Tri-n-butylphosphine, CAS No. 998-40-3

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998-40-3

Catalog No. EBD489937

CAS 998-40-3

Name Tri-n-butylphosphine

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Basic Information

Synonyms: Tri-n-butylphosphine Tributylphosphinetech ZukunftnuralsS15-5801Tri-n-butylphosphine Trinbutylphosphinemincolorlesslightyellowliq Trinbutylphosphineinhexane Tributylphosphine phosphorustri-n-butyl phosphine,tributyl tris(butyl)phosphine (n-c4h9)3p n-Bu3P

Molecular Formula: C12H27P

Molecular Weight: 202.32

MDL Number: MFCD00009462

Categories: Synthetic Chemistry > Catalysts and Ligands > Phosphorus Ligands Synthetic Chemistry > Organic Building Blocks > Phosphorus Compounds

Product Description:

Tributylphosphine is a tertiary phosphine with the chemical formula (C₄H₉)₃P. It is a colorless to pale yellow liquid with a characteristic, unpleasant odor. It is highly air-sensitive, readily oxidizing in air to form tributylphosphine oxide, and is typically handled under an inert atmosphere such as nitrogen or argon. Its primary application is as a versatile reagent in organic synthesis and catalysis. It serves as a strong nucleophile and an effective reducing agent, commonly used in the Staudinger reaction for the conversion of azides to amines and in the Mitsunobu reaction for the formation of esters and ethers. Tributylphosphine is also widely employed as a ligand in transition metal catalysis, particularly in palladium-catalyzed cross-coupling reactions (e.g., Sonogashira, Suzuki-Miyaura) and in gold-catalyzed transformations, where it can modulate the catalyst's activity and selectivity. Due to its pyrophoric nature and toxicity, it requires careful handling. It finds significant use in the synthesis of pharmaceuticals, agrochemicals, and fine chemicals, as well as in polymer chemistry as a catalyst or chain transfer agent.

Physical Properties

Melting Point: -65 °C

Boiling Point: 150 °C/50 mmHg(lit.)

Flash Point: 37 °C

Density: 9 (vs air)

Solubility: Insoluble in water. Miscible with ether, methanol, ethanol and benzene.

Refractivity: n20/D 1.462(lit.)

Storage: 2-8°C

Safety Information

Packing Level: I

Hazard Category: 4.2

Transport Codes: 3254

Analytical Data

Appearance: colourless liquid