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Tetrakis(triphenylphosphin)palladium

Tetrakis(triphenylphosphine)palladium Struktur
14221-01-3
CAS-Nr.
14221-01-3
Bezeichnung:
Tetrakis(triphenylphosphin)palladium
Englisch Name:
Tetrakis(triphenylphosphine)palladium
Synonyma:
PD(PPH3)4;TETRAKIS(TRIPHENYLPHOSPHINE)PALLADIUM(0);etrakis(triphenylphosphine)palladiuM;TETRAKIS(TRIPHENYLPHOSPHINE)PALLADIUM(O);PALLADIUM (0) TETRAKIS(TRIPHENYLPHOSPHINE);Tetra(triphenylphosphine) palladium;Tetrakis(triphenylphosphine)palladiu;PALLADIUM-TETRAKIS(TRIPHENYLPHOSPHINE);Tetrakis(triphenylphosphine)palladium, tech;Tetrakis(triphenylphosphine)palladium(0), 99.8% (metals basis), Pd 9% min
CBNumber:
CB6163934
Summenformel:
C72H60P4Pd
Molgewicht:
1155.561844
MOL-Datei:
14221-01-3.mol

Tetrakis(triphenylphosphin)palladium Eigenschaften

Schmelzpunkt:
103-107 °C
Dampfdruck
0Pa at 25℃
storage temp. 
2-8°C
L?slichkeit
Chloroform (Slightly), Ethyl Acetate (Slightly), Methanol (Slightly)
Aggregatzustand
Fine Powder or Platelets
Farbe
Bright yellow to khaki
Wasserl?slichkeit
insoluble
Hydrolytic Sensitivity
7: reacts slowly with moisture/water
Sensitive 
Light Sensitive/Air Sensitive
BRN 
6704828
Stabilit?t:
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
  • Risiko- und Sicherheitserkl?rung
  • Gefahreninformationscode (GHS)
Kennzeichnung gef?hrlicher Xi,Xn
R-S?tze: 20/22-40-36/37/38
S-S?tze: 22-24/25-36/37-37/39-26
WGK Germany  3
8-10-23
Hazard Note  Air sensitive/Light sensitive/Irritant
TSCA  No
HazardClass  MOISTURE SENSITIVE, STORED UNDER ARGON
HS Code  28439090
Bildanzeige (GHS) GHS hazard pictograms
Alarmwort Warnung
Gefahrenhinweise
Code Gefahrenhinweise Gefahrenklasse Abteilung Alarmwort Symbol P-Code
H302 Gesundheitssch?dlich bei Verschlucken. Akute Toxizit?t oral Kategorie 4 Warnung GHS hazard pictogramssrc="/GHS07.jpg" width="20" height="20" /> P264, P270, P301+P312, P330, P501
Sicherheit
P264 Nach Gebrauch gründlich waschen.
P264 Nach Gebrauch gründlich waschen.
P270 Bei Gebrauch nicht essen, trinken oder rauchen.
P301+P312 BEI VERSCHLUCKEN: Bei Unwohlsein GIFTINFORMATIONSZENTRUM/Arzt/... (geeignete Stelle für medizinische Notfallversorgung vom Hersteller/Lieferanten anzugeben) anrufen.
P501 Inhalt/Beh?lter ... (Entsorgungsvorschriften vom Hersteller anzugeben) zuführen.

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

R-S?tze Betriebsanweisung:

R20/22:Gesundheitssch?dlich beim Einatmen und Verschlucken.
R40:Verdacht auf krebserzeugende Wirkung.
R36/37/38:Reizt die Augen, die Atmungsorgane und die Haut.

S-S?tze 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

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.
Palladium-Catalyzed Three-Component Reaction for the Synthesis of Imidazolidinones.gif
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.
    Tetrakis(triphenylphosphine)palladium Reaction 1
    Tetrakis(triphenylphosphine)palladium Reaction 2

l?uterung 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(triphenylphosphin)palladium Upstream-Materialien And Downstream Produkte

Upstream-Materialien

Downstream Produkte


Tetrakis(triphenylphosphin)palladium Anbieter Lieferant Produzent Hersteller Vertrieb H?ndler.

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