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Bis(diphenylphosphino)methane

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1,1-bis(diphenylphosphino)­methane
Names
Preferred IUPAC name Methylenebis(diphenylphosphane)
Other names Methylenebis(diphenylphosphine)
dppm
Identifiers
CAS Number
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.016.541 Edit this at Wikidata
EC Number
  • 218-194-2
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • 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,21H2Key: XGCDBGRZEKYHNV-UHFFFAOYSA-N
  • 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,21H2Key: XGCDBGRZEKYHNV-UHFFFAOYAH
SMILES
  • P(c1ccccc1)(c2ccccc2)CP(c3ccccc3)c4ccccc4
Properties
Chemical formula C25H22P2
Molar mass 384.399 g·mol
Appearance White crystalline powder
Melting point 118 to 122 °C (244 to 252 °F; 391 to 395 K)
Solubility in water Insoluble in water
Hazards
GHS labelling:
Pictograms GHS07: Exclamation mark
Signal word Warning
Hazard statements H315, H319, H335
Precautionary statements 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 , 100 kPa). checkY verify (what is  ?) Infobox references
Chemical compound

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. 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°.

Synthesis and reactivity

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

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 CH22 (E = O, S). The methylene group is even more acidic in these derivatives.

Coordination chemistry

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.

Ball-and-stick model of .

References

  1. Humphrey, Mark G.; Lee, Jeanne; Hockless, David C.R.; Skelton, Brian W.; White, Allan H. (1993). "Mixed-Metal Cluster Chemistry". Organometallics. 12 (3468): 3468. doi:10.1021/om00033a017.
  2. Birkholz, Mandy-Nicole; Freixa, Zoraida; van Leeuwen, Piet W. N. M. (2009). "Bite angle effects of diphosphines in C–C and C–X bond forming cross coupling reactions". Chemical Society Reviews. 38 (4): 1099. doi:10.1039/B806211K. PMID 19421583.
  3. W. Hewertson & H. R. Watson (1962). "The preparation of di- and tri-tertiary phosphines". J. Chem. Soc. 12: 1490–1494. doi:10.1039/JR9620001490.
  4. Albéniz, Ana C. & Espinet, Pablo (2006). "Palladium: Inorganic & Coordination Chemistry". Encyclopedia of Inorganic Chemistry. Encyclopedia of Inorganic Chemistry. doi:10.1002/0470862106.ia178. ISBN 0-470-86078-2.
  5. G. Besenyei; L. Párkányia; E. Gács-Baitza; B. R. James (January 2002). "Crystallographic characterization of the palladium(I) dimers, syn-Pd2Cl2(dppmMe)2 and Pd2Cl2(dppm)2; solution conformational behavior of syn- and anti-Pd2Cl2(dppmMe)2 and their (μ-Se) adducts ". Inorg. Chim. Acta. 327 (1): 179–187. doi:10.1016/S0020-1693(01)00682-X.
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