Chemistry:Dimethylamidophosphoric dichloride

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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
Properties
C2H6Cl2NOP
Molar mass 161.95 g·mol−1
Melting point < 0 °C (32 °F; 273 K)
Hazards
GHS pictograms GHS05: CorrosiveGHS06: ToxicGHS09: Environmental hazard
GHS Signal word Danger
H314
P260, P264, P280, P301+330+331, P303+361+353, P304+340, P305+351+338, P310, P321, P363, P405, P501
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 acidNFPA 704 four-colored diamond
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
Tracking categories (test):

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" (in en). https://www.chemsrc.com/en/cas/677-43-0_981880.html. 
  2. ↑ "N,N-DIMETHYL PHOSPHORAMIDIC DICHLORIDE | CAMEO Chemicals | NOAA". https://cameochemicals.noaa.gov/chemical/30043. 
  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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