Tributylphosphine

Tributylphosphine (TBP) (CAS 998-40-3) is a clear, colorless to pale yellow liquid that is one of the most widely utilized tertiary alkylphosphines in synthetic chemistry. It is characterized by its strong, pungent, and highly characteristic garlic-like odor. TBP is valued for its powerful reducing capabilities and its function as a soft, sterically non-hindered ligand for transition metals, particularly palladium and nickel. Its solubility profile and relatively low cost make it a practical choice for large-scale industrial and laboratory synthesis. TBP is a crucial reagent in many carbon-carbon and carbon-heteroatom bond-forming reactions.

Basic Information of TBP

CAS No.:	998-40-3
EC No.:	213-651-2
Linear Formula:	C12H27P
Molecular Weight:	202.32
Appearance:	Colorless to pale yellow, clear liquid
Odor:	Strong, highly pungent, garlic-like
Melting Point:	-65 °C
Boiling Point:	150 °C50 mm Hg(lit.)
Density:	0.81 g/mL at 25 °C(lit.)
Solubility:	Insoluble in water; highly soluble in organic solvents (toluene, hexane, THF).
Flash Point:	99 °F
RIDADR:	UN 3254 4.2/PG 1
Chemical Structure:

Application Overview

Tributylphosphine's versatility stems from its strong nucleophilicity, high ligand properties, and reducing power, making it key in various high-demand chemical syntheses:

• Catalysis (Transition Metal Ligand): It serves as a fundamental phosphine ligand in many industrial transition-metal catalyzed coupling reactions, including various Suzuki, Heck, and Negishi couplings, particularly in cross-coupling reactions where moderate steric bulk is preferred.

• Reducing Agent: Used as a non-metallic reducing agent in reactions such as the Staudinger reaction (reduction of azides to amines) and the Mitsunobu reaction (in combination with diethyl azodicarboxylate).

• Polymerization: TBP is employed as a specialized catalyst or initiator in certain polymerization processes, particularly for ring-opening and addition polymerizations, influencing the molecular weight and structure of the final polymer.

• Pharmaceutical Intermediates: It is a crucial reagent in the synthesis of complex pharmaceutical and agrochemical intermediates, often for forming specific functional groups or constructing complex molecular skeletons.

• Inert Gas and Specialized Packaging: Due to TBP's extreme sensitivity to oxygen (leading to immediate oxidation), we utilize high-integrity, seamless stainless steel containers or glass ampoules under a rigorously maintained argon atmosphere. This packaging guarantees the integrity and purity of the reactive phosphine upon delivery.

• Batch-Specific Spectroscopic Analysis: Every batch is accompanied by detailed ${}^{31}\text{P NMR}$ data alongside the Certificate of Analysis (CoA). This provides a direct, highly accurate measure of phosphine purity, giving chemists absolute confidence in the material's identity and reactivity.

• Controlled Supply Chain for Safety: We adhere to the strictest global regulatory standards for handling and shipping corrosive and flammable materials (UN 2920). Our specialized logistics team ensures safe, compliant, and timely delivery directly to your secure storage facilities.

Hazards Classification

• GHS Classification: Pyr. Liq. 1 (GHS02), Flam. Liq. 1 (GHS02), Acute Tox. 2 (Inhalation) (GHS06), Skin Corr. 1A (GHS05), Eye Dam. 1 (GHS05), STOT SE 3 (GHS08), Aquatic Acute 1 (GHS09), Aquatic Chronic 1 (GHS09)

• Hazard Statements: Catches fire spontaneously if exposed to air; Extremely flammable liquid and vapour; Fatal if inhaled; Causes severe skin burns and eye damage; May cause respiratory irritation; Very toxic to aquatic life with long lasting effects

• UN Number: UN 3254

• Hazard Class: 4.2 (Spontaneously combustible); Subsidiary hazard 6.1 (Toxic inhalation hazard)

• Packing Group: I