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 ;
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

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

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[iupac2013-1] Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book). Cambridge: The Royal Society of Chemistry. 2014. 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: 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.