Tris(4-chlorphenyl)phosphin

Bezeichnung:Tris(4-chlorphenyl)phosphin

CAS-Nr1159-54-2

Englisch Name:TRIS(4-CHLOROPHENYL)PHOSPHINE

CBNumberCB3372856

SummenformelC18H12Cl3P

Molgewicht365.62

MOL-Datei1159-54-2.mol

Synonyma

Tris(4-chlorphenyl)phosphin

Tris(4-chlorphenyl)phosphin physikalisch-chemischer Eigenschaften

Schmelzpunkt	100-103 °C (lit.)
Siedepunkt	427.6±40.0 °C(Predicted)
storage temp.	Inert atmosphere,Room Temperature
Aggregatzustand	crystal
Farbe	white
Sensitive	Air Sensitive
BRN	751458
InChI	1S/C18H12Cl3P/c19-13-1-7-16(8-2-13)22(17-9-3-14(20)4-10-17)18-11-5-15(21)6-12-18/h1-12H
InChIKey	IQKSLJOIKWOGIZ-UHFFFAOYSA-N
SMILES	Clc1ccc(cc1)P(c2ccc(Cl)cc2)c3ccc(Cl)cc3
CAS Datenbank	1159-54-2(CAS DataBase Reference)

Sicherheit

Kennzeichnung gefährlicher	Xi
R-Sätze:	36/37/38
S-Sätze:	26-37/39
RIDADR	3278
WGK Germany	3
TSCA	No
PackingGroup	III
HS Code	29310099
Speicherklasse	11 - Combustible Solids
Hazard Classifications	Eye Irrit. 2 Skin Irrit. 2 STOT SE 3

Gefahreninformationscode (GHS)

TRIS(4-CHLOROPHENYL)PHOSPHINE Chemische Eigenschaften,Einsatz,Produktion Methoden

R-Sätze Betriebsanweisung:
R36/37/38:Reizt die Augen, die Atmungsorgane und die Haut.
S-Sätze Betriebsanweisung:
S26:Bei Berührung mit den Augen sofort gründlich mit Wasser abspülen und Arzt konsultieren.
S37/39:Bei der Arbeit geeignete Schutzhandschuhe und Schutzbrille/Gesichtsschutz tragen.
Chemische Eigenschaften
white to light yellow crystal powde
Verwenden
Catalyst for:
- Preparation of chromans and (E,E)-1,3-dienes via reaction of γ-substituted allenoates with aldehydes
- Solvent-free Heck reactions
Cocatalyst in:
- Regioselective carbomagnesiation of terminal alkynes and enynes with alkyl Grignard reagents
- Rhodium-catalyzed coordination-assisted regioselective alkenylation of aromatic C-H bonds with terminal silylacetylenes
- Rhodium-catalyzed hydrogenation reactions
- Platinum-catalyzed allylation reactions
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
reaction type: Cross Couplings
Synthese

4576-56-1

1159-54-2

The general procedure for the synthesis of tris(4-chlorophenyl)phosphine oxide from tris(4-chlorophenyl)phosphine oxide was as follows: 5100 mg (0.262 mmol) of tris(4-chlorophenyl)phosphine oxide was reacted with 6 mg of I (26 μmol) and 130 μL (0.52 mmol) of tributylphosphine in 1 mL of mixed solvent of acetonitrile/THF (1:1, v/v) under nitrogen protection The reaction was carried out at room temperature for 10 min. After stirring for 10 min at room temperature, the reaction was quenched with 100 μL HO. The reaction mixture was diluted with 10 mL of ethyl acetate and washed three times (5 mL each) with saturated aqueous NaHCOsolution. The organic phase was dried with NaSO, filtered and concentrated under reduced pressure. The residue was recrystallized with 2 mL of methanol, the crystals were collected by filtration, washed and dried under vacuum to give 95 mg (0.260 mmol, 99%) of tris(4-chlorophenyl)phosphine.
Einzelnachweise
[1] Patent: WO2011/123037, 2011, A1. Location in patent: Page/Page column 23-24
[2] Journal of Organic Chemistry, 2008, vol. 73, # 4, p. 1524 - 1531
[3] Chinese Chemical Letters, 2014, vol. 25, # 1, p. 176 - 178
[4] Russian Journal of General Chemistry, 2015, vol. 85, # 5, p. 1156 - 1160
[5] Zh. Obshch. Khim.,

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