Dimethylaminophosphorus dichloride

Dimethylaminophosphorus dichloride is an organophosphorus compound with the formula Me2NPCl2 (Me = methyl). A colorless liquid, it is a reagent in the preparation of other organophosphorus compounds. Many analogous compounds can be prepared from the reactions of secondary amines and phosphorus trichloride:[1]

2 R2NH + PCl3 → R2NPCl2 + R2NH2Cl
Dimethylaminophosphorus dichloride
Names
Other names
dimethylaminochlorophosphine, dimethylphosphoramidous dichloride
Identifiers
3D model (JSmol)
ChemSpider
  • InChI=1S/C2H6Cl2NP/c1-5(2)6(3)4/h1-2H3
    Key: XPWWDZRSNFSLRQ-UHFFFAOYSA-N
  • CN(C)P(Cl)Cl
Properties
C2H6Cl2NP
Molar mass 145.95 g·mol−1
Appearance colorless liquid
Density 1.264 g/cm3
Boiling point 40 °C (104 °F; 313 K) 10 torr
Hazards
GHS labelling:
GHS02: FlammableGHS05: Corrosive
Danger
H225, H314
P210, P233, P240, P241, P242, P243, P260, P264, P280, P301+P330+P331, P303+P361+P353, P304+P340, P305+P351+P338, P310, P321, P363, P370+P378, P403+P235, P405, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Reactions

Further equivalents of amine react with dialkylaminophosphorus dichlorides:

2 R2NH + R2NPCl2 → (R2N)2PCl + R2NH2Cl

Since the P-NR2 bond is not attacked by Grignard reagents, dimethylaminophosphorus dichloride can be selectively dimethylated:

2 MeMgBr + Me2NPCl2 → Me2NPMe2 + 2 MgBrCl

The resulting dimethylphosphino derivative, a structural relative of tetramethylhydrazine, reacts with hydrogen chloride to give chlorodimethylphosphine:[2]

Me2NPMe2 + 2 HCl → ClPMe2 + Me2NH2Cl

References
  1. Morse, J. G.; Cohn, K.; Rudolph, R. W.; Parry, R. W. (1967). "Substituted Difluoro- and Dichlorophosphines". Inorganic Syntheses. 22: 147–156. doi:10.1002/9780470132418.ch22.
  2. Burg, Anton B.; Slota, Peter J. (1958). "Dimethylaminodimethylphosphine". Journal of the American Chemical Society. 80 (5): 1107–1109. doi:10.1021/ja01538a023.
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