Dimethylamidophosphoric dichloride

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 checkY
3D model (JSmol)
  • Interactive image
ChemSpider
  • 12152
PubChem CID
  • 12673
UNII
  • XG32RK7L5Q checkY
CompTox Dashboard (EPA)
  • DTXSID4074801 Edit this at Wikidata
InChI
  • InChI=1S/C2H6Cl2NOP/c1-5(2)7(3,4)6/h1-2H3
    Key: YNHXBEVSSILHPI-UHFFFAOYSA-N
  • 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
 GHS05: CorrosiveGHS06: ToxicGHS09: Environmental hazard
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)
NFPA 704 four-colored diamondHealth 3: Short exposure could cause serious temporary or residual injury. E.g. chlorine gasFlammability 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. gasolineInstability 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
W
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references
Chemical compound

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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