Methylidynephosphane

Methylidynephosphane
IUPAC name Methylidynephosphane
Other names Phosphaethyne
Identifiers
CAS number	6829-52-3
PubChem	138843 Y
ChemSpider	122445 Y
Jmol-3D images	Image 1
SMILES C#P
InChI InChI=1S/CHP/c1-2/h1H Key: DPYPSJGRRFKXBE-UHFFFAOYSA-N
Properties
Molecular formula	CHP
Molar mass	43.99 g mol−1
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

Methylidynephosphane (phosphaethyne) is a chemical compound which was the first phosphaalkyne compound discovered, containing the unusual C≡P carbon-phosphorus triple bond. It is thus the phosphorus analogue of hydrogen cyanide, with the nitrile nitrogen replaced by phosphorus. Methylidynephosphane can be synthesised by reaction of phosphine with carbon,^[1] but is extremely reactive and polymerises readily at temperatures above −120 °C. However several derivatives substituted on the carbon atom with bulky groups such as t-butyl or trimethylsilyl are much more stable and are useful reagents for the synthesis of various organophosphorus compounds,^[2] and the PCO⁻ and PCS⁻ anions are also known.^[3]

References

1. ^ Gier TE (1961). "HCP, A Unique Phosphorus Compound". J. Am. Chem. Soc. 83: 1769. doi:10.1021/ja01468a058. 
2. ^ Regitz M (1990). "Phosphaalkynes: new building blocks in synthetic chemistry". Chem. Rev. 90: 191. doi:10.1021/cr00099a007. 
3. ^ Hubler K, Schwerdtfeger P. (1999). "Theoretical Studies of NMR Chemical Shifts and Vibrational Frequencies in λ³-Phosphaalkynes P≡C-R". Inorg. Chem. 38: 157–164. doi:10.1021/ic9811291.