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Other names
* (2S,3S)-(–)-Bis(diphenylphosphino)butane
  • (2R,3R)-(+)-Bis(diphenylphosphino)butane (for the corresponding enantiomer)
74839-84-2 (R,R-Enantiomer) YesY
64896-28-2 (S, S-Enantiomer) YesY
ChemSpider 8288775 YesY
Jmol interactive 3D Image
PubChem 10113249
Molar mass 426.47 g/mol
Appearance White powder
Melting point 104 to 109 °C (219 to 228 °F; 377 to 382 K)
Irritant (XI)
R-phrases R36/37/38
S-phrases S26 S37/39
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Chiraphos is a chiral diphosphine employed as a ligand in organometallic chemistry. This bidentate ligand chelates metals via the two phosphine groups. Its name is derived from its description — being both chiral and a phosphine. Chiraphos is available in two enantiomeric forms, S,S and R,R, each with C2 symmetry.


Chiraphos is prepared from S,S or R,R-2,3-butanediol, which are derived from commercially available S,S or R,R-tartaric acid; the technique of using cheaply available enantiopure starting materials is known as chiral pool synthesis. The diol is tosylated and then the ditosylate is treated with lithium diphenylphosphide.[1] The ligand was an important demonstration of how the conformation of the chelate ring can affect asymmetric induction by a metal catalyst. Prior to this work, in most chiral phosphines, e.g., DIPAMP, phosphorus was the stereogenic center.



  1. ^ M. D. Fryzuk, B. Bosnich (1977). "Asymmetric synthesis. Production of optically active amino acids by catalytic hydrogenation". J. Am. Chem. Soc. 99 (19): 6262–6267. doi:10.1021/ja00461a014. PMID 893889.