Soman

Soman (or GD, EA 1210, Zoman, PFMP, A-255, systematic name: O-pinacolyl methylphosphonofluoridate) is an extremely toxic chemical substance. It is a nerve agent, interfering with normal functioning of the mammalian nervous system by inhibiting the enzyme cholinesterase. It is an inhibitor of both acetylcholinesterase and butyrylcholinesterase. As a chemical weapon, it is classified as a weapon of mass destruction by the United Nations according to UN Resolution 687. Its production is strictly controlled, and stockpiling is outlawed by the Chemical Weapons Convention of 1993 where it is classified as a Schedule 1 substance. Soman was the third of the so-called G-series nerve agents to be discovered along with GA (tabun), GB (sarin), and GF (cyclosarin).

Soman
Names
Preferred IUPAC name
3,3-Dimethylbutan-2-yl methylphosphonofluoridate
Other names
GD; Phosphonofluoridic acid, methyl-, 1, 2, 2-trimethylpropyl ester; 2-(Fluoromethylphosphoryl)oxy-3,3-dimethylbutane; Pinacolyl methylphosphonofluoridate; 1,2,2-Trimethylpropyl methylphosphonofluoridate; Methylpinacolyloxyfluorophosphine oxide; Pinacolyloxymethylphosphonyl fluoride; Pinacolyl methanefluorophosphonate; Methylfluoropinacolylphosphonate; Fluoromethylpinacolyloxyphosphine oxide; Methylpinacolyloxyphosphonyl fluoride; Pinacolyl methylfluorophosphonate; 1,2,2-Trimethylpropoxyfluoromethylphosphine oxide
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
UNII
  • InChI=1S/C7H16FO2P/c1-6(7(2,3)4)10-11(5,8)9/h6H,1-5H3 Y
    Key: GRXKLBBBQUKJJZ-UHFFFAOYSA-N Y
  • InChI=1/C7H16FO2P/c1-6(7(2,3)4)10-11(5,8)9/h6H,1-5H3
    Key: GRXKLBBBQUKJJZ-UHFFFAOYAY
  • FP(=O)(OC(C)C(C)(C)C)C
Properties
C7H16FO2P
Molar mass 182.175 g·mol−1
Appearance When pure, colorless liquid with odor resembling rotten fruit. With impurities, amber or dark brown, with odor of camphor oil.
Density 1.022 g/cm3
Melting point −42 °C (−44 °F; 231 K)
Boiling point 198 °C (388 °F; 471 K)
Moderate
Vapor pressure 0.40 mmHg (53 Pa)
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
Highly Toxic
NFPA 704 (fire diamond)
4
1
1
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

When pure, soman is a volatile, corrosive, and colorless liquid with a faint odor like that of mothballs or rotten fruit. More commonly, it is a yellow to brown color and has a strong odor described as similar to camphor. The LCt50 for soman is 70 mg·min/m3 in humans.

GD can be thickened for use as a chemical spray using an acryloid copolymer. It can also be deployed as a binary chemical weapon; its precursor chemicals are methylphosphonyl difluoride and a mixture of pinacolyl alcohol and an amine.

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