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2,4,6-Trichlorophenol

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2,4,6-Trichlorophenol
Chemical structure of 2,4,6-trichlorophenol
Names
Preferred IUPAC name 2,4,6-Trichlorophenol
Identifiers
CAS Number
3D model (JSmol)
Beilstein Reference 776729
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.001.633 Edit this at Wikidata
EC Number
  • 201-795-9
Gmelin Reference 3766
KEGG
PubChem CID
RTECS number
  • SN1575000
UNII
UN number 2020
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C6H3Cl3O/c7-3-1-4(8)6(10)5(9)2-3/h1-2,10HKey: LINPIYWFGCPVIE-UHFFFAOYSA-N
SMILES
  • OC1=C(C=C(C=C1Cl)Cl)Cl
Properties
Chemical formula C6H2Cl3OH/C6H3Cl3O
Molar mass 197.45 g/mol
Appearance yellow-whitish lumps or powder
Density 1.4901 g/cm at 75 °C
Melting point 69.5 °C (157.1 °F; 342.6 K)
Boiling point 249 °C (480 °F; 522 K)
Solubility in water 0.069 g/100 g H2O
Hazards
GHS labelling:
Pictograms GHS07: Exclamation markGHS08: Health hazardGHS09: Environmental hazard
Signal word Warning
Hazard statements H302, H315, H319, H351, H410
Precautionary statements P201, P202, P264, P270, P273, P280, P281, P301+P312, P302+P352, P305+P351+P338, P308+P313, P321, P330, P332+P313, P337+P313, P362, P391, P405, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). ☒N verify (what is  ?) Infobox references
Chemical compound

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, defoliant, and glue preservative. 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:

Health effects

In animal models, consumption of 2,4,6-trichlorophenol leads to an increased incidence of lymphomas, leukemia, and liver cancer. It is classified as Group B2 (probable human carcinogen) by the United States Environmental Protection Agency. The technical grade of this substance may contain polychlorinated dibenzodioxins (PCDDs), polychlorinated dibenzofurans (PCDFs), and other contaminants.

Environmental effects

2,4,6-Trichlorophenol is an environmental pollutant that has been found in fresh water lakes such as the Great Lakes.

See also

References

  1. ^ Haynes, p. 3.522
  2. William M. Haynes, ed. (2016). CRC handbook of chemistry and physics : a ready-reference book of chemical and physical data (97th ed.). Boca Raton, Florida: CRC Press. ISBN 978-1-4987-5428-6. OCLC 930681942.
  3. Ogunniyi TA, Oni PO, Juba A, Asaolu SO, Kolawole DO (2000-01-05). "Disinfectants/antiseptics in the management of guinea worm ulcers in the rural areas". Acta Tropica. 74 (1): 33–38(6). doi:10.1016/S0001-706X(99)00057-1. PMID 10643905.
  4. "Safety data for 2,4,6-trichlorophenol". University of Oxford. 2005-09-05. Archived from the original on 2007-10-14. Retrieved 2007-11-16.
  5. Muller, François; Caillard, Liliane (2011-10-15), "Chlorophenols", in Wiley-VCH Verlag GmbH & Co. KGaA (ed.), Ullmann's Encyclopedia of Industrial Chemistry, 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, retrieved 2022-03-13
  6. "2,4,6-Trichlorophenol". The Carcinogenic Potency Database Project, University of Berkeley. 2007-10-03. Archived from the original on 4 December 2007. Retrieved 2007-11-16.
  7. ^ "2,4,6 Trichlorophenol". United States Environmental Protection Agency. Jan 2000. Retrieved 2007-11-16.
  8. "2,4,6-Trichlorophenol". IPCS. Nov 1998. Archived from the original on 2013-06-27. Retrieved 2007-11-16.
  9. 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. Bibcode:1985WASP...24..189H. doi:10.1007/BF00285444. S2CID 96067556.

Cited sources

External links

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