Dimethylamidophosphoric dichloride
Dimethyl amidophosphoric dichloride 3D balls
Dimethylamidophosphoric dichloride 2D skeletal
Names
IUPAC name
N-Dichlorophosphoryl-N-methylmethanamine
Other names
(Dimethylamido)phosphoryl dichloride
N,N-Dimethylphosphoramidodichloridate
Identifiers
3D model (JSmol)
ChemSpider
UNII
  • InChI=1S/C2H6Cl2NOP/c1-5(2)7(3,4)6/h1-2H3
    Key: YNHXBEVSSILHPI-UHFFFAOYSA-N
  • CN(C)P(=O)(Cl)Cl
Properties
C2H6Cl2NOP
Molar mass 161.95 g·mol−1
Melting point < 0 °C (32 °F; 273 K)
Hazards
GHS labelling:
GHS05: CorrosiveGHS06: ToxicGHS09: Environmental hazard
Danger
H314
P260, P264, P280, P301+P330+P331, P303+P361+P353, P304+P340, P305+P351+P338, P310, P321, P363, P405, P501
NFPA 704 (fire diamond)
NFPA 704 four-colored diamond
3
3
2
W
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Dimethylamidophosphoric dichloride is a chemical used in industrial applications. It is used for synthesizing phosphoramidates as well as Nerve agent GA which is used as a chemical weapon.

Safety

Due to its nature, this chemical is corrosive, flammable, and neurotoxic if ingested or absorbed through the skin.[1] In contact with water, it is expected to give off hydrogen chloride and dimethylamidophosphoric acid vapors.[2]

History

First synthesis of the substance dates back to turn of the 19th century, when a student of German chemistry professor August Michaelis Ernst Ratzlaff made dimethylamidophosphoric dichloride as well as its diethyl analog for experiments of another PhD student of Michaelis Adolph Schall.[3] He obtained a PhD at University of Rostock with a thesis titled Über die Einwirkung primärer und sekundärer Amine auf Phosphoroxychlorid und Äthoxylphosphoroxychlorid later in 1901. The high toxicity of the substance (as well as the high toxicity of ethyl diethylaminocyanophosphonate, an analog of tabun synthesised by Schall) wasn't noticed at the time, most likely due to the low yield of synthetic reactions used.

See also

References

  1. ↑ "Dimethylamidophosphoric dichloride". www.chemsrc.com. Retrieved 2023-09-19.
  2. ↑ "N,N-DIMETHYL PHOSPHORAMIDIC DICHLORIDE | CAMEO Chemicals | NOAA". cameochemicals.noaa.gov. Retrieved 2023-11-15.
  3. ↑ Petroianu, Georg (2014). "Pharmacists Adolf Schall and Ernst Ratzlaff and the synthesis of tabun-like compounds: a brief history". Die Pharmazie. 69 (October 2014): 780–784. doi:10.1691/ph.2014.4028. PMID 25985570.
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