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2176-62-7

Basic Information
CAS No.: 2176-62-7
Name: Pentachloropyridine
Article Data: 40
Molecular Structure:
Molecular Structure of 2176-62-7 (Pentachloropyridine)
Formula: C5Cl5N
Molecular Weight: 251.327
Synonyms: Pyridine,pentachloro- (6CI,7CI,8CI,9CI);2,3,4,5,6-Pentachloropyridine;NSC 26286;Pentachloropyridine;Perchloropyridine;
EINECS: 218-535-5
Density: 1.764 g/cm3
Melting Point: 124 °C
Boiling Point: 282.3 °C at 760 mmHg
Flash Point: 151.5 °C
Appearance: white to off-white flake
Hazard Symbols: HarmfulXn,IrritantXi
Risk Codes: 22-36/37/38-42/43
Safety: 22-26-36-24/25
PSA: 12.89000
LogP: 4.34860
Synthetic route
2402-79-1

2,3,5,6-tetrachloropyridine

2176-62-7

2,3,4,5,6-pentachloropyridine

Conditions
ConditionsYield
With sodium hydroxide; hexachloroethane; tetrabutylammomium bromide In dichloromethane at 55℃;71%
With phosphorus pentachloride
72012-23-8

tetrachlo-5-iodoropyridine

A

14121-36-9

2,3,4,6-Tetrachloropyridine

B

2176-62-7

2,3,4,5,6-pentachloropyridine

C

octachloro-3,3'-bipyridyl

Conditions
ConditionsYield
With copper In N,N-dimethyl-formamide at 150℃;A 3%
B n/a
C 71%
23995-94-0

4-Bromo-2,3,5,6-tetrachloropyridine

A

2402-79-1

2,3,5,6-tetrachloropyridine

B

14121-36-9

2,3,4,6-Tetrachloropyridine

C

2176-62-7

2,3,4,5,6-pentachloropyridine

D

18725-60-5

octachloro-4,4'-bipyridyl

Conditions
ConditionsYield
With Isopropylbenzene; copper In N,N-dimethyl-formamide at 150℃; for 1h; Further byproducts given;A 63%
B 15%
C 16%
D 17%
30332-35-5

tetrachloro-4-iodopyridine

A

2402-79-1

2,3,5,6-tetrachloropyridine

B

2176-62-7

2,3,4,5,6-pentachloropyridine

C

18725-60-5

octachloro-4,4'-bipyridyl

Conditions
ConditionsYield
With copper In N,N-dimethyl-formamide at 150℃;A 22%
B 4%
C 52%
39873-38-6

bis(2,3,5,6-tetrachloropyridin-4-yl)sulfane

A

2176-62-7

2,3,4,5,6-pentachloropyridine

B

63954-14-3

hexachlorodipyrido<5,4-b;3,4-d>thiophen

Conditions
ConditionsYield
In tetrachloromethane for 24h; Irradiation;A 6.5%
B 44%
23995-94-0

4-Bromo-2,3,5,6-tetrachloropyridine

A

2402-79-1

2,3,5,6-tetrachloropyridine

B

14121-36-9

2,3,4,6-Tetrachloropyridine

C

2176-62-7

2,3,4,5,6-pentachloropyridine

D

octachloro-3,4'-bipyridyl

E

18725-60-5

octachloro-4,4'-bipyridyl

Conditions
ConditionsYield
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%
23995-94-0

4-Bromo-2,3,5,6-tetrachloropyridine

A

2402-79-1

2,3,5,6-tetrachloropyridine

B

2176-62-7

2,3,4,5,6-pentachloropyridine

C

octachloro-3,4'-bipyridyl

D

18725-60-5

octachloro-4,4'-bipyridyl

Conditions
ConditionsYield
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%
74894-12-5

tetrachloro-4-(2-pyridylthio)pyridine

A

2176-62-7

2,3,4,5,6-pentachloropyridine

B

74894-22-7

1,3,4-trichlorodipyrido<2,3-b;3,4-d>thiophen

Conditions
ConditionsYield
In tetrahydrofuran; ethanol for 6h; Irradiation;A 39%
B 13%
56-23-5

tetrachloromethane

2402-79-1

2,3,5,6-tetrachloropyridine

A

2176-62-7

2,3,4,5,6-pentachloropyridine

B

37665-08-0

4-dichloromethyl-2,3,5,6-tetrachloropyridine

C

4-trichloromethyl-2,3,5,6-tetrachloropyridine

Conditions
ConditionsYield
With tetrachloromethane; tetrabutylammomium bromide In sodium hydroxide at 50℃; for 4h;A n/a
B 30%
C n/a
27425-94-1

tetrachloro-4-pyridylcopper

98-88-4

benzoyl chloride

A

2402-79-1

2,3,5,6-tetrachloropyridine

B

18613-89-3

4-benzoyltetrachloropyridine

C

2176-62-7

2,3,4,5,6-pentachloropyridine

D

18725-60-5

octachloro-4,4'-bipyridyl

Conditions
ConditionsYield
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%
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    Product Name: Pentachloropyridine CAS: 2176-62-7 MF: C5Cl5N MW: 251.33 EINECS: 218-535-5 Mol File: 2176-62-7.mol Pentachloropyridine Structure Pentachloropyridine Chemical Properties Melting point 124 °C Boiling point

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Consensus Reports

Reported in EPA TSCA Inventory.

Specification

The Pentachloropyridine is an organic compound with the formula C5Cl5N. The IUPAC name of this chemical is 2,3,4,5,6-pentachloropyridine. With the CAS registry number 2176-62-7, it is also named as pyridine, 2,3,4,5,6-pentachloro-. The product's categories are Chloropyridines; Halopyridines; C5Heterocyclic Building Blocks; Halogenated Heterocycles; Heterocyclic Building Blocks; Pyridines. Besides, it is white to off-white flake, which should be stored in a closed cool and dry place. It is used as a pesticide and pharmaceutical intermediates, which can be used for production pesticides of chlorpyrifos and dichloro-pyridine acid.

Physical properties about Pentachloropyridine are: (1)ACD/LogP: 3.61; (2)ACD/LogD (pH 5.5): 3.61; (3)ACD/LogD (pH 7.4): 3.61; (4)ACD/BCF (pH 5.5): 323.72; (5)ACD/BCF (pH 7.4): 323.72; (6)ACD/KOC (pH 5.5): 2179.63; (7)ACD/KOC (pH 7.4): 2179.63; (8)#H bond acceptors: 1; (9)Polar Surface Area: 12.89 Å2; (10)Index of Refraction: 1.601; (11)Molar Refractivity: 48.81 cm3; (12)Molar Volume: 142.4 cm3; (13)Polarizability: 19.35×10-24cm3; (14)Surface Tension: 51.1 dyne/cm; (15)Density: 1.764 g/cm3; (16)Flash Point: 151.5 °C; (17)Enthalpy of Vaporization: 50.02 kJ/mol; (18)Boiling Point: 282.3 °C at 760 mmHg; (19)Vapour Pressure: 0.00579 mmHg at 25°C.

Preparation: this chemical can be prepared by octachloro-4,4'-sulfanediyl-bis-pyridine. This reaction will need reagent CCl4. The reaction time is 22 hours. The yield is about 44%.



Uses of Pentachloropyridine: it can be used to produce 3,5-dichloro-2,4,6-trifluoro-pyridine at temperature of 190 °C. It will need reagent KF and solvent tetrahydrothiophene 1,1-dioxide with reaction time of 3 days. The yield is about 93%.

When you are using this chemical, please be cautious about it as the following:
It is harmful if swallowed and may cause sensitisation by inhalation and skin contact. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. Besides, this chemical is irritating to eyes, respiratory system and skin. When you are using it, wear suitable protective clothing, do not breathe dust and avoid contact with skin and eyes.

You can still convert the following datas into molecular structure:
(1)SMILES: Clc1c(Cl)c(Cl)nc(Cl)c1Cl
(2)InChI: InChI=1/C5Cl5N/c6-1-2(7)4(9)11-5(10)3(1)8
(3)InChIKey: DNDPLEAVNVOOQZ-UHFFFAOYAW
(4)Std. InChI: InChI=1S/C5Cl5N/c6-1-2(7)4(9)11-5(10)3(1)8
(5)Std. InChIKey: DNDPLEAVNVOOQZ-UHFFFAOYSA-N

The toxicity data is as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 intraperitoneal 235mg/kg (235mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

BEHAVIORAL: ANTIPSYCHOTIC

LIVER: FATTY LIVER DEGERATION
Toxicology and Applied Pharmacology. Vol. 11, Pg. 361, 1967.
rat LD50 oral 435mg/kg (435mg/kg) SENSE ORGANS AND SPECIAL SENSES: LACRIMATION: EYE

BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD
National Technical Information Service. Vol. OTS0536503,