2,4,6-Trichlorophenol

2,4,6-Trichlorophenol
	Chemical structure of 2,4,6-trichlorophenol source ↗
source ↗	source ↗
	source ↗
Names
	Preferred IUPAC name 2,4,6-Trichlorophenol
Identifiers
CAS Number	88-06-2 Y;
3D model (JSmol)	Interactive image;
Beilstein Reference	776729
ChEBI	CHEBI:28755 Y;
ChEMBL	ChEMBL309917;
ChemSpider	6648 Y;
ECHA InfoCard	100.001.633
EC Number	201-795-9;
Gmelin Reference	3766
KEGG	C07098;
PubChem CID	6914;
RTECS number	SN1575000;
UNII	MHS8C5BAUZ Y;
UN number	2020
CompTox Dashboard (EPA)	DTXSID5021386 ;
	InChI InChI=1S/C6H3Cl3O/c7-3-1-4(8)6(10)5(9)2-3/h1-2,10H Key: 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/cm3 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
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 [77 °F], 100 kPa). N verify (what is YN ?) 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.⁶⁷ 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.⁸⁹

Environmental effects

2,4,6-Trichlorophenol is an environmental pollutant that has been found in fresh water lakes such as the Great Lakes.¹⁰

References

Haynes, p. 3.522
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.
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.
"Safety data for 2,4,6-trichlorophenol". University of Oxford. 2005-09-05. Retrieved 2007-11-16.{{cite web}}: CS1 maint: deprecated archival service (link)
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
"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.
"2,4,6 Trichlorophenol". United States Environmental Protection Agency. Jan 2000. Retrieved 2007-11-16.{{cite web}}: CS1 maint: deprecated archival service (link)
Briois, C.; Ryan, S.; Tabor, D.; Touati, A.; Gullett, B. K. (2007). "Formation of polychlorinated dibenzo-p-dioxins and dibenzofurans from a mixture of chlorophenols over fly ash: Influence of water vapor". Environmental Science & Technology. 41 (3): 850–856. Bibcode:2007EnST...41..850B. doi:10.1021/es0613761. PMID 17328193.
"2,4,6-Trichlorophenol". IPCS. Nov 1998. Archived from the original on 2013-06-27. Retrieved 2007-11-16.
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

Haynes, William M., ed. (2016). CRC Handbook of Chemistry and Physics (97th ed.). CRC Press. ISBN 9781498754293.

External links

[crc-1] Haynes, p. 3.522

[CRC97-2] 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.

[msds-4] "Safety data for 2,4,6-trichlorophenol". University of Oxford. 2005-09-05. Retrieved 2007-11-16.{{cite web}}: CS1 maint: deprecated archival service (link)

[ullmannchlorophenols-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

[berkeley-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.

[epa-7] "2,4,6 Trichlorophenol". United States Environmental Protection Agency. Jan 2000. Retrieved 2007-11-16.{{cite web}}: CS1 maint: deprecated archival service (link)

[8] Briois, C.; Ryan, S.; Tabor, D.; Touati, A.; Gullett, B. K. (2007). "Formation of polychlorinated dibenzo-p-dioxins and dibenzofurans from a mixture of chlorophenols over fly ash: Influence of water vapor". Environmental Science & Technology. 41 (3): 850–856. Bibcode:2007EnST...41..850B. doi:10.1021/es0613761. PMID 17328193.

[9] "2,4,6-Trichlorophenol". IPCS. Nov 1998. Archived from the original on 2013-06-27. Retrieved 2007-11-16.

[halappagowdal-10] 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.

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