2,4-Dichlorophenol

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 Edit this at Wikidata
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 diamondHealth 0: Exposure under fire conditions would offer no hazard beyond that of ordinary combustible material. E.g. sodium chlorideFlammability 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
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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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]

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.[dubious – discuss]

See also

References

  1. ^ a b Haynes, p. 3.166
  2. ^ Haynes, p. 5.12
  3. ^ Haynes, p. 16.20
  4. ^ a b François Muller, Liliane Caillard (2011). "Chlorophenols". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a07_001.pub2. ISBN 978-3527306732.
  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. Bibcode:2002EnST...36.4998S. 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. S2CID 19322739.
  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. S2CID 23764834.