Chlorfenvinphos

Chlorfenvinphos
Skeletal formulas of (E)-chlorfenvinphos (left) and (Z)-chlorfenvinphos (right)
Space-filling model of the (Z)-chlorfenvinphos molecule
Names
IUPAC name
[(EZ)-2-Chloro-1-(2,4-dichlorophenyl)ethenyl] diethyl phosphate
Other names
Clofenvinfos; Chlorfenvinfos; Chlorphenvinfos; Chlofenvinphos; Chlofenvinfos; Vinylphate; Apachlor; Birlane; Dermaton; Enolofos; Haptarax; Haptasol; Dermaton; Sapercon; Steladone; Supona
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.006.758 Edit this at Wikidata
EC Number
  • 207-432-0
KEGG
RTECS number
  • TB8750000
UNII
UN number 3018
  • InChI=1S/C12H14Cl3O4P/c1-3-17-20(16,18-4-2)19-12(8-13)10-6-5-9(14)7-11(10)15/h5-8H,3-4H2,1-2H3/b12-8- checkY
    Key: FSAVDKDHPDSCTO-WQLSENKSSA-N checkY
  • InChI=1/C12H14Cl3O4P/c1-3-17-20(16,18-4-2)19-12(8-13)10-6-5-9(14)7-11(10)15/h5-8H,3-4H2,1-2H3/b12-8-
    Key: FSAVDKDHPDSCTO-WQLSENKSBC
  • Clc1cc(Cl)ccc1C(OP(=O)(OCC)OCC)=[C@H]Cl
Properties
C12H14Cl3O4P
Molar mass 359.56 g·mol−1
Appearance Amber liquid
145 mg/L
Hazards
GHS labelling:[1]
GHS06: ToxicGHS09: Environmental hazard
Danger
H300, H311, H330, H410
P260, P262, P264, P270, P271, P273, P280, P284, P301+P316, P302+P352, P304+P340, P316, P320, P321, P330, P361+P364, P391, P403+P233, P405, P501
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 hazards (white): no code
4
1
0
Lethal dose or concentration (LD, LC):
15  mg/kg (rat, oral)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)

Chlorfenvinphos is an organophosphorus compound that was widely used as an insecticide and an acaricide.[2] The molecule itself can be described as an enol ester derived from dichloroacetophenone and diethylphosphonic acid. Chlorfenvinphos has been included in many products since its first use in 1963. However, because of its toxic effect as a cholinesterase inhibitor it has been banned in several countries, including the United States and the European Union. Its use in the United States was discontinued in 1991.[3]

The pure chemical is a colorless solid, but for commercial purposes, it is often marketed as an amber liquid. The insecticides, mostly used in liquid form, contain between 50% and 90% chlorfenvinphos. The substance easily mixes with acetone, ethanol, and propylene glycol. Furthermore, chlorfenvinphos is corrosive to metal and hydrolyzes in the environment.[4]

It is classified as an extremely hazardous substance in the United States as defined in Section 302 of the U.S. Emergency Planning and Community Right-to-Know Act (42 U.S.C. 11002), and is subject to strict reporting requirements by facilities which produce, store, or use it in significant quantities.[5]

  1. ^ "Clofenvinfos". pubchem.ncbi.nlm.nih.gov.
  2. ^ CID 10107 from PubChem
  3. ^ [REFS. 1995. Reference Files System. Chemistry for chlorfenvinphos data report.]
  4. ^ [U.S. Department of Health and Human Services. 1997. Toxicological Profile for Chlorfenvinphos.]
  5. ^ "40 C.F.R.: Appendix A to Part 355—The List of Extremely Hazardous Substances and Their Threshold Planning Quantities" (PDF) (July 1, 2008 ed.). Government Printing Office. Archived from the original (PDF) on February 25, 2012. Retrieved October 29, 2011. {{cite journal}}: Cite journal requires |journal= (help)