1,2-Bis(dichlorophosphino)ethane

1,2-Bis(dichlorophosphino)ethane
Names
	Preferred IUPAC name (Ethane-1,2-diyl)bis(phosphonous dichloride)
	Other names 1,2-Ethanebis(phosphonous dichloride)
Identifiers
CAS Number	28240-69-9;
3D model (JSmol)	Interactive image;
ChemSpider	107057;
ECHA InfoCard	100.156.519
PubChem CID	119904;
CompTox Dashboard (EPA)	DTXSID3067368;
	InChI InChI=1S/C2H4Cl4P2/c3-7(4)1-2-8(5)6/h1-2H2 Key: SBWAJHLQMFBNIN-UHFFFAOYSA-N;
	SMILES C(CP(Cl)Cl)P(Cl)Cl;
Properties
Chemical formula	C2H4Cl4P2
Molar mass	231.80 g·mol−1
Appearance	colorless liquid
Boiling point	68 °C (154 °F; 341 K) 1 mmHg
Hazards
	GHS labelling:
Pictograms
Signal word	Danger
Hazard statements	H314
Precautionary statements	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). Infobox references

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

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

1,2-Bis(dichlorophosphino)benzene

References

^ 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 (2): 203–206. doi:10.1016/S0022-328X(00)94383-3.
^ 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 (29): 7696–7710. doi:10.1021/ja00134a014.

[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 (2): 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 (29): 7696–7710. doi:10.1021/ja00134a014.

[1]

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