3-Chloropyridine supplier | CasNO.626-60-8

Name
3-Chloropyridine
EINECS 210-955-7
CAS No. 626-60-8
Article Data63
CAS DataBase
Density 1.2 g/cm³
Solubility Soluble in water 10 g/L.
Melting Point -0.5oC
Formula C₅H₄ClN
Boiling Point 143.1 °C at 760 mmHg
Molecular Weight 113.546
Flash Point 49.7 °C
Transport Information UN 2822
Appearance clear colorless to yellow liquid
Safety 36/37/39-26
Risk Codes 20/21/22-36/37/38
Molecular Structure
Hazard Symbols Xn,Xi
Synonyms m-Chloropyridine;Pyridine, 3-chloro-;5-20-05-00406 (Beilstein Handbook Reference);3-Pyridinyl chloride;
PSA 12.89000
LogP 1.73500

Synthetic route

: 462-08-8
pyridin-3-ylamine

: 626-60-8
3-Chloropyridine

Conditions

Conditions	Yield
With tert-Butyl thionitrate; copper dichloride In acetonitrile at 25℃; for 6h;	95%
With hydrogenchloride; copper; sodium nitrite Diazotization;

: 1851-22-5
3-chloropyridine-N-oxide

: 626-60-8
3-Chloropyridine

Conditions

Conditions	Yield
With hydrogen; triethyl phosphite In isopropyl alcohol at 100℃; under 4500.45 Torr; for 12h; Glovebox; chemoselective reaction;	93%
With aluminium(III) iodide In acetonitrile for 6h; Heating;	80%
With 1,1,2,2-tetrabutyl-1,2-dichloro distannane In tetrahydrofuran for 1h; Heating;	75%

: 626-55-1
3-Bromopyridine

: 626-60-8
3-Chloropyridine

Conditions

Conditions	Yield
With trans-bis(glycinato)copper(II) monohydrate; tetramethlyammonium chloride In ethanol at 100℃; for 20h; Finkelstein Reaction; Schlenk technique; Inert atmosphere;	90%
With copper(I) oxide; tetramethlyammonium chloride; L-proline In ethanol at 110℃; for 36h; Inert atmosphere;	89 %Chromat.
With iron(III) chloride; sodium chloride In acetonitrile for 4h; Kinetics; Irradiation; Green chemistry;

: 29955-47-3
3,5-Dinitro-N-phenyl-benzimidoyl chloride

A: 626-60-8
3-Chloropyridine

B: 7461-51-0
3,5-dinitro-(N-phenyl)benzamide

C: 16527-88-1
Pyridine 1-oxide hydrochloride

Conditions

Conditions	Yield
With pyridine N-oxide In 1,2-dichloro-ethane for 24h; Heating;	A 3.7% B 89.8% C n/a

...Expand

: 87282-02-8
2,4-Dinitro-N-phenyl-benzimidoyl chloride

A: 626-60-8
3-Chloropyridine

B: 22978-56-9
2,4-dinitro-benzoic acid anilide

C: 16527-88-1
Pyridine 1-oxide hydrochloride

Conditions

Conditions	Yield
With pyridine N-oxide In 1,2-dichloro-ethane for 24h; Heating;	A 19.4% B 85.3% C n/a

...Expand

: 30435-62-2
C19H14N2O2

A: 626-60-8
3-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 82% B n/a C n/a D n/a

...Expand

: 694-59-7
pyridine N-oxide

: 57761-80-5
N-Phenyl-o-nitrobenzimidoyl chloride

A: 626-60-8
3-Chloropyridine

B: 2385-27-5
N-phenyl-2-nitrobenzamide

C: 16527-88-1
Pyridine 1-oxide hydrochloride

D: 87281-92-3
2-Nitro-N-phenyl-N-pyridin-2-yl-benzamide

Conditions

Conditions	Yield
In 1,2-dichloro-ethane for 24h; Heating;	A 29.8% B 66% C n/a D 30.7%

...Expand

: 57761-80-5
N-Phenyl-o-nitrobenzimidoyl chloride

A: 626-60-8
3-Chloropyridine

B: 2385-27-5
N-phenyl-2-nitrobenzamide

C: 16527-88-1
Pyridine 1-oxide hydrochloride

D: 87281-92-3
2-Nitro-N-phenyl-N-pyridin-2-yl-benzamide

Conditions

Conditions	Yield
With pyridine N-oxide In 1,2-dichloro-ethane for 24h; Heating;	A 29.8% B 66% C n/a D 30.7%

...Expand

: 694-59-7
pyridine N-oxide

: 5509-90-0
3-nitro-N-phenyl-benzimidoyl chloride

A: 626-60-8
3-Chloropyridine

B: 2243-73-4
5-nitrobenzanilide

C: 16527-88-1
Pyridine 1-oxide hydrochloride

D: 87281-93-4
2-pyridine

Conditions

Conditions	Yield
In 1,2-dichloro-ethane for 24h; Heating;	A 41.3% B 62.7% C n/a D 30.1%

...Expand

: 694-59-7
pyridine N-oxide

A: 626-60-8
3-Chloropyridine

B: 2243-73-4
5-nitrobenzanilide

C: 16527-88-1
Pyridine 1-oxide hydrochloride

D: 87281-93-4
2-pyridine

Conditions

Conditions	Yield
With N-Phenyl-m-nitrobenzimidoyl chloride In 1,2-dichloro-ethane for 24h; Heating;	A 41.3% B 62.7% C n/a D 30.1%

...Expand

: 5509-90-0
3-nitro-N-phenyl-benzimidoyl chloride

A: 626-60-8
3-Chloropyridine

B: 2243-73-4
5-nitrobenzanilide

C: 16527-88-1
Pyridine 1-oxide hydrochloride

D: 87281-93-4
2-pyridine

Conditions

Conditions	Yield
With pyridine N-oxide In 1,2-dichloro-ethane for 24h; Heating;	A 41.3% B 62.7% C n/a D 30.1%

...Expand

: 694-59-7
pyridine N-oxide

: 51619-51-3
2-methyl-N-phenyl-benzimidoyl chloride

A: 626-60-8
3-Chloropyridine

B: 7055-03-0
2-methyl-N-phenylbenzamide

C: 16527-88-1
Pyridine 1-oxide hydrochloride

D: 87281-82-1
2-Methyl-N-phenyl-N-pyridin-2-yl-benzamide

Conditions

Conditions	Yield
In 1,2-dichloro-ethane for 24h; Heating;	A 17.9% B 39.3% C n/a D 58.6%

...Expand

: 51619-51-3
2-methyl-N-phenyl-benzimidoyl chloride

A: 626-60-8
3-Chloropyridine

B: 7055-03-0
2-methyl-N-phenylbenzamide

C: 16527-88-1
Pyridine 1-oxide hydrochloride

D: 87281-82-1
2-Methyl-N-phenyl-N-pyridin-2-yl-benzamide

Conditions

Conditions	Yield
With pyridine N-oxide In 1,2-dichloro-ethane for 24h; Heating;	A 17.9% B 39.3% C n/a D 58.6%

...Expand

: 694-59-7
pyridine N-oxide

: 4903-36-0
N-phenyl-benzimidoyl chloride

A: 626-60-8
3-Chloropyridine

B: 93-98-1
N-phenyl benzoyl amide

C: 16527-88-1
Pyridine 1-oxide hydrochloride

D: 20107-78-2
N-phenyl-N-(2-pyridinyl)benzamide

Conditions

Conditions	Yield
In 1,2-dichloro-ethane for 24h; Product distribution; Mechanism; Heating; var. N-Phenylarenimidoyl chlorides + fluorides;	A 28.1% B 36.8% C n/a D 57.2%

...Expand

: 694-59-7
pyridine N-oxide

: 87282-00-6
2,4-Dichloro-N-phenyl-benzimidoyl chloride

A: 626-60-8
3-Chloropyridine

B: 6043-39-6
2,4-dichloro-N-phenylbenzamide

C: 16527-88-1
Pyridine 1-oxide hydrochloride

D: 87281-90-1
2,4-Dichloro-N-phenyl-N-pyridin-2-yl-benzamide

Conditions

Conditions	Yield
In 1,2-dichloro-ethane for 24h; Heating;	A 30.5% B 54.9% C n/a D 39.5%

...Expand

: 87282-00-6
2,4-Dichloro-N-phenyl-benzimidoyl chloride

A: 626-60-8
3-Chloropyridine

B: 6043-39-6
2,4-dichloro-N-phenylbenzamide

C: 16527-88-1
Pyridine 1-oxide hydrochloride

D: 87281-90-1
2,4-Dichloro-N-phenyl-N-pyridin-2-yl-benzamide

Conditions

Conditions	Yield
With pyridine N-oxide In 1,2-dichloro-ethane for 24h; Heating;	A 30.5% B 54.9% C n/a D 39.5%

...Expand

: 694-59-7
pyridine N-oxide

: 87281-98-9
N-Phenyl-2,4-dimethoxybenzimidoyl chloride

A: 626-60-8
3-Chloropyridine

B: 1718-94-1
2,4-dimethoxy-benzoic acid anilide

C: 16527-88-1
Pyridine 1-oxide hydrochloride

D: 87308-16-5
2,4-Dimethoxy-N-phenyl-N-pyridin-2-yl-benzamide

Conditions

Conditions	Yield
In 1,2-dichloro-ethane for 24h; Heating;	A 10.4% B 54% C n/a D 45.5%

...Expand

: 87281-98-9
N-Phenyl-2,4-dimethoxybenzimidoyl chloride

A: 626-60-8
3-Chloropyridine

B: 1718-94-1
2,4-dimethoxy-benzoic acid anilide

C: 16527-88-1
Pyridine 1-oxide hydrochloride

D: 87308-16-5
2,4-Dimethoxy-N-phenyl-N-pyridin-2-yl-benzamide

Conditions

Conditions	Yield
With pyridine N-oxide In 1,2-dichloro-ethane for 24h; Heating;	A 10.4% B 54% C n/a D 45.5%

...Expand

: 694-59-7
pyridine N-oxide

: 87281-96-7
3,5-Dimethyl-N-phenyl-benzimidoyl chloride

A: 626-60-8
3-Chloropyridine

B: 16527-88-1
Pyridine 1-oxide hydrochloride

C: 87282-03-9
3,5-dimethyl-N-phenylbenzamide

D: 87281-85-4
3,5-Dimethyl-N-phenyl-N-pyridin-2-yl-benzamide

Conditions

Conditions	Yield
In 1,2-dichloro-ethane for 24h; Heating;	A 24.2% B n/a C 45.3% D 53.6%

...Expand

: 87281-96-7
3,5-Dimethyl-N-phenyl-benzimidoyl chloride

A: 626-60-8
3-Chloropyridine

B: 16527-88-1
Pyridine 1-oxide hydrochloride

C: 87282-03-9
3,5-dimethyl-N-phenylbenzamide

D: 87281-85-4
3,5-Dimethyl-N-phenyl-N-pyridin-2-yl-benzamide

Conditions

Conditions	Yield
With pyridine N-oxide In 1,2-dichloro-ethane for 24h; Heating;	A 24.2% B n/a C 45.3% D 53.6%

...Expand

: 694-59-7
pyridine N-oxide

: 87281-95-6
2,4-Dimethyl-N-phenyl-benzimidoyl chloride

A: 626-60-8
3-Chloropyridine

B: 5180-83-6
2,4-dimethyl-benzoic acid anilide

C: 16527-88-1
Pyridine 1-oxide hydrochloride

D: 87281-84-3
2,4-Dimethyl-N-phenyl-N-pyridin-2-yl-benzamide

Conditions

Conditions	Yield
In 1,2-dichloro-ethane for 24h; Heating;	A 9.8% B 44.8% C n/a D 51.5%

...Expand

: 87281-95-6
2,4-Dimethyl-N-phenyl-benzimidoyl chloride

A: 626-60-8
3-Chloropyridine

B: 5180-83-6
2,4-dimethyl-benzoic acid anilide

C: 16527-88-1
Pyridine 1-oxide hydrochloride

D: 87281-84-3
2,4-Dimethyl-N-phenyl-N-pyridin-2-yl-benzamide

Conditions

Conditions	Yield
With pyridine N-oxide In 1,2-dichloro-ethane for 24h; Heating;	A 9.8% B 44.8% C n/a D 51.5%

...Expand

: 694-59-7
pyridine N-oxide

: 87281-94-5
3-methyl-N-phenyl-benzimidoyl chloride

A: 626-60-8
3-Chloropyridine

B: 23099-05-0
3-methyl-N-phenylbenzamide

C: 16527-88-1
Pyridine 1-oxide hydrochloride

D: 87281-83-2
3-Methyl-N-phenyl-N-pyridin-2-yl-benzamide

Conditions

Conditions	Yield
In 1,2-dichloro-ethane for 24h; Heating;	A 21.6% B 45.9% C n/a D 51.4%

...Expand

: 87281-94-5
3-methyl-N-phenyl-benzimidoyl chloride

A: 626-60-8
3-Chloropyridine

B: 23099-05-0
3-methyl-N-phenylbenzamide

C: 16527-88-1
Pyridine 1-oxide hydrochloride

D: 87281-83-2
3-Methyl-N-phenyl-N-pyridin-2-yl-benzamide

Conditions

Conditions	Yield
With pyridine N-oxide In 1,2-dichloro-ethane for 24h; Heating;	A 21.6% B 45.9% C n/a D 51.4%

...Expand

: 694-59-7
pyridine N-oxide

: 87281-99-0
3,5-Dimethoxy-N-phenyl-benzimidoyl chloride

A: 626-60-8
3-Chloropyridine

B: 87282-04-0
3,5-dimethoxy-N-phenylbenzamide

C: 16527-88-1
Pyridine 1-oxide hydrochloride

D: 87281-87-6
3,5-Dimethoxy-N-phenyl-N-pyridin-2-yl-benzamide

Conditions

Conditions	Yield
In 1,2-dichloro-ethane for 24h; Heating;	A 28.8% B 50.9% C n/a D 43.7%

...Expand

: 87281-99-0
3,5-Dimethoxy-N-phenyl-benzimidoyl chloride

A: 626-60-8
3-Chloropyridine

B: 87282-04-0
3,5-dimethoxy-N-phenylbenzamide

C: 16527-88-1
Pyridine 1-oxide hydrochloride

D: 87281-87-6
3,5-Dimethoxy-N-phenyl-N-pyridin-2-yl-benzamide

Conditions

Conditions	Yield
With pyridine N-oxide In 1,2-dichloro-ethane for 24h; Heating;	A 28.8% B 50.9% C n/a D 43.7%

...Expand

: 694-59-7
pyridine N-oxide

: 87282-01-7
3,4-Dichloro-N-phenyl-benzimidoyl chloride

A: 626-60-8
3-Chloropyridine

B: 6043-42-1
3,4-dichloro-N-phenylbenzamide

C: 16527-88-1
Pyridine 1-oxide hydrochloride

D: 87281-91-2
3,4-Dichloro-N-phenyl-N-pyridin-2-yl-benzamide

Conditions

Conditions	Yield
In 1,2-dichloro-ethane for 24h; Heating;	A 22.6% B 39.5% C n/a D 48.9%

...Expand

: 87282-01-7
3,4-Dichloro-N-phenyl-benzimidoyl chloride

A: 626-60-8
3-Chloropyridine

B: 6043-42-1
3,4-dichloro-N-phenylbenzamide

C: 16527-88-1
Pyridine 1-oxide hydrochloride

D: 87281-91-2
3,4-Dichloro-N-phenyl-N-pyridin-2-yl-benzamide

Conditions

Conditions	Yield
With pyridine N-oxide In 1,2-dichloro-ethane for 24h; Heating;	A 22.6% B 39.5% C n/a D 48.9%

...Expand

: 694-59-7
pyridine N-oxide

: 55832-04-7
N-phenyl-m-chlorobenzimidoyl chloride

A: 626-60-8
3-Chloropyridine

B: 6832-92-4
3-chloro-N-phenylbenzamide

C: 16527-88-1
Pyridine 1-oxide hydrochloride

D: 87281-89-8
3-Chloro-N-phenyl-N-pyridin-2-yl-benzamide

Conditions

Conditions	Yield
In 1,2-dichloro-ethane for 24h; Heating;	A 32.3% B 48.7% C n/a D 45.3%

...Expand

: 55832-04-7
N-phenyl-m-chlorobenzimidoyl chloride

A: 626-60-8
3-Chloropyridine

B: 6832-92-4
3-chloro-N-phenylbenzamide

C: 16527-88-1
Pyridine 1-oxide hydrochloride

D: 87281-89-8
3-Chloro-N-phenyl-N-pyridin-2-yl-benzamide

Conditions

Conditions	Yield
With pyridine N-oxide In 1,2-dichloro-ethane for 24h; Heating;	A 32.3% B 48.7% C n/a D 45.3%

...Expand

: 626-60-8
3-Chloropyridine

: 98-80-6
phenylboronic acid

: 1008-88-4
3-phenylpyridine

Conditions

Conditions	Yield
With potassium phosphate; bis(tricyclohexylphosphine)nickel(II) dichloride In tert-Amyl alcohol for 12h; Solvent; Suzuki-Miyaura Coupling; Heating;	100%
With cesiumhydroxide monohydrate; 2-dicyclohexylphosphino-2′,6′-diisopropoxybiphenyl; palladium diacetate In water; butan-1-ol at 25℃; for 0.25h; Solvent; Reagent/catalyst; Suzuki-Miyaura Coupling; Inert atmosphere;	100%
With potassium phosphate; catacxium A; palladium diacetate In toluene at 100℃; for 20h; Suzuki reaction;	99%

: 626-60-8
3-Chloropyridine

: 16419-60-6
2-Methylphenylboronic acid

: 90395-49-6
3-(p-methylphenyl)pyridine

Conditions

Conditions	Yield
With potassium phosphate monohydrate; R-Phos; bis(dibenzylideneacetone)-palladium(0) In 1,4-dioxane at 100℃; for 0.333333h; Suzuki-Miyaura reaction; Inert atmosphere;	100%
With NHC-Pd(II)-Im; potassium tert-butylate In water at 80℃; for 12h; Suzuki-Miyaura coupling;	99%
With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; potassium phosphate; palladium diacetate In tetrahydrofuran; toluene at 100℃; for 10h; Suzuki-Miyaura reaction;	97%

: 626-60-8
3-Chloropyridine

: (2,3-dimethylphenyl)zinc chloride

: 3-(2,3-dimethylphenyl)pyridine

Conditions

Conditions	Yield
With tris(dibenzylideneacetone)dipalladium (0); ruphos In tetrahydrofuran at 70℃; for 15h; Negishi coupling;	100%

: 626-60-8
3-Chloropyridine

starch-iodine: starch-iodine

: 1851-22-5
3-chloropyridine-N-oxide

Conditions

Conditions	Yield
With dihydrogen peroxide; paraformaldehyde In methanol; acetic acid	100%

: 626-60-8
3-Chloropyridine

: 1256768-10-1
3-isopropyl-1-phenyl-1H-imidazol-3-ium iodide

: 3375-31-3
palladium diacetate

: [PdI2(CN(C6H5)CHCHN(CH(CH3)2))(NC5H4Cl)]

Conditions

Conditions	Yield
With K2CO3; KI In neat (no solvent) (Ar); mixt. of Pd salt, imidazolium salt, K2CO3, KI and chloropyridine was heated at 80°C for 16 h; cooled to room temp.; evapd. (vac.); dissolved in CH2Cl2; filtered through Celite; evapd.; washed (pentane); elem. anal.;	100%

...Expand

: 626-60-8
3-Chloropyridine

: 1256768-12-3
[PdI2(CC(C6H5)N(CH3)C(C6H5)N(CH(CH3)2))]2

: 1256768-15-6
[PdI2(CC(C6H5)N(CH3)C(C6H5)N(CH(CH3)2))(NC5H4Cl)]

Conditions

Conditions	Yield
In dichloromethane (Ar); chloropyridine was added to Pd complex in CH2Cl2; stirred at room temp. for 2 h; evapd. (vac.); washed (pentane); elem. anal.;	100%

: 626-60-8
3-Chloropyridine

: 75-03-6
ethyl iodide

: 79698-48-9
3-chloro-4-ethylpyridine

Conditions

Conditions	Yield
Stage #1: 3-Chloropyridine With lithium diisopropyl amide In tetrahydrofuran; n-heptane; ethylbenzene at -78℃; for 1h; Inert atmosphere; Stage #2: ethyl iodide In tetrahydrofuran; n-heptane; ethylbenzene at -78 - 20℃; Inert atmosphere; regioselective reaction;	100%

: 110-85-0
piperazine

: 626-60-8
3-Chloropyridine

: 1,4-di(pyridin-3-yl)piperazine

Conditions

Conditions	Yield
With C48H56ClN3Pd; potassium tert-butylate In tetrahydrofuran at 70℃; for 24h; Schlenk technique; Inert atmosphere;	100%

: 626-60-8
3-Chloropyridine

: μ2-chlorido[3-(2-(piperidinyl)pyrimidin-4-yl-5-ido)-1-mesityl-1Himidazolylidene]palladium(II) dimer

: chlorido[3-(2-(piperidinyl)pyrimidin-4-yl-5-ido)-1-mesityl-1H-imidazolylidene](3-chloropyridine)palladium(II)

Conditions

Conditions	Yield
for 0.0833333h; Reflux;	100%

: 626-60-8
3-Chloropyridine

: 557-42-6
zinc(II) thiocyanate

: Cd(NCS)2(3-chloropyridine)2

Conditions

Conditions	Yield
In water	99.4%

: 110-91-8
morpholine

: 626-60-8
3-Chloropyridine

: 92670-29-6
N-(3-pyridyl)morpholine

Conditions

Conditions	Yield
With (C5H5)Fe(C5H3C(CH3)NC6H4CH3)PdCl(CN2(C6H3(CH(CH3)2)2)2C2H2); potassium tert-butylate In 1,4-dioxane at 110℃; for 1h; Catalytic behavior; Time; Reagent/catalyst; Temperature; Buchwald-Hartwig Coupling; Inert atmosphere; Schlenk technique;	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%
With C28H29Cl2N3OPd; potassium tert-butylate In toluene at 110℃; for 15h; Buchwald-Hartwig Coupling; Schlenk technique; Inert atmosphere;	99%

: 626-60-8
3-Chloropyridine

: 100-61-8
N-methylaniline

: N-methyl-N-phenylpyridin-3-amine

Conditions

Conditions	Yield
With palladium diacetate; sodium t-butanolate; ruphos In neat (no solvent) at 110℃; for 12h; Buchwald-Hartwig Coupling; Green chemistry;	99%
With tris-(dibenzylideneacetone)dipalladium(0); dicyclohexyl(2',4',6'-triisopropyl-[1,1':3',1''-terphenyl]-2-yl)phosphane; sodium t-butanolate In tetrahydrofuran at 100℃; for 15h; Solvent; Sealed tube;	99%
With dichloro(3-chloropyridinyl)(1,3-(diisopropylphenyl)-4,5-bis(dimethylamino)imidazol-2-ylidene)palladium(II); potassium tert-butylate In 1,4-dioxane at 80℃; for 18h; Catalytic behavior; Solvent; Temperature; Reagent/catalyst; Buchwald-Hartwig Coupling; Inert atmosphere; Schlenk technique; Sealed tube;	98%

: 626-60-8
3-Chloropyridine

: 5720-05-8
4-methylphenylboronic acid

: 4423-09-0
4-(3-pyridyl)toluene

Conditions

Conditions	Yield
Stage #1: 3-Chloropyridine; 4-methylphenylboronic acid With palladium diacetate; (R)-6-dicyclohexylphoshino-6'-diphenylphosphino-3,3'-dimethoxy-2,2',4,4'-tetramethyl-1,1'-biphenyl In dodecane; butan-1-ol at 25℃; for 0.0833333h; Suzuki-Miyaura Coupling; Inert atmosphere; Glovebox; Stage #2: With cesiumhydroxide monohydrate In dodecane; water; butan-1-ol at 80℃; for 4h; Suzuki-Miyaura Coupling; Inert atmosphere; Glovebox;	99%
With potassium phosphate; 2-(dicyclohexylphosphino)biphenyl based D-gluconamide; palladium diacetate In water at 80℃; for 16h;	96%
With potassium phosphate; chloro(crotyl)(2-dicyclohexylphosphino-2’,4’,6’-triisopropybiphenyl)palladium(II) In tetrahydrofuran; water at 20℃; for 2h; Reagent/catalyst; Suzuki-Miyaura Coupling; Schlenk technique; Inert atmosphere;	95%

: 626-60-8
3-Chloropyridine

: 62-53-3
aniline

: 5024-68-0
Phenyl-pyridin-3-yl-amine

Conditions

Conditions	Yield
With tris-(dibenzylideneacetone)dipalladium(0); dicyclohexyl(2',4',6'-triisopropyl-[1,1':3',1''-terphenyl]-2-yl)phosphane; sodium t-butanolate In tetrahydrofuran at 100℃; for 15h; Solvent; Sealed tube;	99%
With tris(dibenzylideneacetone)dipalladium (0); potassium tert-butylate; 1,3-bis[2,6-diisopropylphenyl]imidazolium chloride In 1,4-dioxane at 100℃; for 3h;	98%
With C48H56ClN3Pd; potassium tert-butylate In tetrahydrofuran at 70℃; for 24h; Catalytic behavior; Reagent/catalyst; Temperature; Time; Schlenk technique; Inert atmosphere;	98%

: 626-60-8
3-Chloropyridine

: 960-16-7
tributylphenylstannane

: 1008-88-4
3-phenylpyridine

Conditions

Conditions	Yield
With P(i-BuNCH2CH2)3N; cesium fluoride; tris(dibenzylideneacetone)dipalladium (0) In 1,4-dioxane at 100 - 110℃; for 36h; Stille reaction;	99%
With tris(dibenzylideneacetone)dipalladium (0); cesium fluoride; 2,8,9-tris(2-methylpropyl)-2,5,8,9-tetraaza-1-phosphabicyclo[3.3.3]undecane In 1,4-dioxane at 110℃; for 36h; Stille cross-coupling;	99%
With Pd(OAc)2/XPhos (1:3); cesium fluoride In 1,4-dioxane at 100℃; for 4h; Stille coupling; Inert atmosphere;	91%

: 626-60-8
3-Chloropyridine

: 110-86-1
pyridine

Conditions

Conditions	Yield
With ammonium formate In water; isopropyl alcohol at 20℃; for 3h;	99%
With ammonium formate In water at 20℃; for 6h;	99%
With potassium fluoride; polymethylhydrosiloxane; palladium diacetate In tetrahydrofuran at 20℃; for 1h;	97 % Spectr.

: 626-60-8
3-Chloropyridine

: 111-86-4
n-Octylamine

: N-(1-octyl)-3-aminopyridine

Conditions

Conditions	Yield
With sodium t-butanolate; palladium diacetate; (R)-(-)-1-[(S)-2-(dicyclohexylphosphino)ferrocenyl]ethyl di-t-butylphosphine In 1,2-dimethoxyethane at 100℃; for 24h;	99%
With bis(1,5-cyclooctadiene)nickel (0); sodium t-butanolate In toluene at 80℃; for 20h; Inert atmosphere; Sealed tube;	94%
With (R)-(-)-1-[(S)-2-(dicyclohexylphosphino)ferrocenyl]ethyl di-t-butylphosphine; sodium t-butanolate; palladium diacetate In 1,2-dimethoxyethane at 70℃; for 24h;	93%

: 626-60-8
3-Chloropyridine

: 5350-57-2
benzophenone hydrazone

: 3-(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%

: 626-60-8
3-Chloropyridine

: 60-35-5
acetamide

: 5867-45-8
N-(pyridin-3-yl)acetamide

Conditions

Conditions	Yield
With potassium phosphate; tris-(dibenzylideneacetone)dipalladium(0) In tert-butyl alcohol at 110℃; for 4h;	99%
With 5-(di-tert-butylphosphino)-1′, 3′, 5′-triphenyl-1′H-[1,4′]bipyrazole; bis[chloro(1,2,3-trihapto-allylbenzene)palladium(II)]; potassium carbonate In 1,4-dioxane at 90℃; for 18h; Buchwald-Hartwig Coupling; Inert atmosphere; Glovebox;	82%

: 626-60-8
3-Chloropyridine

: 98-92-0
nicotinamide

: 13160-06-0
N-(pyridin-3-yl)pyridine-3-carboxamide

Conditions

Conditions	Yield
With 2-di-tertbutylphosphino-3,4,5,6-tetramethyl-2',4',6'-triisopropyl-1,1'-biphenyl; potassium phosphate; water; palladium diacetate In tert-butyl alcohol at 110℃; for 3h; Inert atmosphere;	99%
With potassium phosphate; tris-(dibenzylideneacetone)dipalladium(0) In tert-butyl alcohol at 110℃; for 24h;	97%

: 626-60-8
3-Chloropyridine

: 90-04-0
2-methoxy-phenylamine

: 1028223-83-7
N-methyl-N-phenylpyridin-3-amine

Conditions

Conditions	Yield
With sodium t-butanolate; palladium diacetate; (R)-(-)-1-[(S)-2-(dicyclohexylphosphino)ferrocenyl]ethyl di-t-butylphosphine In 1,2-dimethoxyethane at 100℃; for 24h;	99%
With (C5H5)Fe(C5H3C(CH3)NC6H4CH3)PdCl(CN2(C6H3(CH(CH3)2)2)2C2H2); potassium tert-butylate In 1,4-dioxane at 110℃; for 8h; Buchwald-Hartwig Coupling; Inert atmosphere; Schlenk technique;	91%
With C29H37O2P; bis(dibenzylideneacetone)-palladium(0); sodium t-butanolate In neat (no solvent) at 110℃; for 24h; Buchwald-Hartwig Coupling; Sealed tube; Inert atmosphere;	49%

: 626-60-8
3-Chloropyridine

: 108-98-5
thiophenol

: 28856-77-1
3-phenylthiopyridine

Conditions

Conditions	Yield
With tetrakis(tri-p-tolylphosphite)nickel(0); potassium tert-butylate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; zinc In toluene at 110℃; for 16h; Sealed tube; Inert atmosphere;	99%
With copper(I) oxide; caesium carbonate; ethyl 2-oxocyclohexane carboxylate In dimethyl sulfoxide at 80℃; for 24h;	77%
With potassium hydroxide In water for 8h; Reflux;	69%
With 1,1'-bis-(diphenylphosphino)ferrocene; bis(η3-allyl-μ-chloropalladium(II)); sodium t-butanolate In toluene at 120℃; for 17h;	65%
With fac-tris[2-phenylpyridinato-C2,N]iridium(III); caesium carbonate In N,N-dimethyl-formamide at 25℃; for 24h; Schlenk technique; Inert atmosphere; Irradiation;	61%

: 626-60-8
3-Chloropyridine

: potassium phenyltrifluoborate

: 1008-88-4
3-phenylpyridine

Conditions

Conditions	Yield
With N-methyl-2-phenyl-3-(dicyclohexylphosphino)-1H-indole; palladium diacetate; triethylamine; sodium t-butanolate In water at 100℃; for 18h; Suzuki-Miyaura Coupling; Inert atmosphere; Schlenk technique;	99%
With potassium phosphate monohydrate; 1-methyl-2-(2-(dicyclohexylphosphino)phenyl)-1H-benzoimidazole; bis(dibenzylideneacetone)-palladium(0) In toluene; tert-butyl alcohol at 135℃; for 24h; Suzuki coupling; Inert atmosphere;	98%
With C16H16Cl2N2O4Pd2; tetrabutylammomium bromide; potassium carbonate In water for 16h; Reflux; Darkness; Inert atmosphere;	73%
With water; palladium diacetate; sodium carbonate at 100℃; for 15h; Suzuki Coupling; Green chemistry;	10%

: 626-60-8
3-Chloropyridine

: 13922-41-3
1-Naphthylboronic acid

: 189193-21-3
3-(naphthalen-1-yl)pyridine

Conditions

Conditions	Yield
With NHC-Pd(II)-Im; potassium tert-butylate In water at 80℃; for 12h; Suzuki-Miyaura coupling;	99%
With dichloro bis((p-dimethylaminophenyl)-ϖ-di-tert-butylphosphine)palladium(II); triethylamine In water at 40℃; for 24h; Suzuki-Miyaura coupling; Inert atmosphere;	97%
Stage #1: 3-Chloropyridine; 1-Naphthylboronic acid With palladium diacetate; (R)-6-dicyclohexylphoshino-6'-diphenylphosphino-3,3'-dimethoxy-2,2',4,4'-tetramethyl-1,1'-biphenyl In dodecane; butan-1-ol at 25℃; for 0.0833333h; Suzuki-Miyaura Coupling; Inert atmosphere; Glovebox; Stage #2: With cesiumhydroxide monohydrate In dodecane; water; butan-1-ol at 80℃; for 4h; Suzuki-Miyaura Coupling; Inert atmosphere; Glovebox;	97%

: 626-60-8
3-Chloropyridine

: 42599-16-6
(E)-1-octen-1-ylboronic acid

: (E)-3-(oct-1-en-1-yl)pyridine

Conditions

Yield

With chloro-(1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene)(2-(N-acetylamino)-phenyl-C1,O)-palladium(II); sodium hydroxide In tetrahydrofuran; methanol at 20℃; for 18h; Suzuki-Miyaura coupling; Inert atmosphere; Sealed tube;

99%

Stage #1: 3-Chloropyridine; (E)-1-octen-1-ylboronic acid With palladium diacetate; (R)-6-dicyclohexylphoshino-6'-diphenylphosphino-3,3'-dimethoxy-2,2',4,4'-tetramethyl-1,1'-biphenyl In dodecane; butan-1-ol at 25℃; for 0.0833333h; Suzuki-Miyaura Coupling; Inert atmosphere; Glovebox;
Stage #2: With cesiumhydroxide monohydrate In dodecane; water; butan-1-ol at 80℃; for 4h; Suzuki-Miyaura Coupling; Inert atmosphere; Glovebox;

98%

: 626-60-8
3-Chloropyridine

: 81745-84-8
2-thienylzinc chloride

: 21298-53-3
3-thiophen-2-yl-pyridine

Conditions

Conditions	Yield
With tris-(dibenzylideneacetone)dipalladium(0); XPhos In tetrahydrofuran at 65℃; for 2h; Negishi cross-coupling; Inert atmosphere;	99%

: 626-60-8
3-Chloropyridine

: 75-09-2
dichloromethane

: Tp(Me2)Ir((E)-C(CO2Me)=CH(Co2Me))(H2O)(benzoic acid(-H))

: Tp(Me2)Ir((E)-C(CO2Me)=CH(Co2Me))(m-chloromopyridine)(benzoic acid(-H))*0.5CH2Cl2

Conditions

Conditions	Yield
In dichloromethane N2 or Ar; Ir compd. and m-Brpyridine (1:3 molar ratio) stirred in pyridine at 60°C for 5 h; evapd., recrystd. (hexane, -20°C), elem. anal.;	99%

...Expand

: 626-60-8
3-Chloropyridine

: 1268340-97-1
4-trifluoroboratomethylpiperazine-1-carboxylic acid tert-butyl ester internal salt

: 150812-36-5
tert-butyl 4-(pyridin-3-ylmethyl)piperazine-1-carboxylate

Conditions

Conditions	Yield
With palladium diacetate; caesium carbonate; XPhos In tetrahydrofuran; water at 80℃; for 45h; Suzuki-Miyaura coupling;	99%

: 626-60-8
3-Chloropyridine

: 5720-07-0
4-methoxyphenylboronic acid

: 5958-02-1
3-(4-methoxyphenyl)pyridine

Conditions

Conditions	Yield
With NHC-Pd(II)-Im; potassium tert-butylate In water at 80℃; for 12h; Suzuki-Miyaura coupling;	99%
With potassium phosphate; 1,3-bis[(diphenylphosphino)propane]dichloronickel(II) In 1,4-dioxane at 100 - 110℃; Suzuki-Miyaura coupling; Inert atmosphere;	98%
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;	96%

: 626-60-8
3-Chloropyridine

: 5720-07-0
4-methoxyphenylboronic acid

: 91258-43-4
3-(4-methoxybenzyl)pyridine

Conditions

Yield

Stage #1: 3-Chloropyridine; 4-methoxyphenylboronic acid With palladium diacetate; (R)-6-dicyclohexylphoshino-6'-diphenylphosphino-3,3'-dimethoxy-2,2',4,4'-tetramethyl-1,1'-biphenyl In dodecane; butan-1-ol at 25℃; for 0.0833333h; Suzuki-Miyaura Coupling; Inert atmosphere; Glovebox;
Stage #2: With cesiumhydroxide monohydrate In dodecane; water; butan-1-ol at 80℃; for 4h; Suzuki-Miyaura Coupling; Glovebox; Inert atmosphere;

99%

3-Chloropyridine Consensus Reports

Reported in EPA TSCA Inventory.

3-Chloropyridine Specification

This product is an organic compound with the formula C₅H₄ClN. The systematic name of this chemical is 3-Chloropyridine. It belongs to the product categories of Blocks; Pyridines; Pyridine; Chlorine Compounds; Miscellaneous Compounds; Chloropyridines; Halopyridines; C5 Heterocyclic Building Blocks; Halogenated Heterocycles; Heterocyclic Building Blocks; Pyridine series. Its EINECS number is 210-955-7. With the CAS registry number 626-60-8, it is also named as 3-Pyridinyl chloride. Its classification code is Mutation data. In addition, the molecular weight is 113.54. It is used as a pharmaceutical intermediate. It should be sealed and stored in a cool and dry place. Moreover, it should be protected from oxides.

Physical properties of 3-Chloropyridine are: (1)ACD/LogP: 1.57; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 1.57; (4)ACD/LogD (pH 7.4): 1.57; (5)ACD/BCF (pH 5.5): 9.15; (6)ACD/BCF (pH 7.4): 9.18; (7)ACD/KOC (pH 5.5): 169.65; (8)ACD/KOC (pH 7.4): 170.12; (9)#H bond acceptors: 1; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 0; (12)Polar Surface Area: 12.89 Å²; (13)Index of Refraction: 1.53; (14)Molar Refractivity: 29.23 cm³; (15)Molar Volume: 94.6 cm³; (16)Polarizability: 11.59×10^-24cm³; (17)Surface Tension: 39.5 dyne/cm; (18)Density: 1.2 g/cm³; (19)Flash Point: 49.7 °C; (20)Enthalpy of Vaporization: 36.46 kJ/mol; (21)Boiling Point: 143.1 °C at 760 mmHg; (22)Vapour Pressure: 6.8 mmHg at 25°C.

Preparation: this chemical can be prepared by pyridin-3-ylamine at the temperature of 25 °C. This reaction will need reagents t-butyl thionitrate, CuCl₂ and solvent acetonitrile with the reaction time of 6 hours. The yield is about 95%.

3-Chloropyridine can be prepared by pyridin-3-ylamine at the temperature of 25 °C

Uses of 3-Chloropyridine: it can be used to produce 3-chloro-pyridine-1-oxide at the ambient temperature. It will need reagents MeReO₃, H₂O₂ and solvents H₂O, CH₂Cl₂ with the reaction time of 17 hours. The yield is about 84%.

3-Chloropyridine can be used to produce 3-chloro-pyridine-1-oxide at the ambient temperature

When you are using this chemical, please be cautious about it as the following:
This chemical is harmful by inhalation, in contact with skin and if swallowed. 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. When using it, you need wear suitable protective clothing, gloves and eye/face protection.

You can still convert the following datas into molecular structure:
(1)SMILES: Clc1cccnc1
(2)Std. InChI: InChI=1S/C5H4ClN/c6-5-2-1-3-7-4-5/h1-4H
(3)Std. InChIKey: PWRBCZZQRRPXAB-UHFFFAOYSA-N

The toxicity data is as follows:

Organism	Test Type	Route	Reported Dose (Normalized Dose)	Effect	Source
bird - wild	LD50	oral	750mg/kg (750mg/kg)		Archives of Environmental Contamination and Toxicology. Vol. 12, Pg. 355, 1983.
mouse	LD50	intraperitoneal	235mg/kg (235mg/kg)	BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) BEHAVIORAL: ANTIPSYCHOTIC LIVER: FATTY LIVER DEGERATION	Toxicology and Applied Pharmacology. Vol. 11, Pg. 361, 1967.

Product Name

3-Chloropyridine

Synthetic route

3-Chloropyridine Consensus Reports

3-Chloropyridine Specification

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