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Chiraphos information


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) checkY
  • 64896-28-2 (S,S) checkY
3D model (JSmol)
  • Interactive image
ChemSpider
  • 8288775 checkY
ECHA InfoCard 100.152.152 Edit this at Wikidata
PubChem CID
  • 10113249
UNII
  • 1T086B9Q1J (R,R) checkY
  • 6QR78GZL9B (S,S) checkY
CompTox Dashboard (EPA)
  • DTXSID60435814 Edit this at Wikidata
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 checkY
    Key: FWXAUDSWDBGCMN-ZEQRLZLVSA-N checkY
  • 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
 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
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.

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Chiraphos

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As a C2-symmetric ligand, 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...

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Chiral pool

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derived from abundantly available tartaric acid, is used to synthesize chiraphos, a component of catalysts used for asymmetric hydrogenation: Diisopinocampheylborane...

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Diphosphine ligands

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S)-DIOP (O-isopropylidene-2,3-dihydroxy-1,4-bis(diphenylphosphino)butane) Chiraphos 2,3-Bis(diphenylphosphino)butane BINAP 2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl...

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Negishi coupling

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The ligand L in the catalyst can be triphenylphosphine, dppe, BINAP, chiraphos or XPhos. Palladium catalysts in general have higher chemical yields and...

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C28H28P2

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mass: 426.1666 u) may refer to: 1,4-Bis(diphenylphosphino)butane (dppb) Chiraphos This set index page lists chemical structure articles associated with...

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DuPhos

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diphosphine ligands were known at the time of invention, e.g. DIOP, DIPAMP, CHIRAPHOS, but DuPhos was found to be more effective. The ligand consists of two...

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Brice Bosnich

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diphosphine ligands, the premier member being chiraphos. Unlike previous chiral ligands, the chirality of chiraphos arose from the backbone of the chelate....

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