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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: H226-H250-H302-H312-H314-H335
Flammable liquid and vapour. Catches fire spontaneously if exposed to air. Harmful if swallowed. Harmful in contact with skin. Causes severe skin burns and eye damage. May cause respiratory irritation.
Precautionary Statements: P210-P222-P233-P235-P240-P241-P242-P243-P260-P264b-P270-P271-P280-P302+P334-P304+P340-P305+P351+P338-P310-P330-P331-P363-P370+P378q-P501c
Keep away from heat/sparks/open flames/hot surfaces. - No smoking. Do not allow contact with air. Keep container tightly closed. Keep cool. Ground/bond container and receiving equipment. Use explosion-proof electrical/ventilating/lighting/ equipment. Use only non-sparking tools. Take precautionary measures against static discharge. Do not breathe dust/fume/gas/mist/vapours/spray. Wash face, hands and any exposed skin thoroughly after handling Do not eat, drink or smoke when using this product. Use only outdoors or in a well-ventilated area. Wear protective gloves/protective clothing/eye protection/face protection. IF ON SKIN: Immerse in cool water/wrap in wet bandages. IF INHALED: Remove to fresh air and keep at rest in a position comfortable for breathing. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. Immediately call a POISON CENTER or doctor/physician. Rinse mouth. Do NOT induce vomiting. Wash contaminated clothing before reuse. In case of fire: Use CO2, dry chemical, or foam Dispose of contents/ container to an approved waste disposal plant