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00676

Sigma-Aldrich

Trioctylphosphine oxide

for extraction analysis, ≥98.5%

Synonym(s):

(Oct)3PO, TOPO®

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About This Item

Linear Formula:
[CH3(CH2)7]3PO
CAS Number:
78-50-2
Molecular Weight:
386.63
Beilstein:
1796648
EC Number:
201-121-3
MDL number:
MFCD00002083
UNSPSC Code:
12352001
PubChem Substance ID:
329747118
NACRES:
NA.22

grade

for extraction analysis

Quality Level

200

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 oxide

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
GHS05

Signal Word

Danger

Hazard Statements

H315,H318,H412

Hazard Classifications

Aquatic Chronic 3 - Eye Dam. 1 - Skin Irrit. 2

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

446.0 °F - closed cup

Flash Point(C)

230 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

JAN Code

00676-VAR:
00676-BULK:
00676-10G:
00676-50G:

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Certificates of Analysis (COA)

Lot/Batch Number
BCCF5419
BCCC1862
BCBX3954
BCBW0967
BCBT6998

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Wettling, T.; et al.
Ger. Offen., 1993-1993 null
Belyakova, Z. V.; et al
Russ. J. Gen. Chem., 80, 728-728 (2010)
Niemeyer, J.; et al.
European Journal of Inorganic Chemistry, 680-680 (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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