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731374

Sigma-Aldrich

Tri-n-butylphosphine

99%

Synonym(s):
Tributylphosphine, TBP, P(n-Bu)3, NSC 91700
Linear Formula:
[CH3(CH2)3]3P
CAS Number:
Molecular Weight:
202.32
Beilstein:
1738261
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.22

vapor density

9 (vs air)

Quality Level

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

Packaging

25, 100 g in Sure/Seal™

Signal Word

Danger

Hazard Statements

Hazard Classifications

Acute Tox. 4 Oral - Aquatic Chronic 2 - Self-heat. 1 - Skin Corr. 1B

Storage Class Code

4.2 - Pyrophoric and self-heating hazardous materials

WGK

WGK 3

Certificate of Analysis

Enter Lot Number to search for Certificate of Analysis (COA).

Certificate of Origin

Enter Lot Number to search for Certificate of Origin (COO).

A. A. Vasil'ev, et al.,
Russian Chemical Bulletin, 59, 605-610 (2010)
A. S. Singh, et al.,
Tetrahedron Letters, 52, 2383-2386 (2011)
X. Guan, et al.,
European Journal of Organic Chemistry, 14, 2673-2677 (2011)
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)
Y. Zou, et al.,
Synlett, 7, 1000-1004 (2011)

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