Tributylphosphine Property

Melting point:

-65 °C

Boiling point:

150 °C50 mm Hg(lit.)

Density 

0.81 g/mL at 25 °C(lit.)

vapor density 

9 (vs air)

vapor pressure 

1.9Pa at 20℃

refractive index 

n20/D 1.462(lit.)

Flash point:

99 °F

storage temp. 

2-8°C

form 

liquid

color 

Clear colorless to pale yellow

Specific Gravity

0.820 (20/4℃)

Water Solubility 

insoluble

Sensitive 

Moisture Sensitive/Air Sensitive

BRN 

1738261

Stability:

Stable, but pyrophoric - spontaneously inflammable in air. Incompatible with oxidizing agents. Moisture sensitive.

InChIKey

TUQOTMZNTHZOKS-UHFFFAOYSA-N

CAS DataBase Reference

998-40-3(CAS DataBase Reference)

NIST Chemistry Reference

Phosphine, tributyl-(998-40-3)

EPA Substance Registry System

Phosphine, tributyl- (998-40-3)

Safety

Hazard Codes 

Xi,F,C,T

Risk Statements 

36/38-34-21/22-17-11-37-36/37/38-61

Safety Statements 

41-36/37/39-26-16-45-43-17-5-53

RIDADR 

UN 3254 4.2/PG 1

WGK Germany 

3

RTECS 

SZ3270000

F 

10-13-23

Autoignition Temperature

392 °F

TSCA 

Yes

HazardClass 

4.2

PackingGroup 

I

HS Code 

29319090

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Danger

Hazard statements

H251Self-heating; may catch fire

H302Harmful if swallowed

H314Causes severe skin burns and eye damage

H411Toxic to aquatic life with long lasting effects

Precautionary statements

P235Keep cool.

P273Avoid release to the environment.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P301+P312IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.

P303+P361+P353IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

Tributylphosphine Chemical Properties,Usage,Production

Chemical Properties

Clear liquid

Uses

1,4-addition catalyst; used with disulfides for the thioetherification of alcohols; acylation catalyst; used to prepare active esters.

Uses

suzuki reaction

Uses

Tributylphosphine is usually used as catalyst for Domino reactions of activated conjugated dienes with β,γ-unsaturated-α-ketoesters, [3+2]-Cycloadditions,Umpolung addition reactions,Reductive carbonylation, Allylation reactions.

Reactions

Tributylphosphine (TBP) is a versatile chemical reagent similar to tributylamine but more reactive, showing catalytic activity in a variety of reactions.
(1) TBP reacts with oxygen to form the corresponding phosphine oxide (i.e., tributylphosphine oxide) according to the following reaction equation:

Since this reaction is very fast, the compound is usually handled under an inert atmosphere. Phosphine is also easily alkylated.
(2) TBP is used as an anionic polymerization initiator in the reaction of aldehydes, olefins, or active vinyl compounds. Condensation reactions are usually catalyzed by TBP. In some cases, TBP can induce condensation reactions that are not catalyzed by the corresponding amine. TBP catalysis has been used for isocyanates, active vinyl compounds, and epoxy esters^[1].

Synthesis Reference(s)

Tetrahedron Letters, 25, p. 2493, 1984 DOI: 10.1016/S0040-4039(01)81213-2

General Description

Tributylphosphane is a colorless to yellowish liquid with a strong garlic-like odor. Tributylphosphane is insoluble in water. Tributylphosphane is liable to heat and ignite spontaneously in air. If involved in a fire phosphine gas, a highly flammable and toxic gas, will evolve. Tributylphosphane is irritating to mucous membranes.

Air & Water Reactions

Highly flammable. May ignite on contact with air or moist air. Insoluble in water.

Reactivity Profile

Organophosphates, such as Tributylphosphane, are susceptible to formation of highly toxic and flammable phosphine gas in the presence of strong reducing agents such as hydrides. Partial oxidation by oxidizing agents may result in the release of toxic phosphorus oxides.

Health Hazard

Fire will produce irritating, corrosive and/or toxic gases. Inhalation of decomposition products may cause severe injury or death. Contact with substance may cause severe burns to skin and eyes. Runoff from fire control may cause pollution.

Fire Hazard

Flammable/combustible material. May ignite on contact with moist air or moisture. May burn rapidly with flare-burning effect. Some react vigorously or explosively on contact with water. Some may decompose explosively when heated or involved in a fire. May re-ignite after fire is extinguished. Runoff may create fire or explosion hazard. Containers may explode when heated.

Purification Methods

Fractionally distil it under reduced pressure in an inert atmosphere (N2) through an 8inch gauze-packed column (b 110-111o/10mm) and redistil it in a vacuum, then seal it in thin glass ampoules. It is easily oxidised by air to tri-n-butylphosphine oxide, b 293-296o/745mm. It has a characteristic odour, it is soluble in EtOH, Et2O, and *C6H6 but is insoluble in H2O and less easily oxidised by air than the lower molecular weight phosphines. It forms complexes, e.g. with CS2 (1:1) m 65.5o (from EtOH). [Davies & Jones J Chem Soc 33 1929, Chernick & Skinner J Chem Soc 1401 1956, Beilstein 4 IV 3436.]

References

[1] CATALYZE with TRIBUTYLPHOSPHINE[J]. C&EN Global Enterprise, 1967, 45 3: 11. DOI:10.1021/cen-v045n003.p011.