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90827

Tributylphosphine

Name: Tributylphosphine
Brand: ALDRICH

≥97% (Tri-N-butylphospine + isomers),≥93.5% (Tri-N-butylphosphine, GC), liquid

Synonym(s):

P(n-Bu)₃, TBP

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About This Item

Linear Formula:

[CH₃(CH₂)₃]₃P

CAS Number:

998-40-3

Molecular Weight:

202.32

NACRES:

NA.22

PubChem Substance ID:

57653412

UNSPSC Code:

12352128

EC Number:

213-651-2

MDL number:

MFCD00009462

Beilstein/REAXYS Number:

1738261

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Properties

Product Name

Tributylphosphine, ≥93.5% (Tri-N-butylphosphine, GC)

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. It is an efficient promoting reagent for the ring-opening reaction of various epoxides and aziridines. TBP in conjugation with 1,1′-(azodicarbonyl)dipiperidine (ADDP) constitutes Mitsunobu reagent. This reactive phosphine allows the formation of a strained lactone.

Application

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

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