875-35-4

Basic information

• Product Name: 2,6-Dichloro-4-methylnicotinonitrile
• Synonyms: BUTTPARK 43\57-14;IFLAB-BB F0907-8363;3-PYRIDINECARBONITRILE, 2,6-DICHLORO-4-METHYL-;3-CYANO-2,6-DICHLORO-4-METHYLPYRIDINE;3-Cyano-4-methyl-2,6-dichloropyridine;2,6-DICHLORO-4-METHYL-3-CYANOPYRIDINE;2,6-DICHLORO-4-METHYLNICOTINONITRILE;2,6-DICHLORO-4-METHYLPYRIDINE-3-CARBONITRILE
• CAS NO: 875-35-4
• Molecular Formula: C₇H₄Cl₂N₂
• Molecular Weight: 187.03
• EINECS: 212-873-7
• Product Categories: Pyridine series;API intermediates;Pyridines;Chloropyridines;Halopyridines;C7 and C8Heterocyclic Building Blocks;Halogenated Heterocycles;Heterocyclic Building Blocks;Building Blocks;C7 to C18;C7 to C8;Chemical Synthesis;Halogenated Heterocycles;Heterocyclic Building Blocks
• Mol File: 875-35-4.mol
• Article Data: 25

Chemical Properties

• Melting Point: 108-112 °C(lit.)
• Boiling Point: 118 °C / 5mmHg
• Flash Point: 145.5 °C
• Appearance: /
• Density: 1.42 g/cm³
• Vapor Pressure: 0.000395mmHg at 25°C
• Refractive Index: 1.574
• Storage Temp.: Store below +30°C.
• Solubility: 0.4g/l
• PKA: -4.53±0.10(Predicted)
• CAS DataBase Reference: 2,6-Dichloro-4-methylnicotinonitrile(CAS DataBase Reference)
• NIST Chemistry Reference: 2,6-Dichloro-4-methylnicotinonitrile(875-35-4)
• EPA Substance Registry System: 2,6-Dichloro-4-methylnicotinonitrile(875-35-4)

Safety Data

• Hazard Codes: T,Xi
• Statements: 20/21-25-37/38-41-43-36/37/38
• Safety Statements: 26-36/37/39-45-36
• RIDADR: UN 2811 6.1/PG 3
• WGK Germany: 3
• HazardClass: 6.1
• PackingGroup: III
• Hazardous Substances Data: 875-35-4(Hazardous Substances Data)

Usage

InChI:InChI=1/C7H4Cl2N2/c1-4-2-6(8)11-7(9)5(4)3-10/h2H,1H3

Synthetic route

2,6-dihydroxy-3-cyano-4-methylpyrimidine (5444-02-0) → 2,6-dichloro-4-methylnicotinonitrile (875-35-4)

Conditions	Yield
With trichlorophosphate at 200℃; for 7h;	98%
With trichlorophosphate at 180℃; for 6h;	92%
With trichlorophosphate at 180℃; for 6h; Sealed tube;	92%

3-cyano-4-methyl-6-hydroxypyrid-2-one (5444-02-0) → 2,6-dichloro-4-methylnicotinonitrile (875-35-4)

Conditions	Yield
With trichlorophosphate at 120℃; for 6h;	98%
With trichlorophosphate at 80℃; Temperature;	84%

3-ethynyl-4-methylpyridine-2,6-diol → 2,6-dichloro-4-methylnicotinonitrile (875-35-4)

Conditions	Yield
With trichlorophosphate at 180℃; for 6h; Sealed tube;	92%

C9H17N2(1+)*C7H5N2O2(1-) → 2,6-dichloro-4-methylnicotinonitrile (875-35-4)

Conditions	Yield
With benzyltrimethylammonium chloride; trichlorophosphate at 120℃; for 8h;	91%
With tetramethlyammonium chloride; trichlorophosphate for 8h; Reflux;	88%
With trichlorophosphate for 8h; Reflux;	50%

2-hydroxy-4-methyl-6-oxo-1,6-dihydropyridine-3-carbonitrile → 2,6-dichloro-4-methylnicotinonitrile (875-35-4)

Conditions	Yield
With N-benzyl-N,N,N-triethylammonium chloride; trichlorophosphate at 90℃; for 10h;	65%

1-butyl-6-hydroxy-4-methyl-2-oxo-1,2-dihydropyridine-3-carbonitrile (39108-47-9) → 2,6-dichloro-4-methylnicotinonitrile (875-35-4) + 1-butyl-6-chloro-1,2-dihydro-4-methyl-2-oxo-3-pyridinecarbonitrile (168697-58-3) + 1-butyl-2-chloro-1,6-dihydro-4-methyl-6-oxo-3-pyridinecarbonitrile

Conditions	Yield
With trichlorophosphate at 105℃; for 3h;	A 1% B 62% C 0.12 g

6-Chloro-4-methyl-2-oxo-1,2-dihydro-pyridine-3-carbonitrile → 2,6-dichloro-4-methylnicotinonitrile (875-35-4)

Conditions	Yield
With trichlorophosphate at 120℃;

(Z)-4-Butylcarbamoyl-2-cyano-3-methyl-but-2-enoic acid ethyl ester (1026543-43-0) → 2,6-dichloro-4-methylnicotinonitrile (875-35-4)

Conditions	Yield
Multi-step reaction with 2 steps 1: NaOH / 2 h / 140 °C 2: 1 percent / POCl3 / 3 h / 105 °C View Scheme

2,6-dihydroxy-3-cyano-4-methylpyrimidine (5444-02-0) + ethanolamine (141-43-5) → 2,6-dichloro-4-methylnicotinonitrile (875-35-4)

Conditions	Yield
With sodium carbonate; trichlorophosphate In quinoline

2,6-dichloro-4-methylnicotinonitrile (875-35-4) + 2-(4'-aminophenyl)ethyl alcohol (104-10-9) → 2,6-bis[4-(2-hydroxyethyl)phenylamino]-3-cyano-4-methylpyridine (631899-53-1)

Conditions	Yield
Stage #1: 2,6-dichloro-4-methylnicotinonitrile; 2-(4'-aminophenyl)ethyl alcohol With sodium carbonate at 120 - 195℃; for 18h; Stage #2: With hydrogenchloride In water	98%

2,6-dichloro-4-methylnicotinonitrile (875-35-4) → 2,6-dichloro-4-methyl-nicotinic acid (62774-90-7)

Conditions	Yield
With sulfuric acid; water; nitric acid at 70 - 105℃; for 2h;	96%
Multi-step reaction with 2 steps 1: 93 percent / aq. H2SO4 / 6 h / 98 °C 2: 88 percent / H2SO4; aq. NaNO2 / 20 - 25 °C View Scheme
Multi-step reaction with 2 steps 1: 66 percent / DIBALH / CH2Cl2; toluene / 2 h / -78 - 20 °C 2: 78 percent / NaClO2; NaH2PO4*2H2O / 2-methyl-propan-2-ol; H2O / 4 h / 10 - 25 °C View Scheme
With sulfuric acid; nitric acid at 110℃;
With sulfuric acid; nitric acid at 110℃;

2,6-dichloro-4-methylnicotinonitrile (875-35-4) → 6-hydrazinyl-4-methyl-2H-pyrazolo[3,4-b]pyridine-3-amine

Conditions	Yield
With hydrazine hydrate at 120℃; for 3h;	93.6%
With hydrazine

3-(2-ethylhexoxy)propylamine (5397-31-9) + 2,6-dichloro-4-methylnicotinonitrile (875-35-4) → C29H52N4O2 (861395-95-1)

Conditions	Yield
In water at 120℃; for 4h;	93.2%

2,6-dichloro-4-methylnicotinonitrile (875-35-4) → 2,6-dichloro-4-methyl-3-pyridinecarboxamide (38841-54-2)

Conditions	Yield
With sulfuric acid at 98℃; for 6h;	93%
With sulfuric acid at 80℃; for 4h;	91%
With sulfuric acid at 80℃; for 4h;	80.9%

2,6-dichloro-4-methylnicotinonitrile (875-35-4) → 3-cyano-4-methylpyridine (5444-01-9)

Conditions	Yield
With hydrogen; sodium acetate; palladium dichloride In methanol at 23℃; under 760.051 Torr; for 14h;	93%
With hydrogen; sodium acetate; palladium dichloride In methanol at 23℃; under 760.051 Torr; for 14h;	93%
With hydrogen; sodium acetate; palladium 10% on activated carbon In methanol at 20℃; for 16h;	86%
With ammonium hydroxide; zinc In tetrahydrofuran at 70℃; for 4h; Catalytic behavior; Reagent/catalyst; Solvent; Temperature; Large scale;	81%

2,6-dichloro-4-methylnicotinonitrile (875-35-4) → 2,6-diamino-4-methyl-3-pyridinecarbonitrile (38841-52-0)

Conditions	Yield
With ammonia at 150℃; for 16h;	91%
With ammonium hydroxide In dimethyl sulfoxide at 130℃; for 3h; Microwave irradiation;	67%

2,6-dichloro-4-methylnicotinonitrile (875-35-4) → 6-amino-2-chloro-4-methyl-3-pyridinecarbonitrile (51561-20-7)

Conditions	Yield
With ammonia In methanol at 150℃; Microwave irradiation; regioselective reaction;	90%
With ammonia In methanol at 150℃; for 0.416667h; Microwave irradiation;	45%

2,6-dichloro-4-methylnicotinonitrile (875-35-4) + methylhydrazine (60-34-4) → C9H14N6 (1352830-90-0)

Conditions	Yield
In 1,4-dioxane for 20h; Reflux;	89%

2,6-dichloro-4-methylnicotinonitrile (875-35-4) → 2-chloro-4-methyl-3-pyridinecarbonitrile (65169-38-2)

Conditions	Yield
With 5%-palladium/activated carbon; ammonium formate In methanol at 20℃; for 72h;	87%

2,6-dichloro-4-methylnicotinonitrile (875-35-4) + N,N-dimethyl-formamide dimethyl acetal (4637-24-5) → 2,6-dichloro-4-[(E)-2-(dimethylamino)ethenyl]pyridine-3-carbonitrile (1175559-53-1)

Conditions	Yield
In N,N-dimethyl-formamide at 100℃; for 2h;	86%
In isopropyl alcohol at 65℃; for 18h;	26%
In isopropyl alcohol at 65℃; for 18h;	26%

2,6-dichloro-4-methylnicotinonitrile (875-35-4) → 2,6-diazido-4-methylnicotinonitrile

Conditions	Yield
With sodium azide In water; N,N-dimethyl-formamide at 20℃; Solvent;	86%

3,5-dimethyl-1H-pyrazole (67-51-6) + 2,6-dichloro-4-methylnicotinonitrile (875-35-4) → 2,6-bis(3,5-dimethyl-1H-pyrazol-1-yl)-4-methyl-nicotinonitrile (935747-88-9)

Conditions	Yield
With sodium hydrogencarbonate; potassium iodide In N,N-dimethyl-formamide for 0.166667h; Microwave irradiation;	85.6%

2,6-dichloro-4-methylnicotinonitrile (875-35-4) + palladium dichloride → 3-cyano-4-methylpyridine (5444-01-9)

Conditions	Yield
With sodium acetate In methanol	85%

morpholine (110-91-8) + 2,6-dichloro-4-methylnicotinonitrile (875-35-4) → 2-chloro-4-methyl-6-morpholinonicotinonitrile

Conditions	Yield
In methanol at 0 - 20℃; Inert atmosphere;	85%
In methanol at 0 - 20℃; Inert atmosphere;	85%
In methanol at 0 - 20℃; Inert atmosphere;	85%
In methanol at 0 - 20℃; Inert atmosphere;	85%

cyclopentylzinc bromide lithium chloride + 2,6-dichloro-4-methylnicotinonitrile (875-35-4) → 2,6-dicyclopentyl-4-methylnicotinonitrile (1448351-74-3)

Conditions	Yield
With 1-methyl-1H-imidazole; Pd-PEPPSI-IPrAn In tetrahydrofuran; 1,4-dioxane at 0 - 80℃; for 6h; Negishi Coupling; Schlenk technique; Inert atmosphere;	81%

2,6-dichloro-4-methylnicotinonitrile (875-35-4) + 3-methoxypropylamine (5332-73-0) → 2-chloro-3-cyano-4-methyl-6-(3'-methoxypropylamino)-pyridine (56331-52-3)

Conditions	Yield
In ethanol at 90℃;	78%
With sodium carbonate In water; toluene
With triethylamine In toluene at 50℃; for 16h;

2-fluoro-5-methoxy-N-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)benzenesulfonamide + 2,6-dichloro-4-methylnicotinonitrile (875-35-4) → N-(4-(6-chloro-5-cyano-4-methylpyridin-2-yl)phenyl)-2-fluoro-5-methoxybenzenesulfonamide

Conditions	Yield
With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; caesium carbonate In 1,4-dioxane; water at 90℃; for 18h; Inert atmosphere;	78%

5-methoxypentan-1-amine (71259-63-7) + 2,6-dichloro-4-methylnicotinonitrile (875-35-4) → C13H18ClN3O

Conditions	Yield
In ethanol at 80℃;	78%

8-methoxyoctan-1-amine + 2,6-dichloro-4-methylnicotinonitrile (875-35-4) → C16H24ClN3O

Conditions	Yield
In ethanol at 100℃;	78%

2,6-dichloro-4-methylnicotinonitrile (875-35-4) + pinacol vinylboronate (75927-49-0) → 2-chloro-4-methyl-6-vinylnicotinonitrile

Conditions	Yield
With bis-triphenylphosphine-palladium(II) chloride; cesium fluoride In 1,4-dioxane; water at 85℃; for 12h; Suzuki Coupling; Inert atmosphere;	76%

2-Ethylhexylamine (104-75-6) + 2,6-dichloro-4-methylnicotinonitrile (875-35-4) → C23H40N4 (861396-01-2)

Conditions	Yield
In water at 130℃; for 4h;	75.6%

2,6-dichloro-4-methylnicotinonitrile (875-35-4) + 3-methoxypropylamine (5332-73-0) → 2,6-bis-(3'-methoxy-n-propylamino)-3-cyano-4-methylpyridine (51560-72-6)

Conditions	Yield
for 3h; Reflux;	75%
at 10 - 120℃; for 3h;	72.5%
at 10 - 20℃;	72.5%

4-fluoroboronic acid (1765-93-1) + 2,6-dichloro-4-methylnicotinonitrile (875-35-4) → 2-chloro-6-(4-fluorophenyl)-4-methylnicotinonitrile (943117-82-6)

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In 1,4-dioxane; water at 100℃; for 3.5h; Suzuki Coupling; Inert atmosphere;	75%

2,6-dichloro-4-methylnicotinonitrile (875-35-4) + 3-amino-2-propanol (78-96-6, 1674-56-2) → C13H20N4O2 (845531-60-4)

Conditions	Yield
In water at 130℃; for 3h;	74.5%
at 120℃; for 3h;	74.6%

2,6-dichloro-4-methylnicotinonitrile (875-35-4) + N,N-dimethylethylenediamine (108-00-9) → 2-(2-dimethylaminoethylamino)-3-cyano-4-methyl-6-chloropyridine + 2-chloro-6-(2-(dimethylamino)ethylamino)-4-methylnicotinonitrile

Conditions	Yield
In ethanol at 20℃; for 48h;	A n/a B 68%

Upstream product

• 5444-02-0 2,6-dihydroxy-3-cyano-4-methylpyrimidine 
• 39108-47-9 1-butyl-6-hydroxy-4-methyl-2-oxo-1,2-dihydropyridine-3-carbonitrile 
• 5444-02-0 3-cyano-4-methyl-6-hydroxypyrid-2-one 
• 1026543-43-0 (Z)-4-Butylcarbamoyl-2-cyano-3-methyl-but-2-enoic acid ethyl ester 
• 141-43-5 ethanolamine 

Downstream Products

• 52982-90-8 2-amino-6-chloro-4-methyl-3-pyridinecarbonitrile 
• 51561-20-7 6-amino-2-chloro-4-methyl-3-pyridinecarbonitrile 
• 38841-52-0 2,6-diamino-4-methyl-3-pyridinecarbonitrile 
• 38841-54-2 2,6-dichloro-4-methyl-3-pyridinecarboxamide 
• 51564-29-5 2-chloro-6-methoxy-4-methylpyridine-3-carbonitrile 
• 243469-65-0 6-chloro-2-methoxy-4-methylnicotinonitrile 
• 149379-71-5 2-methoxy-4-methylpyridine-3-carbonitrile 
• 243469-66-1 6-methoxy-4-methylpyridine-3-carbonitrile 
• 91591-70-7 2,6-dichloro-4-methyl-3-pyridinecarboxaldehyde 
• 62774-90-7 2,6-dichloro-4-methyl-nicotinic acid 
• 220559-34-2 methyl 4.6-dichloro-3-(diethylamino)furo[3,4-c]pyridine-1-carboxylate 
• 243469-62-7 3-hydroxymethyl-2-methoxy-4-methylpyridine 
• 243469-67-2 4-(2-hydroxy-2-phenylethyl)-2-methoxypyridine-3-carbonitrile 
• 243469-68-3 methanesulfonic acid 2-(3-cyano-2-methoxy-pyridin-4-yl)-1-phenyl-ethyl ester 

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