Dimethylamidophosphoric dichloride

Dimethylamidophosphoric dichloride is an important chemical for few industrial purposes. It is an important chemical for synthesizing phosphoramidates as well as Nerve agent GA which is used as a chemical weapon.

Dimethylamidophosphoric dichloride
Names
IUPAC name
N-Dichlorophosphoryl-N-methylmethanamine
Other names
(Dimethylamido)phosphoryl dichloride
N,N-Dimethylphosphoramidodichloridate
Identifiers
3D model (JSmol)
ChemSpider
Properties
C2H6Cl2NOP
Molar mass 161.95 g·mol−1
Melting point < 0 °C (32 °F; 273 K)
Hazards
C N T
NFPA 704 (fire diamond)
Flammability code 3: Liquids and solids that can be ignited under almost all ambient temperature conditions. Flash point between 23 and 38 °C (73 and 100 °F). E.g. gasolineHealth code 3: Short exposure could cause serious temporary or residual injury. E.g. chlorine gasReactivity code 2: Undergoes violent chemical change at elevated temperatures and pressures, reacts violently with water, or may form explosive mixtures with water. E.g. white phosphorusSpecial hazard W: Reacts with water in an unusual or dangerous manner. E.g. sodium, sulfuric acid
3
3
2
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Safety

This chemical is also corrosive, flammable and will cause mild nerve agent symptoms if ingested or absorbed through skin due to its nature. It will react with water giving off hydrogen chloride vapors and dimethylamidophosphoric acid.

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.[1] 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 high toxicity of ethyl diethylaminocyanophosphonate, an analog of tabun synthesised by Schall) wasn't noticed at time, most likely due to the low yield of synthethic reactions used.

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See also

References
  1. 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.
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