EA-1763

Last updated
EA-1763
N-propyl S-2-di-isopropylaminoethyl methylphosphonothioate.svg
Names
Other names
N-[2-[methyl(propoxy)phosphoryl]sulfanylethyl]-N-propan-2-ylpropan-2-amine
Identifiers
3D model (JSmol)
PubChem CID
  • 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
  • CCCOP(=O)(C)SCCN(C(C)C)C(C)C
Properties
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).

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 the propyl analogue of VX. It is part of the V-series.

Contents

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. Impure, or in the crude form, it has a characteristic viscous amber color, giving it an appearance similar to motor oil. The impure form varies 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, estimating the hydrolysis rate between ethyl and n-propyl paraoxon, is 1.6 times more persistent in 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.

Related Research Articles

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Germanium compounds are chemical compounds formed by the element germanium (Ge). Germanium is insoluble in dilute acids and alkalis but dissolves slowly in hot concentrated sulfuric and nitric acids and reacts violently with molten alkalis to produce germanates ([GeO
3
]2−
). Germanium occurs mostly in the oxidation state +4 although many +2 compounds are known. Other oxidation states are rare: +3 is found in compounds such as Ge2Cl6, and +3 and +1 are found on the surface of oxides, or negative oxidation states in germanides, such as −4 in Mg
2
Ge
. Germanium cluster anions (Zintl ions) such as Ge42−, Ge94−, Ge92−, [(Ge9)2]6− have been prepared by the extraction from alloys containing alkali metals and germanium in liquid ammonia in the presence of ethylenediamine or a cryptand. The oxidation states of the element in these ions are not integers—similar to the ozonides O3.

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References

  1. 1 2 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.
  4. Ledgard, J. A Laboratory History of Chemical Warfare Agents. p 223-225.
  5. 1 2 3 cit-OPDC. The preparatory manual to chemical warfare. Vol 1: V1
  6. CHEMICAL REVIEWS VOLUME6 4, NUMBER 4. JULY 24, 1964. page 318.