16063-70-0

Basic information

• Product Name: 2,3,5-Trichloropyridine
• Synonyms: 2,3,5-trichloro-pyridin;2,3,5-TRICHLOROPYRIDINE;Trichloropyridine,98%;2,3,5-TRICHLOROPYRIDINE 98+%;3,5,6-Trichloropyridine;Pyridine, 2,3,5-trichloro-;5-Trichloropyridine;2,3,5 - cross-linked with pyridine
• CAS NO: 16063-70-0
• Molecular Formula: C₅H₂Cl₃N
• Molecular Weight: 182.44
• EINECS: 407-270-2
• Product Categories: Pyridine;Chloropyridines;Halopyridines;C5Heterocyclic Building Blocks;Halogenated Heterocycles;Heterocyclic Building Blocks;Pyridines;Chlorinated heterocyclic series;Building Blocks;C5;C5 to C6;Chemical Synthesis;Halogenated Heterocycles;Heterocyclic Building Blocks;alkyl chloride
• Mol File: 16063-70-0.mol

Chemical Properties

• Melting Point: 46-50 °C(lit.)
• Boiling Point: 219 °C(lit.)
• Flash Point: >230 °F
• Appearance: Off-white to pale yellow/Solid
• Density: 1.539 g/cm³
• Vapor Pressure: 0.213mmHg at 25°C
• Refractive Index: 1.572
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• PKA: -2.92±0.10(Predicted)
• Water Solubility: Slightly soluble in water.
• BRN: 119384
• CAS DataBase Reference: 2,3,5-Trichloropyridine(CAS DataBase Reference)
• NIST Chemistry Reference: 2,3,5-Trichloropyridine(16063-70-0)
• EPA Substance Registry System: 2,3,5-Trichloropyridine(16063-70-0)

Safety Data

• Hazard Codes: Xi
• Statements: 52/53-36/37/38
• Safety Statements: 61-37/39-26
• RIDADR: UN 2811 6.1/PG 3
• WGK Germany: 2
• RTECS: UU0525000
• Hazardous Substances Data: 16063-70-0(Hazardous Substances Data)

Usage

Uses

Used in Chemical Synthesis:
2,3,5-Trichloropyridine is used as a chemical intermediate for the synthesis of various compounds, including 3,5-dichloro-2-arylpyridines. This synthesis is achieved through a palladium acetate-catalyzed ligand-free Suzuki reaction with arylboronic acids. The compound plays a crucial role in the development of new chemical entities and materials.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 2,3,5-trichloropyridine may be utilized as a building block for the development of new drugs. Its unique chemical properties and reactivity make it a valuable component in the synthesis of various pharmaceutical compounds, potentially leading to the discovery of novel therapeutic agents.
Used in Material Science:
The study of the separation and migration behavior of 2,3,5-trichloropyridine, as well as its crystal structure, suggests that it may have applications in material science. Understanding its structural properties can help in designing new materials with specific characteristics, such as improved stability or enhanced reactivity.
Used in Ionic Liquid Research:
2,3,5-Trichloropyridine's nucleophilic displacement reaction in ionic liquids opens up possibilities for its use in the development of new ionic liquid systems. These systems can be employed in various applications, such as solvents for chemical reactions, electrolytes for batteries, or components in other advanced materials.

InChI:InChI=1/C5H2Cl3N/c6-3-1-4(7)5(8)9-2-3/h1-2H

Synthetic route

2,3,5,6-tetrachloropyridine (2402-79-1) → 2,3,5-trichloropyridine (16063-70-0)

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

2,3,4,5,6-pentachloropyridine (2176-62-7) → 2,3,6-trichloropyridine (6515-09-9) + 2,3,5-trichloropyridine (16063-70-0) + 2,3,5,6-tetrachloropyridine (2402-79-1)

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%

2,3,4,5-tetrachloro-pyridine (2808-86-8) → 2,3,5-trichloropyridine (16063-70-0)

Conditions	Yield
With tetramethylammonium methylphosphonic acid methyl ester; dimethyl methane phosphonate; zinc In water at 85℃; other ammonium salts; other methylphosphonates;other solvent(s). Object of study: selectivity of reaction;	96.4%
With ammonium chloride; zinc In methanol; water at 72℃; for 2h; Solvent; Temperature;	90%
With pyridine; 5%-palladium/activated carbon; hydrogen In methanol; water at 50℃; under 3750.38 Torr; Reagent/catalyst; Temperature; Pressure;	86.2%
With tetramethylammonium methylphosphonic acid methyl ester; dimethyl methane phosphonate; zinc In water at 85℃; for 1h; Yield given;
With ammonium chloride; zinc In methanol; water at 70 - 80℃; Temperature; Solvent; Large scale;	1.4 kg

3,5,6-trichloro-2-hydrazinopyridine (55933-94-3) → 2,3,5-trichloropyridine (16063-70-0)

Conditions	Yield
	95%
With sodium hypochlorite; sodium hydroxide In water at 70 - 75℃; for 1h; Green chemistry;	95%
	93%

2,4,4-trichloro-4-formylbutyronitrile (75272-53-6) → 2,3,5-trichloropyridine (16063-70-0)

Conditions	Yield
With hydrogenchloride; phosphorus pentachloride In N,N-dimethyl-formamide at 60 - 100℃; for 1h;	89%
With hydrogenchloride at 180℃; for 2h;	85%
With hydrogenchloride at 80℃; for 3h;	82.1%

3,5-Dichloro-2-pyridinol (5437-33-2) → 2,3,5-trichloropyridine (16063-70-0)

Conditions	Yield
With trichlorophosphate at 190℃; for 3h; in sealed tube;	87%

2,2,4'-trichloro-5-oxopentanonitrile (98775-57-6) → 2,3,5-trichloropyridine (16063-70-0)

Conditions	Yield
With hydrogenchloride; trichlorophosphate In N,N-dimethyl-formamide at 115℃; for 0.333333h;	79%
With trichlorophosphate In benzene at 190℃; for 1h; in autoclave;	76%
Multi-step reaction with 2 steps 1: 91 percent / dry HCl / dimethylformamide / 0.25 h / 110 °C 2: 87 percent / POCl3 / 3 h / 190 °C / in sealed tube View Scheme
Multi-step reaction with 3 steps 1: 90 percent / dry HCl / dibutyl ether / 1 h / 90 °C 2: 95 percent / triethylamine / benzene / 4 h / Heating 3: 87 percent / POCl3 / 3 h / 190 °C / in sealed tube View Scheme

2,3,4,5,6-pentachloropyridine (2176-62-7) → 2,3,5-trichloropyridine (16063-70-0)

Conditions	Yield
With tetrabutylammomium bromide; sodium hydroxide; zinc In toluene at 50℃; for 6h; Green chemistry;	73%
With ammonium hydroxide In toluene
With sodium hydroxide; zinc In benzene
With sodium hypochlorite; sodium hydrogencarbonate; hydrazine In propylene glycol dimethyl ether; water

chloral (75-87-6) + acrylonitrile (107-13-1) → 2,3,5-trichloropyridine (16063-70-0)

Conditions	Yield
copper(l) chloride In acetonitrile at 190℃; for 0.5h;	65%
copper(l) chloride In acetonitrile at 190℃; for 0.5h;	65%
With [bmim]BF4; copper(l) chloride In acetonitrile at 120℃;	41%
In acetonitrile at 105 - 190℃; Product distribution; various inorg. catalyst, various yield;
copper(l) chloride In acetonitrile at 120 - 175℃; for 19h;

Pyridin-Palladium(II)-chlorid-Komplex → 2-chloropyridine (109-09-1) + 2,3-dichloro-pyridine (2402-77-9) + 2,3,5-trichloropyridine (16063-70-0)

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

3,5-dichloropyridine-2-carboxylic acid (81719-53-1) → 2,3,5-trichloropyridine (16063-70-0)

Conditions	Yield
With tert-butylhypochlorite; dichloromethane; oxygen; sodium hydrogencarbonate at 60℃; for 20h; Green chemistry;	42%

pyridine (110-86-1) → 2,3,5-trichloropyridine (16063-70-0)

Conditions	Yield
With hydrogenchloride; chlorine at 115 - 120℃;
With phosphorus pentachloride at 210 - 220℃;

phosgene (75-44-5) + 3,5-dichloro-1-methyl-1H-pyridin-2-one (4214-83-9) → 2,3,5-trichloropyridine (16063-70-0)

Conditions	Yield
With toluene at 150℃;

trichloroacetonitrile (545-06-2) + acrolein (107-02-8) → 2,3,5-trichloropyridine (16063-70-0)

Conditions	Yield
With copper(I) chloride; trichlorophosphate 1. 5 h, 90 deg C, benzene, autoclave; 2. 30 min, 180 deg C.; Yield given. Multistep reaction;

1-methyl-3.5-dichloro-pyridone-(2) → 2,3,5-trichloropyridine (16063-70-0)

Conditions	Yield
With phosphorus pentachloride; trichlorophosphate at 180℃; im Rohr;

3,5-dichloro-1-methyl-1H-pyridin-2-one (4214-83-9) + phosphorus pentachloride (10026-13-8, 874483-75-7) + trichlorophosphate (10025-87-3, 12599-09-6, 63736-95-8) → 2,3,5-trichloropyridine (16063-70-0)

Conditions	Yield
at 180℃;

barium salt of/the/ pyridine-disulfonic acid-(3.5) → 2,3,5-trichloropyridine (16063-70-0) + 3,5-dichloropyridine (2457-47-8)

Conditions	Yield
With phosphorus pentachloride at 200℃;

3,5-dichloropyridin-2-amine (4214-74-8) → 2,3,5-trichloropyridine (16063-70-0) + 3.5-dichloro-2-oxy-pyridine

Conditions	Yield
With hydrogenchloride; potassium nitrite

hydrogenchloride (7647-01-0) + 3,5-dichloropyridin-2-amine (4214-74-8) + potassium nitrite → 2,3,5-trichloropyridine (16063-70-0) + 3.5-dichloro-2-oxy-pyridine

2-(trichloromethyl)-3,5-dichloropyridine (1128-16-1) → tetrachloromethane (56-23-5) + 2,3,5-trichloropyridine (16063-70-0) + 2,3,5-trichloro-6-(trichloromethyl)pyridine (7041-24-9) + HCl

Conditions	Yield
With chlorine at 200℃; Title compound not separated from byproducts;
With chlorine at 200℃; Rate constant;

2-hydroxy-3,3,5-trichloro-3,4-dihydropyridine (115168-33-7) → 2,3,5-trichloropyridine (16063-70-0)

Conditions	Yield
Multi-step reaction with 2 steps 1: 95 percent / triethylamine / benzene / 4 h / Heating 2: 87 percent / POCl3 / 3 h / 190 °C / in sealed tube View Scheme

2-aminopyridine (504-29-0) → 2,3,5-trichloropyridine (16063-70-0)

Conditions	Yield
Multi-step reaction with 3 steps 1: alcohol; chlorine 2: alcohol; chlorine 3: potassium nitrite; hydrochloric acid View Scheme
Multi-step reaction with 2 steps 1: alcohol; chlorine 2: potassium nitrite; hydrochloric acid View Scheme

5-chloro-2-pyridylamine (1072-98-6) → 2,3,5-trichloropyridine (16063-70-0)

Conditions	Yield
Multi-step reaction with 2 steps 1: alcohol; chlorine 2: potassium nitrite; hydrochloric acid View Scheme

2,3,5,6-tetrachloropyridine (2402-79-1) → 2,3,5-trichloropyridine (16063-70-0) + 3,5-dichloropyridine (2457-47-8)

Conditions	Yield
With ammonium chloride; zinc In 1,4-dioxane; water at 90 - 92℃; for 12h; Product distribution / selectivity;	A 7.7 %Chromat. B 77.8 %Chromat.

3,5-dichloropyridin-2-amine (4214-74-8) → 2,3,5-trichloropyridine (16063-70-0)

Conditions	Yield
With sodium nitrite In hydrogenchloride; hexane; water
With hydrogenchloride; sodium nitrite In water at -20 - 20℃; for 4h;

chloral (75-87-6) + acrylonitrile (107-13-1) + copper(l) chloride → 2,3,5-trichloropyridine (16063-70-0)

Conditions	Yield
In acetonitrile	11.1 g (61% theory)

ruthenium(II)dichloro-tris-triphenylphosphine + 3-Methoxypropionitrile (110-67-8) + chloral (75-87-6) + acrylonitrile (107-13-1) → 2,3,5-trichloropyridine (16063-70-0)

ammonium hydroxide (1336-21-6) + 2,3,4,5,6-pentachloropyridine (2176-62-7) + 1-methoxy-2-propanol (107-98-2) → 2,3,5-trichloropyridine (16063-70-0)

Conditions	Yield
In water; toluene

2,3,5-trichloro-4-hydrazino-pyridine (55933-95-4) → 2,3,5-trichloropyridine (16063-70-0)

Conditions	Yield
With sodium hypochlorite In tetrahydrofuran

2,3,5-trichloropyridine (16063-70-0) + propargyl alcohol (107-19-7) → 3,5-dichloro-2-(prop-2-ynyloxy)-pyridine

Conditions	Yield
Stage #1: propargyl alcohol With sodium hydride In tetrahydrofuran at 0 - 45℃; Stage #2: 2,3,5-trichloropyridine In tetrahydrofuran at 20 - 45℃; for 24h;	100%

2,3,5-trichloropyridine (16063-70-0) + 2-amino-benzenethiol (137-07-5) → 3-chloro-1-azaphenothiazine (3493-96-7)

Conditions	Yield
With potassium hydroxide In water; N,N-dimethyl-formamide for 4h; Reflux;	99.7%

2,3,5-trichloropyridine (16063-70-0) → 3,5-dichloro-2-bromopyridine (14482-51-0)

Conditions	Yield
With trimethylsilyl bromide In propiononitrile at 100℃; for 14h;	99%
With hydrogen bromide; propionic acid In water at 80℃; Reagent/catalyst; Solvent;	96.8%

2,3,5-trichloropyridine (16063-70-0) → (3,5-dichloro-2-pyridyl)hydrazine (104408-23-3)

Conditions	Yield
With hydrazine hydrate In ethanol at 80℃; for 24h;	96%
With hydrazine hydrate	95%
With hydrazine hydrate In ethanol at 80 - 90℃;	94.5%

2,3,5-trichloropyridine (16063-70-0) → 5-chloro-2,3-difluoropyridine (89402-43-7)

Conditions	Yield
With potassium fluoride; C6H10BNO4 In dimethyl sulfoxide at 60℃; for 5h; Solvent; Temperature;	95%
With potassium fluoride; 18-crown-6 ether; potassium carbonate; cesium fluoride In sulfolane; dimethyl sulfoxide at 120 - 200℃; for 3h;	90%
Multi-step reaction with 2 steps 1: 36.1 percent / KF; CsF; K2CO3 / [Bmim]BF4 / 10 h / 200 °C 2: 68.8 percent / CsF; K2CO3; [Bmim]BF4 / 8 h / 100 - 110 °C / 200 Torr View Scheme

2,3,5-trichloropyridine (16063-70-0) + 2-methoxy-phenylamine (90-04-0) → 3,5-dichloro-N-(2-methoxyphenyl)pyridine-2-amine

Conditions	Yield
With potassium carbonate; palladium diacetate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene In 1,2-dimethoxyethane at 85℃; for 2.5h;	94.7%

2,3,5-trichloropyridine (16063-70-0) + 2-methyl-7-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-2H-indazole (845751-67-9) → 7-(3,5-dichloro-pyridin-2-yl)-2-methyl-2H-indazole (845751-68-0)

Conditions	Yield
With potassium phosphate; tetrakis(triphenylphosphine) palladium(0) In DMF (N,N-dimethyl-formamide); water at 65℃; for 16h;	93%

2,3,5-trichloropyridine (16063-70-0) + p-cresol (106-44-5) → 2-(4-Methylphenoxy)-3,5-dichlorpyridin (28232-17-9)

Conditions	Yield
With copper(l) iodide; N,N,N,N,-tetramethylethylenediamine; caesium carbonate In dimethyl sulfoxide at 110℃; for 24h; Inert atmosphere; regioselective reaction;	93%

2,3,5-trichloropyridine (16063-70-0) + 4-Chlorophenylboronic acid (1679-18-1) → 3,5-dichloro-2-(4-chlorophenyl)pyridine (161949-47-9)

Conditions	Yield
With palladium diacetate; sodium carbonate In water; N,N-dimethyl-formamide at 60℃; for 12h; Suzuki coupling;	91%

2,3,5-trichloropyridine (16063-70-0) + 4-methylphenylboronic acid (5720-05-8) → 3,5-dichloro-2-p-tolylpyridine (1204385-79-4)

Conditions	Yield
With palladium diacetate; sodium carbonate In water; N,N-dimethyl-formamide at 60℃; for 12h; Suzuki coupling;	90%

2,3,5-trichloropyridine (16063-70-0) + (RS)-2-(4-hydroxyphenoxy)propionic acid (94050-90-5, 95977-31-4, 105118-15-8, 67648-61-7) → D-2-[4-(3,5-dichloro-pyridin-2-yloxy)-phenoxy]-propionic acid (60074-25-1)

Conditions	Yield
With potassium carbonate at 75℃; for 4.5h; Reagent/catalyst; Temperature;	90%

2,3,5-trichloropyridine (16063-70-0) + 2-Methoxyphenylboronic acid (5720-06-9) → C12H9Cl2NO

Conditions	Yield
With potassium fluoride; tetrakis(triphenylphosphine) palladium(0) In toluene at 100℃; for 5h;	90%
With potassium fluoride; tetrakis(triphenylphosphine) palladium(0) In toluene at 100℃; for 5h;	90%

2,3,5-trichloropyridine (16063-70-0) → 2,3,5-trichloro-4-iodopyridine (406676-23-1)

Conditions	Yield
With iodine; lithium diisopropyl amide In tetrahydrofuran; hexane at -75℃;	89%
Stage #1: 2,3,5-trichloropyridine With lithium diisopropyl amide In tetrahydrofuran at -78℃; for 2h; Inert atmosphere; Stage #2: With iodine In tetrahydrofuran at -78℃; for 2h; Inert atmosphere;	75%

2,3,5-trichloropyridine (16063-70-0) + 4-fluoroboronic acid (1765-93-1) → 3,5-dichloro-2-(4-fluorophenyl)pyridine (1204385-81-8)

Conditions	Yield
With palladium diacetate; sodium carbonate In water; N,N-dimethyl-formamide at 60℃; for 12h; Suzuki coupling;	89%

2,3,5-trichloropyridine (16063-70-0) + 1-Naphthylboronic acid (13922-41-3) → 3,5-dichloro-2-(naphthalen-1-yl)pyridine (1204385-86-3)

Conditions	Yield
With palladium diacetate; sodium carbonate In water; N,N-dimethyl-formamide at 60℃; for 12h; Suzuki coupling;	89%

2,3,5-trichloropyridine (16063-70-0) + phenylboronic acid (98-80-6) → 3,5-dichloro-2-phenylpyridine (10469-01-9)

Conditions	Yield
With palladium diacetate; sodium carbonate In water; N,N-dimethyl-formamide at 60℃; for 12h; Suzuki coupling;	89%
With palladium diacetate; potassium carbonate; triphenylphosphine In methanol; acetonitrile at 50℃; for 24h; Suzuki Coupling; Inert atmosphere; regioselective reaction;	86%

6-methoxypyridine-3-ol (51834-97-0) + 2,3,5-trichloropyridine (16063-70-0) → 5-(3,5-dichloro-pyridin-2-yloxy)-2-methoxy-pyridine (548763-85-5)

Conditions	Yield
With potassium hydroxide In dimethyl sulfoxide	88%

2,3,5-trichloropyridine (16063-70-0) + (meta-(trifluoromethyl)phenyl)boronic acid (1423-26-3) → 3,5-dichloro-2-(3-(trifluoromethyl)phenyl)pyridine (1204385-83-0)

Conditions	Yield
With palladium diacetate; sodium carbonate In water; N,N-dimethyl-formamide at 60℃; for 12h; Suzuki coupling;	88%

2,3,5-trichloropyridine (16063-70-0) → 3,5-dichloropyridine (2457-47-8)

Conditions	Yield
With acetic acid; zinc In water at 65 - 95℃; for 1 - 5.25h; Product distribution / selectivity;	87.3%

2,3,5-trichloropyridine (16063-70-0) + 2-Methylphenylboronic acid (16419-60-6) → 3,5-dichloro-2-o-tolylpyridine (1204385-80-7)

Conditions	Yield
With palladium diacetate; sodium carbonate In water; N,N-dimethyl-formamide at 60℃; for 12h; Suzuki coupling;	87%

2,3,5-trichloropyridine (16063-70-0) → 2-Fluoro-3,5-dichloropyridine (823-56-3)

Conditions	Yield
With potassium fluoride In sulfolane at 180℃; for 20h;	86%
With potassium fluoride In sulfolane at 155 - 160℃; for 8h; Solvent; Temperature;

Thien-3-ylboronic acid (6165-69-1) + 2,3,5-trichloropyridine (16063-70-0) → 3,5-dichloro-2-(thiophen-3-yl)pyridine (1204385-85-2)

Conditions	Yield
With palladium diacetate; sodium carbonate In water; N,N-dimethyl-formamide at 60℃; for 12h; Suzuki coupling;	86%

2,3,5-trichloropyridine (16063-70-0) + 4-methoxyphenylboronic acid (5720-07-0) → 3,5-dichloro-2-(4-methoxyphenyl)pyridine (1204385-82-9)

Conditions	Yield
With palladium diacetate; sodium carbonate In water; N,N-dimethyl-formamide at 60℃; for 12h; Suzuki coupling;	85%

2,3,5-trichloropyridine (16063-70-0) + sodium methylate (124-41-4) → 5-chloro-1,2-dimethoxypyridine

Conditions	Yield
In dimethyl sulfoxide at 90℃; for 2h; methoxylation;	83%

Upstream product

• 110-86-1 pyridine 
• 75-44-5 phosgene 
• 4214-83-9 3,5-dichloro-1-methyl-1H-pyridin-2-one 
• 2808-86-8 2,3,4,5-tetrachloro-pyridine 
• 2176-62-7 2,3,4,5,6-pentachloropyridine 
• 5437-33-2 3,5-Dichloro-2-pyridinol 
• 75272-53-6 2,4,4-trichloro-4-formylbutyronitrile 
• 75-87-6 chloral 
• 107-13-1 acrylonitrile 
• 545-06-2 trichloroacetonitrile 
• 107-02-8 acrolein 
• 98775-57-6 2,2,4'-trichloro-5-oxopentanonitrile 
• 10026-13-8 phosphorus pentachloride 
• 10025-87-3 trichlorophosphate 

Downstream Products

• 13472-58-7 3,5-dichloro-2-methoxypyridine 
• 4214-74-8 3,5-dichloropyridin-2-amine 
• 104408-23-3 (3,5-dichloro-2-pyridyl)hydrazine 
• 284040-73-9 5-chloro-1,2-dimethoxypyridine 
• 2457-47-8 3,5-dichloropyridine 
• 406676-23-1 2,3,5-trichloro-4-iodopyridine 
• 2402-79-1 2,3,5,6-tetrachloropyridine 
• 60074-46-6 methyl 2-[4-(3,5-dichloropyridin-2-yloxy)-phenoxy]-propionate 
• 60074-47-7 ethyl 2-{p-[(3,5-dichloro-pyridin-2-yl)oxy]phenoxy}propionate 
• 72280-52-5 2-[4-(3,5-dichloropyridin-2-yloxy)-phenoxy]-propionic acid propargyl ester 
• 60074-56-8 benzyl 2-[4-(3,5-dichloropyridin-2-yloxy)-phenoxy]-propionate 
• 823-56-3 2-Fluoro-3,5-dichloropyridine 
• 89402-43-7 5-chloro-2,3-difluoropyridine 
• 40360-44-9 3,5,6-trichloropicolinic acid 

Relevant articles and documents

Eine neue, einfache Synthese von 2,3,5-Trichlorpyridin

A simple synthesis of 2,3,5-trichloropyridine by the copper-catalyzed free radical addition of chloral to acrylonitrile with or without isolation of the primary 1:1 adduct, 4-formyl-2,4,4-trichlorobutyronitrile (1), is described.

Direct formation of 2,3,5-trichloropyridine and its nucleophilic displacement reactions in ionic liquid

Reaction of trichloroacetaldehyde and acrylonitrile in the presence of a catalytic amount of copper (I) chloride in ionic liquid afforded 2,3,5-trichloropyridine, fluprination of which with KF and CsF in ionic liquid afforded 3,5-dichloro-2-fluoropyridihe and 5-chloro-2,3-dichloropyridine. Reaction of 2,3,5-trichloropyridine, 3,5-dichloro-2-fluoropyridine, or 5-chloro-2,3-dichloropyride with 2-(4-hydroxyphenoxy) propionates in ionic liquid afforded the corresponding 2-aryloxylpropionates in good yields.

Halopyridines. I. Synthesis of 3,5-Dichloro-2-pyridone and 2,3,5-Trichloropyridine

Trichloroacetonitrile reacts with acrolein to give 2,2,4-trichloro-5-oxopentanonitrile, the cyclization of which to chloropyridines has been examined.

Synthesis method of 2, 3, 5-trichloropyridine

The invention relates to a synthesis method of 2, 3, 5-trichloropyridine. The method comprises the following steps: (1) in the presence of a phase transfer catalyst and a polymerization inhibitor, carrying out chemical reaction on trichloroacetaldehyde, acrylonitrile and the catalyst at 60-90 DEG C to prepare an intermediate product 2, 4, 4-trichloro-4-formyl butyronitrile; and (2) heating a reaction solution obtained in the step (1) to 60-100 DEG C, and slowly introducing hydrogen chloride gas into the reaction solution to carry out cyclization reaction, thereby preparing the target compound2, 3, 5-trichloropyridine. The synthesis method has the advantages of mild reaction conditions, no need of harsh reaction conditions, such as high temperature, high pressure and reaction solvent, recyclable catalyst, less heavy metal pollution, high target product yield (up to 80%), high purity (up to 99%), simple post-treatment of the product, and reduced cost, and is suitable for industrial production.

Continuous production process of 2, 3, 5-trichloropyridine

According to a continuous production process of 2, 3, 5-trichloropyridine, a continuous tubular chlorinator is adopted, pyridine is taken as a starting raw material, chlorination reaction is continuously carried out step by step by virtue of a catalyst 1 and a catalyst 2 which are independently researched and developed, and 2, 5-dichloropyridine and 2, 3, 5-trichloropyridine are prepared in sequence. In the preparation process of a catalyst 1 and a catalyst 2, the mass ratio of 1-chloropropane to imidazole to 2-chloroethyl diphenylphosphine to nickel tetracarbonyl is 1.2: 1: 3.7: 2.5, and the mass ratio of 1-chloropropane to imidazole to 2-chloroethyl diphenylphosphine to sodium hexachlororhodate hydrate is 1.2: 1: 3.7: 15. By means of the continuous tubular chlorinator, cheap and easily available pyridine is used as a starting raw material, chlorine atoms are introduced step by step through catalytic chlorination, the atom economy is good, the reaction selectivity is good, the yield of 2, 3, 5-trichloropyridine can be stabilized at 80% or above, the production efficiency is high, the process is easy to control, and the method is environmentally friendly and suitable for industrial production.

Preparation method of 2, 3, 5-trichloropyridine

The invention relates to the field of organic synthesis, in particular to a preparation method of 2, 3, 5-trichloropyridine. According to the invention, in a mixed solvent composed of an organic solvent and water, 2, 3, 4, 5-tetrachloropyridine is reduced by using zinc powder, such that 2, 3, 5-trichloropyridine is prepared. The preparation method of 2, 3, 5-trichloropyridine has the advantages ofhigh yield and high purity, and is environment-friendly, simple and convenient to operate.

Resourceful treatment method of picloram solid residues

The invention relates to a picloram solid residue resourceful treatment method which comprises the following steps: a) carrying out decarboxylation reaction on picloram solid residues, performing filtering, taking filtrate, and separating out solid; b) sequentially carrying out diazotization and chlorination reaction on the solid obtained in the step a), separating out the solid, performing filtering, taking a filter cake, and performing separating to obtain 2, 3, 4, 5-tetrachloropyridine; c) subjecting the 2, 3, 4, 5-tetrachloropyridine obtained in the step b) to a dechlorination reaction soas to obtain 2, 3, 5-trichloropyridine and/or 2, 5-dichloropyridine. According to the resourceful treatment method provided by the invention, the picloram solid residues can be converted into 2, 3, 5-trichloropyridine products with good market demand prospects and relatively high economic values, and further efficient utilization of the picloram solid residues is realized.

Method for preparing 2,3,5-trichloropyridine from 2,3,5,6-tetrachloropyridine

The invention discloses a method for preparing 2,3,5-trichloropyridine from 2,3,5,6-tetrachloropyridine. The method comprises the following steps: (1) adding 2,3,5,6-tetrachloropyridine, an organic solvent, a catalyst, an acid-binding agent and water input a high-pressure kettle, performing nitrogen displacement for three times, further performing hydrogen displacement for three times, and performing a reaction in a hydrogen atmosphere, wherein the catalyst is prepared from at least one of Pd and Pt as active components and aluminum oxide or activated carbon as a carrier; (2) performing cooling to the room temperature, discharging gases in the high-pressure kettle, performing nitrogen displacement for three times, filtering the reaction product so as to obtain a catalyst, and performing standing and layering on filtrate so as to obtain an organic phase; and (3) performing vacuum distillation on the organic phase so as to obtain a light yellow solid, that is, 2,3,5-trichloropyridine, and recycling the fraction for later use. The 2,3,5,6-tetrachloropyridine which is easy to purchase is adopted as a raw material of the method disclosed by the invention, the method is green and environment-friendly, and in addition the product is high in yield and high in purity.

Transition-metal-free decarboxylative halogenation of 2-picolinic acids with dihalomethane under oxygen conditions

A convenient and efficient method for the synthesis of 2-halogen-substituted pyridines is described. The decarboxylative halogenation of 2-picolinic acids with dihalomethane proceeded smoothly via N-chlorocarbene intermediates to afford 2-halogen-substituted pyridines in satisfactory to excellent yields under transition-metal-free conditions. This new type of decarboxylative halogenation is operationally simple and exhibits high functional-group tolerance.

Method for synthesizing 2, 3, 5-trichloropyridine

The invention discloses a method for synthesizing 2, 3, 5-trichloropyridine. The method mainly comprises: (1) synthesis of 2, 3, 5-trichloro-6-hydrated hydrazinyl pyridine: adding hydrazine hydrate and a reaction solvent into 2, 3, 5, 6-tetrachloropyridine as a raw material, carrying out a reaction process at a certain temperature for some time and carrying out treatment to obtain 2, 3, 5-trichloro-6-hydrated hydrazinyl pyridine, and (2) reaction of 2, 3, 5-trichloro-6-hydrated hydrazinyl pyridine and a sodium hypochlorite aqueous solution in an alkaline environment at a certain temperature for a certain period of time, then treatment and reduced pressure distillation. The method has the advantages of low reaction raw material price, no high toxic, no irritation, small three waste amount,environmentally friendly processes, relatively thorough reaction, simple process control and high product yield.