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287822

Sigma-Aldrich

Tri(o-tolyl)phosphine

97%

Synonym(s):

P(o-tol)3, Tris(o-tolyl)phosphine

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About This Item

Linear Formula:
(CH3C6H4)3P
CAS Number:
6163-58-2
Molecular Weight:
304.37
Beilstein:
661212
EC Number:
228-193-9
MDL number:
MFCD00008514
UNSPSC Code:
12352128
PubChem Substance ID:
24857295
NACRES:
NA.22

Quality Level

200

Assay

97%

reaction suitability

reaction type: Cross Couplings
reaction type: Silylations
reagent type: ligand
reaction type: Buchwald-Hartwig Cross Coupling Reaction
reagent type: ligand
reaction type: Heck Reaction
reagent type: ligand
reaction type: Negishi Coupling
reagent type: ligand
reaction type: Stille Coupling
reagent type: ligand
reaction type: Suzuki-Miyaura Coupling

mp

123-125 °C (lit.)

functional group

phosphine

SMILES string

Cc1ccccc1P(c2ccccc2C)c3ccccc3C

InChI

1S/C21H21P/c1-16-10-4-7-13-19(16)22(20-14-8-5-11-17(20)2)21-15-9-6-12-18(21)3/h4-15H,1-3H3

InChI key

COIOYMYWGDAQPM-UHFFFAOYSA-N

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General description

Tri(o-tolyl)phosphine is a ligand used in the heck reaction and suzuki coupling of propargylic carbonates.

Application

Ligand used in a ruthenium-catalyzed direct amination of alcohols.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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Valerio Cinà et al.
ChemPlusChem, 85(3), 391-398 (2020-03-03)
Hybrid nanostructures with switchable and reversible "blue-red-green" emission were efficiently synthesized. These nanostructures comprise polyhedral oligomeric silsesquioxanes (POSS) that behave as a nanocage that can be functionalized with terpyridine-based organic ligands, which can be easily complexed with europium (III) ions.
Wenhan Xu et al.
Small (Weinheim an der Bergstrasse, Germany), 15(28), e1901582-e1901582 (2019-05-16)
Polymer dielectrics are ubiquitous in advanced electric energy storage systems. However, the relatively low operating temperature significantly menaces their widespread application at high temperatures, such as for hybrid vehicles and aerospace power electronics. Spider silk, a natural nanocomposite comprised of
Yih-Chun Chen et al.
ChemSusChem, 11(18), 3225-3233 (2018-07-08)
We have demonstrated two novel donor-acceptor-donor (D-A-D) hole-transport material (HTM) with spiro[fluorene-9,9'-phenanthren-10'-one] as the core structure, which can be synthesized through a low-cost process in high yield. Compared to the incorporation of the conventional HTM of commonly used 2,2',7,7'-tetrakis[N,N-di(4-methoxyphenyl)amino]-9,9'-spirobifluorene (Spiro-OMeTAD)
Tri (o-tolyl) phosphine for highly efficient Suzuki coupling of propargylic carbonates with boronic acids
Junzhe X et al.
Chemical Communications (Cambridge, England), 54, 10451-10454 (2018)
Coordination chemistry and mechanisms of metal-catalyzed CC-coupling reactions. Part 7. Heck vinylation of aryl halides with n-butyl acrylate: relevance of PC bond cleavage to catalyst deactivation
Wolfgang H A et al.
Journal of Molecular Catalysis. B, Enzymatic, 103, 133-146 (1995)
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Catalyst Screening with Catalexis

The Catalexis platform enhances catalysis by digitally optimizing catalyst selection to identify the most effective phosphine ligands for cross-coupling reactions.

Catalyst Screening with Catalexis

The Catalexis platform enhances catalysis by digitally optimizing catalyst selection to identify the most effective phosphine ligands for cross-coupling reactions.

Catalyst Screening with Catalexis

The Catalexis platform enhances catalysis by digitally optimizing catalyst selection to identify the most effective phosphine ligands for cross-coupling reactions.

Catalyst Screening with Catalexis

The Catalexis platform enhances catalysis by digitally optimizing catalyst selection to identify the most effective phosphine ligands for cross-coupling reactions.

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