2-Chloropyridine supplier | CasNO.109-09-1

Name
2-Chloropyridine
EINECS 203-646-3
CAS No. 109-09-1
Article Data114
CAS DataBase
Density 1.2 g/cm³
Solubility 27 g/L (20 °C) in water
Melting Point -46 °C
Formula C₅H₄ClN
Boiling Point 170 °C at 760 mmHg
Molecular Weight 113.546
Flash Point 65 °C
Transport Information UN 2822 6.1/PG 2
Appearance clear colourless to light yellow liquid
Safety 26-36/37/39-45-28A-27
Risk Codes 23/24/25-36/37/38
Molecular Structure
Hazard Symbols T
Synonyms AI3-19231;Pyridine, 2-chloro-;2-Chloropyridine [UN2822] [Poison];alpha-Chloropyridine;NSC 4649;CCRIS 1724;o-Chloropyridine;UN2822;
PSA 12.89000
LogP 1.73500

Synthetic route

: 142-08-5
2-hydroxypyridin

: 109-09-1
2-chloropyridine

Conditions

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.

: 20295-64-1
2-chloropyridine N-oxide hydrochloride

: 109-09-1
2-chloropyridine

Conditions

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

: 504-29-0
2-aminopyridine

: 109-09-1
2-chloropyridine

Conditions

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.

: 2402-95-1
2-chloropyridine-N-oxide

: 109-09-1
2-chloropyridine

Conditions

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%

: 109-04-6
2-bromo-pyridine

: 109-09-1
2-chloropyridine

Conditions

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.

: 694-59-7
pyridine N-oxide

: 109-09-1
2-chloropyridine

Conditions

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: Pyridin-Palladium(II)-chlorid-Komplex

: 109-09-1
2-chloropyridine

Conditions

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

: 110-86-1
pyridine

: 109-09-1
2-chloropyridine

Conditions

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;

: 2127-03-9
2,2'-dipyridyldisulphide

: 109-09-1
2-chloropyridine

Conditions

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

: 93845-11-5
C19H14N2O2

A: 109-09-1
2-chloropyridine

B: 119-61-9
benzophenone

C: 67-72-1
hexachloroethane

D: 983-79-9
benzophenone azine

Conditions

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

...Expand

: 2127-03-9
2,2'-dipyridyldisulphide

A: 109-09-1
2-chloropyridine

B: 66715-65-9
pyridine-2-sulfonyl chloride

Conditions

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

: 2587-00-0
2,6-dichloropyridine N-oxide

A: 109-09-1
2-chloropyridine

B: 2402-78-0
2,6-dichloropyridine

Conditions

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

: 110-86-1
pyridine

: 78948-09-1
acetyl hypofluorite

A: 109-09-1
2-chloropyridine

B: 3847-19-6
2-acetoxypyridine

Conditions

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

...Expand

: 110-86-1
pyridine

A: 109-09-1
2-chloropyridine

B: 3847-19-6
2-acetoxypyridine

Conditions

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%

: 2402-95-1
2-chloropyridine-N-oxide

A: 110-86-1
pyridine

B: 109-09-1
2-chloropyridine

Conditions

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

: 110-86-1
pyridine

: 1984-23-2
p-nitrophenyl isocyanide

A: 109-09-1
2-chloropyridine

B: 61349-99-3
pyridine-2-carboxylic acid (4-nitro-phenyl)amide

C: N-(4-nitro-phenyl)-2-oxo-2-pyridin-2-yl-acetamide

Conditions

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

...Expand

: 98-98-6
2-Picolinic acid

: 109-09-1
2-chloropyridine

Conditions

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.

: 110-86-1
pyridine

: 2769-64-4
n-butyl isonitrile

A: 109-09-1
2-chloropyridine

B: 10354-51-5
N-butyl-pyridine-2-carboxylic acid amide

C: N-butyl-2-oxo-2-pyridin-2-yl-acetamide

Conditions

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

...Expand

: 107263-95-6
N-fluoropyridinium triflate

A: 109-09-1
2-chloropyridine

B: 65007-00-3
pyridin-2-yl trifluoromethanesulfonate

C: 372-48-5
2-fluoropyridine

Conditions

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.

...Expand

Pyridin-Palladium(II)-chlorid-Komplex: Pyridin-Palladium(II)-chlorid-Komplex

A: 109-09-1
2-chloropyridine

B: 2402-77-9
2,3-dichloro-pyridine

C: 16063-70-0
2,3,5-trichloropyridine

Conditions

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

...Expand

: 110-86-1
pyridine

: 931-53-3
Cyclohexyl isocyanide

A: 109-09-1
2-chloropyridine

B: 10354-50-4
N-picolinoylcyclohexylamine

C: N-cyclohexyl-2-oxo-2-pyridin-2-yl-acetamide

Conditions

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

...Expand

: 110-86-1
pyridine

: 2170-06-1
1-Phenyl-2-(trimethylsilyl)acetylene

A: 109-09-1
2-chloropyridine

B: 13141-42-9
2-(2-phenylethynyl)pyridine

C: 372-48-5
2-fluoropyridine

Conditions

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;

...Expand

: 110-86-1
pyridine

: 3-trifluoromethylphenyl isonitrile

A: 109-09-1
2-chloropyridine

B: 61350-01-4
N-[3-(trifluoromethyl)phenyl]-2-pyridinecarboxamide

C: 2-oxo-2-pyridin-2-yl-N-(3-trifluoromethyl-phenyl)-acetamide

Conditions

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

...Expand

: 110-86-1
pyridine

: 119072-55-8, 7188-38-7
tert-butylisonitrile

A: 109-09-1
2-chloropyridine

B: 71653-50-4
pyridine-2-carboxylic acid N-tert-butylamide

C: N-tert-butyl-2-oxo-2-pyridin-2-yl-acetamide

Conditions

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

...Expand

: 110-86-1
pyridine

: 1197040-29-1
phenyl isocyanate

A: 109-09-1
2-chloropyridine

B: 10354-53-7
N-phenylpicolinamide

C: 57152-71-3
2-Oxo-N-phenyl-2-pyridin-2-yl-acetamide

Conditions

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

...Expand

: 110-86-1
pyridine

: 2999-46-4
Ethyl isocyanoacetate

A: 109-09-1
2-chloropyridine

B: 39484-31-6
N-(2-pyridinecarbonyl)-glycine ethyl ester

C: (2-oxo-2-pyridin-2-yl-acetylamino)-acetic acid ethyl ester

Conditions

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

...Expand

: 462-08-8
pyridin-3-ylamine

: 67-66-3
chloroform

A: 110-86-1
pyridine

B: 626-60-8
3-Chloropyridine

C: 109-09-1
2-chloropyridine

D: 100-54-9
pyridine-3-carbonitrile

Conditions

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

...Expand

: 142-08-5
2-Pyridone

: 109-09-1
2-chloropyridine

Conditions

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

: 1628-89-3
2-methoxypyridine

: 109-09-1
2-chloropyridine

Conditions

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%

: 110-86-1
pyridine

: 88333-03-3, 10340-91-7
Benzyl isocyanide

A: 109-09-1
2-chloropyridine

B: 18904-38-6
N-benzyl-2-pyridinecarboxamide

C: N-benzyl-2-oxo-2-pyridin-2-yl-acetamide

Conditions

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

...Expand

: 109-09-1
2-chloropyridine

: 104-94-9
4-methoxy-aniline

: 78644-78-7
N-(4-methoxyphenyl)pyridin-2-amine

Conditions

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℃;

: 110-91-8
morpholine

: 109-09-1
2-chloropyridine

: 24255-25-2
4-(pyridin-2-yl)morpholine

Conditions

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%

: 109-09-1
2-chloropyridine

: 395071-05-3
2-chloro-[6-(2)H]pyridine

Conditions

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;

: 109-09-1
2-chloropyridine

: LiZnPh3

: 1008-89-5
2-phenylpyridine

Conditions

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

: 109-09-1
2-chloropyridine

: 536-74-3
phenylacetylene

: 13141-42-9
2-(2-phenylethynyl)pyridine

Conditions

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%

: 109-09-1
2-chloropyridine

: 122-39-4
diphenylamine

: 50910-08-2
2-N,N-diphenylaminopyridine

Conditions

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%

: 109-09-1
2-chloropyridine

: 4294-57-9
para-methylphenylmagnesium bromide

: 4467-06-5
2-(4-methylphenyl)pyridine

Conditions

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%

: 109-09-1
2-chloropyridine

: 120-72-9
indole

: 61798-24-1, 67579-81-1, 68737-65-5, 75599-23-4, 99295-66-6, 87583-89-9
(1S,2S)-N,N'-dimethyl-1,2-diaminocyclohexane

: 3419-91-8
N-(2-pyridyl)indole

Conditions

Conditions	Yield
With potassium phosphate; CuI In toluene	100%

...Expand

: 109-09-1
2-chloropyridine

: 1765-93-1
4-fluoroboronic acid

: 58861-53-3
4-fluorophenylpyridine

Conditions

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%

: 109-09-1
2-chloropyridine

: 24856-58-4
1,1-dimethoxy-1-(4-bromophenyl)methane

: 127406-56-8
2-(4-formylphenyl)pyridine

Conditions

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%

: 109-09-1
2-chloropyridine

: 177-11-7
4,4-ethylenedioxy-piperidine

: 264608-40-4
(8-pyridin-2-yl)-1,4-dioxa-8-azaspiro[4.5]decane

Conditions

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%

: 109-09-1
2-chloropyridine

: 141459-53-2
1-tert-butyl-3-methyl-1H-pyrazol-5-amine

: 1416439-41-2
N-(1-tert-butyl-3-methyl-1H-pyrazol-5-yl)pyridin-2-amine

Conditions

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%

: 109-09-1
2-chloropyridine

: 147-85-3
L-proline

: 1104077-35-1
(S)-1-(pyridin-2-yl)-pyrrolidine-2-carboxylic acid

Conditions

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

: 109-09-1
2-chloropyridine

: 767-00-0
4-cyanophenol

: 270260-33-8
4-(pyridin-2-yloxy)benzonitrile

Conditions

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

: 109-09-1
2-chloropyridine

: 106-38-7
para-bromotoluene

: 4467-06-5
2-(4-methylphenyl)pyridine

Conditions

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%

: 504-29-0
2-aminopyridine

: 109-09-1
2-chloropyridine

: 1202-34-2
di(pyridin-2-yl)amine

Conditions

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%

: 109-09-1
2-chloropyridine

: 62-53-3
aniline

: 6631-37-4
2-(phenylamino)pyridine

Conditions

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%

: 110-89-4
piperidine

: 109-09-1
2-chloropyridine

: 68654-52-4
2-(piperidin-1-yl)pyridine

Conditions

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%

: 109-09-1
2-chloropyridine

: 100-61-8
N-methylaniline

: 62093-17-8
N-2-pyridyl-N-methylaniline

Conditions

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%

: 109-09-1
2-chloropyridine

: 109-83-1
(2-hydroxyethyl)(methyl)amine

: 122321-04-4
2-(N-methyl-N-(pyridin-2-yl)amino)ethanol

Conditions

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%

: 123-75-1
pyrrolidine

: 109-09-1
2-chloropyridine

: 54660-06-9
2-pyrrolidinopyridine

Conditions

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%

: 109-09-1
2-chloropyridine

: 98-80-6
phenylboronic acid

: 1008-89-5
2-phenylpyridine

Conditions

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%

: 109-09-1
2-chloropyridine

: 333-27-7
methyl trifluoromethanesulfonate

: N-methyl-2-chloropyridinium trifluoromethanesulfonate

Conditions

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%

: 109-09-1
2-chloropyridine

: 103-67-3
benzyl-methyl-amine

: 20173-75-5
N-benzyl-N-methyl-N-(2-pyridyl)amine

Conditions

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%

: 109-09-1
2-chloropyridine

: 5720-05-8
4-methylphenylboronic acid

: 4467-06-5
2-(4-methylphenyl)pyridine

Conditions

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%

: 109-09-1
2-chloropyridine

: 16419-60-6
2-Methylphenylboronic acid

: 10273-89-9
2-(2-methylphenyl)pyridine

Conditions

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%

: 109-09-1
2-chloropyridine

: 13139-86-1
4-methoxyphenyl magnesium bromide

: 5957-90-4
4-(2-pyridinyl)anisole

Conditions

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%

: 109-09-1
2-chloropyridine

: 5350-57-2
benzophenone hydrazone

: 19848-68-1
2-[2-(diphenylmethylene)hydrazinyl]pyridine

Conditions

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%

: 109-09-1
2-chloropyridine

: C24H20Zn(2-)*2Li(1+)

: 1008-89-5
2-phenylpyridine

Conditions

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

: 109-09-1
2-chloropyridine

: 5720-07-0
4-methoxyphenylboronic acid

: 5957-90-4
4-(2-pyridinyl)anisole

Conditions

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%

2-Chloropyridine Chemical Properties

Molecular structure of 2-Chloropyridine (CAS NO.109-09-1) is:

Product Name: 2-Chloropyridine
CAS Registry Number: 109-09-1
IUPAC Name: 2-Chloropyridine
Molecular Weight: 113.54496 [g/mol]
Molecular Formula: C₅H₄ClN
XLogP3: 1.2
H-Bond Donor: 0
H-Bond Acceptor: 1
EINECS: 203-646-3
Melting Point: -46 °C
Water Solubility: 27 g/L (20 °C)
Surface Tension: 39.5 dyne/cm
Density: 1.2 g/cm³
Flash Point: 65 °C
Enthalpy of Vaporization: 38.97 kJ/mol
Boiling Point: 170 °C at 760 mmHg
Vapour Pressure: 1.99 mmHg at 25°C
Product Categories: Pyridines, Pyrimidines, Purines and Pteredines; Pyridines derivates; Chloropyridines; Halopyridines; C5Heterocyclic Building Blocks; Halogenated Heterocycles; Heterocyclic Building Blocks; Pyridines

2-Chloropyridine Uses

2-Chloropyridine (CAS NO.109-09-1) can be primarily used to make fungicides and insecticides in industry. It also serves to make antihistamines and antiarrythymics for pharmaceutical purposes.

2-Chloropyridine Toxicity Data With Reference

Organism	Test Type	Route	Reported Dose (Normalized Dose)	Effect	Source
bird - wild	LD50	oral	1gm/kg (1000mg/kg)		Archives of Environmental Contamination and Toxicology. Vol. 12, Pg. 355, 1983.
mouse	LD50	intraperitoneal	130mg/kg (130mg/kg)	BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) BEHAVIORAL: ANTIPSYCHOTIC LIVER: FATTY LIVER DEGERATION	Toxicology and Applied Pharmacology. Vol. 11, Pg. 361, 1967.
mouse	LD50	oral	110mg/kg (110mg/kg)	BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) BEHAVIORAL: ANTIPSYCHOTIC LIVER: OTHER CHANGES	Toxicology and Applied Pharmacology. Vol. 11, Pg. 361, 1967.
rabbit	LD50	intraperitoneal	48mg/kg (48mg/kg)	BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) LIVER: FATTY LIVER DEGERATION BEHAVIORAL: ANTIPSYCHOTIC	Toxicology and Applied Pharmacology. Vol. 11, Pg. 361, 1967.
rabbit	LD50	skin	64mg/kg (64mg/kg)	LIVER: OTHER CHANGES	Toxicology and Applied Pharmacology. Vol. 11, Pg. 361, 1967.
rat	LCLo	inhalation	100ppm/4H (100ppm)	BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) BEHAVIORAL: ANTIPSYCHOTIC LIVER: OTHER CHANGES	Toxicology and Applied Pharmacology. Vol. 11, Pg. 361, 1967.

2-Chloropyridine Consensus Reports

Reported in EPA TSCA Inventory.

2-Chloropyridine Safety Profile

Safty information about 2-Chloropyridine (CAS NO.109-09-1) is:
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⁻, NO_x, and phosgene.
Hazard Codes: Toxic T
Risk Statements: 23/24/25-36/37/38
R23/24/25:Toxic by inhalation, in contact with skin and if swallowed.
R36/37/38:Irritating to eyes, respiratory system and skin.
Safety Statements: 26-36/37/39-45-28A-27
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection.
S45:In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.)
S28:After contact with skin, wash immediately with plenty of soap-suds.
S27:Take off immediately all contaminated clothing.
RIDADR: UN 2822 6.1/PG 2
WGK Germany: 3
RTECS: US5950000
Hazard Note: Toxic
HazardClass: 6.1
PackingGroup: II
HS Code: 29333999

2-Chloropyridine Specification

2-Chloropyridine , its cas register number is 109-09-1. It also can be called AI3-19231 ; CCRIS 1724 ; NSC 4649 ; alpha-Chloropyridine ; o-Chloropyridine ; Pyridine, 2-chloro- ; 2-Chloropyridine [UN2822] [Poison] ; UN2822 . It is a clear colourless to light yellow liquid. It slightly soluble in water and denser than water. And it reacts with nucleophiles to generate pyridine derivatives substituted at the second and fourth carbons on the heterocycle.

Product Name

2-Chloropyridine

Synthetic route

2-Chloropyridine Chemical Properties

2-Chloropyridine Uses

2-Chloropyridine Toxicity Data With Reference

2-Chloropyridine Consensus Reports

2-Chloropyridine Safety Profile

2-Chloropyridine Specification

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