2,4-Dichlorophenol

2,4-Dichlorophenol
	Template:Chembox image sbs cell
Names
	IUPAC name 2,4-Dichlorophenol
Identifiers
CAS Number	120-83-2 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:16738 ;
ChEMBL	ChEMBL1143 ;
ChemSpider	8140 ;
ECHA InfoCard	Lua error in Module:Wikidata at line 879: attempt to index field 'wikibase' (a nil value). Lua error in Module:Wikidata at line 879: attempt to index field 'wikibase' (a nil value).
KEGG	C02625 ;
PubChem CID	8449;
UNII	R669TG1950 ;
	InChI InChI=1S/C6H4Cl2O/c7-4-1-2-6(9)5(8)3-4/h1-3,9H Key: HFZWRUODUSTPEG-UHFFFAOYSA-N ; InChI=1/C6H4Cl2O/c7-4-1-2-6(9)5(8)3-4/h1-3,9H Key: HFZWRUODUSTPEG-UHFFFAOYAU;
	SMILES Clc1cc(Cl)c(O)cc1;
Properties
Chemical formula	C6H4Cl2O
Molar mass	163.00 g/mol
Hazards
	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

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Editor-In-Chief: C. Michael Gibson, M.S., M.D. [1]

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Overview

2,4-Dichlorophenol (2,4-DCP) is a chlorinated derivative of phenol with the molecular formula C₆H₄Cl₂O. 2,4-DCP is used primarily as an intermediate in the preparation of the herbicide 2,4-dichlorophenoxyacetic acid (2,4-D). Annual worldwide production is estimated at 88 million pounds.^[1] It is also a photo-degradation product of the common antibacterial and antifungal agent triclosan along with the dioxin 2,8-dichlorodibenzo-p-dioxin.^[2]^[3]

Liquid (molten) 2,4-DCP is readily absorbed through the skin and contact with large amounts may be fatal.^[4] Solid 2,4-DCP does not readily absorb through skin and has a lower NFPA H=3 rating (versus H=4 for molten 2,4-DCP). This is primarily caused by instantaneous renal failure, liver damage and various other organ failure.

References

↑ Desmurs J, Ratton S. Chlorophenols. In: Kirk-Othmer Encyclopedia of Chemical Technology, 4th Edition. Kroschwitz JI, Howe-Grant M, eds. New York: John Wiley and Sons, 1993;6:156-168
↑ Singer H, Muller S, Tixier C, Pillonel L. (2002). "Triclosan: occurrence and fate of a widely used biocide in the aquatic environment: field measurements in wastewater treatment plants, surface waters, and lake sediments". Environ Sci Technol. 36 (23): 4998–5004. doi:10.1021/es025750i. PMID 12523412.
↑ Latch DE, Packer JL, Stender BL, VanOverbeke J, Arnold WA, McNeill K (2005). "Aqueous photochemistry of triclosan: formation of 2,4-dichlorophenol, 2,8-dichlorodibenzo-p-dioxin, and oligomerization products". Environ. Toxicol. Chem. 24 (3): 517–25. doi:10.1897/04-243R.1. PMID 15779749.
↑ Kintz P, Tracqui A, Mangin P (1992). "Accidental death caused by the absorption of 2,4-dichlorophenol through the skin". Arch. Toxicol. 66 (4): 298–9. doi:10.1007/BF02307178. PMID 1514931.

[1] Desmurs J, Ratton S. Chlorophenols. In: Kirk-Othmer Encyclopedia of Chemical Technology, 4th Edition. Kroschwitz JI, Howe-Grant M, eds. New York: John Wiley and Sons, 1993;6:156-168

[pmid12523412-2] Singer H, Muller S, Tixier C, Pillonel L. (2002). "Triclosan: occurrence and fate of a widely used biocide in the aquatic environment: field measurements in wastewater treatment plants, surface waters, and lake sediments". Environ Sci Technol. 36 (23): 4998–5004. doi:10.1021/es025750i. PMID 12523412.

[pmid15779749-3] Latch DE, Packer JL, Stender BL, VanOverbeke J, Arnold WA, McNeill K (2005). "Aqueous photochemistry of triclosan: formation of 2,4-dichlorophenol, 2,8-dichlorodibenzo-p-dioxin, and oligomerization products". Environ. Toxicol. Chem. 24 (3): 517–25. doi:10.1897/04-243R.1. PMID 15779749.

[4] Kintz P, Tracqui A, Mangin P (1992). "Accidental death caused by the absorption of 2,4-dichlorophenol through the skin". Arch. Toxicol. 66 (4): 298–9. doi:10.1007/BF02307178. PMID 1514931.

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2,4-Dichlorophenol

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