Chemistry:EA-1763

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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)
Properties
C12H28NO2PS
Molar mass 281.39 g·mol−1
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. It is part of the V-series. The substitution of a proton for methyl makes its properties more similar to those of VX.

Chemical characteristics

The effects of the propyl group are based on the effects of propyl[3]/ethyl[4] acetate on VX.[5][6] Little information about EA-1763's physicochemical properties has been reported.[1] V1 is a more viscous and less dense liquid than VX.[7] 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.[6]

V1 has a boiling point of 316,5 degrees C. Its larger paraffin 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 considerably 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.[8]

A methyl group on the β-carbon adjacent to the O-bonded α-carbon tends to stabilize the induction of electrons from P to O, making P less electrophilic.[8] 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.[9]

The lower volatility and minimal persistence difference makes VX preferable to V1.[8]

Preparation

The manufacture of S-(2-dialkylaminoethyl) O-alkyl alkylphosphonothiolates essentially involves the conditions reported by Eckhaus et al.[10]

References

  1. ↑ 1.0 1.1 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. doi:10.1016/j.cbi.2016.03.016. ISSN 1872-7786. PMID 27000540. https://pubmed.ncbi.nlm.nih.gov/27000540/. 
  3. ↑ PubChem. "Propyl acetate" (in en). https://pubchem.ncbi.nlm.nih.gov/compound/7997. 
  4. ↑ PubChem. "Ethyl acetate" (in en). https://pubchem.ncbi.nlm.nih.gov/compound/8857. 
  5. ↑ PubChem. "O-Ethyl S-(2-diisopropylaminoethyl) methylphosphonothioate" (in en). https://pubchem.ncbi.nlm.nih.gov/compound/39793. 
  6. ↑ 6.0 6.1 Ledgard, J. A Laboratory History of Chemical Warfare Agents. p 223-225.
  7. ↑ 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.
  8. ↑ 8.0 8.1 8.2 cit-OPDC. The preparatory manual to chemical warfare. Vol 1: V1
  9. ↑ CHEMICAL REVIEWS VOLUME6 4, NUMBER 4. JULY 24, 1964. page 318.
  10. ↑ Eckhaus et al. US 3,911,059



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