Tetraphenyldiphosphine
Names
Preferred IUPAC name
Tetraphenyldiphosphane
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
EC Number
  • 214-155-9
  • InChI=1S/C24H20P2/c1-5-13-21(14-6-1)25(22-15-7-2-8-16-22)26(23-17-9-3-10-18-23)24-19-11-4-12-20-24/h1-20H
    Key: DAPZRBJQPPDZGH-UHFFFAOYSA-N
  • C1=CC=C(C=C1)P(C2=CC=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4
Properties
C24H20P2
Molar mass 370.372 g·mol−1
Appearance white solid
Density 1.292 g/cm3
Melting point 125 °C (257 °F; 398 K)
Hazards
GHS labelling:
GHS02: Flammable
Danger
H250
P210, P222, P280, P302+P334, P370+P378, P422
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Tetraphenyldiphosphine is the organophosphorus compound with the formula [PPh2]2, where Ph = phenyl (C6H5). It is a white, air-sensitive solid that dissolves in nonpolar solvents. It is a centrosymmetric molecule with a P-P bond of 2.2592 Å.[1]

Tetraphenyldiphosphine is produced by reductive coupling of chlorodiphenylphosphine:

2 Ph2PCl + 2 Na → Ph2P-PPh2 + 2 NaCl

The compound is used as a source of the Ph2P− group.[2]

Ph2P-PPh2 + 2 Na → + 2 NaPPh2

References

  1. ^ Tam, Eric C. Y.; Maynard, Nicola A.; Apperley, David C.; Smith, J. David; Coles, Martyn P.; Fulton, J. Robin (17 August 2012). "Group 14 Metal Terminal Phosphides: Correlating Structure with ‖ JMP ‖". Inorganic Chemistry. 51 (17): 9403–9415. doi:10.1021/ic301208d. PMID 22900884.
  2. ^ Kuchen, Wilhelm; Buchwald, Hans (1959). "Zur Kenntnis der Organophosphorverbindungen, III. Umsetzungen mit Diphenylphosphin-natrium". Chem. Ber. 92: 227–231. doi:10.1002/cber.19590920126.
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