2,4-Dichlorophenol

2,4-Dichlorophenol (2,4-DCP) is a chlorinated derivative of phenol with the molecular formula Cl2C6H3OH. It is a white solid that is mildly acidic (pKa = 7.9). It is produced on a large scale as a precursor to the herbicide 2,4-dichlorophenoxyacetic acid (2,4-D).[1]

2,4-Dichlorophenol
Skeletal formula
Ball-and-stick model
Names
Preferred IUPAC name
2,4-Dichlorophenol
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.004.027
KEGG
UNII
Properties
C6H4Cl2O
Molar mass 163.00 g·mol−1
Appearance White solid
Odor Phenolic
Density 1.38 g/cm3
Melting point 42 to 43 °C (108 to 109 °F; 315 to 316 K)
Boiling point 209 to 210 °C (408 to 410 °F; 482 to 483 K)
5 g/100mL
Hazards
Safety data sheet External MSDS
R-phrases (outdated) R22 R24 R34 R51/53
S-phrases (outdated) S26 S36/37/39 S45 S61
NFPA 704 (fire diamond)
Flash point 114 °C (237 °F; 387 K)
Lethal dose or concentration (LD, LC):
47.0 mg/kg (Oral in rats)
790.0 mg/kg (Dermal exposure in mammals)
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

Production and use

2,4-DCP is produced by chlorination of phenol.[1]

Annual worldwide production is estimated at 88 million pounds.[2] It is also a photo-degradation product of the common antibacterial and antifungal agent triclosan along with the dioxin 2,8-dichlorodibenzo-p-dioxin.[3][4]

Safety

The LD50 is 580 mg/kg (rats, oral). Liquid (molten) 2,4-DCP is readily absorbed through the skin.[5] 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 kidney failure, liver failure, and failure of various other organs.

See also

References
  1. François Muller, Liliane Caillard (2011). "Chlorophenols". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a07_001.pub2.CS1 maint: uses authors parameter (link)
  2. 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
  3. 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.
  4. 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.
  5. 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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