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.: 2023-03-03 19:00

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1. Names and Identifiers

1.1 Name: Bis(triphenylphosphine)palladium(II) chloride
1.2 Synonyms: BIS(TRIPHENYLPHOSPHINE)PALLADIUM CHLORIDE BIS-(TRIPHENYLPHOSPHINE)-PALLADIUM DICHLORIDE BIS(TRIPHENYLPHOSPHINE)PALLADIUM(II) DICHLORIDE DICHLOROBIS(TRIPHENYLPHOSPHINE)PALLADATE (II) DICHLOROBIS(TRIPHENYLPHOSPHINE)PALLADIUM DICHLOROBIS(TRIPHENYLPHOSPHINE)PALLADIUM(II) PALLADIUM BIS(TRIPHENYLPHOSPHINE) DICHLORIDE PALLADIUM(II)BIS(TRIPHENYLPHOSPHINE) DICHLORIDE

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 InChkey: 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

603-35-0 290 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. Other Information

7.0 BRN: 4935975

7.1 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.

7.2 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.

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

7.4 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.

7.5 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.

7.6 Flammability and Explosibility: Nonflammable

8. Question & Answer

Bis(triphenylphosphine)palladium(II) chloride – a coordination compound of palladium Aug 25 2020
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 rea...

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