Chiraphos

Chiraphos

Names

Preferred IUPAC name

rel-[(2R,3R)-Butane-2,3-diyl]bis(diphenylphosphane)

Other names

(2S,3S)-(–)-Bis(diphenylphosphino)butane
(2R,3R)-(+)-Bis(diphenylphosphino)butane

Identifiers

CAS Number

74839-84-2 (R,R)^Y
64896-28-2 (S,S)^Y

3D model (JSmol)

Interactive image

ChemSpider

8288775^Y

ECHA InfoCard

100.152.152

PubChem CID

10113249

UNII

1T086B9Q1J (R,R)^Y
6QR78GZL9B (S,S)^Y

CompTox Dashboard (EPA)

DTXSID60435814

InChI

InChI=1S/C28H28P2/c1-23(29(25-15-7-3-8-16-25)26-17-9-4-10-18-26)24(2)30(27-19-11-5-12-20-27)28-21-13-6-14-22-28/h3-24H,1-2H3/t23-,24-/m0/s1^Y
Key: FWXAUDSWDBGCMN-ZEQRLZLVSA-N^Y
InChI=1/C28H28P2/c1-23(29(25-15-7-3-8-16-25)26-17-9-4-10-18-26)24(2)30(27-19-11-5-12-20-27)28-21-13-6-14-22-28/h3-24H,1-2H3/t23-,24-/m0/s1
Key: FWXAUDSWDBGCMN-ZEQRLZLVBA

SMILES

P(c1ccccc1)(c2ccccc2)[C@H]([C@@H](P(c3ccccc3)c4ccccc4)C)C

Properties

Chemical formula

C₂₈H₂₈P₂

Molar mass

426.47 g/mol

Appearance

White powder

Melting point

104 to 109 °C (219 to 228 °F; 377 to 382 K)

Hazards

GHS labelling:

Pictograms

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

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. As a C₂-symmetric ligand, chiraphos is available in two enantiomeric forms, S,S and R,R, each with C₂ symmetry.

Preparation

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.

References

^ Fryzuk, M. D.; Bosnich, B. (1977). "Asymmetric synthesis. Production of optically active amino acids by catalytic hydrogenation". Journal of the American Chemical Society. 99 (19): 6262–6267. doi:10.1021/ja00461a014. PMID 893889.

This page was last edited on 6 May 2021, at 12:40

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Preparation

References