Pentachloropyridine
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Pentachloropyridine
structure -
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CAS No:
2176-62-7
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Formula:
C5Cl5N
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Chemical Name:
Pentachloropyridine
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Synonyms:
Pyridine,2,3,4,5,6-pentachloro-;Pyridine,pentachloro-;2,3,4,5,6-Pentachloropyridine;Pentachloropyridine;Perchloropyridine;NSC 26286
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CAS No:
Pentachloropyridine Basic Attributes
251.312
251.33
218-535-5
6MM852KA6T
26286
DTXSID2022179
2933399090
Characteristics
12.9
4.7
OtherSolid
1.8±0.1 g/cm3
125.5 °C
280 °C
151.5±11.5 °C
1.602
Very soluble in benzene, ethanol, ligroin
Store in a tightly closed container. Store in a cool, dry, well-ventilated area away from incompatible substances.
0.01 mm Hg ( 20 °C)
8.4 (vs air)
LD50 ipr-mus: 235 mg/kg TXAPA9 11,361,67
pKa= -1.00
Safety Information
3
R36/37/38
S22-S26-S36-S24/25
UT7000000
Xi:Irritant;
Stable at room temperature in closed containers under normal storage and handling conditions.
P261, P264, P270, P271, P272, P273, P280, P285, P301+P312, P302+P352, P304+P340, P304+P341, P305+P351+P338, P312, P321, P330, P332+P313, P333+P313, P337+P313, P342+P311, P362, P363, P391, P403+P233, P405, P501
H302
SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.
|Danger|H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]|P261, P264, P270, P271, P272, P273, P280, P285, P301+P312, P302+P352, P304+P340, P304+P341, P305+P351+P338, P312, P321, P330, P332+P313, P333+P313, P337+P313, P342+P311, P362, P363, P391, P403+P233, P405, and P501|Aggregated GHS information provided by 98 companies from 4 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Depending on the extent of possible contact, workers should be provided with personal protective equipment. A charcoal gas mask canister respirator has been found to be effective against a 2% pyridine concentration at 30 l/min for 1 hr. Rubber and plastic gloves should not be relied upon to prevent skin contact because pyridine and many of its derivatives penetrate these materials ... . /Pyridine, homologs, and derivatives/
SRP: The scientific literature for the use of contact lenses in industry is conflicting. The benefit or detrimental effects of wearing contact lenses depend not only upon the substance, but also on factors including the form of the substance, characteristics and duration of the exposure, the uses of other eye protection equipment, and the hygiene of the lenses. However, there may be individual substances whose irritating or corrosive properties are such that the wearing of contact lenses would be harmful to the eye. In those specific cases, contact lenses should not be worn. In any event, the usual eye protection equipment should be worn even when contact lenses are in place.
Pyridine and its derivatives cause local irritation on contact with the skin, mucous membranes and cornea. /Pyridine and its derivatives/
Toxicity
LD50 Mouse ip 235 mg/kg
Pentachloropyridine's production and possible use as a chemical intermediate in the production of pesticides such as chlorpyrifos and triclopyr(1) may result in its release to the environment through various waste streams(SRC).
TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 2000(SRC), determined from a log Kow of 3.53(2) and a regression-derived equation(3), indicates that pentachloropyridine is expected to have low to slight mobility in soil(SRC). Volatilization of pentachloropyridine from moist soil surfaces may be an important fate process(SRC) given an estimated Henry's Law constant of 6.3X10-3 atm-cu m/mole(SRC), using a fragment constant estimation method(4) although adsorption to soil surfaces may attenuate the rate of this process(SRC). Pentachloropyridine is not expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 1.4X10-2 mm Hg(5). Pentachloropyridine is expected to be resistant to biodegradation under aerobic conditions in soil based on data from structurally-similar compounds(SRC). Only <0.1% and 3% of the available nitrogen was released over 64 days following the application of 2,3- and 2,6-dichloropyridine to soil(6). Pentachloropyridine may be susceptible to anaerobic biodegradation via dehalogenation(7).|AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 2000(SRC), determined from a log Kow of 3.53(2) and a regression-derived equation(3), indicates that pentachloropyridine may adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces may occur(3) based upon an estimated Henry's Law constant of 6.3X10-3 atm-cu m/mole(SRC), developed using a fragment constant estimation method(4). Using this Henry's Law constant and an estimation method(3), volatilization half-lives for a model river and model lake are 5 hours and 6 days, respectively(SRC). However, volatilization from water surfaces is expected to be attenuated by adsorption to suspended solids and sediment in the water column. The estimated volatilization half-life from a model pond is 4.3 years if adsorption is considered(7). According to a classification scheme(5), an estimated BCF of 105(SRC), from its log Kow(2) and a regression-derived equation(6), suggests the potential for bioconcentration in aquatic organisms is high(SRC).Pentachloropyridine is expected to be resistant to biodegradation under aerobic conditions in water based on soil data from structurally-similar compounds(SRC). Only <0.1% and 3% of the available nitrogen was released over 64 days following the application of 2,3- and 2,6-dichloropyridine to soil(8). This compound may be susceptible to anaerobic biodegradation via dehalogenation(9).|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), pentachloropyridine, which has a vapor pressure of 1.40X10-2 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase pentachloropyridine is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC); the half-life for this reaction in air is estimated to be approximately 4 years(SRC), calculated from its rate constant of 1.10X10-14 cu cm/molecule-sec at 25 °C(SRC), determined using a structure estimation method(3).
The rate constant for the vapor-phase reaction of pentachloropyridine with photochemically-produced hydroxyl radicals has been estimated as 1.10X10-14 cu cm/molecule-sec at 25 °C(SRC), using a structure estimation method(1). This corresponds to an atmospheric half-life of about 4 years at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). Pentachloropyridine is not expected to undergo hydrolysis in the environment due to the lack of hydrolyzable functional groups(2). Pyridine has a weak absorption band that extends into the environmental UV spectrum(3), which suggests that direct photolysis is not likely to be an important fate process for pentachloropyridine(SRC).
An estimated BCF of 105 was calculated for pentachloropyridine(SRC), using a log Kow of 3.53(1) and a regression-derived equation(2). According to a classification scheme(3), this BCF suggests the potential for bioconcentration in aquatic organisms is high(SRC).
The Koc of pentachloropyridine is estimated as 2000(SRC), using a log Kow of 3.53(1) and a regression-derived equation(2). According to a classification scheme(3), this estimated Koc value suggests that pentachloropyridine is expected to have low to slight mobility in soil.
The Henry's Law constant for pentachloropyridine is estimated as 6.3X10-3 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This Henry's Law constant indicates that pentachloropyridine is expected to volatilize from water surfaces(2). Based on this Henry's Law constant, the volatilization half-life from a model river (1 m deep, flowing 1 m/sec, wind velocity of 3 m/sec)(2) is estimated as 5 hours(SRC). The volatilization half-life from a model lake (1 m deep, flowing 0.05 m/sec, wind velocity of 0.5 m/sec)(2) is estimated as 6 days(SRC). However, volatilization from water surfaces is expected to be attenuated by adsorption to suspended solids and sediment in the water column. The estimated volatilization half-life from a model pond is 4.3 years if adsorption is considered(3). Pentachloropyridine's Henry's Law constant(1) indicates that volatilization from moist soil surfaces may occur(SRC). Pentachloropyridine is not expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 1.40X10-2 mm Hg(4).
DRINKING WATER: Pentachloropyridine was qualitatively listed as a contaminant found in drinking water for a survey of US cities that included Pomona, Escondido, Lake Tahoe and Orange Co, CA and Dallas, Washington, DC, Cincinnati, Philadelphia, Miami, New Orleans, Ottumwa, IA, and Seattle(1).
NIOSH (NOES Survey 1981-1983) has statistically estimated that 487 workers are potentially exposed to pentachloropyridine in the US(1). Occupational exposure to pentachloropyridine may occur through inhalation of dusts and dermal contact with this compound at workplaces where pentachloropyridine is produced or used(SRC). Monitoring data indicate that the general population may be exposed to pentachloropyridine via ingestion of drinking water, and dermal contact with this compound and other products containing pentachloropyridine(SRC).
Drug Information
PYRIDINE & ITS ALKYL DERIVATIVES ARE ABSORBED FROM GI TRACT, INTRAPERITONEAL CAVITY & LUNGS. PERITONEAL ABSORPTION IS APPARENTLY ONLY SLIGHTLY MORE RAPID & COMPLETE THAN GI ABSORPTION... IN GENERAL THE BASES ARE RAPIDLY ABSORBED THROUGH INTACT SKIN. /ALKYL DERIVATIVES OF PYRIDINE/
/SRP:/ Basic treatment: Establish a patent airway. Suction if necessary. Watch for signs of respiratory insufficiency and assist ventilations if needed. Administer oxygen by nonrebreather mask at 10 to 15 L/min. Monitor for pulmonary edema and treat if necessary ... . Monitor for shock and treat if necessary ... . Anticipate seizures and treat if necessary ... . For eye contamination, flush eyes immediately with water. Irrigate each eye continuously with normal saline during transport ... . Do not use emetics. For ingestion, rinse mouth and administer 5 ml/kg up to 200 ml of water for dilution if the patient can swallow, has a strong gag reflex, and does not drool ... . Cover skin burns with dry sterile dressings after decontamination ... . /Poison A and B/|/SRP:/ Advanced treatment: Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious, has severe pulmonary edema, or is in respiratory arrest. Positive pressure ventilation techniques with a bag valve mask device may be beneficial. Monitor cardiac rhythm and treat arrhythmias as necessary ... . Start an IV with D5W /SRP: "To keep open", minimal flow rate/. Use lactated Ringer's if signs of hypovolemia are present. Watch for signs of fluid overload. Consider drug therapy for pulmonary edema ... . For hypotension with signs of hypovolemia, administer fluid cautiously. Watch for signs of fluid overload ... . Treat seizures with diazepam (Valium) ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Poison A and B/
Pentachloropyridine Use and Manufacturing
Direct chlorination of pyridine occurs in the vapor phase at over 300 °C in the presence of a diluent. ... Vigorous chlorination of pyridine ... eventually gives pentachloropyridine.
Intermediates
Pesticide, fertilizer, and other agricultural chemical manufacturing|Pyridine, 2,3,4,5,6-pentachloro-: ACTIVE|Pentachloropyridine is most reactive at the 4- position. Reduction with zinc, or electrochemically, yields 2,3,5,6-tetrachloropyridine. Partial hydrolysis and phosphorylation gives the insecticide chlorpyrifos.
VARIOUS TLC SYSTEMS FOR THE SEPARATION OF 2-, 3-, & 4-SUBSTITUTED PYRIDINES ARE DESCRIBED.
Computed Properties
Molecular Weight:251.3
XLogP3:4.7
Hydrogen Bond Acceptor Count:1
Exact Mass:250.844387
Monoisotopic Mass:248.847337
Topological Polar Surface Area:12.9
Heavy Atom Count:11
Complexity:129
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
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