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14221-01-3

Basic Information
CAS No.: 14221-01-3
Name: Tetrakis(triphenylphosphine)palladium
Article Data: 90
Molecular Structure:
Molecular Structure of 14221-01-3 (Tetrakis(triphenylphosphine)palladium)
Formula: C72H60P4Pd
Molecular Weight: 1155.58
Synonyms: Palladium, tetrakis(triphenylphosphine)-, (T-4)-;Tetra(triphenylphosphine)palladium;Tetrakis(triphenylphosphine)palladium(o);Tetrakis(triphenylphosphine);Tetrakis(tripheny1phosphine)palladium (Pd(PPh3)4);
EINECS: 238-086-9
Melting Point: 103-107 ºC
Boiling Point: 360oC at 760 mmHg
Flash Point: 181.7oC
Solubility: insoluble in water
Appearance: yellow crystals
Hazard Symbols: HarmfulXn,IrritantXi
Risk Codes: 20/22-40
Safety: 22-24/25-36/37
PSA: 54.36000
LogP: 13.77920
Synthetic route

palladium tetraammine di(hydrogen carbonate)

603-35-0

triphenylphosphine

14221-01-3

tetrakis(triphenylphosphine) palladium(0)

Conditions
ConditionsYield
In methanol for 1.5h; Heating / reflux;98%
603-35-0

triphenylphosphine

palladium dichloride

14221-01-3

tetrakis(triphenylphosphine) palladium(0)

Conditions
ConditionsYield
With sodium hydrogencarbonate; ascorbic acid In dimethyl sulfoxide at 20 - 60℃; for 2.33333h; Reagent/catalyst;97.6%
Stage #1: triphenylphosphine; palladium dichloride In N,N-dimethyl-formamide at 140℃; for 0.5h;
Stage #2: With hydrazine hydrate In N,N-dimethyl-formamide at 80℃;
95%
Stage #1: triphenylphosphine; palladium dichloride In dimethyl sulfoxide at 20 - 145℃; Inert atmosphere; Schlenk technique;
Stage #2: With hydrazine hydrate In dimethyl sulfoxide at 23℃;
94%

palladium dichloride

14221-01-3

tetrakis(triphenylphosphine) palladium(0)

Conditions
ConditionsYield
With triphenylphosphine; hydrazine In water; N,N-dimethyl-formamide N2; refluxing PdCl2 and PPh3 (30 min), addn. of aq. N2H4 (80°C); pptn., filtration, washing (MeOH, ether), drying;95%

(1S),(2R),(3R)-acetylacetonato(1-methyl-3-phenyl-π-allyl)palladium(II)

A

14221-01-3

tetrakis(triphenylphosphine) palladium(0)

B

118578-64-6

(R)-<1-((E)-styryl)ethyl>acetylacetone

Conditions
ConditionsYield
With triphenylphosphine In tetrahydrofuran excess PPh3, stirring (room temp., 50 min), pptn.; filtration, org. product isolated by preparative TLC (silica, hexane/ethyl acetate);A n/a
B 94%

[(P((C6H5)3))Pd((C6H4)2NH)]2

A

14221-01-3

tetrakis(triphenylphosphine) palladium(0)

B

86-74-8

9H-carbazole

Conditions
ConditionsYield
1 h, room temp.;A n/a
B 92%

HPd2(1+)*4P(C6H5)3*CO*ClO4(1-)={HPd2(P(C6H5)3)4(CO)(ClO4)}

14221-01-3

tetrakis(triphenylphosphine) palladium(0)

Conditions
ConditionsYield
With triphenylphosphine In benzene dissolving freshly prepd. (HPd2(P(C6H5)3)4(CO)(ClO4))(n) and P(C6H5)3 in benzene, stirring for 1 h at 20°C; evapn. of benzene under vac. to dryness, treating residue successively with several portions of 50% alc., washing with C6H6 and drying under vac.; elem. anal.;91%

2Pd(2+)*4CH3COO(1-)*2P(C6H5)3=[Pd(P(C6H5)3)(CH3COO)2]2

14221-01-3

tetrakis(triphenylphosphine) palladium(0)

Conditions
ConditionsYield
With hydrogen; triphenylphosphine In toluene High Pressure; at 50°C under 40 atm of H2 for 3 h; mixed with pentane (Ar), ppt. washed with ether and pentane, dried (vac.); elem. anal.;90%

palladium(II) acetylacetonate

14221-01-3

tetrakis(triphenylphosphine) palladium(0)

Conditions
ConditionsYield
With anthracene; magnesium; triphenylphosphine In tetrahydrofuran byproducts: magnesium acetylacetonate; Sonication; addn. of anthracene and EtBr to Mg in THF under Ar, ultrasonic bath (35 kH), addn. of the phosphine at 65°C, then of the Pd-salt during 20 min; the mixt. is cooled to 23°C, filtn., washed (pentane), dried (vac.);89.5%

Pd8(CO)10(P(C6H5)3)4

14221-01-3

tetrakis(triphenylphosphine) palladium(0)

Conditions
ConditionsYield
With triphenylphosphine In acetone excess of P(C6H5)3 under inert gas atmosphere;;86%
13965-03-2

bis-triphenylphosphine-palladium(II) chloride

14221-01-3

tetrakis(triphenylphosphine) palladium(0)

Conditions
ConditionsYield
With sodium hydroxide; tetra(n-butyl)ammonium hydrogensulfate; triphenylphosphine In tetrahydrofuran byproducts: NaCl, HCl, (C6H5)3PO; stirred at 25°C for 24 h; aq. layer removed, org. layer evaporated at 40°C in vacuo, residue treated with abs. C2H5OH, stirred at 60°C for 20 min, filtered, kept at -15°C for 30 min, filtered (Ar), washed (cold abs. C2H5OH), dried in vacuo; IR, NMR;84%
With sodium borohydride; triphenylphosphine In ethanol the soln. was cooled in cold water, ppt. was filtered, washed with water, EtOH, heptane;83%
With hydrazine Inorg. Synth. 13 (1972) 121;
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Specification

The Tetrakis(triphenylphosphine)palladium, with the cas registry number 14221-01-3, has the IUPAC name of palladium; triphenylphosphane. This is a kind of yellow crystals and is insoluble in water, ether and alcohol while soluble in benzene, toluene. Besides, it is sensitive to light and air. Besides, its product categories are various, including Straight chain compounds; Metal Compounds; blocks; pharmacetical; Catalysts-Ligands; Catalysts for Organic Synthesis; Classes of Metal Compounds; Homogeneous Catalysts; Metal Complexes; Pd (Palladium) Compounds; Synthetic Organic Chemistry; Transition Metal Compounds; Fine Chemical Catalysts.

The characteristics of this chemical are as follows: (1)ACD/LogP: 5.69; (2)# of Rule of 5 Violations: 1 ; (3)#H bond acceptors: 0 ; (4)#Freely Rotating Bonds: 3 ; (5)Polar Surface Area: 13.59 ; (6)Flash Point: 181.7 °C ; (7)Enthalpy of Vaporization: 58.18 kJ/mol ; (8)Boiling Point: 360 °C at 760 mmHg ; (9)Vapour Pressure: 4.74E-05 mmHg at 25°C ; (10)Exact Mass: 1154.268031; (11)MonoIsotopic Mass: 1154.268031; (12)Topological Polar Surface Area: 0; (13)Heavy Atom Count: 77; (14)Formal Charge: 0; (15)Complexity: 202.

Preparation of Tetrakis(triphenylphosphine)palladium:Tetrakis(triphenylphosphine)palladium was first prepared by Lamberto Malatesta and his group in Milan in the 1960s by reduction of sodium chloropalladate with hydrazine in the presence of the phosphine. It is commercially available, but can be prepared in two steps from Pd(II) precursors:
PdCl2 + 2 PPh3 → cis-PdCl2(PPh3)2
cis-PdCl2(PPh3)2 + 2 PPh3 + 2.5 N2H4 → Pd(PPh3)4 + 0.5 N2 + 2 N2H5+Cl-

Use of Tetrakis(triphenylphosphine)palladium: As to its usage, it is widely applied in many ways. It could be used in synthetize the catalytic agent in pharmaceutic and pesticide, such as being used in coupling reaction of Suzuki, Kumada and Negishi; It could also be used widely in important isomerization reaction. 

When deal with this chemical, you should be very cautious. Firstly, being irritating to eyes, respiratory system and skin, it may may cause inflammation to the skin or other mucous membranes. Seconldy, it is harmful and may cause damage to health. If by inhalation and if swallowed, it will be very dangerous. And it also has limited evidence of a carcinogenic effect. Therefore, you should take the following instructions to protect yourself. Wear suitable protective clothing, gloves and eye/face protection, and if in case of contacting with eyes, rinse immediately with plenty of water and seek medical advice. Then remember to avoid contacting with skin and eyes and do not breathe dust.

In addition, you could obtain the molecular structure by converting the following datas:
(1)Canonical SMILES: C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=
CC=C3.C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3.[Pd]
(2)InChI: InChI=1S/4C18H15P.Pd/c4*1-4-10-16(11-5-1)19(17-12-6-2-7-13-17)18-14-8-3-9-15-18;/h4*1-15H; (3)InChIKey: NFHFRUOZVGFOOS-UHFFFAOYSA-N