EA-1763

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EA-1763
Names
Other names
N-[2-[methyl(propoxy)phosphoryl]sulfanylethyl]-N-propan-2-ylpropan-2-amine
Identifiers
3D model (
JSmol
)
  • 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
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

EA-1763,

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

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. ^ 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.
  2. PMID 27000540
    .
  3. ^ PubChem. "Propyl acetate". pubchem.ncbi.nlm.nih.gov. Retrieved 2022-05-29.
  4. ^ PubChem. "Ethyl acetate". pubchem.ncbi.nlm.nih.gov. Retrieved 2022-05-29.
  5. ^ PubChem. "O-Ethyl S-(2-diisopropylaminoethyl) methylphosphonothioate". pubchem.ncbi.nlm.nih.gov. Retrieved 2022-05-29.
  6. ^ a b 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. ^ a b c 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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