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90827 Aldrich

Tributylphosphine

≥93.5% (Tri-N-butylphosphine, GC)

Synonym: P(n-Bu)3, TBP

  • CAS Number 998-40-3

  • Linear Formula [CH3(CH2)3]3P

  • Molecular Weight 202.32

  •  Beilstein Registry Number 1738261

  •  EC Number 213-651-2

  •  MDL number MFCD00009462

  •  PubChem Substance ID 57653412

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Properties

Related Categories Catalysis and Inorganic Chemistry, Chemical Synthesis, Phosphine Compounds, Phosphine Ligands
vapor density   9 (vs air)
InChI Key   TUQOTMZNTHZOKS-UHFFFAOYSA-N
assay   ≥93.5% (Tri-N-butylphosphine, GC)
  ≥97% (Tri-N-butylphospine + isomers)
autoignition temp.   392 °F
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.)
suitable for   Acetylations

Description

Packaging

25, 100, 500 mL in Sure/Seal™

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.

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.

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Suggested Laboratory Gloves


Laboratory GlovesThis substance has been tested against several types of hand protection for CE compliance. Click below to find the recommended gloves for handling this product.




Cross-Coupling Guide
Safety & Documentation

Safety Information

Symbol 
Signal word 
Danger
Hazard statements 
Precautionary statements 
RIDADR 
UN 3254 4.2 / PGI
WGK Germany 
3
RTECS 
SZ3270000
Flash Point(F) 
98.6 °F
Flash Point(C) 
37 °C
Protocols & Articles
Peer-Reviewed Papers
15

References

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