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90827

Tributylphosphine

≥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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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

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.

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Danger

Hazard Classifications

Acute Tox. 4 Oral - Aquatic Chronic 2 - Eye Dam. 1 - Pyr. Liq. 1 - Skin Corr. 1A

Storage Class

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

ppe

Faceshields, Gloves, Goggles, type ABEK (EN14387) respirator filter

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Certificates of Analysis (COA)

Lot/Batch Number
SDBB4930
SDBB3131
STBL3004
STBL2618
STBL1193

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C Battocchio et al.
Physical chemistry chemical physics : PCCP, 16(23), 11719-11728 (2014-05-09)
Silver nanoparticles (AgNPs) functionalized with an organometallic bifunctional thiol containing Pt(ii) centers, generated in situ from trans-trans-[thioacetyl-bistributylphosphine-diethynylbiphenyl-diplatinum(ii)], were synthesized with different sulphur/metal molar ratios (i.e. AgNPs-1 and AgNPs-2) with the aim to obtain nanosystems of different mean size and self-organization
High Yielding and Practical Synthesis of Rotaxanes by Acylative End-Capping Catalyzed by Tributylphosphine.
Kawasaki H, et al.
Chemistry Letters (Jpn), 28(10), 1015-1016 (1999)
Ren-Hua Fan et al.
The Journal of organic chemistry, 68(3), 726-730 (2003-02-01)
Tributylphosphine was found to be an effective promoting reagent for the ring-opening reaction of various epoxides and aziridines with nucleophile to produce corresponding anti-bifunctional products in moderate to excellent yields in water.
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