Bis(triphenylphosphine)palladium(II) chloride structure

3D Mol Similar

Bis(triphenylphosphine)palladium(II) chloride

: Iupac Name：ethane;methane;palladium(2+);triphenylphosphane;dichloride; CAS No.: 13965-03-2; Molecular Weight：701.9; Modify Date.: 2024-03-10 19:57; Introduction:
Bis(triphenylphosphine)palladium(II) chloride, with the chemical formula PdCl2(C6H5)3P2 and CAS registry number 13965-03-2, is a compound known for its applications in various chemical reactions. This coordination compound consists of a central palladium atom bonded to two chloride ions and two triphenylphosphine ligands. It is commonly used as a catalyst in organic synthesis, particularly in cross-coupling reactions such as the Suzuki-Miyaura and Heck reactions. Bis(triphenylphosphine)palladium(II) chloride is a yellow crystalline solid that is air-stable and soluble in organic solvents. It is an important reagent in the synthesis of pharmaceuticals, agrochemicals, and fine chemicals. This compound has been extensively studied and its structure and properties are well-documented in the scientific literature.
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1. Names and Identifiers

: 1.1 Name; Bis(triphenylphosphine)palladium(II) chloride; 1.2 Synonyms; 237-744-2 Bis(Triphenylphosphine)palladium (II) chloride BIS(TRIPHENYLPHOSPHINE)PALLADIUM CHLORIDE BIS-(TRIPHENYLPHOSPHINE)-PALLADIUM DICHLORIDE BIS(TRIPHENYLPHOSPHINE)PALLADIUM(II) DICHLORIDE bis(triphenylphosphino)palladium dichloride DICHLOROBIS(TRIPHENYLPHOSPHINE)PALLADATE (II) DICHLOROBIS(TRIPHENYLPHOSPHINE)PALLADIUM DICHLOROBIS(TRIPHENYLPHOSPHINE)PALLADIUM(II) MFCD00009593 PALLADIUM BIS(TRIPHENYLPHOSPHINE) DICHLORIDE PALLADIUM(II)BIS(TRIPHENYLPHOSPHINE) DICHLORIDE Phosphine, triphenyl-, palladium salt, hydrochloride (2:1:2) trans-Dichlorobis-(triphenylphosphine) palladium(II) trans-Dichlorobis(triphenylphosphine)palladium(II) Triphenylphosphonium chloride - palladium (2:2:1); View all

1.3 CAS No.: 13965-03-2

1.4 EINECS(EC#): 237-744-2

1.5 Molecular Formula: C36H30Cl2P2Pd (isomer)

1.6 Inchi: InChI=1S/2C18H15P.2ClH.Pd/c2*1-4-10-16(11-5-1)19(17-12-6-2-7-13-17)18-14-8-3-9-15-18;;;/h2*1-15H;2*1H;/q;;;;+2/p-2

1.7 InChIkey: YNHIGQDRGKUECZ-UHFFFAOYSA-L

1.8 Canonical Smiles: Cl[Pd]Cl.C1=CC=C(C=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.C1=CC=C(C=C1)P(C1=CC=CC=C1)C1=CC=CC=C1

1.9 Isomers Smiles: C.CC.CC.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.[Cl-].[Cl-].[Pd+2]

2. Properties

2.1 Melting point: 260°C

2.1 StorageTemp: Store below +30°C.

3. Safety and Handling

3.1 Hazard Codes: Xn

3.1 Risk Statements: 36/37/38-22-40-19

3.1 Safety Statements: 37/39-26-36/37

3.1 WGK Germany: 3

3.1 RTECS: RT3578000

4. MSDS

2.Hazard identification

2.1 Classification of the substance or mixture

Skin sensitization, Category 1A

Hazardous to the aquatic environment, long-term (Chronic) - Category Chronic 4

2.2 GHS label elements, including precautionary statements

Pictogram(s)
Signal word	Warning
Hazard statement(s)	H317 May cause an allergic skin reaction H413 May cause long lasting harmful effects to aquatic life
Precautionary statement(s)
Prevention	P261 Avoid breathing dust/fume/gas/mist/vapours/spray. P272 Contaminated work clothing should not be allowed out of the workplace. P280 Wear protective gloves/protective clothing/eye protection/face protection. P273 Avoid release to the environment.
Response	P302+P352 IF ON SKIN: Wash with plenty of water/... P333+P313 If skin irritation or rash occurs: Get medical advice/attention. P321 Specific treatment (see ... on this label). P362+P364 Take off contaminated clothing and wash it before reuse.
Storage	none
Disposal	P501 Dispose of contents/container to ...

2.3 Other hazards which do not result in classification

none

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5. NMR Spectrum

IR : KBr disc

IR : nujol mull

6. Synthesis Route

13965-03-2Total: 39 Synthesis Route

603-35-0 288 Suppliers

13965-03-2 288 Suppliers

Literatures:
Organometallics, , vol. 24, # 10 p. 2516 - 2527
Yield: null

15617-18-2

13965-03-2 288 Suppliers

Literatures:
Journal of the American Chemical Society, , vol. 110, p. 803
Yield: ~92%

14552-67-1

13965-03-2 288 Suppliers

Literatures:
Zeitschrift fuer Anorganische und Allgemeine Chemie, , vol. 576, p. 139 - 150
Yield: ~54%

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7. Precursor and Product

precursor:

14552-67-1

14323-43-4

256227-56-2

80182-10-1

12107-56-1

74593-76-3

612-12-4

852993-44-3

75-77-4

852993-45-4

98-88-4

14221-01-3

15617-18-2

114129-99-6

87841-34-7

10025-98-6

26973-01-3

603-35-0

157319-21-6

83965-84-8

108-90-7

84181-01-1

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product :

34876-51-2

868528-45-4

100-56-1

14221-01-3

15130-25-3

556112-20-0

1066-45-1

2189-60-8

31989-57-8

111-65-9

14243-64-2

751-38-2

8. Other Information

8.0 BRN: 4935975

8.1 Chemical Properties: Bis(triphenylphosphine)palladium chloride is a coordination compound of palladium containing two triphenylphosphine and two chloride ligands. It is a yellow solid that is soluble in some organic solvents. It is used for palladium-catalyzed coupling reactions, e.g. the Sonogashira–Hagihara reaction. The complex is square planar. Many analogous complexes are known with different phosphine ligands.

8.2 Uses: Bis(triphenylphosphine)palladium(II) chloride is used primarily in organometallic catalytic reactions due to the palladium content of the compound. It is also involved in crystalized structures of me tallacyclic complexes which show antiinflammatory and antifungal properties.

8.3 Synthesis: Bis(triphenylphosphine)palladium(II) chloride may be synthesized by treating palladium(II) chloride with triphenylphosphine:
PdCl2 + 2 PPh3 → PdCl2(PPh3)2

8.4 Reactions: Precatalyst for the carbonylative cyclization of malonate derivatives.
Catalyst used in the double allylation of activated olefins.
Precatalyst for the three-component preparation of 3-arylidene- (or 3-alkenylidene) tetrahydrofurans.
Precatalyst for the homocoupling of terminal alkynes.
Precatalyst in the cross-coupling of alkynylsilanols and aryl halides.
Catalyst for direct Pd-catalyzed alkynylation of N-fused heterocycles.
Catalyst for a tandem Heck reaction/C-H functionalization.
Catalyst for direct arylation of tautomerizable heterocycles.

8.5 General Description: Bis(triphenylphosphine)palladium(II) dichloride is an organometallic complex. It is an efficient cross-coupling catalyst for C-C coupling reaction, such as Negishi coupling, Suzuki coupling, Sonogashira coupling and Heck coupling reaction. Detection of bis(triphenylphosphine)palladium(II) dichloride by electrospray ionization quadrupole ion trap mass spectrometry using different imidazolium salts as the charge carrier has been reported. It is employed as catalyst for the Heck reaction medium.

8.6 Flammability and Explosibility: Nonflammable

9. Question & Answer

What is the Role of Bis(triphenylphosphine)palladium(II) Chloride in Organic Synthesis and Antiviral Drug Production? Aug 08 2023
General Description Bis(triphenylphosphine)palladium(II) chloride, a coordination complex of palladium and triphenylphosphine, is a valuable catalyst in organic synthesis. It is particularly useful in..
What is the production process of Bis(triphenylphosphine)palladium(II) chloride? Feb 11 2023
Bis(triphenylphosphine)palladium(II) chloride, with the molecular formula C36H30Cl2P2Pd and structural formula C36H30Cl2P2Pd, is insoluble in water but soluble in toluene and benzene. It is slightly s..
What is Bis(triphenylphosphine)palladium(II) chloride used for and how is it prepared? Nov 07 2020
Background and Overview[1] Bis(triphenylphosphine)palladium(II) chloride is insoluble in water. It is soluble in toluene and benzene, and slightly soluble in acetone and chloroform. It has a melting p..