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Substance Name: Pentachlorophenol [BSI:ISO]
RN: 87-86-5
UNII: D9BSU0SE4T
InChIKey: IZUPBVBPLAPZRR-UHFFFAOYSA-N

Note

  • An insecticide and herbicide that has also been used as a wood preservative. Pentachlorphenol is a widespread environmental pollutant. Both chronic and acute pentachlorophenol poisoning are medical concerns. The range of its biological actions is still being actively explored, but it is clearly a potent enzyme inhibitor and has been used as such as an experimental tool.

Molecular Formula

  • C6-H-Cl5-O

Molecular Weight

  • 266.338
 

Classification Codes

Classification Codes

  • Agricultural Chemical
  • Environmental Pollutants
  • Enzyme Inhibitors
  • Fungicide, Bactericide, Wood Preservative
  • Herbicide
  • Herbicides
  • Human Data
  • Insecticide
  • Insecticides
  • Mutation Data
  • Noxae
  • Pesticides
  • Poisons
  • Reproductive Effect
  • Skin / Eye Irritant
  • Tumor Data
  • Uncoupling Agents

Superlist Classification Codes

  • 2007 CERCLA Priority List, Rank: 45
  • 2011 CERCLA Priority List, Rank: 53
  • Reasonably Anticipated to be a Human Carcinogen.
  • Reportable Quantity (RQ) = 10 lb
  • TWA 0.5 mg/m3; skin
  • TWA 0.5 mg/m3; skin; Confirmed animal carcinogen with unknown relevance to humans; BEI

Names and Synonyms

Results Name

  • Pentachlorophenol [BSI:ISO]

Name of Substance

  • Pentachlorophenol
  • Pentachlorophenol [BSI:ISO]

MeSH Heading

  • Pentachlorophenol

Synonyms

  • 1-Hydroxy-2,3,4,5,6-pentachlorobenzene
  • 1-Hydroxypentachlorobenzene
  • 2,3,4,5,6-Pentachlorophenol
  • 4-06-00-01025 (Beilstein Handbook Reference)
  • AD 73
  • AI3-00134
  • BRN 1285380
  • Caswell No. 641
  • CCRIS 1663
  • Chem-Penta
  • Chem-Tol
  • Chlon
  • Chlorophen
  • CM 613
  • CP 1309
  • Dow pentachlorophenol DP-2 antimicrobial
  • Dowicide 7
  • Dowicide 7 Antimicrobial
  • Dowicide EC-7
  • Dura Treet II
  • Durotox
  • EINECS 201-778-6
  • EP 30 (pesticide)
  • EPA Pesticide Chemical Code 063001
  • Forpen-50 Wood Preservative
  • Fungifen
  • Glazd penta
  • Grundier arbezol
  • HSDB 894
  • Lauxtol
  • Liroprem
  • MB 333
  • NCI-C54933
  • NCI-C55378
  • NCI-C56655
  • NSC 263497
  • Ontrack WE Herbicide
  • Ortho Triox Liquid Vegetation Killer
  • Osmose Wood Preserving Compound
  • PCP (pesticide)
  • Penchlorol
  • Penta
  • Penta Concentrate
  • Penta ready
  • Penta WR
  • Penta-kil
  • Pentachloorfenol
  • Pentachloorfenol [Dutch]
  • Pentachlorofenol
  • Pentachlorophenate
  • Pentachlorophenol
  • Pentachlorophenol, DP-2
  • Pentachlorphenol
  • Pentachlorphenol [German]
  • Pentaclorofenolo
  • Pentaclorofenolo [Italian]
  • Pentacon
  • Penwar
  • Peratox
  • Permacide
  • Permagard
  • Permasan
  • Permatox DP-2
  • Permatox penta
  • Permite
  • Phenol, pentachloro-
  • Pol Nu
  • Pole topper fluid
  • Preventol P
  • RCRA waste number U242
  • Santophen
  • Santophen 20
  • Sinituho
  • Term-i-trol
  • Thompson's wood fix
  • UNII-D9BSU0SE4T
  • Watershed Wood Preservative
  • Weed and Brush Killer
  • Weedone
  • Witophen P
  • Woodtreat A

Systematic Names

  • Pentachlorophenol
  • Phenol, 2,3,4,5,6-pentachloro-
  • Phenol, pentachloro-

Superlist Names

  • PCP
  • Pentachlorophenol
  • Pentachlorophenol [Polychlorophenols and their sodium salts]
  • Pentachlorophenol [UN3155] [Poison]
  • Pentachlorophenol, dowicide EC-7
  • Pentachlorophenol, technical
  • Phenol, pentachloro-
  • RCRA waste no. U242
  • UN3155

Registry Numbers

CAS Registry Number

  • 87-86-5

FDA UNII

  • D9BSU0SE4T

Other Registry Numbers

  • 101802-54-4
  • 1135443-67-2
  • 39390-77-7

System Generated Number

  • 0000087865

Structure Descriptors

InChI

1S/C6HCl5O/c7-1-2(8)4(10)6(12)5(11)3(1)9/h12H

InChIKey

IZUPBVBPLAPZRR-UHFFFAOYSA-N

Smiles

c1(c(c(c(Cl)c(c1Cl)Cl)Cl)Cl)O

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
dog LD50 unreported 70mg/kg (70mg/kg)   Phytiatrie-Phytopharmacie. Vol. 1, Pg. 3, 1953.
dog LDLo subcutaneous 135mg/kg (135mg/kg)   "Handbook of Toxicology," 4 vols., Philadelphia, W.B. Saunders Co., 1956-59Vol. 5, Pg. 123, 1959.
duck LD50 oral 380mg/kg (380mg/kg)   Down to Earth. Vol. 35, Pg. 25, 1979.
frog LD50 unreported 36mg/kg (36mg/kg)   Phytiatrie-Phytopharmacie. Vol. 1, Pg. 3, 1953.
gerbil LD50 oral 294mg/kg (294mg/kg)   Archives of Toxicology. Vol. 40, Pg. 63, 1978.
guinea pig LD50 unreported 100mg/kg (100mg/kg)   Phytiatrie-Phytopharmacie. Vol. 1, Pg. 3, 1953.
hamster LD50 oral 168mg/kg (168mg/kg)   Toxicology and Applied Pharmacology. Vol. 48, Pg. A192, 1979.
man LDLo oral 401mg/kg (401mg/kg)   Ecotoxicology and Environmental Safety. Vol. 1, Pg. 343, 1977.
man LDLo oral 401mg/kg (401mg/kg) BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY)

SKIN AND APPENDAGES (SKIN): SWEATING: OTHER
Ecotoxicology and Environmental Safety. Vol. 1, Pg. 343, 1977.
mouse LC50 inhalation 225mg/m3 (225mg/m3) LUNGS, THORAX, OR RESPIRATION: DYSPNEA

BEHAVIORAL: MUSCLE CONTRACTION OR SPASTICITY)

BEHAVIORAL: EXCITEMENT
Gigiena Truda i Professional'nye Zabolevaniya. Labor Hygiene and Occupational Diseases. Vol. 13(9), Pg. 58, 1969.
mouse LD50 intraperitoneal 32mg/kg (32mg/kg)   Archives of Toxicology. Vol. 40, Pg. 63, 1978.
mouse LD50 oral 36mg/kg (36mg/kg)   Archives of Toxicology. Vol. 40, Pg. 63, 1978.
rabbit LDLo intraperitoneal 135mg/kg (135mg/kg)   "Handbook of Toxicology," 4 vols., Philadelphia, W.B. Saunders Co., 1956-59Vol. 5, Pg. 123, 1959.
rabbit LDLo oral 70mg/kg (70mg/kg) KIDNEY, URETER, AND BLADDER: URINE VOLUME INCREASED

BEHAVIORAL: MUSCLE WEAKNESS

VASCULAR: BP ELEVATION NOT CHARACTERIZED IN AUTONOMIC SECTION
Journal of Pharmacology and Experimental Therapeutics. Vol. 76, Pg. 104, 1942.
rabbit LDLo skin 40mg/kg (40mg/kg) VASCULAR: BP ELEVATION NOT CHARACTERIZED IN AUTONOMIC SECTION

BEHAVIORAL: MUSCLE WEAKNESS

KIDNEY, URETER, AND BLADDER: URINE VOLUME INCREASED
Journal of Pharmacology and Experimental Therapeutics. Vol. 76, Pg. 104, 1942.
rabbit LDLo subcutaneous 70mg/kg (70mg/kg) VASCULAR: BP ELEVATION NOT CHARACTERIZED IN AUTONOMIC SECTION

KIDNEY, URETER, AND BLADDER: URINE VOLUME INCREASED

BEHAVIORAL: MUSCLE WEAKNESS
Journal of Pharmacology and Experimental Therapeutics. Vol. 76, Pg. 104, 1942.
rat LC50 inhalation 355mg/m3 (355mg/m3) BEHAVIORAL: EXCITEMENT

LUNGS, THORAX, OR RESPIRATION: DYSPNEA

BEHAVIORAL: MUSCLE CONTRACTION OR SPASTICITY)
Gigiena Truda i Professional'nye Zabolevaniya. Labor Hygiene and Occupational Diseases. Vol. 13(9), Pg. 58, 1969.
rat LD50 intraperitoneal 56mg/kg (56mg/kg) LUNGS, THORAX, OR RESPIRATION: DYSPNEA

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD
British Journal of Pharmacology and Chemotherapy. Vol. 13, Pg. 20, 1958.
rat LD50 oral 27mg/kg (27mg/kg) ENDOCRINE: HYPERGLYCEMIA

VASCULAR: BP ELEVATION NOT CHARACTERIZED IN AUTONOMIC SECTION
Journal of Pharmacology and Experimental Therapeutics. Vol. 76, Pg. 104, 1942.
rat LD50 skin 96mg/kg (96mg/kg) BEHAVIORAL: EXCITEMENT

BEHAVIORAL: MUSCLE CONTRACTION OR SPASTICITY)

LUNGS, THORAX, OR RESPIRATION: DYSPNEA
Gigiena Truda i Professional'nye Zabolevaniya. Labor Hygiene and Occupational Diseases. Vol. 13(9), Pg. 58, 1969.

Physical Properties

Physical Property Value Units Temp (deg C) Source
Melting Point 174 deg C   EXP
Boiling Point 309.5 deg C   EXP
pKa Dissociation Constant 4.7 (none) 25 EXP
log P (octanol-water) 5.12 (none)   EXP
Water Solubility 14 mg/L 25 EXP
Vapor Pressure 1.10E-04 mm Hg 25 EXP
Henry's Law Constant 2.45E-08 atm-m3/mole 22 EXP
Atmospheric OH Rate Constant 5.50E-13 cm3/molecule-sec 25 EST

Physical property data is provided to ChemIDplus by SRC, Inc.