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Phosphorus triiodide

Phosphorus triiodide
Phosphorus triiodide
Space-filling model of the phosphorus triiodide molecule
Names
IUPAC names
Phosphorus triiodide
Phosphorus(III) iodide
Other names
Triiodophosphine
Identifiers
13455-01-1 N
3D model (Jmol) Interactive image
ChemSpider 75323 YesY
ECHA InfoCard 100.033.302
PubChem 83485
Properties
PI3
Molar mass 411.68717 g/mol
Appearance dark red solid
Density 4.18 g/cm3
Melting point 61.2 °C (142.2 °F; 334.3 K)
Boiling point 200 °C (392 °F; 473 K) (decomposes)
Decomposes
Structure
Trigonal pyramidal
Hazards
Safety data sheet See: data page
not listed
NFPA 704
Flammability code 0: Will not burn. E.g., water Health code 3: Short exposure could cause serious temporary or residual injury. E.g., chlorine gas Reactivity code 2: Undergoes violent chemical change at elevated temperatures and pressures, reacts violently with water, or may form explosive mixtures with water. E.g., phosphorus Special hazards (white): no codeNFPA 704 four-colored diamond
Flash point non-flammable
Supplementary data page
Refractive index (n),
Dielectric constant (εr), etc.
Thermodynamic
data
 Phase behaviour
solid–liquid–gas
UV, IR, NMR, MS
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N  (what is YesYN ?)
Infobox references

Phosphorus triiodide (PI3) is an unstable red solid which reacts violently with water. It is a common misconception that PI3 is too unstable to be stored; it is, in fact, commercially available. It is widely used in organic chemistry for converting alcohols to alkyl iodides. It is also a powerful reducing agent. Note that phosphorus also forms a lower iodide, P2I4, but the existence of PI5 is doubtful at room temperature.

PI3 has essentially zero dipole moment in carbon disulfide solution, because the P-I bond has almost no dipole. The P-I bond is also weak; PI3 is much less stable than PBr3 and PCl3, with a standard enthalpy of formation for PI3 of only −46 kJ/ mol (solid). The phosphorus atom has an NMR chemical shift of 178 ppm (downfield of H3PO4).

Phosphorus triiodide reacts vigorously with water, producing phosphorous acid (H3PO3) and hydroiodic acid (HI), along with smaller amounts of phosphine and P-P compounds. Alcohols likewise form alkyl iodides, this providing the main use for PI3.

PI3 is also a powerful reducing agent and deoxygenating agent. It reduces sulfoxides to thioethers, even at −78 °C. Meanwhile, heating a 1-iodobutane solution of PI3 with red phosphorus causes reduction to P2I4.


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