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Tri-n-butylphosphine is used as a catalyst modifier in the cobalt-catalyzed hydroformylation of alkenes for industrial use. It is also used as a strong reducing agent and polymerization cross-linking catalyst. It is a used as an intermediate for phase transfer catalysts.
K. Sonogashira; S. Takahashi; N. Hagihara. A New Extended Chain Polymer, Poly[trans-bis(tri-n-butylphosphine)platinum 1,4-butadiynediyl]. Macromolecules. 1977, 10(4), 879-880.
JA Maclaren; BJ Sweetman. The preparation of reduced and S-alkykated wool keratins using Tri-n-butylphosphine. Australian Journal of Chemistry. 1966, 19(12), 2355 - 2360.
A useful alternative to Triphenylphosphine, L02502 in many applications. Advantages include its greater reactivity and the water-solubility of the by-product phosphine oxide, simplifying its removal.
In combination with phenyl isocyanate and a Pd catalyst, converts cinnamyl alcohol directly to a phosphorane, which reacts with aldehydes to give conjugated dienes: Chem. Lett., 1449 (1988):
Can behave as a hypernucleophilic catalyst in acylation reactions, with similar results to 4-(Dimethylamino)pyridine, A13016: J. Am. Chem. Soc., 115, 3358 (1993).
Effective catalyst for the Baylis-Hillman reaction with less tendency than the usual DABCO (1,4-Diazabicyclo[2.2.2]octane, A14003) to promote aldol type side reactions: J. Org. Chem., 62, 1521 (1997).
For example of its use in Mitsunobu-type reactions, see Diisopropyl azodicarboxylate, L10386.
Hazard Statements: H250-H252-H302-H312-H314-H318
Catches fire spontaneously if exposed to air. Self-heating in large quantities; may catch fire. Harmful if swallowed. Harmful in contact with skin. Causes severe skin burns and eye damage. Causes serious eye damage.
Precautionary Statements: P210-P303+P361+P353-P305+P351+P338-P405-P422a-P501a
Keep away from heat/sparks/open flames/hot surfaces. - No smoking. IF ON SKIN (or hair): Remove/Take off immediately all contaminated clothing. Rinse skin with water/shower. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. Store locked up. Store contents under inert gas. Dispose of contents/container in accordance with local/regional/national/international regulations.