247049

Sigma-Aldrich

Tributylphosphine

mixture of isomers, 97%

Synonym(s):
TBP, P(n-Bu)3
Linear Formula:
CH3(CH2)33P
CAS Number:
Molecular Weight:
202.32
Beilstein/REAXYS Number:
1738261
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.22
Pricing and availability is not currently available.

vapor density

9 (vs air)

Quality Level

assay

97%

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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Packaging

100, 500 g in Sure/Seal™

Application

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

Signal Word

Danger

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

Hazard Codes

F,C

Risk Statement

17-21/22-34

Safety Statement

17-26-36/37/39-43-45

RIDADR

UN 3254 4.2 / PGI

WGK Germany

WGK 3

Flash Point(F)

99.0 °F - closed cup

Flash Point(C)

37.2 °C - closed cup

J. Mol. Catal. A: Chem., 271, 145-145 (2007)
Bradley G Jellerichs et al.
Journal of the American Chemical Society, 125(26), 7758-7759 (2003-06-26)
Upon exposure of mono-enone mono-allylic carbonates to tributylphosphine and 1 mol % Pd(Ph3P)4, efficient conversion to the corresponding cycloallylated products is achieved. This transformation combines the nucleophilic features of the Morita-Baylis-Hillman reaction with the electrophilic features of the Trost-Tsuji reaction.
Solvent effects on hydrogen bonding.
Joanne L Cook et al.
Angewandte Chemie (International ed. in English), 46(20), 3706-3709 (2007-04-07)
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...
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...
Articles
Solvothermal synthesis is a method for preparing a variety of materials such as metals, semiconductors, ceramics, and polymers.
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