyl hypofluorite (78948-09-1) → 2-chloropyridine (109-09-1) + 2-acetoxypyridine (3847-19-6)

Conditions	Yield
With dichloromethane Ambient temperature;	A 70% B 15%
In dichloromethane Mechanism; Ambient temperature; other N-heterocycles, other solvents;	A 70% B 15%

pyridine (110-86-1) → 2-chloropyridine (109-09-1) + 2-acetoxypyridine (3847-19-6)

Conditions	Yield
With dichloromethane; acetyl hypofluorite In trichlorofluoromethane Product distribution; Mechanism; Ambient temperature; var. halogenomethanes or primary alcohols; other substituted pyridines;	A 70% B 15%

2-chloropyridine-N-oxide (2402-95-1) → pyridine (110-86-1) + 2-chloropyridine (109-09-1)

Conditions	Yield
With copper(l) iodide; zinc In ethanol at 55 - 60℃; for 3h;	A n/a B 70%

pyridine (110-86-1) + p-nitrophenyl isocyanide (1984-23-2) → 2-chloropyridine (109-09-1) + pyridine-2-carboxylic acid (4-nitro-phenyl)amide (61349-99-3) + N-(4-nitro-phenyl)-2-oxo-2-pyridin-2-yl-acetamide

Conditions	Yield
Stage #1: pyridine With fluorine In dichloromethane at -78 - -50℃; Stage #2: p-nitrophenyl isocyanide In dichloromethane at -50 - 0℃; for 4h;	A 11% B 69% C n/a

2-Picolinic acid (98-98-6) → 2-chloropyridine (109-09-1)

Conditions	Yield
With N-chloro-succinimide; tert-butylhypochlorite; potassium carbonate In dichloromethane at 150℃; for 10h; Schlenk technique;	68%
With tert-butylhypochlorite; dichloromethane; sodium hydrogencarbonate at 60℃; for 20h; Green chemistry;	73 %Spectr.

pyridine (110-86-1) + n-butyl isonitrile (2769-64-4) → 2-chloropyridine (109-09-1) + N-butyl-pyridine-2-carboxylic acid amide (10354-51-5) + N-butyl-2-oxo-2-pyridin-2-yl-acetamide

Conditions	Yield
Stage #1: pyridine With fluorine In dichloromethane at -78 - -50℃; Stage #2: n-butyl isonitrile In dichloromethane at -50 - 0℃; for 4h;	A 12% B 64% C n/a

N-fluoropyridinium triflate (107263-95-6) → 2-chloropyridine (109-09-1) + pyridin-2-yl trifluoromethanesulfonate (65007-00-3) + 2-fluoropyridine (372-48-5)

Conditions	Yield
With dichloromethane; triethylamine for 0.0833333h; Product distribution; Ambient temperature; other time; various bases;	A 62% B 21% C 5%
With dichloromethane; triethylamine for 0.0833333h; Ambient temperature; further bases;	A 62 % Chromat. B 21 % Chromat. C 5 % Chromat.
With 2,6-di-tert-butyl-pyridine; dichloromethane for 48h; Ambient temperature;	A 68 % Chromat. B 3 % Chromat. C 9 % Chromat.
With Benzotrichlorid; triethylamine for 0.0833333h; Ambient temperature;	A 11 % Chromat. B 58 % Chromat. C 20 % Chromat.
With dichloromethane; diethylamine for 0.0833333h; Mechanism; Ambient temperature;	A 63 % Chromat. B 22 % Chromat. C 6 % Chromat.

Pyridin-Palladium(II)-chlorid-Komplex → 2-chloropyridine (109-09-1) + 2,3-dichloro-pyridine (2402-77-9) + 2,3,5-trichloropyridine (16063-70-0)

Conditions	Yield
With chlorine In cyclohexane at 75℃; for 1h;	A 9% B 62% C 4.5%

pyridine (110-86-1) + Cyclohexyl isocyanide (931-53-3) → 2-chloropyridine (109-09-1) + N-picolinoylcyclohexylamine (10354-50-4) + N-cyclohexyl-2-oxo-2-pyridin-2-yl-acetamide

Conditions	Yield
Stage #1: pyridine With fluorine In dichloromethane at -78 - -50℃; Stage #2: Cyclohexyl isocyanide In dichloromethane at -50 - 0℃; for 4h;	A 15% B 62% C n/a

pyridine (110-86-1) + 1-Phenyl-2-(trimethylsilyl)acetylene (2170-06-1) → 2-chloropyridine (109-09-1) + 2-(2-phenylethynyl)pyridine (13141-42-9) + 2-fluoropyridine (372-48-5)

Conditions	Yield
With tetrabutyl ammonium fluoride; fluorine Mechanism; multistep reaction; other trimethylsilyl derivatives;	A n/a B 61% C n/a
With tetrabutyl ammonium fluoride; fluorine 1.) CH2Cl2, -50 deg C, 2.) CH2Cl2, a) -50 deg C, 1 h, b) -50 to 0 deg C, 1 h, c) 0 deg C, 0.5 h; Yield given. Multistep reaction. Yields of byproduct given;

pyridine (110-86-1) + 3-trifluoromethylphenyl isonitrile → 2-chloropyridine (109-09-1) + N-[3-(trifluoromethyl)phenyl]-2-pyridinecarboxamide (61350-01-4) + 2-oxo-2-pyridin-2-yl-N-(3-trifluoromethyl-phenyl)-acetamide

Conditions	Yield
Stage #1: pyridine With fluorine In dichloromethane at -78 - -50℃; Stage #2: 3-trifluoromethylphenyl isonitrile In dichloromethane at -50 - 0℃; for 4h;	A 21% B 61% C n/a

pyridine (110-86-1) + tert-butylisonitrile (119072-55-8, 7188-38-7) → 2-chloropyridine (109-09-1) + pyridine-2-carboxylic acid N-tert-butylamide (71653-50-4) + N-tert-butyl-2-oxo-2-pyridin-2-yl-acetamide

Conditions	Yield
Stage #1: pyridine With fluorine In dichloromethane at -78 - -50℃; Stage #2: tert-butylisonitrile In dichloromethane at -50 - 0℃; for 4h;	A 11% B 60% C n/a

pyridine (110-86-1) + phenyl isocyanate (1197040-29-1) → 2-chloropyridine (109-09-1) + N-phenylpicolinamide (10354-53-7) + 2-Oxo-N-phenyl-2-pyridin-2-yl-acetamide (57152-71-3)

Conditions	Yield
Stage #1: pyridine With fluorine In dichloromethane at -78 - -50℃; Stage #2: phenyl isocyanate In dichloromethane at -50 - 0℃; for 4h;	A 24% B 55% C n/a

pyridine (110-86-1) + Ethyl isocyanoacetate (2999-46-4) → 2-chloropyridine (109-09-1) + N-(2-pyridinecarbonyl)-glycine ethyl ester (39484-31-6) + (2-oxo-2-pyridin-2-yl-acetylamino)-acetic acid ethyl ester

Conditions	Yield
Stage #1: pyridine With fluorine In dichloromethane at -78 - -50℃; Stage #2: Ethyl isocyanoacetate In dichloromethane at -50 - 0℃; for 4h;	A 15% B 46% C n/a

pyridin-3-ylamine (462-08-8) + chloroform (67-66-3) → pyridine (110-86-1) + 3-Chloropyridine (626-60-8) + 2-chloropyridine (109-09-1) + pyridine-3-carbonitrile (100-54-9)

Conditions	Yield
at 550℃;	A 3% B 24% C 29% D 44%

2-Pyridone (142-08-5) → 2-chloropyridine (109-09-1)

Conditions	Yield
With N-chloro-succinimide; triphenylphosphine In 1,4-dioxane for 4h; Heating;	43%
With phosphorus pentachloride; trichlorophosphate at 130℃;

2-methoxypyridine (1628-89-3) → 2-chloropyridine (109-09-1)

Conditions	Yield
With N,N-dimethyl-formamide; trichlorophosphate at 80℃; for 2h;	40%
With N,N-dimethyl-formamide; trichlorophosphate 0 deg C, 1 h; 80 deg C, 2 h;	39%

pyridine (110-86-1) + Benzyl isocyanide (88333-03-3, 10340-91-7) → 2-chloropyridine (109-09-1) + N-benzyl-2-pyridinecarboxamide (18904-38-6) + N-benzyl-2-oxo-2-pyridin-2-yl-acetamide

Conditions	Yield
Stage #1: pyridine With fluorine In dichloromethane at -78 - -50℃; Stage #2: Benzyl isocyanide In dichloromethane at -50 - 0℃; for 4h;	A 20% B 39% C n/a

2-chloropyridine (109-09-1) + 4-methoxy-aniline (104-94-9) → N-(4-methoxyphenyl)pyridin-2-amine (78644-78-7)

Conditions	Yield
at 160℃; for 6h; Inert atmosphere; Neat (no solvent);	100%
With palladium 10% on activated carbon; sodium t-butanolate; CyJohnPhos In tert-Amyl alcohol at 110℃; Buchwald-Hartwig amination; Inert atmosphere;	73%
With sodium dispersion In tetrahydrofuran at 50℃; for 1h;	65.6%
With zinc(II) chloride at 220 - 230℃;

morpholine (110-91-8) + 2-chloropyridine (109-09-1) → 4-(pyridin-2-yl)morpholine (24255-25-2)

Conditions	Yield
With dichloro(3-chloropyridinyl)(1,3-(diisopropylphenyl)-4,5-bis(dimethylamino)imidazol-2-ylidene)palladium(II); caesium carbonate In 1,2-dimethoxyethane at 80℃; for 24h; Buchwald-Hartwig Coupling; Schlenk technique; Sealed tube; Inert atmosphere;	100%
With tris(dibenzylideneacetone)dipalladium (0); potassium tert-butylate; 1,3-bis[2,6-diisopropylphenyl]imidazolium chloride In 1,4-dioxane at 100℃; for 3h;	99%
With Pd-PEPPSI-IPrAn; potassium tert-butylate In 1,4-dioxane at 80℃; for 24h; Inert atmosphere;	99%

2-chloropyridine (109-09-1) → 2-chloro-[6-(2)H]pyridine (395071-05-3)

Conditions	Yield
Stage #1: 2-chloropyridine With n-butyllithium; BuLi-LiDMAE In hexane at -78℃; for 1h; Metallation; Stage #2: With deuteromethanol In tetrahydrofuran at -78 - 0℃; for 1h; Condensation;	100%
Stage #1: 2-chloropyridine With n-butyllithium; 2-(N,N-dimethylamino)ethanol In hexane at -78℃; for 1h; Stage #2: With diclazuril; water-d2 In hexane at -78℃; for 0.25h; Further stages.;	65%
Stage #1: 2-chloropyridine With n-butyllithium; 2-(N,N-dimethylamino)ethanol In hexane at -78℃; for 1h; Inert atmosphere; Stage #2: With deuteromethanol In hexane at -78 - 0℃; for 0.666667h; Inert atmosphere; regioselective reaction;	33%
With Crabtree's catalyst; rhodium; deuterium In tetrahydrofuran; dichloromethane at 20℃; for 4h;

2-chloropyridine (109-09-1) + LiZnPh3 → 2-phenylpyridine (1008-89-5)

Conditions	Yield
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride	100%

2-chloropyridine (109-09-1) + phenylacetylene (536-74-3) → 2-(2-phenylethynyl)pyridine (13141-42-9)

Conditions	Yield
With pyrrolidine; bis(η3-allyl-μ-chloropalladium(II)); triphenylphosphine; 1-butyl-3-methylimidazolium Tetrafluoroborate at 100℃; for 4h; Heck alkynylation; Inert atmosphere;	100%
With palladium 10% on activated carbon; potassium carbonate; XPhos In N,N-dimethyl acetamide at 110℃; for 2h; Sonogashira coupling; Inert atmosphere;	99%
With piperidine; tetrabutylammomium bromide In water at 60℃; for 5h; Sonogashira coupling;	96%

2-chloropyridine (109-09-1) + diphenylamine (122-39-4) → 2-N,N-diphenylaminopyridine (50910-08-2)

Conditions	Yield
With sodium t-butanolate; tris(dibenzylideneacetone)dipalladium (0); P(i-BuNCH2CH2)3N In toluene at 100℃; for 20h; Buchwald-Hartwig amination;	100%
With palladium diacetate; sodium t-butanolate; ruphos In neat (no solvent) at 110℃; for 12h; Buchwald-Hartwig Coupling; Green chemistry;	99%
With (1,3-bis(2,6-diisopropylphenyl)-3,4,5,6-tetrahydropyrimidin-2-ylidene)Pd(cinnamyl, 3-phenylallyl)Cl; sodium t-butanolate In neat (no solvent) at 110℃; for 12h; Buchwald-Hartwig Coupling; Inert atmosphere; Green chemistry;	99%

2-chloropyridine (109-09-1) + para-methylphenylmagnesium bromide (4294-57-9) → 2-(4-methylphenyl)pyridine (4467-06-5)

Conditions	Yield
With C32H41N12Ni2O(3+)*3F6P(1-) In tetrahydrofuran at 25℃; for 5h; Inert atmosphere; Schlenk technique;	100%
With N-heterocyclic carbene-based nickel(II) complex In tetrahydrofuran at 20℃; for 12h; Kumada reaction;	99%
With chloro(1,3-bis(pyridin-2-ylmethyl)imidazolylidene)nickel(II) hexafluorophosphate In tetrahydrofuran at 20℃; for 12h; Kumada-Corriu coupling reaction; Inert atmosphere;	99%

2-chloropyridine (109-09-1) + indole (120-72-9) + (1S,2S)-N,N'-dimethyl-1,2-diaminocyclohexane (61798-24-1, 67579-81-1, 68737-65-5, 75599-23-4, 99295-66-6, 87583-89-9) → N-(2-pyridyl)indole (3419-91-8)

Conditions	Yield
With potassium phosphate; CuI In toluene	100%

2-chloropyridine (109-09-1) + 4-fluoroboronic acid (1765-93-1) → 4-fluorophenylpyridine (58861-53-3)

Conditions	Yield
With palladium diacetate; potassium carbonate; triphenylphosphine In 1,2-dimethoxyethane Suzuki Coupling; Inert atmosphere; Reflux;	100%
With potassium phosphate tribasic trihydrate; (2-(anthracen-9-yl)-1H-inden-3-yl)dicyclohexylphosphine; palladium diacetate In water; isopropyl alcohol; toluene at 90℃; for 16h; Suzuki-Miyaura Coupling; Schlenk technique; Inert atmosphere;	90%
With (1,3-bis(2,6-diisopropylphenyl)-3,4,5,6-tetrahydropyrimidin-2-ylidene)Pd(cinnamyl, 3-phenylallyl)Cl; tetrabutylammomium bromide; sodium hydrogencarbonate In water for 1h; Catalytic behavior; Suzuki-Miyaura Coupling; Reflux;	82%

2-chloropyridine (109-09-1) + 1,1-dimethoxy-1-(4-bromophenyl)methane (24856-58-4) → 2-(4-formylphenyl)pyridine (127406-56-8)

Conditions	Yield
Stage #1: 1,1-dimethoxy-1-(4-bromophenyl)methane With iodine; magnesium In tetrahydrofuran at 30 - 35℃; for 2.5h; Stage #2: 2-chloropyridine With 1,4-di(diphenylphosphino)-butane; palladium diacetate; zinc(II) chloride In tetrahydrofuran at 70℃; for 3.5h; Conversion of starting material;	100%
Stage #1: 1,1-dimethoxy-1-(4-bromophenyl)methane With iodine; magnesium In tetrahydrofuran at 30 - 35℃; for 2.5h; Stage #2: 2-chloropyridine; 1,3-bis-(diphenylphosphino)propane; palladium diacetate; zinc(II) chloride In tetrahydrofuran at 70℃; for 3.5h; Stage #3: With hydrogenchloride; ammonia; water Conversion of starting material; more than 3 stages;	99.4%
Stage #1: 1,1-dimethoxy-1-(4-bromophenyl)methane With iodine; magnesium In tetrahydrofuran at 30 - 35℃; for 2.5h; Stage #2: 2-chloropyridine; 1,3-bis-(diphenylphosphino)propane; palladium diacetate; zinc(II) chloride In tetrahydrofuran at 50℃; for 3.5h; Stage #3: With hydrogenchloride; ammonia; water Conversion of starting material; more than 3 stages;	97%

2-chloropyridine (109-09-1) + 4,4-ethylenedioxy-piperidine (177-11-7) → (8-pyridin-2-yl)-1,4-dioxa-8-azaspiro[4.5]decane (264608-40-4)

Conditions	Yield
With [1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene](3-chloropyridyl)palladium(ll) dichloride; potassium tert-butylate In 1,2-dimethoxyethane at 20℃; for 24h; Buchwald-Hartwig Coupling; Inert atmosphere;	100%
With sodium carbonate In acetonitrile at 150℃; for 1.5h; Inert atmosphere;	50%

2-chloropyridine (109-09-1) + 1-tert-butyl-3-methyl-1H-pyrazol-5-amine (141459-53-2) → N-(1-tert-butyl-3-methyl-1H-pyrazol-5-yl)pyridin-2-amine (1416439-41-2)

Conditions	Yield
Stage #1: 2-chloropyridine; 1-tert-butyl-3-methyl-1H-pyrazol-5-amine With tetrabutylammomium bromide; sodium hydroxide In water; toluene for 0.0833333h; Inert atmosphere; Stage #2: With 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; bis(dibenzylideneacetone)-palladium(0) In water; toluene at 87℃; for 24h; Inert atmosphere;	100%

2-chloropyridine (109-09-1) + L-proline (147-85-3) → (S)-1-(pyridin-2-yl)-pyrrolidine-2-carboxylic acid (1104077-35-1)

Conditions	Yield
With caesium carbonate In toluene for 53h; Inert atmosphere; Reflux;	100%
With caesium carbonate In toluene for 53h; Reflux;	100%

2-chloropyridine (109-09-1) + 4-cyanophenol (767-00-0) → 4-(pyridin-2-yloxy)benzonitrile (270260-33-8)

Conditions	Yield
With C45H65FeNO3P2PdS; caesium carbonate In toluene at 100℃; for 24h; Inert atmosphere; Sealed tube;	100%

2-chloropyridine (109-09-1) + para-bromotoluene (106-38-7) → 2-(4-methylphenyl)pyridine (4467-06-5)

Conditions	Yield
Stage #1: para-bromotoluene With lithium Stage #2: With zinc(II) chloride Stage #3: 2-chloropyridine; nickel phosphine amido pincer complex In tetrahydrofuran; 1-methyl-pyrrolidin-2-one at 70℃; for 12h; Negishi cross-coupling; Further stages.;	99.5%
With (2,2'-bipyridine)nickel(II) dibromide; tetrabutylammonium tetrafluoroborate In N,N-dimethyl-formamide Ambient temperature; electrolysis;	80%

2-aminopyridine (504-29-0) + 2-chloropyridine (109-09-1) → di(pyridin-2-yl)amine (1202-34-2)

Conditions	Yield
With lithium amide; sodium t-butanolate In toluene at 100 - 110℃; for 1h; Buchwald-Hartwig amination; Inert atmosphere; Sealed vial;	99%
With caesium carbonate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; tris(dibenzylideneacetone)dipalladium (0) In 1,4-dioxane at 100℃; for 15h;	94%
With potassium tert-butylate In toluene at 3120℃; for 36h; Inert atmosphere;	75.5%

2-chloropyridine (109-09-1) + aniline (62-53-3) → 2-(phenylamino)pyridine (6631-37-4)

Conditions	Yield
With (1,3-bis(2,6-diisopropylphenyl)-3,4,5,6-tetrahydropyrimidin-2-ylidene)Pd(cinnamyl, 3-phenylallyl)Cl; sodium t-butanolate In neat (no solvent) at 110℃; for 12h; Buchwald-Hartwig Coupling; Inert atmosphere; Green chemistry;	99%
With indium(III) chloride In acetonitrile at 120℃; for 0.5h; Microwave irradiation; regioselective reaction;	98%
at 160℃; for 6h; Inert atmosphere; Neat (no solvent);	95%

piperidine (110-89-4) + 2-chloropyridine (109-09-1) → 2-(piperidin-1-yl)pyridine (68654-52-4)

Conditions	Yield
With (IPr)Ni(π-allyl)Cl; sodium t-butanolate In tetrahydrofuran at 25℃; for 1h; Buchwald-Hartwig reaction; Inert atmosphere;	99%
With potassium tert-butylate; C50H75ClP2Pd In tetrahydrofuran at 20℃; for 6h; Schlenk technique; Inert atmosphere;	99%
With potassium tert-butylate; ClPd[N,N-(2,6-iPr2C6H3)2-4,5-dihydroimidazol-2-yl](cinnamyl) In 1,2-dimethoxyethane at 20℃; for 0.0833333h; Buchwald-Hartwig cross-coupling reaction;	98%

2-chloropyridine (109-09-1) + N-methylaniline (100-61-8) → N-2-pyridyl-N-methylaniline (62093-17-8)

Conditions	Yield
With sodium t-butanolate; palladium diacetate In toluene at 80℃; for 11h; Buchwald-Hartwig amination;	99%
With tris-(dibenzylideneacetone)dipalladium(0); 1-methyl-2-(2-(dicyclohexylphosphino)phenyl)-1H-benzoimidazole; sodium t-butanolate In toluene at 20 - 135℃; for 20h; Buchwald-Hartwig reaction; Inert atmosphere;	99%
With [Pd(IPr*)(acac)Cl]; lithium hexamethyldisilazane In 1,4-dioxane at 20℃; for 3h; Buchwald-Hartwig cross coupling; Inert atmosphere;	99%

2-chloropyridine (109-09-1) + (2-hydroxyethyl)(methyl)amine (109-83-1) → 2-(N-methyl-N-(pyridin-2-yl)amino)ethanol (122321-04-4)

Conditions	Yield
for 9h; Reflux;	99%
With triphenylmethyl sodium at 70℃; for 8h; Temperature;	97%
at 140℃; for 0.333333h; Sealed vessel; Neat (no solvent);	92%

pyrrolidine (123-75-1) + 2-chloropyridine (109-09-1) → 2-pyrrolidinopyridine (54660-06-9)

Conditions	Yield
With (IPr)Ni(π-allyl)Cl; sodium t-butanolate In tetrahydrofuran at 25℃; for 3h; Buchwald-Hartwig reaction; Inert atmosphere;	99%
With sodium hydride; 1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazolium chloride; tert-butyl alcohol; bis(acetylacetonate)nickel(II) In tetrahydrofuran at 65℃; for 2h;	95%
With [Pd(2-aminobiphenyl)(PCyp2ArXyl2)](OMs); sodium t-butanolate In tert-butyl alcohol at 80℃; for 19h; Reagent/catalyst; Inert atmosphere; Schlenk technique;	93%

2-chloropyridine (109-09-1) + phenylboronic acid (98-80-6) → 2-phenylpyridine (1008-89-5)

Conditions	Yield
With 4-di-tert-butylphosphanyl-1,5-diphenyl-1H-[1,2,3]triazole; potassium phosphate; bis(dibenzylideneacetone)-palladium(0) In toluene at 100℃; for 12h; Suzuki-Miyaura coupling;	99%
With 4-di-tert-butylphosphanyl-1,5-diphenyl-1H-[1,2,3]triazole; potassium phosphate; bis(dibenzylideneacetone)-palladium(0) In toluene at 100℃; for 12h; Suzuki-Miyaura coupling;	99%
With potassium phosphate; palladium diacetate In tetrahydrofuran at 100℃; for 24h; Suzuki-Miyaura coupling;	99%

2-chloropyridine (109-09-1) + methyl trifluoromethanesulfonate (333-27-7) → N-methyl-2-chloropyridinium trifluoromethanesulfonate

Conditions	Yield
In toluene at 20℃; for 1h;	99%
In dichloromethane Schlenk technique; Inert atmosphere;	95%
In dichloromethane at -78 - 20℃; for 16h; Methylation;	94%
In dichloromethane at -78 - 23℃; for 12.1667h; Inert atmosphere;	93%
In dichloromethane at 20℃; for 18h;	88%

2-chloropyridine (109-09-1) + benzyl-methyl-amine (103-67-3) → N-benzyl-N-methyl-N-(2-pyridyl)amine (20173-75-5)

Conditions	Yield
With PdCl2(C3H3N2(CH3))(C3H2N2(C6H3(C3H7)2)2); potassium tert-butylate In 1,4-dioxane at 70℃; for 3h; Inert atmosphere;	99%
With C36H45Cl2N3OPd; potassium tert-butylate In 1,4-dioxane at 90℃; for 1h; Buchwald-Hartwig Coupling; Inert atmosphere; Schlenk technique;	99%
With bis[chloro(1,2,3-trihapto-allylbenzene)palladium(II)]; 4-(4-diphenylphosphinyl[2.2]paracyclophan-13-yl)morpholine; sodium t-butanolate In toluene at 110℃; for 3h; Reagent/catalyst; Buchwald-Hartwig Coupling; Inert atmosphere;	99%

2-chloropyridine (109-09-1) + 4-methylphenylboronic acid (5720-05-8) → 2-(4-methylphenyl)pyridine (4467-06-5)

Conditions	Yield
With potassium phosphate; palladium diacetate In tetrahydrofuran at 100℃; for 24h; Suzuki-Miyaura coupling;	99%
With potassium phosphate monohydrate; 1-methyl-2-(2-(dicyclohexylphosphino)phenyl)-1H-benzoimidazole; palladium diacetate In 1,4-dioxane; 1,3,5-trimethyl-benzene at 135℃; for 24h; Suzuki-Miyaura coupling; Inert atmosphere;	98%
With 4-di-tert-butylphosphanyl-1-phenyl-5-(2,6-dimethoxyphenyl)-1H-[1,2,3]triazole; potassium phosphate; tris-(dibenzylideneacetone)dipalladium(0) In toluene at 100℃; for 12h; Suzuki coupling; Inert atmosphere;	97%

2-chloropyridine (109-09-1) + 2-Methylphenylboronic acid (16419-60-6) → 2-(2-methylphenyl)pyridine (10273-89-9)

Conditions	Yield
With potassium phosphate; tris(dibenzylideneacetone)dipalladium (0) In toluene at 100℃; for 16h; Suzuki-Miyaura coupling;	99%
With [Pd(μ-Cl)Cl(IPr)]2; sodium methylate In ethanol at 20℃; Suzuki-Miyaura reaction;	99%
With ethanol; [PdCl2(N,N'-bis(2,6-diisopropylphenyl)imidazol-2-ylidene)(P(OMe)3)]; sodium hydroxide at 80℃; for 24h; Suzuki-Miyaura reaction; Inert atmosphere;	99%

2-chloropyridine (109-09-1) + 4-methoxyphenyl magnesium bromide (13139-86-1) → 4-(2-pyridinyl)anisole (5957-90-4)

Conditions	Yield
With [1,3-bis(2,6-diisopropylphenyl)-imidazolium][Ni(PPh3)Cl3] In tetrahydrofuran at 30℃; for 5h; Kumada Cross-Coupling; Schlenk technique; Inert atmosphere;	99%
With ((C6H4)(PPh2)(NCHPhP(O)Ph2))NiCl In diethyl ether at 25℃; for 12h; Kumada cross-coupling; Inert atmosphere;	98%
Stage #1: 2-chloropyridine With Ni(PPh3)(1,3-di-tert-butylimidazol-2-ylidene)Br2 In tetrahydrofuran at 0℃; for 0.0333333h; Inert atmosphere; Schlenk technique; Stage #2: 4-methoxyphenyl magnesium bromide In tetrahydrofuran at 0 - 25℃; for 3h; Inert atmosphere; Schlenk technique;	97%

2-chloropyridine (109-09-1) + benzophenone hydrazone (5350-57-2) → 2-[2-(diphenylmethylene)hydrazinyl]pyridine (19848-68-1)

Conditions	Yield
With (R)-(-)-1-[(S)-2-(dicyclohexylphosphino)ferrocenyl]ethyl di-t-butylphosphine; sodium t-butanolate; palladium diacetate In 1,2-dimethoxyethane at 70℃; for 16h;	99%
With 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; sodium t-butanolate; palladium diacetate In toluene at 100℃; for 16h;	70%

2-chloropyridine (109-09-1) + C24H20Zn(2-)*2Li(1+) → 2-phenylpyridine (1008-89-5)

Conditions	Yield
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride	99%

2-chloropyridine (109-09-1) + 4-methoxyphenylboronic acid (5720-07-0) → 4-(2-pyridinyl)anisole (5957-90-4)

Conditions	Yield
With NHC-Pd(II)-Im; potassium tert-butylate In water at 80℃; for 12h; Suzuki-Miyaura coupling;	99%
With potassium phosphate tribasic trihydrate; PdCl2(C3H3N2(CH3))(C3H2N2(C6H3(C3H7)2)2) In tetrahydrofuran; water at 20℃; for 24h; Suzuki-Miyaura coupling reaction; Inert atmosphere;	99%
With potassium phosphate tribasic trihydrate; (2-mesityl-1H-inden-3-yl)dicyclohexyl phosphine; palladium diacetate; Aliquat 336 In water at 20 - 100℃; for 8h; Suzuki-Miyaura Coupling; Inert atmosphere;	98%

Upstream product

• 52200-48-3 3-bromo-2-chloropyridine 
• 109-65-9 1-bromo-butane 
• 109-72-8 n-butyllithium 
• 142-08-5 2-hydroxypyridin 
• 53939-30-3 5-bromo-2-chloropyridine 
• 5029-67-4 2-iodopyridine 
• 151-10-0 1,3-Dimethoxybenzene 
• 150-78-7 1,4-dimethoxybezene 
• 108-88-3 toluene 
• 108-90-7 chlorobenzene 
• 100-66-3 methoxybenzene 
• 91-16-7 1,2-dimethoxybenzene 
• 93-58-3 benzoic acid methyl ester 
• 462-08-8 pyridin-3-ylamine 

Downstream Products

• 109847-88-3 [1,2']bipyridylium; picrate 
• 1202-34-2 di(pyridin-2-yl)amine 
• 148-65-2 Chlorothen 
• 100-70-9 2-Cyanopyridine 
• 5005-41-4 3,4-dimethoxyphenyl-(2-pyridyl)acetonitrile 
• 123517-65-7 (2-chloro-phenyl)-[2]pyridyl-acetonitrile 
• 96461-91-5 (2,4-dichloro-phenyl)-[2]pyridyl-acetonitrile 
• 106167-23-1 (3-methylsulfanyl-phenyl)-pyridin-2-yl-amine 
• 7477-88-5 bis-{4-[(2-chloro-pyridinio)-acetyl]-phenyl}-ether ; dibromide 
• 6271-67-6 2-chloro-1-[2-oxo-2-(5,6,7,8-tetrahydro-[2]naphthyl)-ethyl]-pyridinium; bromide 
• 71486-42-5 4-(N,N-dimethylamino)-2-phenyl-2-(2-pyridyl)butanenitrile 
• 139764-31-1 2-methyl-2-phenyl-2-(pyridin-2-yl)acetonitrile 
• 19395-42-7 2-phenyl-2-pyridin-2-yl-butyronitrile 
• 27361-16-6 2-butoxypyridine 

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