2-Chloro-4-cyanopyridine supplier

Name
2-Chloro-4-cyanopyridine
EINECS -0
CAS No. 33252-30-1
Article Data12
CAS DataBase
Density 1.33 g/cm³
Solubility
Melting Point 69-73 °C(lit.)
Formula C₆H₃ClN₂
Boiling Point 218.9 °C at 760 mmHg
Molecular Weight 138.556
Flash Point 86.2 °C
Transport Information
Appearance white or light yellow crystal
Safety 26-36-36/37/39
Risk Codes 36/37/38-20/21/22
Molecular Structure
Hazard Symbols Xn,Xi
Synonyms 2-Chloroisonicotinonitrile;2-chloropyridine-4-carbonitrile;
PSA 36.68000
LogP 1.60668

Synthetic route

: 2-chloro-4-cyanopyridine 1-oxide

: 33252-30-1
2-chloro-4-pyridinenitrile

Conditions

Conditions	Yield
With ammonium formate; silica gel; zinc In methanol at 20℃; for 0.166667h; chemoselective reaction;	89%

: 14906-59-3
4-cyanopyridine N-oxide

: 33252-30-1
2-chloro-4-pyridinenitrile

Conditions

Conditions	Yield
With trichlorophosphate at 100℃; for 24h;	69%
With triethylamine; trichlorophosphate In 1,2-dichloro-ethane for 4h;	117.5 g

: 14432-12-3
4-Amino-2-chloropyridine

: 151-50-8
potassium cyanide

: 33252-30-1
2-chloro-4-pyridinenitrile

Conditions

Conditions	Yield
With sulfuric acid; copper(II) sulfate; sodium nitrite Diazotization.weitere Reagentien: Kupfer-Pulver, wss. Na2CO3;

: 38557-82-3
4-pyridine carboxamide 1-oxide

: 33252-30-1
2-chloro-4-pyridinenitrile

Conditions

Conditions	Yield
With phosphorus pentachloride; trichlorophosphate

: 38557-82-3
4-pyridine carboxamide 1-oxide

: 10026-13-8, 874483-75-7
phosphorus pentachloride

: 10025-87-3, 12599-09-6, 63736-95-8
trichlorophosphate

: 33252-30-1
2-chloro-4-pyridinenitrile

...Expand

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

: 33252-30-1
2-chloro-4-pyridinenitrile

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: concentrated sulfuric acid; nitric acid 2: acetic acid; iron-powder / anschliessend mit Zink-Pulver unter Zusatz von wenig wss. HgCl2 3: NaNO2; aqueous H2SO4; CuSO4 / Diazotization.weitere Reagentien: Kupfer-Pulver, wss. Na2CO3 View Scheme

: 14432-16-7
2-chloro-4-nitropyridine-N-oxide

: 33252-30-1
2-chloro-4-pyridinenitrile

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: acetic acid; iron-powder / anschliessend mit Zink-Pulver unter Zusatz von wenig wss. HgCl2 2: NaNO2; aqueous H2SO4; CuSO4 / Diazotization.weitere Reagentien: Kupfer-Pulver, wss. Na2CO3 View Scheme

: 1453-82-3
isonicotinamide

: 33252-30-1
2-chloro-4-pyridinenitrile

Conditions

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

: 14906-59-3
4-cyanopyridine N-oxide

: 7440-44-0
pyrographite

: 33252-30-1
2-chloro-4-pyridinenitrile

Conditions

Conditions	Yield
With sodium hydroxide; trichlorophosphate In n-heptane

: 14906-59-3
4-cyanopyridine N-oxide

: 10026-13-8, 874483-75-7
phosphorus pentachloride

: 33252-30-1
2-chloro-4-pyridinenitrile

Conditions

Conditions	Yield
With trichlorophosphate	8.4 g (24%)

: 33252-30-1
2-chloro-4-pyridinenitrile

: 7486-35-3
tri-n-butyl(vinyl)tin

: 2-vinylpyrimidine-4-carbonitrile

Conditions

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0) In toluene for 2h; Reflux; Inert atmosphere;	100%

: 33252-30-1
2-chloro-4-pyridinenitrile

: 128796-39-4
4-trifluoromethylphenylboronic acid

: 1257437-26-5
2-[4-(trifluoromethyl)phenyl]pyridine 4-carbonitrile

Conditions

Conditions	Yield
With [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II); sodium carbonate In 1,4-dioxane; water at 120℃; for 0.333333h; Microwave irradiation;	99%
With caesium carbonate; palladium diacetate; XPhos In 1,4-dioxane at 100℃; for 4h; Sealed tube;	78%
Stage #1: 2-chloro-4-pyridinenitrile; 4-trifluoromethylphenylboronic acid With sodium hydrogencarbonate In 1,2-dimethoxyethane; water at 20℃; for 5h; Stage #2: With tetrakis(triphenylphosphine) palladium(0) In 1,2-dimethoxyethane; water at 100℃;	47%
With tetrakis(triphenylphosphine) palladium(0); sodium hydrogencarbonate In 1,2-dimethoxyethane; water at 100℃; Inert atmosphere;	47%
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In tetrahydrofuran; water at 80℃; Inert atmosphere;

: 33252-30-1
2-chloro-4-pyridinenitrile

: 100859-84-5
2-chloro-4-pyridine carboxamide

Conditions

Conditions	Yield
With manganese(IV) oxide; water In isopropyl alcohol at 60℃; under 5171.62 Torr; for 0.2h;	98%
With water at 110℃; for 20h;	95%
With ammonium hydroxide; cesiumhydroxide monohydrate at 100℃; for 1h; Schlenk technique; Sealed tube;	89%
With cesium hydroxide; water; dimethyl sulfoxide at 30℃; for 24h; Temperature; Schlenk technique; Green chemistry;	88%
Stage #1: 2-chloro-4-pyridinenitrile With caesium carbonate In 2-pyrrolidinon at 130℃; for 2h; Sealed vessel; Stage #2: With methanol In 2-pyrrolidinon; dichloromethane at 20℃; Filtering through Celite pad;	72%

: 33252-30-1
2-chloro-4-pyridinenitrile

: 1196152-14-3
2-chloro-4-(1H-tetrazole-5-yl)pyridine

Conditions

Conditions	Yield
With sodium azide; ammonium cerium (IV) nitrate In N,N-dimethyl-formamide at 110℃; for 6h; Inert atmosphere; Green chemistry;	98%
With sodium azide In N,N-dimethyl-formamide at 100℃; for 4h; Reagent/catalyst; Temperature;	97%
With sodium azide; gold In N,N-dimethyl-formamide at 80℃; for 1h; Reagent/catalyst; Inert atmosphere;	96%

: 33252-30-1
2-chloro-4-pyridinenitrile

: 124-68-5
2-Amino-2-methyl-1-propanol

: 93639-38-4
2-(2-chloropyridin-4-yl)-4,5-dihydro-4,4-dimethyloxazole

Conditions

Conditions	Yield
With sodium carbonate In methanol at 80℃; for 15h; Inert atmosphere; Schlenk technique;	98%

: 33252-30-1
2-chloro-4-pyridinenitrile

: 1679-18-1
4-Chlorophenylboronic acid

: 1415250-86-0
2-(4-chlorophenyl)isonicotinonitrile

Conditions

Conditions	Yield
With bis-triphenylphosphine-palladium(II) chloride; sodium carbonate In water; acetonitrile at 80℃; for 1h; Inert atmosphere;	98%
With bis-triphenylphosphine-palladium(II) chloride; sodium carbonate In water; acetonitrile for 1h; Suzuki-Miyaura Coupling; Inert atmosphere; Reflux;	96%
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In tetrahydrofuran; water at 80℃; Inert atmosphere;

: 33252-30-1
2-chloro-4-pyridinenitrile

: 1066-54-2
trimethylsilylacetylene

: 4-cyano-2-[2-(trimethylsilyl)ethynyl]pyridine

Conditions

Conditions	Yield
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine In acetonitrile at 60℃; for 3h; Inert atmosphere;	98%

: 33252-30-1
2-chloro-4-pyridinenitrile

: 91447-89-1
2-chloropyridine-4-carbothioamide

Conditions

Conditions	Yield
With triethanolamine; hydrogen sulfide In ethanol	97%
With triethanolamine; ethanol; hydrogen sulfide

: 33252-30-1
2-chloro-4-pyridinenitrile

: 141-43-5
ethanolamine

: 2-(2-chloropyridin-4-yl)-4,5-dihydrooxazole

Conditions

Conditions	Yield
With sodium carbonate In methanol at 80℃; for 15h; Inert atmosphere; Schlenk technique;	97%

: 33252-30-1
2-chloro-4-pyridinenitrile

: 139301-27-2
4-trifluoromethoxyphenylboronic acid

: 1257437-27-6
2-[4-(trifluoromethoxy)phenyl]pyridine-4-carbonitrile

Conditions

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); sodium hydrogencarbonate In 1,2-dimethoxyethane; water at 100℃; for 12h; Inert atmosphere;	96%
With tetrakis(triphenylphosphine) palladium(0); sodium hydrogencarbonate In 1,2-dimethoxyethane; water at 100℃; for 12h; Inert atmosphere;	96%
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In tetrahydrofuran; water at 80℃; Inert atmosphere;

: 33252-30-1
2-chloro-4-pyridinenitrile

: 713-68-8
meta-phenoxyphenol

: 2-chloro-6-(3-phenoxyphenoxy)isonicotinonitrile

Conditions

Conditions	Yield
With caesium carbonate; N,N-dimethylethylenediamine at 20℃; for 16h;	96%

: 33252-30-1
2-chloro-4-pyridinenitrile

: 108-95-2
phenol

: 81249-44-7
2-phenoxyisonicotinonitrile

Conditions

Conditions	Yield
Stage #1: phenol With caesium carbonate; N,N-dimethylethylenediamine at 20℃; for 0.5h; Stage #2: 2-chloro-4-pyridinenitrile at 80℃; for 2h;	95%
Stage #1: phenol With caesium carbonate In N,N-dimethyl acetamide at 20℃; for 0.5h; Stage #2: 2-chloro-4-pyridinenitrile In N,N-dimethyl acetamide at 80℃; for 20h;	95%
With caesium carbonate In 1-methyl-pyrrolidin-2-one at 80℃; for 16h;	57.95%
Stage #1: 2-chloro-4-pyridinenitrile; phenol With potassium carbonate In N,N-dimethyl-formamide at 120℃; Stage #2: With hydrogenchloride In water Cooling;

: 33252-30-1
2-chloro-4-pyridinenitrile

: 82019-89-4
2-chloropyridine-4-carboximidamide hydrochloride

Conditions

Conditions	Yield
With trimethylaluminum; ammonium chloride In toluene at 90℃;	95%

: 3-methoxyazetidine hydrochloride

: 33252-30-1
2-chloro-4-pyridinenitrile

: 2-(3-methoxyazetidin-1-yl)isonicotinonitrile

Conditions

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In 1-methyl-pyrrolidin-2-one at 120℃; for 2h; Microwave irradiation; Inert atmosphere;	95%

: 33252-30-1
2-chloro-4-pyridinenitrile

: 1177559-74-8
1,1-dimethylethyl (2S)-2-methyl-4-{[3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]methyl}-1-piperazinecarboxylate

: 1177559-73-7
1,1-dimethylethyl (2S)-4-{[3-(4-cyano-2-pyridinyl)phenyl]methyl}-2-methyl-1-piperazinecarboxylate

Conditions

Conditions	Yield
With potassium carbonate; tetrakis(triphenylphosphine) palladium(0) In 1,4-dioxane; water at 140℃; for 0.5h;	94%
With potassium carbonate; tetrakis(triphenylphosphine) palladium(0) In 1,4-dioxane; water at 140℃; for 0.5h; Microwave irradiation;	94%

: 33252-30-1
2-chloro-4-pyridinenitrile

: 74-89-5
methylamine

: 137225-13-9
2-(methylamino)isonicotinonitrile

Conditions

Conditions	Yield
In tetrahydrofuran; 1-methyl-pyrrolidin-2-one at 120℃; for 2h; Microwave irradiation;	93%
With sodium hydrogencarbonate In pyridine at 120℃; for 40h;
With sodium hydrogencarbonate In tetrahydrofuran; pyridine at 120℃; for 40h;
In tetrahydrofuran; water at 20℃; for 18h;
In tetrahydrofuran at 80℃; for 16h; Sealed tube;

: 33252-30-1
2-chloro-4-pyridinenitrile

: 693792-82-4
methyl N-[6-(4-hydroxyphenyl)pyrimidin-4-yl]phenylalaninate

: 693792-97-1
methyl N-(6-{4-[(4-cyanopyridin-2-yl)-oxy]phenyl}pyrimidin-4-yl)phenylalaninate

Conditions

Conditions	Yield
With potassium carbonate In dimethyl sulfoxide at 60℃;	93%

: 33252-30-1
2-chloro-4-pyridinenitrile

: 62-53-3
aniline

: 137225-05-9
2-(phenylamino)isonicotinonitrile

Conditions

Conditions	Yield
With palladium diacetate; caesium carbonate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl In 1,4-dioxane at 80℃; for 4h; Buchwald-Hartwig Coupling; Sealed tube; Inert atmosphere;	93%

: 33252-30-1
2-chloro-4-pyridinenitrile

: 6313-54-8
2-chloroisonicotinic acid,

Conditions

Conditions	Yield
With 1-butyl-3-methylimidazolium hydrogen sulfate; water at 60 - 65℃; for 2.4h; Green chemistry;	92%
With hydrogenchloride

: 33252-30-1
2-chloro-4-pyridinenitrile

: 21043-40-3
1-cyclopentylpiperazine

: 892867-16-2
2-(4-cyclopentyl-piperazin-1-yl)-isonicotinonitrile

Conditions

Conditions	Yield
In N,N-dimethyl-formamide at 80℃; for 16h;	92%

: 33252-30-1
2-chloro-4-pyridinenitrile

: 5720-05-8
4-methylphenylboronic acid

: 1039775-36-4
2-(p-tolyl)isonicotinonitrile

Conditions

Conditions	Yield
With sodium tetrachloropalladate(II); dicyclohexyl {2-sulfo-9-[3-(4-sulfophenyl)propyl]-9H-fluoren-9-yl}phosphonium hydrogen sulfate; potassium carbonate In water; butan-1-ol at 100℃; for 12h; Suzuki coupling; Inert atmosphere;	92%

: 33252-30-1
2-chloro-4-pyridinenitrile

: 13922-41-3
1-Naphthylboronic acid

: 1039775-44-4
C16H10N2

Conditions

Conditions	Yield
With sodium tetrachloropalladate(II); dicyclohexyl {2-sulfo-9-[3-(4-sulfophenyl)propyl]-9H-fluoren-9-yl}phosphonium hydrogen sulfate; potassium carbonate In water; butan-1-ol at 100℃; for 12h; Suzuki coupling; Inert atmosphere;	91%

: 33252-30-1
2-chloro-4-pyridinenitrile

: (S)-N-((S)-1-(2-chlorophenyl)-2- ((3,3-difluorocyclobutyl)amino)-2-oxoethyl)-N-(5-fluoropyridin-3-yl)-5-oxopyrrolidine-2-carboxamide

: 1448347-49-6
(2S)-N-{(1S)-1-(2-chlorophenyl)-2-[(3,3-difluorocyclobutyl)amino]-2-oxoethyl}-1-(4-cyanopyridin-2-yl)-N-(5-fluoropyridin-3-yl)-5-oxopyrrolidine-2-carboxamide

Conditions

Conditions	Yield
With tris-(dibenzylideneacetone)dipalladium(0); potassium carbonate; (R)-2,2'-bis(diphenylphosphanyl)-1,1'-binaphthyl In acetic acid methyl ester; toluene Solvent; Reflux; Inert atmosphere;	91%
Stage #1: 2-chloro-4-pyridinenitrile; (S)-N-((S)-1-(2-chlorophenyl)-2- ((3,3-difluorocyclobutyl)amino)-2-oxoethyl)-N-(5-fluoropyridin-3-yl)-5-oxopyrrolidine-2-carboxamide With tris-(dibenzylideneacetone)dipalladium(0); potassium carbonate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl In toluene Inert atmosphere; Reflux; Stage #2: With 1,8-diazabicyclo[5.4.0]undec-7-ene In tetrahydrofuran at 20℃; Reagent/catalyst; Temperature;

Yield

With tris-(dibenzylideneacetone)dipalladium(0); potassium carbonate; (R)-2,2'-bis(diphenylphosphanyl)-1,1'-binaphthyl In acetic acid methyl ester; toluene Solvent; Reflux; Inert atmosphere;

91%

Stage #1: 2-chloro-4-pyridinenitrile; (S)-N-((S)-1-(2-chlorophenyl)-2- ((3,3-difluorocyclobutyl)amino)-2-oxoethyl)-N-(5-fluoropyridin-3-yl)-5-oxopyrrolidine-2-carboxamide With tris-(dibenzylideneacetone)dipalladium(0); potassium carbonate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl In toluene Inert atmosphere; Reflux;
Stage #2: With 1,8-diazabicyclo[5.4.0]undec-7-ene In tetrahydrofuran at 20℃; Reagent/catalyst; Temperature;

: 33252-30-1
2-chloro-4-pyridinenitrile

: 1-(2-chloropyridin-4-yl)methanamine

Conditions

Conditions	Yield
With lithium aluminium tetrahydride In tetrahydrofuran	90%
With fac-1,2-bis(dipropylphosphaneyl)ethane tricarbonyl manganese(I) bromide; potassium tert-butylate; hydrogen In toluene at 100℃; under 37503.8 Torr; for 18h; Autoclave;	72 %Chromat.

: 33252-30-1
2-chloro-4-pyridinenitrile

: 99-03-6
1-(3-aminophenyl)ethanone

: 1438416-83-1
2-((3-acetylphenyl)amino)isonicotinonitrile

Conditions

Conditions	Yield
With palladium diacetate; caesium carbonate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl In 1,4-dioxane at 80℃; for 4h; Buchwald-Hartwig Coupling; Sealed tube; Inert atmosphere;	90%

: 33252-30-1
2-chloro-4-pyridinenitrile

: 100-01-6
4-nitro-aniline

: 58408-94-9
2-((4-nitrophenyl)amino)isonicotinonitrile

Conditions

Conditions	Yield
With palladium diacetate; caesium carbonate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl In 1,4-dioxane at 80℃; for 4h; Buchwald-Hartwig Coupling; Sealed tube; Inert atmosphere;	90%

: 33252-30-1
2-chloro-4-pyridinenitrile

: tetrafluoroboric acid

: C59H48Cl2O2OsP3

: C65H50Cl2N2O2OsP3(1+)*BF4(1-)

Conditions

Conditions	Yield
With dihydrogen peroxide In dichloromethane; water at 20℃; for 3h;	90%

...Expand

: 33252-30-1
2-chloro-4-pyridinenitrile

: 54-85-3
isoniazid

: C12H8ClN5

Conditions

Conditions	Yield
With sodium methylate In methanol at 25℃; for 14h;	90%

: 33252-30-1
2-chloro-4-pyridinenitrile

: 3-ethyl-4-hydroxy-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-benzo[d]imidazol-2(3H)-one

: 2-((3-ethyl-2-oxo-1-((2-(trimethylsilyl)ethoxy)methyl)-2,3-dihydro-1Hbenzo[d]imidazol-4-yl)oxy)isonicotinonitrile

Conditions

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 90℃; for 18h; Inert atmosphere; Schlenk technique;	90%

: 33252-30-1
2-chloro-4-pyridinenitrile

: 591-50-4
iodobenzene

: 80099-88-3
(2-chloropyridin-4-yl)(phenyl)methanone

Conditions

Conditions	Yield
Stage #1: iodobenzene With n-butyllithium In diethyl ether; hexane at -78 - 0℃; for 0.75h; Inert atmosphere; Stage #2: 2-chloro-4-pyridinenitrile In diethyl ether; hexane at -78℃; for 1h; Stage #3: With hydrogenchloride In diethyl ether; hexane at -30℃; for 1h;	90%

2-Chloro-4-cyanopyridine Chemical Properties

IUPAC Name: 2-chloropyridine-4-carbonitrile
2-Chloro-4-cyanopyridine(33252-30-1),its Molecular formula: C₆H₃ClN₂
2-Chloro-4-cyanopyridine(33252-30-1),its Molar mass: 138.55
Melting point: 69-73 °C(lit.)
Boiling Point: 104-106°C at 15mm
Appearance: White crystalline powder.
Synonyms: 4-CYANO-2-CHLORO PYRIDINE;2-CHLORO-4-PYRIDINECARBONITRILE;2-CHLOROPYRIDINE-4-CARBONITRILE;2-CHLORO-4-CYANOPYRIDINE 2-CHLORO-ISONICOTINONITRILE 2-CHLOROISONICOTINONITRILE
Following is the molecular formula of 2-Chloro-4-cyanopyridine(33252-30-1):

2-Chloro-4-cyanopyridine Uses

2-Chloro-4-cyanopyridine(33252-30-1) can be used as intermediates of medicine,pesticide .

2-Chloro-4-cyanopyridine Safety Profile

Safty informations about 2-Chloro-4-cyanopyridine(33252-30-1):
Hazard Codes :Xi,Xn (Irritant;Harmful):

RIDADR 3276
WGK Germany : 3
Risk Statements :
R36/37/38:Irritating to eyes, respiratory system and skin
R20/21/22 :Harmful by inhalation, in contact with skin and if swallowed
Safety Statements :
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

Product Name

2-Chloro-4-cyanopyridine

Synthetic route

2-Chloro-4-cyanopyridine Chemical Properties

2-Chloro-4-cyanopyridine Uses

2-Chloro-4-cyanopyridine Safety Profile

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