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| Names | |
|---|---|
| Preferred IUPAC name
Trimethylphosphane oxide | |
| Other names
Trimethylphosphine oxide
| |
| Identifiers | |
3D model (JSmol)
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| ChemSpider | |
| EC Number |
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PubChem CID
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| UNII | |
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| Properties | |
| 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) |
| high | |
| Solubility in other solvents | polar organic solvents |
| Structure | |
| tetrahedral | |
| Hazards | |
| Occupational safety and health (OHS/OSH): | |
Main hazards
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Causes CNS effects, skin, eye, and lung irritation |
| GHS labelling:[1] | |
| |
| Warning | |
| H302, H315, H319, H335 | |
| P280, P301+P330+P331, P302+P352, P304+P340, P312, P332+P313, P337+P313 | |
| Related compounds | |
Related compounds
|
P(C6H5)3S; P(C6H5)3O; |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
| |
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
editTMPO 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
editTMPO 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
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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
edit- ^ "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.