QL (chemical)

QL
Names
Preferred IUPAC name
2-[Di(propan-2-yl)amino]ethyl ethyl methylphosphonite
Other names
2-(Diisopropylamino)ethyl ethyl methylphosphonite
N-[2-(Ethoxy(methyl)phosphanyl)oxyethyl]-N-isopropyl-propan-2-amine
Isopropyl aminoethylmethyl phosphonite
O-(2-Diisopropylaminoethyl) O'-ethyl methylphosphonite
Identifiers
CAS Number
3D model (JSmol)
Abbreviations QL
ChemSpider
PubChem CID
UNII
InChI
  • InChI=1S/C11H26NO2P/c1-7-13-15(6)14-9-8-12(10(2)3)11(4)5/h10-11H,7-9H2,1-6H3 checkY
    Key: OIQVKKOBTVZIFE-UHFFFAOYSA-N checkY
  • InChI=1/C11H26NO2P/c1-7-13-15(6)14-9-8-12(10(2)3)11(4)5/h10-11H,7-9H2,1-6H3
    Key: OIQVKKOBTVZIFE-UHFFFAOYAN
SMILES
  • O(P(OCCN(C(C)C)C(C)C)C)CC
Properties
Chemical formula
 C11H26NO2P
Molar mass 235.308 g·mol−1
Appearance Colorless liquid
Odor Strong fishy odor
Boiling point 230 °C (446 °F; 503 K)
Solubility in water
 Slightly soluble in water
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 ?)
Infobox references

Isopropyl aminoethylmethyl phosphonite (NATO designation QL), also known as O-(2-diisopropylaminoethyl) O′-ethyl methylphosphonite, is a precursor chemical to the nerve agent VX and VR-56. It is a colorless liquid with a strong fishy odor, and is slightly soluble in water.[1]

Synthesis

QL is manufactured by the transesterification of diethyl methylphosphonite with 2-(diisopropylamino)ethanol.[2][3]

Uses in chemical warfare

QL is a component in binary chemical weapons, mainly VX nerve agent.[4] It, along with methylphosphonyl difluoride (DF), was developed during the 1980s in order to replace an aging stockpile of unitary chemical weapons.[4] QL is listed as a Schedule 1 chemical by the Chemical Weapons Convention.[5]

Toxicity

QL itself is a relatively non-toxic chemical.[6] However, when reacting with sulfur, the corresponding sulfide of QL isomerizes into the highly toxic VX molecule.[4][6]

References

  1. ↑ "Isopropyl aminoethylmethyl phosphonite". PubChem.
  2. ↑ "Isopropyl aminoethylmethyl phosphonite". PubChem.
  3. ↑ Ember, Lois R. (1982-08-23). "Army seeks firm to make nerve gas chemicals: After solicitations to firms this summer, Army finds big firms generally won't touch this controversial area, but some small companies will". Chemical & Engineering News Archive. 60 (34): 32–34. doi:10.1021/cen-v060n034.p032. ISSN 0009-2347.
  4. 1 2 3 National Research Council, et al. Systems and Technologies for the Treatment of Non-stockpile Chemical Warfare Materiel, (Google Books), National Academies Press, 2002, p. 14, (ISBN 0309084520), accessed October 21, 2008.
  5. ↑ "Schedule One Chemicals", Chemical Weapons Convention Archived 2012-01-03 at the Wayback Machine, US Government website, Retrieved November 15, 2008.
  6. 1 2 Croddy, Eric and Wirtz, James J. Weapons of Mass Destruction: An Encyclopedia of Worldwide Policy, Technology, and History, (Google Books), ABC-CLIO, 2005, p. 238, (ISBN 1851094903), accessed October 21, 2008.
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