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).[4]

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)
742467
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.004.027
EC Number
  • 204-429-6
261170
KEGG
RTECS number
  • SK8575000
UNII
UN number 2020
  • 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−1
Appearance White solid
Odor Phenolic
Density 1.38 g/cm3
Melting point 43.2 °C (109.8 °F; 316.3 K)[1]
Boiling point 210 °C (410 °F; 483 K)[1]
50 g/L
Thermochemistry[2]
−226.4 kJ·mol−1 (s)
−156.3 kJ·mol−1 (gas)
Hazards
GHS labelling:
GHS05: CorrosiveGHS06: ToxicGHS07: Exclamation markGHS09: Environmental hazard
Danger
H302, H311, H314, H411
P260, P264, P270, P273, P280, P301+P312, P301+P330+P331, P302+P352, P303+P361+P353, P304+P340, P305+P351+P338, P310, P312, P321, P322, P330, P361, P363, P391, P405, P501
NFPA 704 (fire diamond)
NFPA 704 four-colored diamond
0
1
0
COR
Flash point 114 °C (237 °F; 387 K)[3]
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).
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Infobox references

Production and use

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

Annual worldwide production is estimated at 88 million pounds.[5] It is also a photo-degradation product of the common antibacterial and antifungal agent triclosan along with the dioxin 2,8-dichlorodibenzo-p-dioxin.[6][7]

Safety

The LD50 is 580 mg/kg (rats, oral). Liquid (molten) 2,4-DCP is readily absorbed through the skin.[8] 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. Haynes, p. 3.166
  2. Haynes, p. 5.12
  3. Haynes, p. 16.20
  4. François Muller; Liliane Caillard (2011). "Chlorophenols". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a07_001.pub2.
  5. 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
  6. 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.
  7. 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.
  8. 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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