Difference between revisions of "Trimethylphosphine"
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Latest revision as of 22:30, 21 January 2020
| Names | |
|---|---|
| IUPAC name
Trimethylphosphane
| |
| Other names
TMP
Trimethylphosphorus | |
| Properties | |
| C3H9P P(CH3)3 PMe3 | |
| Molar mass | 76.079 g/mol |
| Appearance | Colorless volatile liquid |
| Odor | Unpleasant, pungent |
| Density | 0.738 g/cm3 (20 °C) |
| Melting point | −86 °C (−123 °F; 187 K) |
| Boiling point | 38 °C (100 °F; 311 K) |
| Soluble | |
| Solubility | Miscible with THF, toluene |
| Vapor pressure | 374.3 mmHg at 20 °C 1232.6 mmHg at 55 °C |
| Acidity (pKa) | 8.65 |
| Hazards | |
| Safety data sheet | Sigma-Aldrich |
| Flash point | −19 °C (−2 °F; 254 K) |
| Related compounds | |
| Related compounds
|
Phosphine Triphenylphosphine |
| Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). | |
| Infobox references | |
Trimethylphosphine is the organophosphorus compound with the formula P(CH3)3, commonly abbreviated as PMe3. This colorless liquid has a strongly unpleasant odor, characteristic of alkylphosphines. It is often used as ligand in coordination chemistry.
Contents
Properties
Chemical
Trimethylphosphine is a weak base, but does form stable salts with strong acids.
Trimethylphosphine is a highly basic ligand that forms complexes with most metals. As a ligand, trimethylphosphine's Tolman cone angle is 118°.
Being a relatively compact phosphine, several can bind to a single transition metal, as illustrated by the existence of Pt(PEt3)4. Its complex with silver iodide, AgI(PMe3) is an air-stable solid that releases PMe3 upon heating.
Physical
Trimethylphosphine is a volatile toxic colorless liquid, with a strong repulsive odor, described by some as somewhere between smelly goat and vomit.[1] It is miscible with many organic solvents.
Availability
This compound is sold by many chemical suppliers, but due to its hazards it's hard to acquire and quite expensive.
Preparation
Trimethylphosphine can be prepared by the treatment of triphenyl phosphite with methylmagnesium chloride:
- 3 CH3MgCl + P(OC6H5)3 → P(CH3)3 + 3 C6H5OMgCl
The synthesis is conducted in dibutyl ether, from which the more volatile PMe3 can be distilled.
Projects
- Ligand in coordination chemistry
- Make trimethylphosphine oxide
Handling
Safety
Trimethylphosphine is pyrophoric and very toxic.
Storage
Trimethylphosphine must be kept in airtight containers, in specially designed storage cabinets, in a dry and well ventilated place. Containers which are opened must be carefully resealed and kept upright to prevent leakage.
Recommended storage temperature 2 - 8 °C
Disposal
Trimethylphosphine is best neutralized by burning it outside or in a special incinerator.
Trimethylphosphine converts to non-pyrophoric phosphine oxide by treatment with dilute bleach.
References
Relevant Sciencemadness threads
- Articles containing unverified chemical infoboxes
- Chembox articles without image
- Chemical compounds
- Organic compounds
- Phosphorus compounds
- Organophosphorus compounds
- Bases
- Organic bases
- Lewis bases
- Things that should NOT be messed with except by professionals
- Things that can kill you very quickly
- Choking agents
- Pyrophoric materials
- Irritants
- Foul smelling compounds
- Liquids
