Phosphinane

Phosphinane
Names
	Preferred IUPAC name Phosphinane
	Other names Phosphacyclohexane
Identifiers
CAS Number	4743-40-2;
3D model (JSmol)	Interactive image;
PubChem CID	138339;
	InChI InChI=1S/C5H11P/c1-2-4-6-5-3-1/h6H,1-5H2 Key: VXTFGYMINLXJPW-UHFFFAOYSA-N;
	SMILES C1CCPCC1;
Properties
Chemical formula	C5H11P
Molar mass	102.117 g·mol−1
Appearance	colorless liquid
Boiling point	118–121 °C (244–250 °F; 391–394 K)
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Phosphinane is the organophosphorus compound with the formula (CH₂)₅PH. This colorless liquid is the parent member of a family of six-membered, saturated rings containing phosphorus. These compounds are mainly of academic interest. The ring adopts a flexible cyclohexane-like chair conformation.^[1]

Phosphinane can be prepared via the Arbuzov reaction of triethylphosphite and 1,5-dibromopentane followed by cyclization and reduction steps.^[1] Phosphinane can also be prepared by reduction of 1-chlorophosphinane, which in turn is obtained by the reaction of 1-phenylphosphinane and phosphorus trichloride.^[2]

References

^ ^a ^b Michael J. Gallagher (2001). "Six-membered rings: Phosphinanes, Dihydro- and Tetrahydro-phosphinines". Phosphorus-Carbon Heterocyclic Chemistry The Rise of a New Domain. pp. 463–483. doi:10.1016/B978-008043952-5/50012-7.
^ K. Sommer (1970). "Zur Spaltung tertiärer Phosphine. II". Zeitschrift für Anorganische und Allgemeine Chemie. 379: 56–62. doi:10.1002/zaac.19703790110.

[Pencycl-1] Michael J. Gallagher (2001). "Six-membered rings: Phosphinanes, Dihydro- and Tetrahydro-phosphinines". Phosphorus-Carbon Heterocyclic Chemistry The Rise of a New Domain. pp. 463–483. doi:10.1016/B978-008043952-5/50012-7.

[2] 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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