EA-1763

EA-1763
Names
	Other names N-[2-[methyl(propoxy)phosphoryl]sulfanylethyl]-N-propan-2-ylpropan-2-amine
Identifiers
CAS Number	52364-45-1;
3D model (JSmol)	Interactive image;
PubChem CID	89671424;
	InChI InChI=1S/C12H28NO2PS/c1-7-9-15-16(6,14)17-10-8-13(11(2)3)12(4)5/h11-12H,7-10H2,1-6H3 Key: WPCWBOZLTXVEHU-UHFFFAOYSA-N;
	SMILES CCCOP(=O)(C)SCCN(C(C)C)C(C)C;
Properties
Chemical formula	C12H28NO2PS
Molar mass	281.39 g·mol−1
Boiling point	316.5 °C (601.7 °F; 589.6 K)
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

EA-1763,^[1] O-PPVX, V1^[2] or propyl S-2-diisopropylaminoethylmethylphosphonothiolate is a military-grade neurotoxic organophosphonate nerve agent related to VX as it is the propyl analogue of VX. It is part of the V-series.

Chemical characteristics

Little information about EA-1763's physicochemical properties has been reported.^[1] V1 is a more viscous and less dense liquid than VX.^[3] It is colorless, odorless and tasteless in its pure form. When impure or in the crude form, it has a characteristic viscous amber color, giving it an appearance similar to motor oil. The appearance of the impure form varies between several shades of amber, from a viscous liquid of a transparent pale yellow color to a pasty liquid of a semi-transparent and cloudy dirty amber color. The smell varies from engine oil to an offensive brew of organosulfur compounds and organoamines.^[4]

Its larger alkane chain pushes its melting point above that of VX. The estimated solubility of V1 in water is 4 times lower compared to VX (6.8 g/L of water at 25 °C). V1 has high solubility in organic solvents and other non-polar compounds. The stability of V1 is roughly the same as that of VX in either environment. Higher insolubility and lower volatility can slow down the process. A vapor pressure at least 3 times lower than VX is speculated.^[5]

The longer alkane chain tends to stabilize the induction of electrons from P to O, making P less electrophilic.^[5] It is expected that the persistence of V1 is slightly higher than that of VX since the hydrolysis rate of ethyl paraoxon is 1.6 times higher than the one of n-propyl paraoxon in a neutral medium.^[6]

The lower volatility and minimal persistence difference makes VX preferable to V1.^[5]

Preparation

It is prepared by the same route as VX using propanol instead of ethanol.

References

^ ^a ^b John B. Samuel, Elwin C. Penski, John J. Callahan. PHYSICAL PROPERTIES OF STANDARD AGENTS, CANDIDATE AGENTS, AND RELATED COMPOUNDS AT SEVERAL TEMPERATURES (U). p 24 and 279.
^ Kirkpatrick, Melanie G.; diTargiani, Robert C.; Sweeney, Richard E.; Otto, Tamara C. (2016-11-25). "Use of V agents and V-analogue compounds to probe the active site of atypical butyrylcholinesterase from Oryzias latipes". Chemico-Biological Interactions. 259 (Pt B): 182–186. Bibcode:2016CBI...259..182K. doi:10.1016/j.cbi.2016.03.016. ISSN 1872-7786. PMID 27000540.
^ Coulter, P. B.; Callahan, J. J.; Link, R.S. Physical Constants of Thirteen V Agents. U. S. Army Chemical Warfare Laboratories Technical Report (Report). CWLR-2346.
^ Ledgard, J. A Laboratory History of Chemical Warfare Agents. p 223-225.
^ ^a ^b ^c cit-OPDC. The preparatory manual to chemical warfare. Vol 1: V1
^ CHEMICAL REVIEWS VOLUME6 4, NUMBER 4. JULY 24, 1964. page 318.

[:0-1] John B. Samuel, Elwin C. Penski, John J. Callahan. PHYSICAL PROPERTIES OF STANDARD AGENTS, CANDIDATE AGENTS, AND RELATED COMPOUNDS AT SEVERAL TEMPERATURES (U). p 24 and 279.

[2] Kirkpatrick, Melanie G.; diTargiani, Robert C.; Sweeney, Richard E.; Otto, Tamara C. (2016-11-25). "Use of V agents and V-analogue compounds to probe the active site of atypical butyrylcholinesterase from Oryzias latipes". Chemico-Biological Interactions. 259 (Pt B): 182–186. Bibcode:2016CBI...259..182K. doi:10.1016/j.cbi.2016.03.016. ISSN 1872-7786. PMID 27000540.

[3] Coulter, P. B.; Callahan, J. J.; Link, R.S. Physical Constants of Thirteen V Agents. U. S. Army Chemical Warfare Laboratories Technical Report (Report). CWLR-2346.

[:1-4] Ledgard, J. A Laboratory History of Chemical Warfare Agents. p 223-225.

[:2-5] t-OPDC. The preparatory manual to chemical warfare. Vol 1: V1

[6] CHEMICAL REVIEWS VOLUME6 4, NUMBER 4. JULY 24, 1964. page 318.

[1]