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Dimethylamidophosphoric dichloride

From Wikipedia, the free encyclopedia
Dimethylamidophosphoric dichloride
Dimethyl amidophosphoric dichloride 3D balls
Dimethyl amidophosphoric dichloride 3D balls
Dimethylamidophosphoric dichloride 2D skeletal
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 mass161.95 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)
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa).
Chemical compound

Dimethylamidophosphoric dichloride is a chemical used in industrial applications. It is used for synthesizingphosphoramidates as well astabun, which is used as achemical weapon.[2]

Safety

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Due to its nature, this chemical iscorrosive,flammable, andneurotoxic if ingested or absorbed through the skin.[3] In contact with water, it is expected to give offhydrogen chloride anddimethylamidophosphoric acid vapors.[4]

History

[edit]

First synthesis of the substance dates back to turn of the 19th century, when a student of German chemistry professorAugust Michaelis Ernst Ratzlaff made dimethylamidophosphoric dichloride as well as its diethyl analog for experiments of another PhD student of Michaelis Adolph Schall.[5] He obtained a PhD atUniversity of Rostock with a thesis titledÜber 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 oftabun synthesised by Schall) wasn't noticed at the time, most likely due to the low yield of synthetic reactions used.

See also

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References

[edit]
  1. ^Petrov, K. A.; Zhurnal Obshchei Khimii, (1961), 31, 1366-71
  2. ^PubChem."N,N-Dimethylaminophosphoryl dichloride".pubchem.ncbi.nlm.nih.gov. Retrieved2025-09-17.
  3. ^"Dimethylamidophosphoric dichloride".www.chemsrc.com. Retrieved2023-09-19.
  4. ^"N,N-DIMETHYL PHOSPHORAMIDIC DICHLORIDE | CAMEO Chemicals | NOAA".cameochemicals.noaa.gov. Retrieved2023-11-15.
  5. ^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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