00676

Sigma-Aldrich

Trioctylphosphine oxide

for extraction analysis, ≥98.5%

Synonym(s):
(Oct)3PO, TOPO®
Linear Formula:
[CH3(CH2)7]3PO
CAS Number:
Molecular Weight:
386.63
Beilstein/REAXYS Number:
1796648
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.22

Quality Level

grade

for extraction analysis

assay

≥98.5% (GC)
≥98.5%

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

impurities

≤0.2% free acid (as H3PO4)
≤0.5% water

bp

201-202 °C/2 mmHg (lit.)

mp

50-52 °C (lit.)
52-55 °C

cation traces

Ca: ≤10 mg/kg
Cd: ≤5 mg/kg
Co: ≤5 mg/kg
Cr: ≤5 mg/kg
Cu: ≤5 mg/kg
Fe: ≤5 mg/kg
K: ≤10 mg/kg
Mg: ≤5 mg/kg
Mn: ≤5 mg/kg
Na: ≤10 mg/kg
Ni: ≤5 mg/kg
Pb: ≤5 mg/kg
Zn: ≤5 mg/kg

functional group

phosphine

SMILES string

CCCCCCCCP(=O)(CCCCCCCC)CCCCCCCC

InChI

1S/C24H51OP/c1-4-7-10-13-16-19-22-26(25,23-20-17-14-11-8-5-2)24-21-18-15-12-9-6-3/h4-24H2,1-3H3

InChI key

ZMBHCYHQLYEYDV-UHFFFAOYSA-N

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Application

Catalyst in:
  • Preparation of tetradentate planar-chiral hydroxy-substituted ferrocenecarboxaldimine Schiff base ligands
  • Reactions of allyl esters with hydrosilanes
  • Asymmetric cyanosilylation of aldehydes
  • Preparation of chlorothiol formates from thiols and phosgene

Legal Information

TOPO is a registered trademark of Life Technologies

Pictograms

Corrosion

Signal Word

Danger

Hazard Statements

Precautionary Statements

hazcat

Eye Dam. 1 - Skin Irrit. 2

storage_class_code

13 - Non Combustible Solids

WGK Germany

WGK 3

Flash Point(F)

230.0 °F - closed cup

Flash Point(C)

110 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

Certificate of Analysis

Certificate of Origin

Niemeyer, J.; et al.
European Journal of Inorganic Chemistry, 680-680 (2010)
Wettling, T.; et al.
Ger. Offen., 1993-1993 null
Belyakova, Z. V.; et al
Russ. J. Gen. Chem., 80, 728-728 (2010)
Zeng, Z.; et al.
European Journal of Organic Chemistry, 1615-1615 (2008)
Wesley E Smith et al.
ACS nano, 6(11), 9475-9484 (2012-10-09)
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