Bis(diphenylphosphino)methane

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1,1-bis(diphenylphosphino)­methane
Names
Preferred IUPAC name
Methylenebis(diphenylphosphane)
Other names
Methylenebis(diphenylphosphine)
dppm
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
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EC Number
  • 218-194-2
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UNII
  • {{#property:P3117}}Lua error in Module:EditAtWikidata at line 29: attempt to index field 'wikibase' (a nil value).
  • InChI=1S/C25H22P2/c1-5-13-22(14-6-1)26(23-15-7-2-8-16-23)21-27(24-17-9-3-10-18-24)25-19-11-4-12-20-25/h1-20H,21H2 checkY
    Key: XGCDBGRZEKYHNV-UHFFFAOYSA-N checkY
  • InChI=1/C25H22P2/c1-5-13-22(14-6-1)26(23-15-7-2-8-16-23)21-27(24-17-9-3-10-18-24)25-19-11-4-12-20-25/h1-20H,21H2
    Key: XGCDBGRZEKYHNV-UHFFFAOYAH
  • P(c1ccccc1)(c2ccccc2)CP(c3ccccc3)c4ccccc4
Properties
C25H22P2
Molar mass 384.399 g·mol−1
Appearance White crystalline powder
Melting point 118 to 122 °C (244 to 252 °F; 391 to 395 K)
Insoluble in water
Hazards
GHS labelling:
GHS07: Exclamation mark
Warning
H315, H319, H335
P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, P501
Safety data sheet (SDS) External MSDS
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

1,1-Bis(diphenylphosphino)methane (dppm), is an organophosphorus compound with the formula CH2(PPh2)2. Dppm, a white, crystalline powder, is used in inorganic and organometallic chemistry as a ligand.[1] It is more specifically a chelating ligand because it is a ligand that can bond to metals with two phosphorus donor atoms. The natural bite angle is 73°.[2]

Synthesis and reactivity

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1,1-Bis(diphenylphosphino)methane was first prepared by the reaction of sodium diphenylphosphide (Ph2PNa) with dichloromethane:[3]

Ph3P + 2 Na → Ph2PNa + NaPh
2NaPPh2 + CH2Cl2 → Ph2PCH2PPh2 + 2 NaCl

The methylene group (CH2) in dppm (and especially its complexes) is mildly acidic. The ligand can be oxidized to give the corresponding oxides and sulfides CH2[P(E)Ph2]2 (E = O, S). The methylene group is even more acidic in these derivatives.

Coordination chemistry

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As a chelating ligand, 1,1-bis(diphenylphosphino)methane forms a four-membered ring with the constituents MP2C. The ligand promotes the formation of bimetallic complexes that feature five-membered M2P2C rings. In this way, dppm promotes the formation of bimetallic complexes. One such example is the dipalladium chloride, Pd2Cl2(dppm)2. In this complex, the oxidation state for the Pd centres are I. Bis(diphenylphosphino)methane gives rise to a family of coordination compounds known as A-frame complexes.[4]

File:Pd2Cl2(dppm)2-from-xtal-3D-ball-stick-hybrid.png
Ball-and-stick model of [Pd2Cl2(dppm)2].[5]

References

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