Chemistry:2,4,6-Trichlorophenol
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| Names | |||
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| Preferred IUPAC name
2,4,6-Trichlorophenol | |||
| Identifiers | |||
3D model (JSmol)
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| 776729 | |||
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| ChEMBL | |||
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| EC Number |
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| 3766 | |||
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PubChem CID
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| UNII | |||
| UN number | 2020 | ||
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| Properties | |||
| C6H2Cl3OH/C6H3Cl3O | |||
| Molar mass | 197.45 g/mol | ||
| Appearance | yellow-whitish lumps or powder | ||
| Density | 1.4901 g/cm3 at 75 °C[1] | ||
| Melting point | 69.5 °C (157.1 °F; 342.6 K)[1] | ||
| Boiling point | 249 °C (480 °F; 522 K)[1] | ||
| 0.069 g/100 g H2O[2] | |||
| Hazards | |||
| GHS pictograms |   
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| GHS Signal word | Warning | ||
| H302, H315, H319, H351, H410 | |||
| P201, P202, P264, P270, P273, P280, P281, P301+312, P302+352, P305+351+338, P308+313, P321, P330, P332+313, P337+313, P362, P391, P405, P501 | |||
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). | |||
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| Infobox references | |||
2,4,6-Trichlorophenol, also known as TCP, phenaclor, Dowicide 2S, Dowcide 2S, omal, is a chlorinated phenol that has been used as a fungicide, herbicide, insecticide, antiseptic,[3] defoliant, and glue preservative.[4] It is a clear to yellowish crystalline solid with a strong, phenolic odor. It decomposes on heating to produce toxic and corrosive fumes including hydrogen chloride and chlorine.
Preparation
2,4,6-Trichlorophenol is produced industrially by the electrophilic chlorination of phenol:[5]
Health effects
In animal models, consumption of 2,4,6-trichlorophenol leads to an increased incidence of lymphomas, leukemia, and liver cancer.[6][7] It is classified as Group B2 (probable human carcinogen) by the United States Environmental Protection Agency.[7] The technical grade of this substance may contain polychlorinated dibenzodioxins (PCDDs), polychlorinated dibenzofurans (PCDFs), and other contaminants.[8]
Environmental effects
2,4,6-Trichlorophenol is an environmental pollutant that has been found in fresh water lakes such as the Great Lakes.[9]
See also
- Trichlorophenol (for other isomers).
References
- ↑ 1.0 1.1 1.2 Haynes, p. 3.522
- ↑ CRC handbook of chemistry and physics : a ready-reference book of chemical and physical data.. William M. Haynes, David R. Lide, Thomas J. Bruno (2016-2017, 97th ed.). Boca Raton, Florida. 2016. ISBN 978-1-4987-5428-6. OCLC 930681942. https://www.worldcat.org/oclc/930681942.
- ↑ "Disinfectants/antiseptics in the management of guinea worm ulcers in the rural areas". Acta Tropica 74 (1): 33–38(6). 2000-01-05. doi:10.1016/S0001-706X(99)00057-1. PMID 10643905.
- ↑ "Safety data for 2,4,6-trichlorophenol". University of Oxford. 2005-09-05. http://physchem.ox.ac.uk/MSDS/TR/2,4,6-trichlorophenol.html.
- ↑ Muller, François; Caillard, Liliane (2011-10-15), Wiley-VCH Verlag GmbH & Co. KGaA, ed. (in en), Chlorophenols, Weinheim, Germany: Wiley-VCH Verlag GmbH & Co. KGaA, pp. a07_001.pub2, doi:10.1002/14356007.a07_001.pub2, ISBN 978-3-527-30673-2, https://onlinelibrary.wiley.com/doi/10.1002/14356007.a07_001.pub2, retrieved 2022-03-13
- ↑ "2,4,6-Trichlorophenol". The Carcinogenic Potency Database Project, University of Berkeley. 2007-10-03. http://potency.berkeley.edu/chempages/2,4,6-TRICHLOROPHENOL.html.
- ↑ 7.0 7.1 "2,4,6 Trichlorophenol". United States Environmental Protection Agency. Jan 2000. http://www.epa.gov/ttn/atw/hlthef/tri-phen.html.
- ↑ "2,4,6-Trichlorophenol". IPCS. Nov 1998. http://www.oit.org/public/english/protection/safework/cis/products/icsc/dtasht/_icsc11/icsc1122.htm.[failed verification]
- ↑ TP Halappa Gowdal; John D Lock; Ruth G Kurtz (Feb 1985). "A comprehensive study of risk assessment for a hazardous compound of public health concern". Water, Air, & Soil Pollution 24 (2): 189. doi:10.1007/BF00285444. Bibcode: 1985WASP...24..189H.
Cited sources
- Haynes, William M., ed (2016). CRC Handbook of Chemistry and Physics (97th ed.). CRC Press. ISBN 9781498754293.
External links
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