2,4-Dichlorophenol

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

Template:Chembox E numberTemplate:Chembox SolubilityInWaterTemplate:Chembox Lethal amounts (set)
2,4-Dichlorophenol
Template:Chembox image sbs cell
Names
IUPAC name
2,4-Dichlorophenol
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
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KEGG
UNII
Properties
C6H4Cl2O
Molar mass 163.00 g/mol
Appearance White/off-white crystalline solid
Odor Phenolic
Density 1.38g/cm3
Melting point
Boiling point
Hazards
R-phrases R22 R24 R34 R51/53
S-phrases S26 S36/37/39 S45 S61
Flash point {{{value}}}
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

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.

See also

References

  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
  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.
  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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