Bis (diphenylphosphino) methane

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Structural formula
Structure of dppm
General
Surname Bis (diphenylphosphino) methane
other names
  • Methylenebis (diphenylphosphine) ( IUPAC )
  • dppm
Molecular formula C 25 H 22 P 2
Brief description

white crystalline powder

External identifiers / databases
CAS number 2071-20-7
EC number 218-194-2
ECHA InfoCard 100.016.541
PubChem 74952
ChemSpider 67509
Wikidata Q419624
properties
Molar mass 384.40 g mol −1
Physical state

firmly

Melting point

118-119 ° C

solubility

practically insoluble in water

safety instructions
GHS labeling of hazardous substances
07 - Warning

Caution

H and P phrases H: 315-319-335
P: 302 + 352-305 + 351 + 338
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Bis (diphenylphosphino) methane is an organic compound from the group of phosphines . It is used as a ligand for catalytically active complexes .

presentation

Dppm can be obtained from the reaction of diphenylphosphine with dichloromethane in the presence of a base . A solution of potassium hydroxide and potassium carbonate is used as the base .

Alternatively, dppm can be represented by the reaction of the less reactive triphenylphosphine with lithium and dichloromethane .

Another possibility is the reaction of chlorodiphenylphosphine with metallic lithium and dichloromethane.

use

Dppm is a common phosphine ligand in homogeneous transition metal catalysis. It usually functions as a bidentate chelating ligand , coordinating via its two phosphorus atoms on the central atom .

Individual evidence

  1. a b c d e f data sheet bis (diphenylphosphino) methane, 97% from AlfaAesar, accessed on December 26, 2019 ( PDF )(JavaScript required) .
  2. EN Tsvetkov, NA Bondarenko, IG Malakhova, MI Kabachnik: A Simple Synthesis and Some Synthetic Applications of Substituted Phosphide and Phosphinite Anions . In: Synthesis . tape 1986 , no. 3 , 1986, ISSN  0039-7881 , pp. 198-208 , doi : 10.1055 / s-1986-31510 ( thieme-connect.de ).
  3. Klaus Sommer: On the splitting of tertiary phosphines. I . In: Journal of Inorganic and General Chemistry . tape 376 , no. 1 , August 1970, ISSN  0044-2313 , pp. 37-43 , doi : 10.1002 / zaac.19703760106 ( wiley.com ).
  4. Kurt Issleib , Dietrich-Wolfgang Müller: Alkali-phosphorus compounds and their reactive behavior, III. Representation ditert. Phosphines R 2 P- [CH 2 ] n -PR 2 . In: Chemical Reports . tape 92 , no. December 12 , 1959, p. 3175-3182 , doi : 10.1002 / cber.19590921221 ( wiley.com ).

See also