Description

Tributylphosphine (CAS 998-40-3) is a highly versatile organophosphorus compound with the molecular formula C₁₂H₂₇P and IUPAC name tributylphosphane. This clear, colorless to pale yellow liquid is widely utilized in organic synthesis, catalysis, and material science due to its strong nucleophilic and reducing properties. With a boiling point of approximately 240°C and a density of 0.82 g/cm³, it is soluble in common organic solvents such as ether, benzene, and alcohol but insoluble in water. Tributylphosphine is packaged under inert gas to ensure stability and purity, making it ideal for sensitive reactions like palladium-catalyzed cross-couplings (e.g., Stille, Suzuki) and as a ligand in transition metal complexes. Its high reactivity also lends itself to applications in polymer chemistry and semiconductor manufacturing. Store in a cool, dry place away from oxidizers and moisture to maintain optimal performance.

Properties

• CAS Number: 998-40-3
• Complexity: 72.1
• IUPAC Name: tributylphosphane
• InChI: InChI=1S/C12H27P/c1-4-7-10-13(11-8-5-2)12-9-6-3/h4-12H2,1-3H3
• InChI Key: TUQOTMZNTHZOKS-UHFFFAOYSA-N
• Exact Mass: 202.185037859
• Molecular Formula: C12H27P
• Molecular Weight: 202.32
• SMILES: CCCCP(CCCC)CCCC
• Monoisotopic Mass: 202.185037859
• Physical Description: Tributylphosphine is a colorless to yellowish liquid with a strong garlic-like odor. It is insoluble in water. It is liable to heat and ignite spontaneously in air. If involved in a fire phosphine gas, a highly flammable and toxic gas, will evolve. It is irritating to mucous membranes.
• Synonyms: Tributylphosphine, Tributylphosphane, Tri-n-butylphosphine, Phosphine, tributyl-, Tributylphosphorus, UNII-0O52FJR7WN, EINECS 213-651-2, 0O52FJR7WN, NSC 91700, BRN 1738261, DTXSID9046998, AI3-28071, PBu(n)3, NSC-91700, Tributylphosphane [UN3254] [Spontaneously combustible], (n-C4H9)3P, DTXCID7026998, EC 213-651-2, phosphine, tributyl, Tributylphosphane (UN3254) (Spontaneously combustible), Trinbutylphosphine, P(nBu)3, 4-16-00-01699 (beilstein handbook reference), inchi=1/c12h27p/c1-4-7-10-13(11-8-5-2)12-9-6-3/h4-12h2,1-3h, tuqotmznthzoks-uhfffaoysa-n, 998-40-3, Tris(butyl)phosphine, tributyl phosphine, Tributylfosfin, Tri-n-butyl phosphine, tributyl-phosphane, MFCD00009462, Tributylfosfin [Czech], UN3254, Tributyl phosphine (TBP), tributyiphophine, tributylphoshine, tributylphospine, Tribuylphosphine, tri-butylphosphine, tributy-lphosphine, Tributyl-phosphine, tri-n-butylphosphin, nBu3P, tri n-butylphosphine, Tri-n-butylphosphane, tri-n-butyl phosphin, tri n-butyl phosphine, tri(n-butyl)phosphine, tri-n-butyl-phosphine, Bu3P, PBu3, n-Bu3P, tris n-butyl phosphine, tri-(n-butyl)phosphine, (n-Bu)3P, SCHEMBL6033, (Bu)3P, P(Bu)3, NCIOpen2_005716, Tri-n-butylphosphine, 97%, Tri-n-butylphosphine, 99%, SCHEMBL821221, P(N-BU)3, CHEMBL3185473, BCP22498, NSC91700, Tox21_301600, SBB058500, AKOS009128712, NCGC00256212-01, BP-10599, CAS-998-40-3, DB-009882, DB-222255, NS00009653, ST51023413, T0361, EN300-27824, A22090, Tris(butyl)phosphine; Tri-n-butylphosphine; TBUP, Q7840573, F0001-2344, Tributylphosphine, >=93.5% (Tri-N-butylphosphine, GC)

Application

Tributylphosphine is a key reagent in organic synthesis, particularly in palladium-catalyzed cross-coupling reactions such as Suzuki-Miyaura and Stille couplings. It serves as an effective reducing agent for converting metal precursors into nanoparticles and as a stabilizing ligand for catalytic systems. In polymer chemistry, it is used to initiate polymerization and modify polymer properties. Additionally, its role in semiconductor processing includes passivation and doping applications.

Safety and Hazards

GHS Hazard Statements

• Not Classified

Precautionary Statements

• P210, P222, P231, P233, P280, P302+P335+P334, and P370+P378

Hazard Classes and Categories

• Flam. Liq. 3 (15.7%)
• Pyr. Liq. 1 (100%)
• Self-heat. 1 (12.9%)
• Acute Tox. 4 (100%)
• Acute Tox. 4 (64.5%)
• Skin Corr. 1B (100%)
• Eye Dam. 1 (48.8%)
• Aquatic Chronic 2 (72.1%)

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