1,2-Bis(dichlorophosphino)ethane

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1,2-Bis(dichlorophosphino)ethane
C2H4(PCl2)2.svg
Names
Preferred IUPAC name
(Ethane-1,2-diyl)bis(phosphonous dichloride)
Other names
1,2-Ethanebis(phosphonous dichloride)
Identifiers
3D model (JSmol)
ChemSpider
  • InChI=1S/C2H4Cl4P2/c3-7(4)1-2-8(5)6/h1-2H2
    Key: SBWAJHLQMFBNIN-UHFFFAOYSA-N
  • C(CP(Cl)Cl)P(Cl)Cl
Properties
C2H4Cl4P2
Molar mass 231.80 g·mol−1
Appearance colorless liquid
Boiling point 68 °C (154 °F; 341 K) 1 mmHg
Hazards
GHS labelling:
GHS05: Corrosive
Danger
H314
P260, P264, P280, P301+P330+P331, P303+P361+P353, P304+P340, P305+P351+P338, 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).

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

Synthesis and reactions[edit]

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.

Related compounds[edit]

References[edit]

  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.