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247049

Sigma-Aldrich

Tributylphosphine

mixture of isomers, 97%

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
Beilstein:
1738261
EC Number:
213-651-2
MDL number:
MFCD00009462
UNSPSC Code:
12352128
PubChem Substance ID:
329752742
NACRES:
NA.22

vapor density

9 (vs air)

Assay

97%

form

liquid

autoignition temp.

392 °F

reaction suitability

reaction type: Buchwald-Hartwig Cross Coupling Reaction
reaction type: Heck Reaction
reaction type: Hiyama Coupling
reaction type: Negishi Coupling
reaction type: Sonogashira Coupling
reaction type: Stille Coupling
reaction type: Suzuki-Miyaura Coupling
reagent type: ligand
reaction type: Acetylations
reagent type: ligand
reaction type: Addition Reactions
reagent type: ligand
reaction type: Stille Coupling

impurities

<1% TBP oxide
5% TBP isomers

refractive index

n20/D 1.462 (lit.)

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

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Related Categories

Application

1,4-addition catalyst; used with disulfides for the thioetherification of alcohols; acylation catalyst; used to prepare active esters.
Used with platinum (II) or (IV) in an intermolecular hydroamination of unactivated alkenes.

Signal Word

Danger

Hazard Statements

H250,H302,H314,H411

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

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Journal of chromatography. A, 813(1), 187-200 (1998-08-11)
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Aziridines underwent cyclization reaction with carbon disulfide and isothiocyanate in the presence of organophosphine to afford thiazolidinone derivatives in good to high yields. The mechanistic study revealed that organophosphine serves as a catalyst in the reaction.
J Krijt et al.
Clinical chemistry, 47(10), 1821-1828 (2001-09-25)
Aminothiols have been implicated in the pathogenesis of arteriosclerosis, and reliable methods are needed to determine their concentrations in body fluids. We present a comparison of two analytical methods and focus on the reduction of low-molecular weight and protein-mixed disulfides
Yin-Wei Sun et al.
Organic letters, 12(24), 5664-5667 (2010-11-13)
P(n)Bu(3)-catalyzed cyclization reactions of salicylaldimines and salicylaldehydes with ethyl 2,3-butadienoate gave the corresponding functionalized chromans in moderate to good yields in THF under mild conditions. The new reaction provides a new method for the synthesis of biologically active chroman products.
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