Trimethylphosphine

Trimethylphosphine

Chembox new
Name = Trimethylphosphine
ImageFile = PMe3.png ImageName = trimethylphosphine
ImageFile1 = Trimethylphosphine-A-3D-balls.png ImageName1 = Ball-and-stick model of trimethylphosphine
IUPACName = Trimethylphosphine
OtherNames = trimethylphosphane
Section1 = Chembox Identifiers
CASNo = 594-09-2
RTECS =
Section2 = Chembox Properties
Formula = C3H9P
MolarMass = 76.07 g/mol
Appearance = Colorless liquid, Pyrophoric
Density = 0.735 g/cm3 liquid
Solubility = low
Solvent = other solvents
SolubleOther = most organic solvents
MeltingPt = -86 °C
BoilingPt = 38-39 °C
Section3 = Chembox Structure
Coordination = Trigonal pyramidal
Dipole = 1.19 Debye
Section7 = Chembox Hazards
MainHazards = toxic
FlashPt =
RPhrases = 11-36/37/38
SPhrases = 9-16-26-36/37/39
Section8 = Chembox Related
OtherCpds = NMe3
PH3
PPh3

Trimethylphosphine is the chemical compound with the formula P(CH3)3, commonly abbreviated PMe3. This colorless liquid has a strongly unpleasant odour, which characteristic of alkylphosphines. It is a pyramidal molecule with C3v symmetry, similar to ammonia (NH3) and phosphine (PH3). As a ligand, its cone angle is 118°. [G. L. Miessler and D. A. Tarr “Inorganic Chemistry” 3rd Ed, Pearson/Prentice Hall publisher, ISBN 0-13-035471-6.]

PMe3 is prepared using Grignard reagents: [cite journal | editor = Robert J. Angelici | journal = Inorganic Syntheses | author = Leutkens, Jr., M. L.; Sattelberger, A. P.; Murray, H. H.; Basil, J. D.; Fackler, Jr., J. P. | year = 1990 | title = Trimethylphosphine | volume = 28 | pages = 305–310 | isbn = 0-471-52619-3 | doi = 10.1002/9780470132593.ch76] : 3 CH3MgBr + P(OC6H5)3 → P(CH3)3 + 3 MgBrOC6H5The synthesis is conducted in a dibutyl ether, from which the more volatile PMe3 can be distilled.

Coordination chemistry

Trimethylphosphine is a highly basic ligand that forms complexes with most metals. The synthesis of an illustrative example is shown::PMe3 + Fe(CO)5 → Fe(CO)4PMe3 + COIts complex with silver iodide, AgI(PMe3) is a weighable, air stable solid that releases PMe3 upon heating.

afety

PMe3 is potentially pyrophoric, as well as toxic. PMe3 can be converted to non-pyrophoric phosphine oxide by treatment with dilute bleach.

References


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