1,2-Bis(dichlorophosphino)ethane

1,2-Bis(dichlorophosphino)ethane is an organophosphorus compound with the formula (CH2PCl2)2. A colorless liquid, it is a precursor to chelating diphosphines.

1,2-Bis(dichlorophosphino)ethane
Names
Other names
1,2-ethanebis(phosphonous dichloride)
Identifiers
3D model (JSmol)
ChemSpider
Properties
C2H4Cl4P2
Molar mass 231.80 g·mol−1
Appearance colorless liquid
Boiling point 68 °C (154 °F; 341 K) 1 mmHg
Hazards
GHS pictograms
GHS Signal word Danger
H314, H318
P260, P264, P280, P301+330+331, P303+361+353, P304+340, P305+351+338, P310, P321, P363, P405, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Synthesis and reactions

It is prepared by the reaction of ethylene, white phosphorus, and phosphorus trichloride:[1]

3 C2H4 + 0.5 P4 + 4 PCl3 → 3 (CH2PCl2)2

The compound reacts with Grignard reagents and secondary amines to give chelating ligands.[2] An often practiced use of this compound is the synthesis of 1,2-bis(dimethylphosphino)ethane.

References

  1. Burt, Roger J.; Chatt, Joseph; Hussain, Wasif; Leigh, G.Jeffery (1979). "A convenient synthesis of 1,2-bis(dichlorophosphino)ethane, 1,2-bis(dimethylphosphino)ethane and 1,2-bis(diethylphosphino)ethane". Journal of Organometallic Chemistry. 182: 203–206. doi:10.1016/S0022-328X(00)94383-3.
  2. Moloy, Kenneth G.; Petersen, Jeffrey L. (1995). "N-Pyrrolyl Phosphines: An Unexploited Class of Phosphine Ligands with Exceptional .pi.-Acceptor Character". Journal of the American Chemical Society. 117: 7696–7710. doi:10.1021/ja00134a014.
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