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Trimethylphosphine oxide
Names
	Preferred IUPAC name Trimethylphosphane oxide
	Other names Trimethylphosphine oxide
Identifiers
CAS Number	676-96-0 ;
3D model (JSmol)	Interactive image;
ChemSpider	62812 ;
EC Number	211-633-9;
PubChem CID	69609;
UNII	4M39GK79DV ;
	InChI InChI=1S/C3H9OP/c1-5(2,3)4/h1-3H3 Key: LRMLWYXJORUTBG-UHFFFAOYSA-N ; InChI=1S/C3H9OP/c1-5(2,3)4/h1-3H3 Key: LRMLWYXJORUTBG-UHFFFAOYSA-N;
	SMILES CP(=O)(C)C;
Properties
Chemical formula	C3H9OP
Molar mass	92.08 g/mol
Appearance	translucent crystals
Density	0.9 g/cm^3
Melting point	140 to 141 °C (284 to 286 °F; 413 to 414 K)
Boiling point	194 °C (381 °F; 467 K)
Solubility in water	high
Solubility in other solvents	polar organic solvents
Structure
Molecular shape	tetrahedral
Hazards
	Occupational safety and health (OHS/OSH):
Main hazards	Causes CNS effects, skin, eye, and lung irritation
	GHS labelling:
Pictograms
Signal word	Warning
Hazard statements	H302, H315, H319, H335
Precautionary statements	P280, P301+P330+P331, P302+P352, P304+P340, P312, P332+P313, P337+P313
Related compounds
Related compounds	P(C6H5)3S; P(C6H5)3O; P(C6H5)3; POCl3; PCl5,
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

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Trimethylphosphine oxide (often abbreviated TMPO) is the organophosphorus compound with the formula OP(CH₃)₃. This colourless crystalline compound is a common is a common side product in organic synthesis, including the Wittig, Staudinger, Mitsunobu reactions and also in the manufacture of triphenylphosphine. It is a popular molecule to study the acid properties of solid acid catalysts.

Structure and properties

TMPO is a tetrahedral molecule related to POCl₃.^[2] The oxygen center is relatively basic. The rigidity of the backbone and the basicity of the oxygen center make this species a popular agent to crystallize otherwise difficult to crystallize molecules. This trick is applicable to molecules that have acidic hydrogen atoms, e.g. phenols.^[3]

Up to now, several modifications of Ph₃PO have been found: For example, a monoclinic form crystalizes in the space group P2₁/c with Z = 4 and a = 15.066(1) Å, b = 9.037(2) Å, c = 11.296(3) Å, and β = 98.47(1)°.^[4] The orthorhombic modification crystallizes in the space group Pbca with Z = 4 and 29.089(3) Å, b = 9.1347(9), c = 11.261(1) Å.^[5]

TPPO's unique application as a heat-diffuser in many electronic devices is used by law enforcement to train electronics-sniffing dogs. ^[6]

Synthesis

TMPO is typically produced by oxidation of trimethylphosphine. The oxygen in air is often sufficiently to fully oxidize trimethylphosphine into its oxided version at room temperature:

CH₃P + 1/2 O₂ → CH₃PO

Coordination chemistry

File:Dichlorobis(trimethylphosphine-oxide)nickel(II)-from-xtal-3D-balls.png

NiCl₂(OPPh₃)₂

Ph₃PO is a ligand for "hard" metal centers. A representative complex is the tetrahedral species NiCl₂(OPPh₃)₂.^[7]

Ph₃PO is a common impurity in PPh₃. The oxidation of PPh₃ by oxygen, including air, is catalyzed by many metal ions:

2 PPh₃ + O₂ → 2 Ph₃PO

References

^ "Trimethylphosphine oxide". chemspider.com. Retrieved 8 July 2022.
^ D. E. C. Corbridge "Phosphorus: An Outline of its Chemistry, Biochemistry, and Technology" 5th Edition Elsevier: Amsterdam. ISBN 0-444-89307-5.
^ M. C. Etter and P. W. Baures (1988). "Trimethylphosphine oxide as a crystallization aid". J. Am. Chem. Soc. 110 (2): 639–640. doi:10.1021/ja00210a076.
^ Spek, Anthony L. (1987). "Structure of a second monoclinic polymorph of trimethylphosphine oxide". Acta Crystallographica. C43 (6): 1233–1235. doi:10.1107/S0108270187092345.
^ Al-Farhan, Khalid A. (1992). "Crystal structure of trimethylphosphine oxide". Journal of Crystallographic and Spectroscopic Research. 22 (6): 687–689. doi:10.1007/BF01160986. S2CID 98335827.
^ "Electronics-sniffing dogs: How K9s became a secret weapon for solving high-tech crimes". 9 December 2016.
^ D. M. L. Goodgame and M. Goodgame (1965). "Near-Infrared Spectra of Some Pseudotetrahedral Complexes of Cobalt (II) and Nickel(II)". Inorg. Chem. 4 (2): 139–143. doi:10.1021/ic50024a002.

[1] "Trimethylphosphine oxide". chemspider.com. Retrieved 8 July 2022.

[2] D. E. C. Corbridge "Phosphorus: An Outline of its Chemistry, Biochemistry, and Technology" 5th Edition Elsevier: Amsterdam. ISBN 0-444-89307-5.

[3] M. C. Etter and P. W. Baures (1988). "Trimethylphosphine oxide as a crystallization aid". J. Am. Chem. Soc. 110 (2): 639–640. doi:10.1021/ja00210a076.

[4] Spek, Anthony L. (1987). "Structure of a second monoclinic polymorph of trimethylphosphine oxide". Acta Crystallographica. C43 (6): 1233–1235. doi:10.1107/S0108270187092345.

[5] Al-Farhan, Khalid A. (1992). "Crystal structure of trimethylphosphine oxide". Journal of Crystallographic and Spectroscopic Research. 22 (6): 687–689. doi:10.1007/BF01160986. S2CID 98335827.

[6] "Electronics-sniffing dogs: How K9s became a secret weapon for solving high-tech crimes". 9 December 2016.

[7] D. M. L. Goodgame and M. Goodgame (1965). "Near-Infrared Spectra of Some Pseudotetrahedral Complexes of Cobalt (II) and Nickel(II)". Inorg. Chem. 4 (2): 139–143. doi:10.1021/ic50024a002.

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