Dimethylaminophosphorus dichloride

Dimethylaminophosphorus dichloride
Names
	Other names dimethylaminochlorophosphine, dimethylphosphoramidous dichloride
Identifiers
CAS Number	683-85-2;
3D model (JSmol)	Interactive image;
ChemSpider	120252;
PubChem CID	136483;
CompTox Dashboard (EPA)	DTXSID90218455;
	InChI InChI=1S/C2H6Cl2NP/c1-5(2)6(3)4/h1-2H3 Key: XPWWDZRSNFSLRQ-UHFFFAOYSA-N;
	SMILES CN(C)P(Cl)Cl;
Properties
Chemical formula	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 pictograms
GHS Signal word	Danger
GHS hazard statements	H225, H314
GHS precautionary statements	P210, P233, P240, P241, P242, P243, P260, P264, P280, P301+330+331, P303+361+353, P304+340, P305+351+338, P310, P321, P363, P370+378, P403+235, P405, P501
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
	Infobox references

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

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

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gollark: Why not `f32(1)`?!

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References

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.
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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[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.