90827

Tributylphosphine

≥93.5% (Tri-N-butylphosphine, GC)

• Synonym(s): P(n-Bu)₃, TBP
• Linear Formula: [CH₃(CH₂)₃]₃P
• CAS Number: 998-40-3
• Molecular Weight: 202.32
• Beilstein: 1738261
• EC Number: 213-651-2
• MDL number: MFCD00009462
• UNSPSC Code: 12352128
• PubChem Substance ID: 57653412
• NACRES: NA.22

Properties

• vapor density: 9 (vs air)
• Quality Level: 200
• Assay: ≥93.5% (Tri-N-butylphosphine, GC); ≥97% (Tri-N-butylphospine + isomers)
• form: liquid
• autoignition temp.: 392 °F
• reaction suitability: reaction type: Acetylations; reagent type: ligand
• refractive index: n20/D 1.462 (lit.); n20/D 1.463
• bp: 150 °C/50 mmHg (lit.)
• density: 0.81 g/mL at 25 °C (lit.)
• functional group: phosphine
• SMILES string: CCCCP(CCCC)CCCC
• 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

Description

General description

Tributylphosphine (TBP) is a potential nucleophile. It acts as a weak base in organic solvents. It is an important catalyst for the acylation reactions.[1] It is an efficient promoting reagent for the ring-opening reaction of various epoxides and aziridines.[2] TBP in conjugation with 1,1′-(azodicarbonyl)dipiperidine (ADDP) constitutes Mitsunobu reagent.[3] This reactive phosphine allows the formation of a strained lactone.[4][5]

Application

Tributylphosphine was used in the preparation of silver nanoparticles (AgNPs) functionalized with an organometallic bifunctional thiol containing Pt(II) centers.[6]
It may be used in the following processes:

• As reducing agent for alkyl disulfides and aromatic disulfides.[7]
• As catalyst for the synthesis of 2-substituted 1,3-benzoselenazoles.[6]
• As promoter for the ring opening of epoxides and aziridines with nucleophiles.[2]
• As a reagent in the preparation of 6-substituted penicillanate esters by reduction of 6-bromo-6-substituted penicillanate esters in high diastereoselectivity.[8]
• As a catalyst in the acylation reaction of alcohols.[1]
• As a catalyst to prepare rotaxanes by the acylation of corresponding pseudorotaxanes using 3,5-dimethylbenzoic anhydride.[9]
• As a catalyst to prepare vinyl thioethers by the Michael addition of ethanethiol to various alkynyl ketones.[10]
• As a promoter in the conjugate addition of non-nucleophilic N-containing compounds with Michael acceptors.[11]

Safety Information

• Pictograms: GHS02,GHS05,GHS07,GHS09
• Signal Word: Danger
• Hazard Statements: H250,H302,H314,H411
• Precautionary Statements: P231 + P232 - P273 - P280 - P303 + P361 + P353 - P305 + P351 + P338 - P370 + P378
• Hazard Classifications: Acute Tox. 4 Oral - Aquatic Chronic 2 - Eye Dam. 1 - Pyr. Liq. 1 - Skin Corr. 1A
• Storage Class Code: 4.2 - Pyrophoric and self-heating hazardous materials
• WGK: WGK 2
• Flash Point(F): 242.6 °F - closed cup
• Flash Point(C): 117 °C - closed cup
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves