2176-62-7

Basic information

• Product Name: Pentachloropyridine
• Synonyms: 2,3,4,5,6-pentachloro-pyridin;2,3,4,5,6-Pentachlorpyridine;pentachloro-pyridin;pentachlorpyridine;Perchloropyridine;Pyridine, 2,3,4,5,6-pentachloro-;2,3,4,5,6-PENTACHLOROPYRIDINE;2,3,4,5,6-PENTCHLOROPYRIDINE
• CAS NO: 2176-62-7
• Molecular Formula: C₅Cl₅N
• Molecular Weight: 251.33
• EINECS: 218-535-5
• Product Categories: Chloropyridines;Halopyridines;C5Heterocyclic Building Blocks;Halogenated Heterocycles;Heterocyclic Building Blocks;Pyridines;Pesticide intermediate
• Mol File: 2176-62-7.mol
• Article Data: 10

Chemical Properties

• Melting Point: 124 °C
• Boiling Point: 280 °C
• Flash Point: 151.5 °C
• Appearance: White to off-white/Flakes
• Density: 1.7500 (estimate)
• Vapor Density: 8.4 (vs air)
• Vapor Pressure: 0.01 mm Hg ( 20 °C)
• Refractive Index: 1.601
• Storage Temp.: Store below +30°C.
• Solubility: 9mg/l
• PKA: -6.23±0.50(Predicted)
• BRN: 155197
• CAS DataBase Reference: Pentachloropyridine(CAS DataBase Reference)
• NIST Chemistry Reference: Pentachloropyridine(2176-62-7)
• EPA Substance Registry System: Pentachloropyridine(2176-62-7)

Safety Data

• Hazard Codes: Xn,Xi
• Statements: 22-36/37/38-42/43
• Safety Statements: 22-26-36-24/25
• WGK Germany: 3
• RTECS: UT7000000
• TSCA: Yes
• HazardClass: 9
• Hazardous Substances Data: 2176-62-7(Hazardous Substances Data)

Usage

Chemical Properties

WHITE TO OFF-WHITE FLAKES

Uses

Pentachloropyridine is a halogenated pyridine with antineoplastic and antiapoptic properties.

Safety Profile

Poison by intraperitoneal route. When heated to decomposition it emits very toxic fumes of Clí and NOx.

Purification Methods

Purify it by recrystallisation from EtOH or aqueous EtOH. It sublimes at 150o/3mm. [den Hertog et al. Recl Trav Chim Pays-Bas 69 673 1950, Schikh et al. Chem Ber 69 2604 1936, Beilstein 20 I 81, 20 III/IV 2503, 20/5 V 422.]

InChI:InChI=1/C5Cl5N/c6-1-2(7)4(9)11-5(10)3(1)8

Synthetic route

2,3,5,6-tetrachloropyridine (2402-79-1) → 2,3,4,5,6-pentachloropyridine (2176-62-7)

Conditions	Yield
With sodium hydroxide; hexachloroethane; tetrabutylammomium bromide In dichloromethane at 55℃;	71%
With phosphorus pentachloride

tetrachlo-5-iodoropyridine (72012-23-8) → 2,3,4,6-Tetrachloropyridine (14121-36-9) + 2,3,4,5,6-pentachloropyridine (2176-62-7) + octachloro-3,3'-bipyridyl

Conditions	Yield
With copper In N,N-dimethyl-formamide at 150℃;	A 3% B n/a C 71%

4-Bromo-2,3,5,6-tetrachloropyridine (23995-94-0) → 2,3,5,6-tetrachloropyridine (2402-79-1) + 2,3,4,6-Tetrachloropyridine (14121-36-9) + 2,3,4,5,6-pentachloropyridine (2176-62-7) + octachloro-4,4'-bipyridyl (18725-60-5)

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%

tetrachloro-4-iodopyridine (30332-35-5) → 2,3,5,6-tetrachloropyridine (2402-79-1) + 2,3,4,5,6-pentachloropyridine (2176-62-7) + octachloro-4,4'-bipyridyl (18725-60-5)

Conditions	Yield
With copper In N,N-dimethyl-formamide at 150℃;	A 22% B 4% C 52%

bis(2,3,5,6-tetrachloropyridin-4-yl)sulfane (39873-38-6) → 2,3,4,5,6-pentachloropyridine (2176-62-7) + hexachlorodipyrido<5,4-b;3,4-d>thiophen (63954-14-3)

Conditions	Yield
In tetrachloromethane for 24h; Irradiation;	A 6.5% B 44%

4-Bromo-2,3,5,6-tetrachloropyridine (23995-94-0) → 2,3,5,6-tetrachloropyridine (2402-79-1) + 2,3,4,6-Tetrachloropyridine (14121-36-9) + 2,3,4,5,6-pentachloropyridine (2176-62-7) + octachloro-3,4'-bipyridyl + octachloro-4,4'-bipyridyl (18725-60-5)

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 (23995-94-0) → 2,3,5,6-tetrachloropyridine (2402-79-1) + 2,3,4,5,6-pentachloropyridine (2176-62-7) + octachloro-3,4'-bipyridyl + octachloro-4,4'-bipyridyl (18725-60-5)

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%

tetrachloro-4-(2-pyridylthio)pyridine (74894-12-5) → 2,3,4,5,6-pentachloropyridine (2176-62-7) + 1,3,4-trichlorodipyrido<2,3-b;3,4-d>thiophen (74894-22-7)

Conditions	Yield
In tetrahydrofuran; ethanol for 6h; Irradiation;	A 39% B 13%

tetrachloromethane (56-23-5) + 2,3,5,6-tetrachloropyridine (2402-79-1) → 2,3,4,5,6-pentachloropyridine (2176-62-7) + 4-dichloromethyl-2,3,5,6-tetrachloropyridine (37665-08-0) + 4-trichloromethyl-2,3,5,6-tetrachloropyridine

Conditions	Yield
With tetrachloromethane; tetrabutylammomium bromide In sodium hydroxide at 50℃; for 4h;	A n/a B 30% C n/a

tetrachloro-4-pyridylcopper (27425-94-1) + benzoyl chloride (98-88-4) → 2,3,5,6-tetrachloropyridine (2402-79-1) + 4-benzoyltetrachloropyridine (18613-89-3) + 2,3,4,5,6-pentachloropyridine (2176-62-7) + octachloro-4,4'-bipyridyl (18725-60-5)

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 (27425-94-1) → 2,3,5,6-tetrachloropyridine (2402-79-1) + 4-benzoyltetrachloropyridine (18613-89-3) + 2,3,4,5,6-pentachloropyridine (2176-62-7) + octachloro-4,4'-bipyridyl (18725-60-5)

Conditions	Yield
With para-xylene; benzoyl chloride In N,N-dimethyl-formamide for 23h; Heating;	A 12% B 13% C 1% D 2.5%

1-pyrrolidino-1-cycloheptene (14092-11-6) + 2,3,4,5,6-pentachloropyridine N-oxide (17573-93-2) → 1-(tetrachloro-2-pyridyl)cyclohexene (71602-56-7) + 2,3,4,5,6-pentachloropyridine (2176-62-7) + 2-chloro-7-(tetrachloro-2-pyridyl)cycloheptanone (76277-93-5)

Conditions	Yield
In toluene for 14h; Heating; Yields of byproduct given;	A 11% B n/a C n/a
In toluene for 14h; Heating; Yields of byproduct given;	A n/a B n/a C 5%

1-(N-morpholino)cyclopent-1-ene (936-52-7) + 2,3,4,5,6-pentachloropyridine N-oxide (17573-93-2) → 2-(tetrachloro-N-oxido-2-pyridyl)cyclopentanone (71602-52-3) + 2,3,4,5,6-pentachloropyridine (2176-62-7)

Conditions	Yield
In toluene for 14h; Heating;	A 6% B 1%

pyridine (110-86-1) → 2,3,4,5,6-pentachloropyridine (2176-62-7)

Conditions	Yield
With phosphorus pentachloride
With chlorine

3-nitropyridine (2530-26-9) → 2,3,4,5,6-pentachloropyridine (2176-62-7)

Conditions	Yield
With chlorine at 130 - 150℃;

pyridine hydrochloride (628-13-7) → 2,3,4,5,6-pentachloropyridine (2176-62-7)

Conditions	Yield
With chlorine at 115 - 120℃;

2,6-dichloropyridine-4-carboxylic acid (5398-44-7) → 2,3,4,5,6-pentachloropyridine (2176-62-7)

Conditions	Yield
With phosphorus pentachloride

2-Cyanopyridine (100-70-9) → 2,3,4,5,6-pentachloropyridine (2176-62-7) + 6-chloro-pyridine-2-carbonitrile (33252-29-8) + 3,4,5,6-tetrachloropicolinonitrile (17824-83-8) + 3,4,5-trichloro-2-picolinonitrile (139485-42-0)

Conditions	Yield
With chlorine In tetrachloromethane at 630℃; for 0.00138889h; Product distribution; var. contact times, temperatures, and solvent systems;	A 6.1 % Chromat. B 2.0 % Chromat. C 75.4 % Chromat. D 7.7 % Chromat.

2,3,4,5-tetrachloro-6-(trichloromethyl)-pyridine (1134-04-9) → tetrachloromethane (56-23-5) + 2,3,4,5,6-pentachloropyridine (2176-62-7)

Conditions	Yield
With chlorine at 200℃; Rate constant;

2,3,5,6-tetrachloropyridine (2402-79-1) + phosphorus pentachloride (10026-13-8, 874483-75-7) → 2,3,4,5,6-pentachloropyridine (2176-62-7)

2,6-dichloropyridine-4-carboxylic acid (5398-44-7) + (excess) phosphorus pentachloride → 2,3,4,5,6-pentachloropyridine (2176-62-7)

Conditions	Yield
at 300℃; im Rohr;

pyridine N-oxide (694-59-7) + hydrogenchloride (7647-01-0) + sulfuryl dichloride (7791-25-5) → 2-chloropyridine (109-09-1) + 4-Chloropyridine (626-61-9) + 2,3,4,5,6-pentachloropyridine (2176-62-7)

Conditions	Yield
at 120℃;

pyridine (110-86-1) + chlorine (7782-50-5) → 3-Chloropyridine (626-60-8) + 3,4,5-trichloropyridine (33216-52-3) + 2,3,4,5,6-pentachloropyridine (2176-62-7) + 3,5-dichloropyridine (2457-47-8)

Conditions	Yield
at 170℃; beim Behandeln des Pyridin-hydrochlorids;

3,4,5-trichloro-2-trichloromethyl pyridine (1201-30-5) → tetrachloromethane (56-23-5) + 2,3,4,5-tetrachloro-pyridine (2808-86-8) + 2,3,4,5,6-pentachloropyridine (2176-62-7) + 2,3,4,5-tetrachloro-6-(trichloromethyl)-pyridine (1134-04-9) + HCl

Conditions	Yield
With chlorine at 200℃; for 18h; Title compound not separated from byproducts;	A n/a B 9.7 % Chromat. C 3.2 % Chromat. D 11.8 % Chromat. E n/a
With chlorine at 200℃; for 18h; Irradiation; Yield given. Yields of byproduct given. Title compound not separated from byproducts;
With chlorine at 245℃; Thermodynamic data; Kinetics; Rate constant; other temperature, irrradiation, activation energies;
With chlorine at 200℃; for 18h; Product distribution; other time;	A n/a B 9.7 % Chromat. C 3.2 % Chromat. D 11.8 % Chromat. E n/a

carbon → 2,3,4,5,6-pentachloropyridine (2176-62-7) + hexachloroethane (67-72-1) + hexachlorobenzene (118-74-1) + octachlorostyrene (29082-74-4)

Conditions	Yield
With aluminium trichloride at 300℃; for 24h; Chlorination; cyclization; Further byproducts given. Title compound not separated from byproducts;

anode graphite → 2,3,4,5,6-pentachloropyridine (2176-62-7) + Hexachlorobutadiene (87-68-3) + hexachlorobenzene (118-74-1) + octachlorostyrene (29082-74-4)

Conditions	Yield
With melt electrolyte at 700℃; Formation of xenobiotics; electrolysis; Further byproducts given. Title compound not separated from byproducts;

graphite → 2,3,4,5,6-pentachloropyridine (2176-62-7)

Conditions	Yield
With oxygen; urea; copper dichloride at 300℃; Formation of xenobiotics;

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

Conditions	Yield
Multi-step reaction with 2 steps 1: C2Cl6; nBu4NBr; aq. NaOH / 4 h / 50 °C 2: 71 percent / C2Cl6; nBu4NBr; aq. NaOH / CH2Cl2 / 55 °C View Scheme

4-Bromo-2,3,5,6-tetrachloropyridine (23995-94-0) → 2,3,4,5,6-pentachloropyridine (2176-62-7)

Conditions	Yield
Multi-step reaction with 2 steps 1: 39 percent / potassium carbonate / acetone / 2 h / Heating 2: 39 percent / tetrahydrofuran; ethanol / 6 h / Irradiation View Scheme

dmap (1122-58-3) + 2,3,4,5,6-pentachloropyridine (2176-62-7) → 1-(4-dimethylamino)-[2,3,5,6-tetrachloro-pyridin-4-yl]pyridinium chloride

Conditions	Yield
In 1,2-dichloro-benzene at 80℃; for 3h;	100%
In 1,2-dichloro-benzene at 60℃;	87%
In 1,2-dichloro-benzene at 80 - 90℃;

dmap (1122-58-3) + 2,3,4,5,6-pentachloropyridine (2176-62-7) → (3,5-dichloropyridine-2,4,6-triyl)-1,1',1''-tris[4-(dimethylamino)pyridinium] trichloride

Conditions	Yield
In 1,2-dichloro-benzene at 120℃; for 3h;	100%
In 1,2-dichloro-benzene Heating;
Heating;

4-aminopyridine (504-24-5) + 2,3,4,5,6-pentachloropyridine (2176-62-7) → 1,1',1''-tris[4-amino-(3,5-dichloropyridine-2,4,6-triyl)-pyridinium] trichloride

Conditions	Yield
In N,N-dimethyl-formamide at 120℃; for 1h;	100%
Heating;

2,3,4,5,6-pentachloropyridine (2176-62-7) + 4-pyrrolidin-1-ylpyridine (2456-81-7) → 1,1',1''-tris[4-pyrrolidino-(3,5-dichloropyridine-2,4,6-triyl)-pyridinium] trichloride

Conditions	Yield
In N,N-dimethyl-formamide at 120℃; for 2h;	100%

2,3,4,5,6-pentachloropyridine (2176-62-7) → 2,3,5,6-tetrachloropyridine (2402-79-1)

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;

2,3,4,5,6-pentachloropyridine (2176-62-7) + tris(trimethylsilyl) phosphite (1795-31-9) → C11H18Cl4NO3PSi2

Conditions	Yield
With nickel dichloride at 150℃; for 0.5h;	99%

2,3,4,5,6-pentachloropyridine (2176-62-7) + phenylboronic acid (98-80-6) → 2,3,4,5,6-pentaphenylpyridine (40249-26-1)

Conditions	Yield
With dichloro bis(acetonitrile) palladium(II); potassium phosphate; 2-dicyclohexylphosphino-2’,6’-dimethoxybiphenyl In toluene at 100℃; for 20h; Catalytic behavior; Solvent; Reagent/catalyst; Temperature; Suzuki-Miyaura Coupling; Inert atmosphere; Schlenk technique; Sealed tube;	99%
With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; dichloro bis(acetonitrile) palladium(II)	99%

2,3,4,5,6-pentachloropyridine (2176-62-7) + 4-methylphenylboronic acid (5720-05-8) → 2,3,4,5,6-pentakis(4-tolyl)pyridine (1639431-10-9)

Conditions	Yield
With dichloro bis(acetonitrile) palladium(II); potassium phosphate; 2-dicyclohexylphosphino-2’,6’-dimethoxybiphenyl In toluene at 100℃; for 20h; Suzuki-Miyaura Coupling; Inert atmosphere; Schlenk technique; Sealed tube;	99%

2,3,4,5,6-pentachloropyridine (2176-62-7) + 4-methoxyphenylboronic acid (5720-07-0) → 2,3,4,5,6-pentakis(4-methoxyphenyl)pyridine (1639431-14-3)

Conditions	Yield
With dichloro bis(acetonitrile) palladium(II); potassium phosphate; 2-dicyclohexylphosphino-2’,6’-dimethoxybiphenyl In toluene at 100℃; for 20h; Suzuki-Miyaura Coupling; Inert atmosphere; Schlenk technique; Sealed tube;	99%

2,3,4,5,6-pentachloropyridine (2176-62-7) → 2,3,5,6-tetrachloro-4-azidopyridine (51379-64-7)

Conditions	Yield
With sodium azide In acetone at 20℃;	98%

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%

2,3,4,5,6-pentachloropyridine (2176-62-7) + sodium thiomethoxide (5188-07-8) → 2,3,5,6-tetrachloro-4-methylmercaptopyridine (22963-62-8)

Conditions	Yield
With sodium iodide In methanol; water at 20℃; for 4h; Solvent; Reagent/catalyst; Cooling with ice;	96%
In tetrahydrofuran; water at 20℃; for 1h; Temperature; Large scale;

2,3,4,5,6-pentachloropyridine (2176-62-7) → 3,5-dichloro-2,4,6-trifluoropyridine (1737-93-5)

Conditions	Yield
With potassium fluoride at 90℃; for 1.5h; Temperature; Reagent/catalyst; Concentration;	95.42%
With hydrogen fluoride; tetramethylammonium fluoride In water; isopropyl alcohol at -10 - 135℃; Temperature; Flow reactor; Green chemistry;	94.7%
With potassium fluoride In sulfolane at 190℃; for 72h;	93%

2,3,4,5,6-pentachloropyridine (2176-62-7) + 4-pyrrolidin-1-ylpyridine (2456-81-7) → 1-(4-pyrrolidino)-[2,3,5,6-tetrachloropyridin-4-yl]-pyridinium chloride

Conditions	Yield
In 1,2-dichloro-benzene at 20℃; for 24h;	95%

2,3,4,5,6-pentachloropyridine (2176-62-7) → 3,5-dichloro-2,4,6-triazido-pyridine (51379-63-6)

Conditions	Yield
With sodium azide In water; acetone at 70℃; for 72h; azidation;	94%
With sodium azide In acetone at 70℃; for 72h;	84%

2,3,4,5,6-pentachloropyridine (2176-62-7) + phenylacetylene (536-74-3) → 2,3,4,5,6-pentakis(phenylethynyl)pyridine (1269423-16-6)

Conditions	Yield
With dichloro bis(acetonitrile) palladium(II); copper(l) iodide; diisopropylamine; XPhos In 1,4-dioxane at 80℃; for 10h; Sonogashira coupling; Inert atmosphere; Sealed tube;	92%

2,3,4,5,6-pentachloropyridine (2176-62-7) → 2,3,5,6-tetrachloro-4-pyridinol (2322-38-5) + 3,4,5,6-tetrachloro-2-pyridinol (17368-22-8)

Conditions	Yield
With potassium hydroxide In tert-butyl alcohol for 10h; Heating;	A n/a B 90%

2,3,4,5,6-pentachloropyridine (2176-62-7) + N-(4-chlorophenyl)formamide (2617-79-0) → 2,3,5,6-tetrachloro-N-(4-chlorophenyl)pyridin-4-amine (33028-83-0)

Conditions	Yield
Stage #1: N-(4-chlorophenyl)formamide With potassium carbonate In acetonitrile for 0.5h; Reflux; Stage #2: 2,3,4,5,6-pentachloropyridine In acetonitrile at 85℃; for 12h; Solvent; Temperature;	90%

2,3,4,5,6-pentachloropyridine (2176-62-7) + 1,3,4-trichloro-9-(4-methylbenzylidene)-6-(p-tolyl)-6,7,8,9-tetrahydrocyclopenta[D]pyrido[4′,3′:4,5]thiazolo[3,2-a]pyrimidine (1141931-76-1) → C27H20Cl3N3S

Conditions	Yield
Stage #1: 1,3,4-trichloro-9-(4-methylbenzylidene)-6-(p-tolyl)-6,7,8,9-tetrahydrocyclopenta[D]pyrido[4′,3′:4,5]thiazolo[3,2-a]pyrimidine With potassium carbonate In acetonitrile at 100 - 110℃; for 0.5h; Stage #2: 2,3,4,5,6-pentachloropyridine In acetonitrile for 24h; Solvent; Reflux;	90%

2,3,4,5,6-pentachloropyridine (2176-62-7) + sodium dimethyldithiocarbamate (128-04-1) → 2,3,5,6-tetrachloro-4-pyridyl N,N-dimethyldithiocarbamate

Conditions	Yield
In acetone for 5h; Heating;	89%
In acetone	89%

2,3,4,5,6-pentachloropyridine (2176-62-7) + 4-tert-Butylphenylacetylene (772-38-3) → 2,3,4,5,6-pentakis(4-tert-butylphenylethynyl)pyridine (1269423-18-8)

Conditions	Yield
With dichloro bis(acetonitrile) palladium(II); copper(l) iodide; diisopropylamine; XPhos In 1,4-dioxane at 80℃; for 10h; Sonogashira coupling; Inert atmosphere; Sealed tube;	89%

2,3,4,5,6-pentachloropyridine (2176-62-7) + 4-tert-butylphenylboronic acid (123324-71-0) → 2,3,4,5,6-pentakis(4-tert-butylphenyl)pyridine (1639431-13-2)

Conditions	Yield
With dichloro bis(acetonitrile) palladium(II); potassium phosphate; 2-dicyclohexylphosphino-2’,6’-dimethoxybiphenyl In toluene at 100℃; for 20h; Suzuki-Miyaura Coupling; Inert atmosphere; Schlenk technique; Sealed tube;	89%

2,3,4,5,6-pentachloropyridine (2176-62-7) + 4-trifluoromethoxyphenylboronic acid (139301-27-2) → 2,3,4,5,6-pentakis[4-(trifluoromethoxy)phenyl]pyridine (1639431-20-1)

Conditions	Yield
With dichloro bis(acetonitrile) palladium(II); potassium phosphate; 2-dicyclohexylphosphino-2’,6’-dimethoxybiphenyl In toluene at 100℃; for 20h; Suzuki-Miyaura Coupling; Inert atmosphere; Schlenk technique; Sealed tube;	89%

2,3,4,5,6-pentachloropyridine (2176-62-7) + 8-(4-methylbenzylidene)-3,4,5,6,7,8-hexahydro-4-(4-methylphenyl)quinazoline-2(1H)-thione (65331-29-5) → C28H22Cl3N3S

Conditions	Yield
Stage #1: 8-(4-methylbenzylidene)-3,4,5,6,7,8-hexahydro-4-(4-methylphenyl)quinazoline-2(1H)-thione With potassium carbonate In acetonitrile at 100 - 110℃; for 0.5h; Stage #2: 2,3,4,5,6-pentachloropyridine In acetonitrile for 22h; Reflux;	89%

2,3,4,5,6-pentachloropyridine (2176-62-7) + C24H26N2O4S → C29H24Cl3N3O4S

Conditions	Yield
Stage #1: C24H26N2O4S With potassium carbonate In acetonitrile at 100 - 110℃; for 0.5h; Stage #2: 2,3,4,5,6-pentachloropyridine In acetonitrile for 25h; Reflux;	89%

1-ethynyl-4-fluorobenzene (766-98-3) + 2,3,4,5,6-pentachloropyridine (2176-62-7) → 2,3,4,5,6-pentakis(4-fluorophenylethynyl)pyridine (1269423-19-9)

Conditions	Yield
With dichloro bis(acetonitrile) palladium(II); copper(l) iodide; diisopropylamine; XPhos In 1,4-dioxane at 80℃; for 8h; Sonogashira coupling; Inert atmosphere; Sealed tube;	88%

2,3,4,5,6-pentachloropyridine (2176-62-7) + 7-(4-methoxybenzylidene)-4-(4-methoxyphenyl)-3, 4, 6,7-tetrahydro-1H cyclopenta[d]pyrimidin-2(5H)-thione (131652-00-1) → C27H20Cl3N3O2S

Conditions	Yield
Stage #1: 7-(4-methoxybenzylidene)-4-(4-methoxyphenyl)-3, 4, 6,7-tetrahydro-1H cyclopenta[d]pyrimidin-2(5H)-thione With potassium carbonate In acetonitrile at 100 - 110℃; for 0.5h; Stage #2: 2,3,4,5,6-pentachloropyridine In acetonitrile for 26h; Reflux;	88%

2,3,4,5,6-pentachloropyridine (2176-62-7) → N-Fluoropentachloropyridinium tetrafluoroborate

Conditions	Yield
With boron trifluoride; fluorine In trifluoroacetic acid at 10℃; for 3h;	87%

2,3,4,5,6-pentachloropyridine (2176-62-7) + potassium S-i-propyltrithiocarbonate (52207-49-5) → 2,3,5,6-tetrachloro-4-(isopropylsulfanyl)pyridine (19050-46-5)

Conditions	Yield
In ethanol at 20℃; for 6h; Substitution;	87%

2,3,4,5,6-pentachloropyridine (2176-62-7) + 8-(4-methoxybenzylidene)-3,4,5,6,7,8-hexahydro-4-(4-methoxyphenyl)quinazoline-2(1H)-thione (65331-30-8) → C28H22Cl3N3O2S

Conditions	Yield
Stage #1: 8-(4-methoxybenzylidene)-3,4,5,6,7,8-hexahydro-4-(4-methoxyphenyl)quinazoline-2(1H)-thione With potassium carbonate In acetonitrile at 100 - 110℃; for 0.5h; Stage #2: 2,3,4,5,6-pentachloropyridine In acetonitrile for 23h; Reflux;	87%

Upstream product

• 110-86-1 pyridine 
• 2530-26-9 3-nitropyridine 
• 2402-79-1 2,3,5,6-tetrachloropyridine 
• 936-52-7 1-(N-morpholino)cyclopent-1-ene 
• 17573-93-2 2,3,4,5,6-pentachloropyridine N-oxide 
• 1134-04-9 2,3,4,5-tetrachloro-6-(trichloromethyl)-pyridine 
• 10026-13-8 phosphorus pentachloride 
• 5398-44-7 2,6-dichloropyridine-4-carboxylic acid 
• 694-59-7 pyridine N-oxide 
• 7647-01-0 hydrogenchloride 
• 7791-25-5 sulfuryl dichloride 
• 7782-50-5 chlorine 
• 1201-30-5 3,4,5-trichloro-2-trichloromethyl pyridine 
• 56-23-5 tetrachloromethane 

Downstream Products

• 2176-63-8 2,3,5,6-tetrachloro-pyridin-4-ylamine 
• 51501-52-1 3,4,5,6-tetrachloro-pyridin-2-ylamine 
• 700-16-3 Pentafluoropyridine 
• 1735-84-8 3-chloro-2,4,5,6-tetrafluoropyridine 
• 1737-93-5 3,5-dichloro-2,4,6-trifluoropyridine 
• 34415-32-2 2,3,5,6-tetrachloro-4-fluoropyridine 
• 38025-75-1 S-(2,3,5,6-tetrachloro-4-pyridyl) ethylxanthate 
• 5439-04-3 3,4,5-trichloropicolinic acid 
• 10469-09-7 3,4,5,6-tetrachloropyridinecarboxylic acid 
• 2402-79-1 2,3,5,6-tetrachloropyridine 
• 17717-16-7 tetrachloro-monofluoropyridine 
• 52074-51-8 2,4,6-trichloro-3,5-difluoropyridine 
• 5958-25-8 2,6-difluoro-3,4,5-trichloropyridine 
• 34415-31-1 2,3-Dichloro-5-chlorodifluoropyridine 

Relevant articles and documents

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Synthesis and crystal structure of 3,5-dichloro-6-morpholinopyridin-2-ol

A new compound having potential bioactivities 3,5-dichloro-6- morpholinopyridin-2-ol (1) was synthesized and characterized by single crystal X-diffraction. The crystal is monoclinic, space group P21/c with a = 10.3609 (6), b = 10.5711 (7), c = 10.3190 (5) A, β = 108.9433 (15)°, V = 1068.99 (11) A3, Z = 4, C9H 10Cl2N2O2, D c = 1.548 g/cm3, μ (MoKα) = 0.71075 A, S = 1.01, F (000) = 512.00, R = 0.0397 and wR = 0.1364. In the unit cell, there are two independent molecules linked by intermolecular O-H???O (2.693(2) A) hydrogen bonds forming onedimensional expanded structure. Graphical Abstract: As part of our ongoing research work on pyridine derivatives, the title compound crystal structure is important to study the relationship between the structure and its biological activities, thus it is urgent to publish in time.[Figure not available: see fulltext.]

Mild electrophilic halogenation of chloropyridines using CCl4 or C2Cl6 under basic phase transfer conditions

Effective chlorination of 2,3,5,6-tetrachloropyridine to pentachloropyridine was realized under mild phase transfer conditions with carbon tetrachloride and 50% NaOH or solid K3PO4. Mechanistic study of this reaction indicated the possibility of an aromatic carbanionic intermediate. Hexachloroethane was established as a more selective electrophilic chlorination agent.

Thermolysis of phenoxyaluminum compounds and formation of PCDD/F and their precursors

Within the study of the formation of chlorinated dioxins and dibenzofurans and their precursors the thermolysis of hexachloroethane over the aluminum melt was investigated. "De novo" synthesis of precursors of PCDD/F was studied in the model system AlCl3/elemental carbon. Totally chlorinated heterocyclic compounds have been detected parallel with the formation of organochlorine compounds. The possibility of inserting oxygen to aluminum organyls was presented. In order to gain more detailed knowledge of the catalytic behaviour of fly ash the chemistry of thermolysis of phenoxy- and chlorophenoxy aluminum compounds at 300°C with the presence and absence of Al2O3 was investigated. Reagent compounds and products of thermolysis were followed by mass spectrometry.