2,4,6-Trichlorophenol

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.

2,4,6-Trichlorophenol

Chemical structure of 2,4,6-trichlorophenol
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[1]
Melting point	69.5 °C (157.1 °F; 342.6 K)[1]
Boiling point	249 °C (480 °F; 522 K)[1]
Solubility in water	0.069 g/100 g H2O[2]
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

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][9]

Environmental effects

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

See also

• Trichlorophenol (for other isomers).