Dimethylamidophosphoric dichloride

Dimethylamidophosphoric dichloride is a chemical used in industrial applications. It is used for synthesizing phosphoramidates as well as tabun, which is used as a chemical weapon.

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
CAS Number	677-43-0 Y
3D model (JSmol)	Interactive image
ChemSpider	12152
PubChem CID	12673
UNII	XG32RK7L5Q Y
CompTox Dashboard (EPA)	DTXSID4074801
InChI InChI=1S/C2H6Cl2NOP/c1-5(2)7(3,4)6/h1-2H3 Key: YNHXBEVSSILHPI-UHFFFAOYSA-N
SMILES CN(C)P(=O)(Cl)Cl
Properties
Chemical formula	C2H6Cl2NOP
Molar mass	161.95 g·mol−1
Melting point	< 0 °C (32 °F; 273 K)
Hazards
GHS labelling:
Pictograms
Signal word	Danger
Hazard statements	H314
Precautionary statements	P260, P264, P280, P301+P330+P331, P303+P361+P353, P304+P340, P305+P351+P338, P310, P321, P363, P405, P501
NFPA 704 (fire 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

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

• Organophosphate poisoning