Conditions | Yield |
---|---|
Stage #1: 2,3,4,5,6-pentachloropyridine With manganese; ammonium acetate In ethanol; water at 40℃; for 6h; Stage #2: With ammonia In ethanol; water at 65℃; for 1h; pH=8 - 9; Concentration; Temperature; | 99.5% |
With ammonium chloride; zinc In acetonitrile at 80℃; for 3h; Reagent/catalyst; Solvent; Temperature; Green chemistry; | 88.4% |
With ammonium chloride; dimethyl methane phosphonate; zinc In water for 0.5h; Yield given; |
Conditions | Yield |
---|---|
With hydrogen; potassium carbonate at 200℃; under 15001.5 Torr; for 2h; Autoclave; | 99.2% |
2,3,4,5,6-pentachloropyridine
A
2,3,6-trichloropyridine
B
2,3,5-trichloropyridine
C
2,3,5,6-tetrachloropyridine
Conditions | Yield |
---|---|
With ammonium chloride; dimethyl methane phosphonate; zinc In water at 85 - 90℃; Product distribution; other ammonium salts; other methylphosphonates/phosphates; | A 0.9% B 1% C 97.6% |
tetrachloro-4-iodopyridine
2,3,5,6-tetrachloropyridine
Conditions | Yield |
---|---|
In diethyl ether for 19h; Irradiation; | 87% |
Multi-step reaction with 2 steps 1: 4 percent / copper bronze / dimethylformamide / 150 °C 2: 3 percent Chromat. / copper bronze / dimethylformamide / 20 h / 150 °C View Scheme |
methyl 4-cyano-2,2,4-trichlorobutyrate
2,3,5,6-tetrachloropyridine
Conditions | Yield |
---|---|
79% |
tetrachloro-4-pyridylcopper
benzoyl chloride
A
2,3,5,6-tetrachloropyridine
B
4-benzoyltetrachloropyridine
Conditions | Yield |
---|---|
In N,N-dimethyl-formamide for 0.5h; Heating; | A 9% B 72% |
4-Bromo-2,3,5,6-tetrachloropyridine
A
2,3,5,6-tetrachloropyridine
B
2,3,4,6-Tetrachloropyridine
C
2,3,4,5,6-pentachloropyridine
D
octachloro-4,4'-bipyridyl
Conditions | Yield |
---|---|
With Isopropylbenzene; copper In N,N-dimethyl-formamide at 150℃; for 1h; Further byproducts given; | A 63% B 15% C 16% D 17% |
4-Bromo-2,3,5,6-tetrachloropyridine
A
2,3,5,6-tetrachloropyridine
B
2,3,4,6-Tetrachloropyridine
D
octachloro-4,4'-bipyridyl
Conditions | Yield |
---|---|
With copper; benzoyl chloride In N,N-dimethyl-formamide at 150℃; for 0.5h; | A 61% B 24% C n/a D 15% |
tetrachloro-4-iodopyridine
A
2,3,5,6-tetrachloropyridine
B
2,3,4,5,6-pentachloropyridine
C
octachloro-4,4'-bipyridyl
Conditions | Yield |
---|---|
With copper In N,N-dimethyl-formamide at 150℃; | A 22% B 4% C 52% |
4-Bromo-2,3,5,6-tetrachloropyridine
A
2,3,5,6-tetrachloropyridine
B
2,3,4,6-Tetrachloropyridine
C
2,3,4,5,6-pentachloropyridine
E
octachloro-4,4'-bipyridyl
Conditions | Yield |
---|---|
With para-xylene; copper In N,N-dimethyl-formamide at 150℃; for 1h; Product distribution; Mechanism; the similar reaction without p-xylene; in presence cumene, benzoyl chloride instead p-xylene; other reagent (CuCl); other polychloroiodoarenes; tetrahalohenopyridylcopper intermediate; evidence against free radical or pyridyne intermediates; | A 42% B 5% C 15% D 4% E 18% |
4-Bromo-2,3,5,6-tetrachloropyridine
A
2,3,5,6-tetrachloropyridine
B
2,3,4,5,6-pentachloropyridine
D
octachloro-4,4'-bipyridyl
Conditions | Yield |
---|---|
With para-xylene; copper In N,N-dimethyl-formamide at 150℃; for 1h; Further byproducts given; | A 42% B 15% C 4% D 18% |
With copper In N,N-dimethyl-formamide at 150℃; for 0.5h; | A 17% B 21% C 8% D 14% |
With copper In N,N-dimethyl-formamide at 150℃; for 0.5h; Further byproducts given; | A 10% B 10% C 9% D 8% |
4-Bromo-2,3,5,6-tetrachloropyridine
A
2,3,5,6-tetrachloropyridine
B
4-bromo-2,3,6-tetrachloropyridine
Conditions | Yield |
---|---|
In diethyl ether for 71h; Irradiation; | A 17% B 6% |
tetrachloro-4-pyridylcopper
A
2,3,5,6-tetrachloropyridine
B
octachloro-4,4'-bipyridyl
Conditions | Yield |
---|---|
In N,N-dimethyl-formamide for 1h; Heating; | A 13.5% B 1% |
tetrachloro-4-pyridylcopper
benzoyl chloride
A
2,3,5,6-tetrachloropyridine
B
4-benzoyltetrachloropyridine
C
2,3,4,5,6-pentachloropyridine
D
octachloro-4,4'-bipyridyl
Conditions | Yield |
---|---|
With para-xylene In N,N-dimethyl-formamide for 23h; Product distribution; Mechanism; Heating; the similar reaction without p-xylene; other reaction times; similar range of products to those obtained from 4-bromotetrachloropyridine; | A 12% B 13% C 1% D 2.5% |
tetrachloro-4-pyridylcopper
A
2,3,5,6-tetrachloropyridine
B
4-benzoyltetrachloropyridine
C
2,3,4,5,6-pentachloropyridine
D
octachloro-4,4'-bipyridyl
Conditions | Yield |
---|---|
With para-xylene; benzoyl chloride In N,N-dimethyl-formamide for 23h; Heating; | A 12% B 13% C 1% D 2.5% |
Conditions | Yield |
---|---|
With phosphorus pentachloride at 210 - 220℃; | |
With sulfur dichloride In tetrachloromethane at 0 - 80℃; for 6h; Temperature; Solvent; Inert atmosphere; |
Conditions | Yield |
---|---|
With phosphorus pentachloride; trichlorophosphate at 180℃; |
Conditions | Yield |
---|---|
bei der Destillation; unter Kohlendioxyd-Entwicklung; |
tetrachloroisonicotic acid
2,3,5,6-tetrachloropyridine
Conditions | Yield |
---|---|
With water at 180℃; | |
With glycerol beim Destillieren; |
2,6-diamino-3,5-dichloropyridine
2,3,5,6-tetrachloropyridine
Conditions | Yield |
---|---|
With hydrogenchloride; sodium nitrite Yield given; |
2,3,4,5,6-pentachloropyridine
N,N-dimethyl-formamide
A
2,3,5,6-tetrachloropyridine
B
2,3,4,6-Tetrachloropyridine
C
2,3,4,5-tetrachloro-pyridine
D
tetrachloro-4-dimethylaminopyridine
Conditions | Yield |
---|---|
With copper In N,N-dimethyl-formamide at 150℃; for 20h; | A 3 % Chromat. B 22 % Chromat. C 2 % Chromat. D 13 % Chromat. |
2,3,4,5,6-pentachloropyridine
A
2,3,5,6-tetrachloropyridine
B
2,3,4,6-Tetrachloropyridine
C
2,3,4,5-tetrachloro-pyridine
D
tetrachloro-4-dimethylaminopyridine
Conditions | Yield |
---|---|
With copper In N,N-dimethyl-formamide at 150℃; for 20h; | A 3 % Chromat. B 22 % Chromat. C 2 % Chromat. D 13 % Chromat. |
2,3,4,5,6-pentachloropyridine
A
2,3,5,6-tetrachloropyridine
B
bis(tetrachloropyridyl)mercury
Conditions | Yield |
---|---|
In N,N-dimethyl-formamide Hg cathode, -1.40 V (S.C.E.), Et4NBF4; | A 0.66 g B 0.59 g |
2,3,4,5,6-pentachloropyridine
A
2,3,5,6-tetrachloropyridine
B
2,3,5,6,2',3',6'-heptachloro-[4,4']bipyridinyl
Conditions | Yield |
---|---|
With carbon dioxide 1.) Hg cathode, DMF, Et4NBF4, -1.30 V (S.C.E.), 2.) 150 deg C, vacuum; Multistep reaction; |
Conditions | Yield |
---|---|
at 180℃; im Rohr; |
2,3,5-trichloropyridine
2,3,5,6-tetrachloropyridine
Conditions | Yield |
---|---|
With sodium hydroxide; hexachloroethane; tetrabutylammomium bromide at 50℃; for 4h; |
2,3,5,6-tetrachloropyridine
Conditions | Yield |
---|---|
With sodium tetrahydroborate In isopropyl alcohol at 20℃; for 6h; |
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 60 percent / aq. HCl, H2O2 2: NaNO2-HCl View Scheme |
2,3,5,6-tetrachloropyridine
2,3,5-trichloropyridine
Conditions | Yield |
---|---|
With 5%-palladium/activated carbon; hydrogen; potassium hydroxide In 5,5-dimethyl-1,3-cyclohexadiene; water at 60℃; under 4500.45 Torr; for 6h; Reagent/catalyst; Solvent; Pressure; Autoclave; | 99.1% |
With sodium hydroxide In benzene |
Conditions | Yield |
---|---|
In N,N-dimethyl-formamide at 120℃; for 3h; | 99% |
2,3,5,6-tetrachloropyridine
(4-methoxystyrene)boronic acid
Conditions | Yield |
---|---|
With potassium phosphate; di-(1-adamantyl)-n-butylphosphine; bis(dibenzylideneacetone)-palladium(0) In 1,4-dioxane at 100℃; for 20h; Suzuki-Miyaura Coupling; Inert atmosphere; | 99% |
2,3,5,6-tetrachloropyridine
4-trifluoromethylstyrenylboronic acid
Conditions | Yield |
---|---|
With potassium phosphate; di-(1-adamantyl)-n-butylphosphine; bis(dibenzylideneacetone)-palladium(0) In 1,4-dioxane at 100℃; for 20h; Suzuki-Miyaura Coupling; Inert atmosphere; | 99% |
2,3,5,6-tetrachloropyridine
4-methylstyrenylboronic acid
Conditions | Yield |
---|---|
With potassium phosphate; di-(1-adamantyl)-n-butylphosphine; bis(dibenzylideneacetone)-palladium(0) In 1,4-dioxane at 100℃; for 20h; Suzuki-Miyaura Coupling; Inert atmosphere; | 99% |
2,3,5,6-tetrachloropyridine
phenylboronic acid
tetraphenyl-2,3,5,6 pyridine
Conditions | Yield |
---|---|
With tris-(dibenzylideneacetone)dipalladium(0); potassium phosphate In toluene at 100℃; for 22h; Reagent/catalyst; Suzuki-Miyaura Coupling; Inert atmosphere; Sealed tube; | 99% |
2,3,5,6-tetrachloropyridine
4-methoxyphenylboronic acid
2,3,5,6-tetrakis(4-methoxyphenyl)pyridine
Conditions | Yield |
---|---|
With tris-(dibenzylideneacetone)dipalladium(0); potassium phosphate In toluene at 100℃; for 22h; Suzuki-Miyaura Coupling; Inert atmosphere; Sealed tube; | 99% |
Conditions | Yield |
---|---|
With potassium carbonate In N,N-dimethyl-formamide at 50℃; for 1h; | 98% |
Conditions | Yield |
---|---|
Stage #1: 2,3,5,6-tetrachloropyridine With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; dichloro bis(acetonitrile) palladium(II); copper(l) iodide; diisopropylamine In 1,4-dioxane at 20℃; for 0.166667h; Inert atmosphere; Stage #2: phenylacetylene In 1,4-dioxane at 90℃; for 20h; | 96% |
2,3,5,6-tetrachloropyridine
4-methylphenylboronic acid
2,3,5,6-tetra-p-tolylpyridine
Conditions | Yield |
---|---|
With tris-(dibenzylideneacetone)dipalladium(0); potassium phosphate In toluene at 100℃; for 22h; Suzuki-Miyaura Coupling; Inert atmosphere; Sealed tube; | 96% |
2,3,5,6-tetrachloropyridine
3,5,6-trichloro-2-hydrazinopyridine
Conditions | Yield |
---|---|
With hydrazine hydrate In methanol at 60 - 65℃; for 2h; Temperature; Green chemistry; | 96% |
With sodium carbonate; hydrazine hydrate; butan-1-ol In water at 90 - 95℃; |
Conditions | Yield |
---|---|
In N,N-dimethyl-formamide at 120℃; for 3h; | 95% |
2,3,5,6-tetrachloropyridine
Dihydroxy-styryl-boran
Conditions | Yield |
---|---|
With potassium phosphate; di-(1-adamantyl)-n-butylphosphine; bis(dibenzylideneacetone)-palladium(0) In 1,4-dioxane at 100℃; for 20h; Reagent/catalyst; Solvent; Suzuki-Miyaura Coupling; Inert atmosphere; | 95% |
Conditions | Yield |
---|---|
With potassium fluoride In sulfolane at 120℃; for 6h; Reagent/catalyst; Solvent; Green chemistry; | 95% |
2,3,5,6-tetrachloropyridine
(4-chloro-2-methoxyphenyl)boronic acid
Conditions | Yield |
---|---|
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In 1,2-dimethoxyethane for 6h; Inert atmosphere; Reflux; | 95% |
2,3,5,6-tetrachloropyridine
2-Methylphenylboronic acid
Conditions | Yield |
---|---|
With potassium fluoride; tetrakis(triphenylphosphine) palladium(0) In toluene at 100℃; for 22h; Suzuki-Miyaura Coupling; Inert atmosphere; | 95% |
2,3,5,6-tetrachloropyridine
4-ethylphenylboronic acid
Conditions | Yield |
---|---|
With tris-(dibenzylideneacetone)dipalladium(0); potassium phosphate In toluene at 100℃; for 22h; Suzuki-Miyaura Coupling; Inert atmosphere; Sealed tube; | 94% |
2,3,5,6-tetrachloropyridine
Conditions | Yield |
---|---|
With N-benzyl-N,N,N-triethylammonium chloride; potassium carbonate In tetrahydrofuran for 5h; Reagent/catalyst; Solvent; Reflux; | 94% |
Conditions | Yield |
---|---|
Stage #1: 2,3,5,6-tetrachloropyridine With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; dichloro bis(acetonitrile) palladium(II); copper(l) iodide; diisopropylamine In 1,4-dioxane at 20℃; for 0.166667h; Inert atmosphere; Stage #2: 4-methoxyphenylacetylen In 1,4-dioxane at 90℃; for 20h; | 93% |
2,3,5,6-tetrachloropyridine
naphthalene-2-boronic acid
Conditions | Yield |
---|---|
With potassium fluoride; tetrakis(triphenylphosphine) palladium(0) In toluene at 100℃; for 22h; Suzuki-Miyaura Coupling; Inert atmosphere; | 91% |
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In water; acetonitrile for 4h; Inert atmosphere; Reflux; | |
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In water; acetonitrile for 4h; Inert atmosphere; Reflux; |
Conditions | Yield |
---|---|
With potassium fluoride; tetrakis(triphenylphosphine) palladium(0) In toluene at 100℃; for 22h; Suzuki-Miyaura Coupling; Inert atmosphere; | 91% |
Conditions | Yield |
---|---|
With potassium fluoride; tetrakis(triphenylphosphine) palladium(0) In toluene at 100℃; for 22h; Suzuki-Miyaura Coupling; Inert atmosphere; | 90% |
With potassium fluoride; tetrakis(triphenylphosphine) palladium(0) In toluene at 100℃; for 22h; Suzuki-Miyaura Coupling; Inert atmosphere; Sealed tube; regioselective reaction; | 77% |
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In water; acetonitrile for 4h; Inert atmosphere; Reflux; | |
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In water; acetonitrile for 4h; Reflux; Inert atmosphere; |
2,3,5,6-tetrachloropyridine
4-tert-butylphenylboronic acid
Conditions | Yield |
---|---|
With tris-(dibenzylideneacetone)dipalladium(0); potassium phosphate In toluene at 100℃; for 22h; Suzuki-Miyaura Coupling; Inert atmosphere; Sealed tube; | 90% |
2,3,5,6-tetrachloropyridine
5'-tert-butyl-(1,1':3',1"-terphenyl)-3,3"-diol
C54H42Cl4N2O4
Conditions | Yield |
---|---|
With caesium carbonate In dimethyl sulfoxide at 120℃; for 0.5h; Inert atmosphere; | 89.4% |
Methyl fluorosulfonate
2,3,5,6-tetrachloropyridine
3,5,6-trichloro-1-methyl-2-pyridone
Conditions | Yield |
---|---|
for 0.5h; Heating; | 89% |
Conditions | Yield |
---|---|
With copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); diisopropylamine In 1,4-dioxane at 90℃; for 20h; Sonogashira Cross-Coupling; Inert atmosphere; Sealed tube; regioselective reaction; | 89% |
Stage #1: 2,3,5,6-tetrachloropyridine With copper(l) iodide; tetrakis(triphenylphosphine) palladium(0) In 1,4-dioxane at 20℃; for 0.166667h; Sonogashira Cross-Coupling; Inert atmosphere; Stage #2: 1-ethynyl-4-fluorobenzene In 1,4-dioxane at 90℃; for 20h; Sonogashira Cross-Coupling; Inert atmosphere; | 68% |
2,3,5,6-Tetrachloropyridine(2402-79-1) can be used as the intermediate of medicine and pesticide.
2,3,5,6-Tetrachloropyridine(2402-79-1) can be used as the main raw material of synthetic herbicides: picloram,too .
1. | ipr-mus LD50:1150 mg/kg | TXAPA9 Toxicology and Applied Pharmacology. 11 (1967),361. |
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