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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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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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J. Mol. Catal. A: Chem., 271, 145-145 (2007)
Kersti B Nilsson et al.
Dalton transactions (Cambridge, England : 2003), (9)(9), 1312-1319 (2004-07-15)
The coordination chemistry of the solvate complexes of the relatively soft electron-pair acceptor copper(I) has been studied in solution and solid state in seven solvents with strong electron-pair donor properties, liquid ammonia, trimethyl, triethyl, triisopropyl, tri-n-butyl and triphenyl phosphite, and
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.
Tien Q Pham et al.
The Journal of organic chemistry, 70(16), 6369-6377 (2005-07-30)
The phosphine-catalyzed [3 + 2]-cycloaddition of 5-methylenehydantoins 4 with the ylides 5, derived from addition of tributylphosphine to the 2-butynoic acid derivatives, 6a-d, gives spiro-heterocyclic products. The camphor sultam derivative 6b gives optically active products. Noteable was that the ylides
Cristina-Maria Vâlcu et al.
Proteomics, 6(5), 1599-1605 (2006-02-04)
Protein extraction procedure and the reducing agent content (DTT, dithioerythritol, tributyl phosphine and tris (2-carboxyethyl) phosphine (TCEP)) of the sample and rehydration buffers were optimised for European beech leaves and roots and Norway spruce needles. Optimal extraction was achieved with
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