| Compound Name |
Pentachlorophenol and its salts and esters |
| Stockholm Annex code | I |
| Key |
Annex I to the regulation are subject to prohibition (with specific exemptions) on manufacturing, placing on the market and use; Annex II to the regulation are subject to restriction on manufacturing, placing on the market and use; Annex III to the regulation are subject to release reduction provisions; and Annex IV to the regulation are subject to waste management provisions. Note that for some substances listed in Annex I, specific exemptions on the prohibition of their use, manufacturing and placing on the market may apply. |
| Classification |
Intentional |
| Category |
Listed under Annex A with specific exemptions for use in utility poles and cross-arms (decision SC-7 |
| Year of Listing Decision |
2015 |
| Persistence |
N/A |
| Specific exemptions associated with its use |
Production: As allowed for the parties listed in the Register in accordance with the provisions of Part VIII of Annex A |
| Acceptable purposes associated with its use |
Use: Pentachlorophenol for utility poles and cross-arms in accordance with the provisions of Part VIII of Annex A Pentachlorophenol has been used as herbicide, insecticide, fungicide, algaecide and disinfectant Has been used as wood preservatives, and as ingredients in alcohol denaturants. |
| Conventions on POPs |
Stockholm Convention Convention on Long-Range Transboundary Air Pollution Rotterdam Convention Basel Convention |
| Name |
Pentachlorophenol and its salts and esters |
| Synonyms |
2,3,4,5,6-Pentachlorophenol Penchlorol Chlorophen Pentachlorophenate Permasan Permatox Phenol, 2,3,4,5,6-pentachloro- 1-Hydroxypentachlorobenzene 2,3,4,5,6-pentachlorophenol 2,6-Dichlorfenol 1-Hydroxy-2,3,4,5,6-pentachlorobenzene |
| Structure | C(Cl)=C(Cl)C(Cl)=C1Cl.png)
Molecular Formula:
C6HCl5O
|
| CAS Number | 87-86-5 |
| European Community (EC) Number | 201-778-6 |
| European Chemicals Agency (ECHA) | 201-778-6 |
| PubChem ID | 992 |
| DSSTOX Substance ID | DTXSID7021106 |
| KEGG | C02575 |
| ChemSpider |
967 |
| Similarity threshold | Name of Related Compound | DSSTox Substance ID | CAS Number | Molecular weight | Molecular formula |
|---|---|---|---|---|---|
| N/A | Pentachlorophenyl N-[[(4-methoxyphenyl)methoxy]carbonyl]-L-serinate | N/A | N/A | N/A g/mol | N/A |
| N/A | Perchlorophenyl 5-oxo-L-prolinate | DTXSID60183186 | 28990-85-4 | 377.42 g/mol | C11H6Cl5NO3 |
| N/A | Pentachlorophenol esters | N/A | N/A | N/A g/mol | N/A |
| N/A | Pentachlorophenol salts | N/A | N/A | N/A g/mol | N/A |
| N/A | Potassium pentachlorophenolate | DTXSID3064801 | 7778-73-6 | 304.41 g/mol | C6Cl5KO |
| N/A | N2-benzyl pentachlorophenyl N2-carboxy-L-(2-aminoglutaramate) | DTXSID00159906 | 13673-51-3 | 528.59 g/mol | C19H15Cl5N2O5 |
| N/A | Perchlorophenyl N-(benzyloxycarbonyl)-L-isoleucinate | DTXSID60159907 | 13673-53-5 | 513.62 g/mol | C20H18Cl5NO4 |
| N/A | Perchlorophenyl S-benzyl-N-(benzyloxycarbonyl)-L-cysteinate | DTXSID20159908 | 13673-54-6 | 593.72 g/mol | C24H18Cl5NO4S |
| N/A | Zinc bis(pentachlorophenolate) | DTXSID80895113 | 2917-32-0 | 596.01 g/mol | C12Cl10O2Zn |
| N/A | Pentachlorophenyl laurate | DTXSID9058078 | 3772-94-9 | 448.63 g/mol | C18H23Cl5O2 |
| N/A | Sodium pentachlorophenolate | DTXSID4040264 | 131-52-2 | 288.3 g/mol | C6Cl5NaO |
| 1.0 | 2,4,5-Trichlorophenol | DTXSID4024359 | 95-95-4 | 197.44 g/mol | C6H3Cl3O |
| 1.0 | 2,3,4-Trichlorophenol | DTXSID5026207 | 15950-66-0 | 197.44 g/mol | C6H3Cl3O |
| 1.0 | 2,3,5-Trichlorophenol | DTXSID0026208 | 933-78-8 | 197.44 g/mol | C6H3Cl3O |
| 1.0 | 2,3,6-Trichlorophenol | DTXSID5026209 | 933-75-5 | 197.44 g/mol | C6H3Cl3O |
| 1.0 | 2,3,5-Trichloro(O-~2~H)phenol | DTXSID60892640 | NOCAS_892640 | 198.45 g/mol | C6H2DCl3O |
| 1.0 | 2,4,5-Trichloro(O-~2~H)phenol | DTXSID10892751 | NOCAS_892751 | 198.45 g/mol | C6H2DCl3O |
| 1.0 | 2,4,5-Trichloro(~2~H_2_)phenol | DTXSID50745676 | 93951-82-7 | 199.45 g/mol | C6HD2Cl3O |
| 1.0 | 1,4-Benzenediol, 2,3,5-trichloro- | DTXSID9073208 | 608-94-6 | 213.44 g/mol | C6H3Cl3O2 |
| 1.0 | 2,3,4,6-Tetrachlorophenol | DTXSID9021716 | 58-90-2 | 231.88 g/mol | C6H2Cl4O |
| 1.0 | 2,3,4,5-Tetrachlorophenol | DTXSID0022220 | 4901-51-3 | 231.88 g/mol | C6H2Cl4O |
| N/A | Full List of Similar compounds | N/A | N/A | N/A g/mol | N/A |
| Description | Reference | Article Link |
|---|---|---|
| PCP (CASRN 87-86-5) is a chlorinated aromatic compound that appears in a solid crystalline state and ranges in color from colorless to white, tan, or brown. The chemical, also referred to as penta, pentachlorofenol, 2,3,4,5,6-PCP, and chlorophen, has a phenolic odor that is pungent when heated. PCP is nonflammable and noncorrosive, and, although solubility is limited in water, it is readily soluble in alcohol (Budavari et al., 1996; NTP, 1989). PCP was first registered in the United States in 1936 as a wood preservative to prevent decay from fungal organisms and insect damage (Ahlborg and Thunberg, 1980). It was widely used as a biocide and could also be found in ropes, paints, adhesives, canvas, insulation, and brick walls (Proudfoot, 2003; ATSDR, 2001). After use by the general public was restricted in 1984, PCP application was limited to industrial areas (e.g., utility poles, cross arms, railroad cross ties, wooden pilings, fence posts, and lumber/timbers for construction). Currently products containing PCP remain registered for wood preservation; utility poles and cross arms represent approximately 92% of all uses for PCP-treated lumber. | EPA. 2010. TOXICOLOGICAL REVIEW OF PENTACHLOROPHENOL accessed 07 October 2020 | Link |
| Pentachlorophenol (PCP) is a synthetic substance made from other chemicals and does not occur naturally in the environment. At one time, it was one of the most widely used biocides in the United States. Since 1984, the purchase and use of PCP have been restricted to certified applications. It is no longer available to the general public. Before use restrictions, PCP was widely used as a wood preservative. It is now used industrially as a wood preservative for power line poles, cross arms, and fence posts. PCP can be found in two forms: PCP and the sodium salt of PCP. The sodium salt dissolves easily in water but PCP does not. The physical properties of these two forms are different but their toxic effects are expected to be similar. Humans are generally exposed to technical-grade PCP, which usually contains toxic impurities such as polychlorinated dibenzo-p-dioxins and dibenzofurans. In addition to workplace exposure, humans can be exposed to very low levels of PCP in indoor and outdoor air, food, soil, and drinking water. Exposure may also result from dermal contact with wood treated with preservatives that contain PCP | Badanthadka and Mehendale., 2014. Chlorophenols | Link |
| Pentachlorophenol (PCP) can be found in two forms: pentachlorophenol itself or as the sodium salt of pentachlorophenol (NaPCP). These two forms have some different physical properties, but are expected to have similar toxic effects. PCP is a synthetic substance, made from other chemicals, and does not occur naturally in the environment. Although PCP was first synthesized in 1841, it was not produced commercially until 1936. It has since been registered for use as an insecticide, fungicide, herbicide, algicide, and disinfectant. By 1967, PCP and its sodium salt, NaPCP, were used extensively in industry and agriculture, due in large part to the solubility of PCP in organic solvents and of NaPCP in water. In 1977, both were listed together as the second most heavily used pesticide in the United States. | Gad and Pham. 2014. Sodium Pentachlorophenate | Link |
| PCR in common with other chlorophenols, has a broad range of biocidal activity. In particular, PCP has been found to be effective as an algicide, bactericide, fungicide, herbicide, insecticide, and molluscicide (WHO, 1987). Collectively, PCP and its sodium salt previously constituted one of the most heavily used pesticides in the United States. Net production of the three U.S. manufacturers active in 1980 was 30,600 tons (Jones, 1981). Usage patterns tabulated around that time indicate that 95-98% of North American PCP production (of which 94% originated in the United States) was employed directly or indirectly in wood treatment (Economist Intelligence Unit, 1981). Wood preservation uses of PCP and NaPCP included commercial wood treatment, fence-post treatment, paint treatment, and sapstain control in pressboard and other woodderived materials (WHO, 1987). | Goodman. 2001. CHAPTER 65 - Pentachlorophenol | Link |