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Sigma-Aldrich

Tri-n-butylphosphine

99%

Synonym(s):

Tributylphosphine, NSC 91700, 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/REAXYS Number:
1738261
EC Number:
213-651-2
MDL number:
MFCD00009462
UNSPSC Code:
12352128
PubChem Substance ID:
329764649
NACRES:
NA.22

vapor density

9 (vs air)

assay

99%

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

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

Catalyst for:
  • Domino reactions of activated conjugated dienes with β,γ−unsaturated-α-ketoesters
  • [3+2]-Cycloadditions
  • Umpolung addition reactions
  • Reductive carbonylation
  • Allylation reactions

signalword

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_germany

WGK 2

flash_point_f

242.6 °F - closed cup

flash_point_c

117 °C - closed cup

Certificates of Analysis (COA)

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Substrate-controlled, phosphine-catalyzed domino reactions of activated conjugated dienes: highly diastereoselective synthesis of bicyclic skeletons.
Jianze Ma et al.
Chemistry (Weinheim an der Bergstrasse, Germany), 17(27), 7418-7422 (2011-05-19)
X. Guan, et al.,
European Journal of Organic Chemistry, 14, 2673-2677 (2011)
A. A. Vasil'ev, et al.,
Russian Chemical Bulletin, 59, 605-610 (2010)
A. S. Singh, et al.,
Tetrahedron Letters, 52, 2383-2386 (2011)
Y. Zou, et al.,
Synlett, 7, 1000-1004 (2011)
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