Tetrakis(triphenylphosphin)palladium

Bezeichnung:Tetrakis(triphenylphosphin)palladium

CAS-Nr14221-01-3

Englisch Name:Tetrakis(triphenylphosphine)palladium

CBNumberCB6163934

SummenformelC72H60P4Pd

Molgewicht1155.561844

MOL-Datei14221-01-3.mol

Synonyma

Tetrakis(triphenylphosphin)palladium

Tetrakis(triphenylphosphin)palladium physikalisch-chemischer Eigenschaften

Schmelzpunkt	103-107 °C
Dampfdruck	0Pa at 25℃
storage temp.	2-8°C
Löslichkeit	Chloroform (Slightly), Ethyl Acetate (Slightly), Methanol (Slightly)
Aggregatzustand	Fine Powder or Platelets
Farbe	Bright yellow to khaki
Wasserlöslichkeit	insoluble
Hydrolytic Sensitivity	7: reacts slowly with moisture/water
Sensitive	Light Sensitive/Air Sensitive
BRN	6704828
Stabilität	Light Sensitive, Moisture Sensitive
InChIKey	NANALCPCPBPJAB-UHFFFAOYSA-N
LogP	5.69 at 20℃
CAS Datenbank	14221-01-3(CAS DataBase Reference)
EPA chemische Informationen	Palladium, tetrakis(triphenylphosphine)-, (T-4)- (14221-01-3)

Sicherheit

Kennzeichnung gefährlicher	Xi,Xn
R-Sätze:	20/22-40-36/37/38
S-Sätze:	22-24/25-36/37-37/39-26
WGK Germany	3
F	8-10-23
Hazard Note	Air sensitive/Light sensitive/Irritant
TSCA	No
HazardClass	MOISTURE SENSITIVE, STORED UNDER ARGON
HS Code	28439090

Gefahreninformationscode (GHS)

Tetrakis(triphenylphosphine)palladium Chemische Eigenschaften,Einsatz,Produktion Methoden

R-Sätze Betriebsanweisung:
R20/22:Gesundheitsschädlich beim Einatmen und Verschlucken.
R40:Verdacht auf krebserzeugende Wirkung.
R36/37/38:Reizt die Augen, die Atmungsorgane und die Haut.
S-Sätze Betriebsanweisung:
S22:Staub nicht einatmen.
S24/25:Berührung mit den Augen und der Haut vermeiden.
S36/37:Bei der Arbeit geeignete Schutzhandschuhe und Schutzkleidung tragen.
S37/39:Bei der Arbeit geeignete Schutzhandschuhe und Schutzbrille/Gesichtsschutz tragen.
S26:Bei Berührung mit den Augen sofort gründlich mit Wasser abspülen und Arzt konsultieren.
Chemische Eigenschaften
yellow crystals
Verwenden
Pd(PPh3)4 is widely used as a catalyst for palladium-catalyzed coupling reactions. Prominent applications include the Heck reaction, Suzuki coupling, Stille coupling, Sonogashira coupling, and Negishi coupling.
Verwenden
A high-yielding catalyst used in coupling reactions.
Verwenden
suzuki reaction
Verwenden
Tetrakis(triphenylphosphine)palladium(0) is widely used as a catalyst for palladium-catalyzed coupling reactions.
Application
Palladium-Catalyzed Three-Component Reaction for the Synthesis of Imidazolidinones.

Once the Schlenk tube containing K2CO3 (55 mg, 0.40 mmol) is flamed, dried, and filled with argon, Tetrakis(triphenylphosphine)palladium (12 mg, 0.010 mmol), PMB-protected 2,3-allenylamine (37 mg, 0.20 mmol), iodobenzene (58 mg, 0.28 mmol), phenyl isocyanate (36 mg, 0.30 mmol), and CH3CN (4 mL) are added sequentially. The resulting solution is heated to and stirred at 70°C. When the reaction is completed as monitored by TLC, the solvent is evaporated under reduced pressure, and the residue is purified by chromatography on silica gel (petroleum ether : ethyl acetate = 7:1) to afford the corresponding imidazolidione (72 mg, Y. 96%) as an oil.
Reaktionen
1. Catalyst for Suzuki coupling of chiral secondary organoboronic esters.
2. Palladium-catalyzed SNAr reactions for the synthesis of heteroaryl ethers.
3. Catalyst for cross-coupling of a-diazocarbonyl compouns with arylboronic acids.
4. Diastereoselective synthesis of trans-1,2-diazetidines.
5. Palladium-catalyzed alkynyl iminium ion cyclization.
6. Widely used reagent in a variety of transformations including Heck arylation, enyne and diyne cycloisomerization.
7. Catalysts for cross-coupling.
Flammability and Explosibility
Non flammable
läuterung methode
The palladium complex is recrystallised from EtOH. It should not be heated excessively as it dissociates to Pd(PPh3)3 and PdPh3 and then further to Pd(PPh3)2 and PPh3. It is also air sensitive as PPh3 is oxidized to PPh3O. It is stable only for short periods because on exposure to heat or air it turns from yellow to orange and dissociates in solution so the solutions should be used directly. However it can always be prepared freshly by mixing Pd(NO3)2 (2mmols) and PPh3(2mmols) in hot *C6H6 when vigorous evolution of nitric oxide occurs and a solid mass separates. This is collected and crystallised from EtOH. Its cryoscopic constant in *C6H6 (at 0.601g/20mL) corresponds to M 1156 [Malatesta & Angoletti J Chem Soc 1186 1957]. It is a useful catalyst for Suzuki coupling reactions [Trost Tetrahedron 33 2615 1977]. [Beilstein 16 IV 954.] This palladium catalyst bound to a polymer support (~0.06mmol/g) is also commercially available [cf Fenger & LeDrain Tetrahedron Lett 39 4287 1998]. [Beilstein 16 IV 954.]

Tetrakis(triphenylphosphine)palladium Upstream-Materialien And Downstream Produkte

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