QL (chemical)

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]

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	57856-11-8 N
3D model (JSmol)	Interactive image
Abbreviations	QL
ChemSpider	148925 Y
PubChem CID	170325
UNII	8154M6X68L
CompTox Dashboard (EPA)	DTXSID70866655
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 Y Key: OIQVKKOBTVZIFE-UHFFFAOYSA-N Y 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 YN ?) Infobox references

Synthesis

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

Uses in chemical warfare

QL is a component in binary chemical weapons, mainly VX nerve agent.^[3] It, along with methylphosphonyl difluoride (DF), was developed during the 1980s in order to replace an aging stockpile of unitary chemical weapons.^[3] QL is listed as a Schedule 1 chemical by the Chemical Weapons Convention.^[4]

Toxicity

QL itself is a relatively non-toxic chemical.^[5] However, when reacting with sulfur, the corresponding sulfide of QL isomerizes into the highly toxic VX molecule.^[3][5]

References

1. "Isopropyl aminoethylmethyl phosphonite". PubChem.
2. "Isopropyl aminoethylmethyl phosphonite". PubChem.
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.
4. "Schedule One Chemicals", Chemical Weapons Convention Archived 2012-01-03 at the Wayback Machine, US Government website, Retrieved November 15, 2008.
5. 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.