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| | 1,4-Bis(diphenylphosphino)butane-palladium(II) chloride Basic information | | Reaction |
| Product Name: | 1,4-Bis(diphenylphosphino)butane-palladium(II) chloride | | Synonyms: | Palladium(ii) chloride 1,4-b;1,4-Bis(diphenylphosphino)butane-palladium(II) chloride,98+%;Dichloro-1,4-bis(diphenylphosphino)butane-palladium(II), Palladium(II) chloride 1,4-bis(diphenylphosphino)butane complex;Dichloro[bis(1,4-diphenylphosphino)butane]palladium(II), Pd 17.6%;1,4-Butylenebis(diphenylphosphine)-palladium dichloride;Dichloro[1,4-bis(diphenylphosphino)butane]palladium (II) ,98%;4-Bis(diphenylphosphino)butane-palladiuM(II) chloride;PDCI2(DPPB) | | CAS: | 29964-62-3 | | MF: | C28H28P2.Cl2Pd | | MW: | 603.8 | | EINECS: | 678-067-6 | | Product Categories: | Pd (Palladium) Compounds;Synthetic Organic Chemistry;Transition Metal Compounds;Catalysts for Organic Synthesis;Classes of Metal Compounds;Homogeneous Catalysts;Metal Complexes;Metal Compounds;Pd | | Mol File: | 29964-62-3.mol |  |
| | 1,4-Bis(diphenylphosphino)butane-palladium(II) chloride Chemical Properties |
| Melting point | 285-305 °C | | storage temp. | under inert gas (nitrogen or Argon) at 2-8°C | | solubility | Soluble in ethanol, benzene, and ethereal solvents. | | form | Powder | | color | light-yellow | | InChI | 1S/C28H28P2.2ClH.Pd/c1-5-15-25(16-6-1)29(26-17-7-2-8-18-26)23-13-14-24-30(27-19-9-3-10-20-27)28-21-11-4-12-22-28;;;/h1-12,15-22H,13-14,23-24H2;2*1H;/q;;;+2/p-2 | | InChIKey | JQXJBXVWVPVTOO-UHFFFAOYSA-L | | SMILES | P(C1=CC=CC=C1)(CCCCP(C1=CC=CC=C1)C1C=CC=CC=1)C1=CC=CC=C1.[Pd](Cl)Cl |
| Hazard Codes | Xn | | Risk Statements | 36/37/38 | | Safety Statements | 24/25-36-27 | | WGK Germany | 3 | | F | 1-10 | | HS Code | 28439000 | | Storage Class | 13 - Non Combustible Solids |
| | 1,4-Bis(diphenylphosphino)butane-palladium(II) chloride Usage And Synthesis |
| Reaction |
- Catalyst for the Grignard coupling for regioand stereoselective monoalkylation and arylation of 1,1-dichloro-1-alkenes
- Synthetic pyrethriods: catalyst for the Negishi coupling of (2,2-dihaloethenyl)cyclopropanecarboxylates
| | Chemical Properties | yellow solid | | Uses | Dichloro[bis(1,4-diphenylphosphino)butane]palladium(II) is used for the catalysis of styrene carbonylation, coupling of alkyl Grignard reagents with organic halides, selective monoalkylation of organic polyhalides, and modification of the dihalovinyl moiety of synthetic pyrethroids. | | Preparation | Dichloro[1,4-bis(diphenylphosphino)butane]palladium(II) (1,4-Bis(diphenylphosphino)butane-palladium(II) chloride) can be prepared conveniently in situ by mixing the bidentate phosphine ligand and
(PhCN)2PdCl2 in either benzene or chloroform.[1] The preparation of (dppb)PdCl2 is also possible through the
reaction of PdCl2 with dppb in acetone, a process that slowly forms the catalyst as a white precipitate which
can be isolated in 51% yield.[2] Preparation of the hydrate complex is possible via the reaction of Na2[PdCl4]
with dppb in a mixture of CH2Cl2 and water. | | reaction suitability | core: palladium
reaction type: Buchwald-Hartwig Cross Coupling Reaction
reaction type: Cross Couplings
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: catalyst | | Synthesis | Example 3
Step 1: 10 mL of palladium sponge was mixed with concentrated hydrochloric acid and concentrated nitric acid in a 3:1 volume ratio until the palladium sponge was completely dissolved. 37% concentrated hydrochloric acid was added to the solution and filtered to remove insoluble material while treating the brown nitrogen oxides produced. The filtrate was concentrated to a solution of chloropalladium acid with a palladium concentration of 0.5 g/mL.
Step 2: An N,N-dimethylformamide solution of bis(diphenylphosphino)butane was prepared by adding 44 g of 1,4-bis(diphenylphosphino)butane to 100 mL of N,N-dimethylformamide, and heating to 50°C. The N,N-dimethylformamide solution of bis(diphenylphosphino)butane was then heated to 50°C.
Step 3: The chloropalladium acid solution prepared in step 1 was added dropwise to the bis(diphenylphosphino)butane solution in step 2 under stirring. The reaction was stirred at 50 °C for 60 minutes. After completion of the reaction, the reaction solution was cooled and filtered, and the filter cake was collected.
Step 4: The filter cake obtained in Step III was washed with anhydrous ethanol and then dried under vacuum at 50 °C for 4 h. A light yellow 1,4-bis(diphenylphosphino)butane-palladium(II) chloride complex (C28H28Cl2P2Pd) of 56.1 g was obtained in 98.9% yield. | | References | 1. Sugi, Y.; Bando, K.-I. CL 1976, 727.
2. Sanger, A. R. JCS(D) 1977, 1971.
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| | 1,4-Bis(diphenylphosphino)butane-palladium(II) chloride Preparation Products And Raw materials |
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