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2,4-Dichlorophenol

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2,4-Dichlorophenol
Skeletal formula
Skeletal formula
Ball-and-stick model
Ball-and-stick model
Names
Preferred IUPAC name
2,4-Dichlorophenol
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.004.027 Edit this at Wikidata
KEGG
UNII
  • InChI=1S/C6H4Cl2O/c7-4-1-2-6(9)5(8)3-4/h1-3,9H checkY
    Key: HFZWRUODUSTPEG-UHFFFAOYSA-N checkY
  • InChI=1/C6H4Cl2O/c7-4-1-2-6(9)5(8)3-4/h1-3,9H
    Key: HFZWRUODUSTPEG-UHFFFAOYAU
  • Clc1cc(Cl)c(O)cc1
Properties
C6H4Cl2O
Molar mass 163.00 g/mol
Appearance White/off-white crystalline solid
Odor Phenolic
Density 1.38g/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
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 4: Very short exposure could cause death or major residual injury. E.g. VX gasFlammability 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oilInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazard COR: Corrosive; strong acid or base. E.g. sulfuric acid, potassium hydroxide
4
1
0
COR
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)
Safety data sheet (SDS) External MSDS
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
checkY verify (what is checkY☒N ?)

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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