1,2-Bis(dichlorophosphino)ethane
{{Chembox
| ImageFile = C2H4(PCl2)2.svg
| ImageSize = 148
| ImageAlt =
| PIN = (Ethane-1,2-diyl)bis(phosphonous dichloride)
| OtherNames = 1,2-Ethanebis(phosphonous dichloride)
|Section1={{Chembox Identifiers
| CASNo = 28240-69-9
| PubChem = 119904
| DTXSID = DTXSID3067368
| ChemSpiderID = 107057
| StdInChI=1S/C2H4Cl4P2/c3-7(4)1-2-8(5)6/h1-2H2
| StdInChIKey = SBWAJHLQMFBNIN-UHFFFAOYSA-N
| SMILES = C(CP(Cl)Cl)P(Cl)Cl
}}
|Section2={{Chembox Properties
| C=2|H=4|P=2|Cl=4
| MolarMass =
| Appearance = colorless liquid
| Density =
| MeltingPt =
| BoilingPtC = 68
| BoilingPt_notes = 1 mmHg
| Solubility = }}
|Section3={{Chembox Hazards
| GHSPictograms = {{GHS05}}
| GHSSignalWord = Danger
| HPhrases = {{H-phrases|314}}
| PPhrases = {{P-phrases|260|264|280|301+330+331|303+361+353|304+340|305+351+338|310|321|363|405|501}}
| MainHazards =
| FlashPt =
| AutoignitionPt = }}
}}
1,2-Bis(dichlorophosphino)ethane is an organophosphorus compound with the formula (CH2PCl2)2. This colorless liquid is a precursor to chelating diphosphines.
Synthesis and reactions
It is prepared by the reaction of ethylene, white phosphorus, and phosphorus trichloride:{{cite journal|doi=10.1016/S0022-328X(00)94383-3|title=A convenient synthesis of 1,2-bis(dichlorophosphino)ethane, 1,2-bis(dimethylphosphino)ethane and 1,2-bis(diethylphosphino)ethane|journal=Journal of Organometallic Chemistry|volume=182|pages=203–206|year=1979|last1=Burt|first1=Roger J.|last2=Chatt|first2=Joseph|last3=Hussain|first3=Wasif|last4=Leigh|first4=G.Jeffery|issue=2 }}
:3 C2H4 + 0.5 P4 + 4 PCl3 → 3 (CH2PCl2)2
The compound reacts with Grignard reagents and secondary amines to give chelating ligands.{{cite journal|doi=10.1021/ja00134a014|title=N-Pyrrolyl Phosphines: An Unexploited Class of Phosphine Ligands with Exceptional .pi.-Acceptor Character|journal=Journal of the American Chemical Society|volume=117|pages=7696–7710|year=1995|last1=Moloy|first1=Kenneth G.|last2=Petersen|first2=Jeffrey L.|issue=29 }} An often practiced use of this compound is the synthesis of 1,2-bis(dimethylphosphino)ethane.
Related compounds
References
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{{DEFAULTSORT:Bis(dichlorophosphino)ethane, 1,2-}}