Triisopropylphosphine

Triisopropylphosphine
Skeletal formula	Space-filling model
Names
	Other names Triisopropylphosphine; PiPr3; Pi-Pr3
Identifiers
CAS Number	6476-36-4 ;
3D model (JSmol)	Interactive image;
ChemSpider	73055 ;
ECHA InfoCard	100.026.667
PubChem CID	24863218;
CompTox Dashboard (EPA)	DTXSID80215074 ;
	InChI InChI=1S/C9H21P/c1-7(2)10(8(3)4)9(5)6/h7-9H,1-6H3 Key: IGNTWNVBGLNYDV-UHFFFAOYSA-N ; InChI=1/C9H21P/c1-7(2)10(8(3)4)9(5)6/h7-9H,1-6H3 Key: IGNTWNVBGLNYDV-UHFFFAOYAM;
	SMILES CC(C)P(C(C)C)C(C)C;
Properties
Chemical formula	C9H21P
Molar mass	160.24 g mol−1
Appearance	colourless liquid
Density	0.839 g/mL
Boiling point	81 °C (178 °F; 354 K) (22 mm Hg)
Solubility in water	good in alkanes
Hazards
Main hazards	spontaneously flammable
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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	Infobox references

Triisopropylphosphine is the tertiary phosphine with the formula P(CH(CH₃)₂)₃. Commonly used as a ligand in organometallic chemistry, it is often abbreviated to Pi-Pr₃ or PⁱPr₃. This ligand is one of the most basic alkyl phosphines with a large ligand cone angle of 160.[1]

Pi-Pr₃ is similar to the more frequently used tricyclohexylphosphine. The triisopropyl derivative however, is a liquid at room temperature and more soluble in hydrocarbons.

References

C. A. Tolman (1977). "Steric Effects of Phosphorus Ligands in Organometallic Chemistry and Homogeneous Catalysis". Chem. Rev. 77 (4): 313–348. doi:10.1021/cr60307a002.

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[1] C. A. Tolman (1977). "Steric Effects of Phosphorus Ligands in Organometallic Chemistry and Homogeneous Catalysis". Chem. Rev. 77 (4): 313–348. doi:10.1021/cr60307a002.