2,4,6-Trichlorophenol

2,4,6-Trichlorophenol
Chemical structure of 2,4,6-trichlorophenol
Chemical structure of 2,4,6-trichlorophenol
Names
Preferred IUPAC name
2,4,6-Trichlorophenol
Identifiers
3D model (JSmol)
776729
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.001.633 Edit this at Wikidata
EC Number
  • 201-795-9
3766
KEGG
RTECS number
  • SN1575000
UNII
UN number 2020
  • InChI=1S/C6H3Cl3O/c7-3-1-4(8)6(10)5(9)2-3/h1-2,10H
    Key: LINPIYWFGCPVIE-UHFFFAOYSA-N
  • OC1=C(C=C(C=C1Cl)Cl)Cl
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 labelling:
GHS07: Exclamation markGHS08: Health hazardGHS09: Environmental hazard
Warning
H302, H315, H319, H351, H410
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 [77 °F], 100 kPa).
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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

References

  1. ^ a b c 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. ^ a b "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.[failed verification]
  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