Phospholane

Phospholane

Names
Preferred IUPAC name Phospholane [1]
Identifiers
CAS Number	3466-00-0
3D model (JSmol)	Interactive image
Beilstein Reference	605298
ChEBI	CHEBI:33133
ChemSpider	69459
ECHA InfoCard	100.020.383
EC Number	222-420-5
Gmelin Reference	323930
PubChem CID	77013
UNII	2BH587UMF9  Y
CompTox Dashboard (EPA)	DTXSID00188216
InChI InChI=1S/C4H9P/c1-2-4-5-3-1/h5H,1-4H2 Key: GWLJTAJEHRYMCA-UHFFFAOYSA-N
SMILES C1CPCC1
Properties
Chemical formula	C4H9P
Molar mass	88.090 g·mol−1
Appearance	colorless liquid
Boiling point	100–103 °C (212–217 °F; 373–376 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Phospholane is the organophosphorus compound with the formula (CH₂)₄PH. This colorless liquid is the parent member of a family of five-membered, saturated rings containing phosphorus. Although phospholane itself is only of minor academic interest, the class of C- and P-substituted phospholanes are valued ligands in asymmetric hydrogenation and related areas of homogeneous catalysis. ^[2] Phospholane is prepared by reduction of 1-chlorophospholane, which in turn is obtained by the reaction of 1-phenylphospholane and phosphorus trichloride. ^[3]

DuPhos is one of several phospholane ligands.

References

1. Favre, Henri A.; Powell, Warren H. (2014). Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book). Cambridge: The Royal Society of Chemistry. pp. 392, 599. doi:10.1039/9781849733069. ISBN   978-0-85404-182-4.
2. Clark, Thomas; Landis, Clark (2004). "Recent developments in chiral phospholane chemistry". Tetrahedron: Asymmetry. 15 (14): 2123–2137. doi:10.1016/j.tetasy.2004.06.025.
3. K. Sommer (1970). "Zur Spaltung tertiärer Phosphine. II". Zeitschrift für Anorganische und Allgemeine Chemie. 379: 56–62. doi:10.1002/zaac.19703790110.