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Tributylphosphine

Tributylphosphine
Tributylphosphine.png
Tributylphosphine-3D-vdW.png
Names
IUPAC name
Tributylphosphane
Preferred IUPAC name
Tributylphosphane
Other names
Tributylphosphine
Identifiers
3D model (Jmol)
ChemSpider
ECHA InfoCard 100.012.410
EC Number 213-651-2
PubChem CID
Properties
C
12H
27P
Molar mass 202.32 g·mol−1
Appearance Colorless oily liquid
Density 0.82 g/ml
Melting point −60 °C; −76 °F; 213 K
Boiling point 240 °C; 464 °F; 513 K (150 °C (302 °F; 423 K) at 50 mmHg)
negligible
Solubility organic solvents such as heptane
Hazards
Main hazards Stench, Flammable, Corrosive
R-phrases R11 R17 R20/21/22 R34 R38
NFPA 704
Flammability code 3: Liquids and solids that can be ignited under almost all ambient temperature conditions. Flash point between 23 and 38 °C (73 and 100 °F). E.g., gasoline) Health code 1: Exposure would cause irritation but only minor residual injury. E.g., turpentine 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 117 °C (243 °F; 390 K)
168 °C (334 °F; 441 K)
Related compounds
Related Tertiary phosphine
 Trimethylphosphine
Triphenylphosphine
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Tributylphosphine is the organophosphorus compound with the formula P(C
4H
9)
3. Abbreviated or PBu
3, it is a tertiary phosphine. It is an oily liquid at room temperature, with a nauseating odor. It reacts slowly with atmospheric oxygen, and rapidly with other oxidizing agents, to give the corresponding phosphine oxide. It is usually handled using air-free techniques.

Tributylphosphine is prepared industrially by the addition of phosphine to butene: the addition proceeds by a free radical mechanism, and so the Markovnikov rule is not followed.

Tributylphosphine can be prepared in the laboratory by reaction of the appropriate Grignard reagent with phosphorus trichloride although, as it is commercially available at reasonable prices, it is rare to have to perform the small-scale preparation.

Tributylphosphine reacts with oxygen to give the phosphine oxide:

Because this reaction is so fast, the compound is usually handled under an inert atmosphere.

The phosphine is also easily alkylated. For example, benzyl chloride gives the phosphonium salt:


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Wikipedia

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