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QL (chemical)

From Wikipedia, the free encyclopedia
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
3D model (JSmol)
AbbreviationsQL
ChemSpider
UNII
  • 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
  • O(P(OCCN(C(C)C)C(C)C)C)CC
Properties
C11H26NO2P
Molar mass235.308 g·mol−1
AppearanceColorless liquid
OdorStrong fishyodor
Boiling point230 °C (446 °F; 503 K)
Slightly soluble inwater
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)
Chemical compound

Isopropyl aminoethylmethyl phosphonite (NATO designationQL), also known asO-(2-diisopropylaminoethyl)O-ethyl methylphosphonite, is aprecursor chemical to thenerve agentVX and VR-56. It is a colorless liquid with a strong fishy odor, and is slightly soluble in water.[1]

Synthesis

[edit]

QL is manufactured by thetransesterification of diethyl methylphosphonite with2-(diisopropylamino)ethanol.[2][3]

Uses in chemical warfare

[edit]

QL is a component inbinary chemical weapons, mainlyVXnerve agent.[4] It, along withmethylphosphonyl difluoride (DF), was developed during the 1980s in order to replace an aging stockpile of unitarychemical weapons.[4] QL is listed as aSchedule 1 chemical by theChemical Weapons Convention.[5]

Toxicity

[edit]

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

References

[edit]
  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. ^abcNational 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 ConventionArchived 2012-01-03 at theWayback Machine, US Government website, Retrieved November 15, 2008.
  6. ^abCroddy, 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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