Phosphorine

Phosphorine
Names
	Preferred IUPAC name Phosphinine
	Other names Phosphabenzene
Identifiers
CAS Number	289-68-9 [PubChem];
3D model (JSmol)	Interactive image;
ChemSpider	109668 ;
MeSH	Phosphinine
PubChem CID	123046;
UNII	A8TY55D4JJ ;
CompTox Dashboard (EPA)	DTXSID70183096 ;
	InChI InChI=1S/C5H5P/c1-2-4-6-5-3-1/h1-5H Key: UNQNIRQQBJCMQR-UHFFFAOYSA-N ; InChI=1/C5H5P/c1-2-4-6-5-3-1/h1-5H Key: UNQNIRQQBJCMQR-UHFFFAOYAZ;
	SMILES C1=CC=PC=C1;
Properties
Chemical formula	C5H5P
Molar mass	96.069 g·mol−1
Appearance	Colorless liquid
Boiling point	93 °C (199 °F; 366 K)
Acidity (pKa)	-16 (conjugate acid)
Related compounds
Related -ines	Pyridine; Arsabenzene; Silabenzene;
Related compounds	Phosphole
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

Phosphorine (IUPAC name: phosphinine) is a heavier element analog of pyridine, containing a phosphorus atom instead of an aza- moiety. It is also called phosphabenzene and belongs to the phosphaalkene class. It is a colorless liquid that is mainly of interest in research.

Phosphorine is an air-sensitive oil but is otherwise stable when handled using air-free techniques (however, substituted derivatives can often be handled under air without risk of decomposition). In contrast, silabenzene, a related heavy-element analogue of benzene, is not only air- and moisture-sensitive but also thermally unstable without extensive steric protection.