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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/REAXYS Number:
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

signalword

Danger

Hazard Classifications

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

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

446.0 °F - closed cup

flash_point_c

230 °C - closed cup

ppe

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
BCCL6305
BCCL6304
BCCJ5012
BCCF5419
BCCC1862

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Wettling, T.; et al.
Ger. Offen., 1993-1993 null
Zeng, Z.; et al.
European Journal of Organic Chemistry, 1615-1615 (2008)
Niemeyer, J.; et al.
European Journal of Inorganic Chemistry, 680-680 (2010)
Belyakova, Z. V.; et al
Russ. J. Gen. Chem., 80, 728-728 (2010)
Sanjeev Kumar Mahto et al.
Toxicology in vitro : an international journal published in association with BIBRA, 24(4), 1070-1077 (2010-04-07)
With the widespread use of quantum dots (QDs), the likelihood of exposure to QDs has been assumed to have increased substantially. Recently, QDs have been employed in numerous biological and medical applications. However, there is a lack of toxicological data
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