Soman

For other uses, see Soman (disambiguation).
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 checkY
    Key: GRXKLBBBQUKJJZ-UHFFFAOYSA-N checkY
  • 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)
NFPA 704 four-colored diamondHealth 4: Very short exposure could cause death or major residual injury. E.g. VX gasFlammability 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oilInstability 1: Normally stable, but can become unstable at elevated temperatures and pressures. E.g. calciumSpecial hazards (white): no code
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 checkY☒N ?)

Soman (or GD, EA 1210, Zoman, PFMP, A-255, systematic name: O-pinacolyl methylphosphonofluoridate)[1] 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.[2] 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).

When pure, soman is a volatile, corrosive, and colorless liquid with a faint odor like that of mothballs or rotten fruit.[3] 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.[citation needed]

  1. ^ [1] Archived 2013-09-12 at the Wayback Machine United States Senate, 103d Congress, 2d Session. (May 25, 1994). Material Safety Data Sheet -- Lethal Nerve Agents Somain (GD and Thickened GD). Retrieved Nov. 6, 2004.
  2. ^ Millard CB, Kryger G, Ordentlich A, et al. (June 1999). "Crystal structures of aged phosphonylated acetylcholinesterase: nerve agent reaction products at the atomic level". Biochemistry. 38 (22): 7032–9. doi:10.1021/bi982678l. PMID 10353814. S2CID 11744952.
  3. ^ "CDC | Facts About Soman". emergency.cdc.gov. Centers for Disease Control and Prevention. Archived from the original on 2017-12-22. Retrieved 2018-03-20.