![Chemical structure of NiCl₂(dppf) ([1,1′-bis(diphenylphosphino)ferrocene]dichloronickel(II), C₃₄H₂₈Cl₂FeNiP₂), CAS 67292-34-6, ≥98% — nickel(II) precatalyst, reduced in situ (for example with zinc or n-butyllithium) to the active nickel(0) catalyst. Used for Suzuki–Miyaura coupling of arylboronic acids with aryl chlorides and aryl sulfonates such as mesylates and tosylates, and for couplings with Grignard and organozinc reagents. Supplied by NorrChemica with DDP shipping. CoA and SDS provided.](http://www.norrchemica.com/cdn/shop/files/NiCl2_dppf.png?v=1792522475&width=1946)
NorrChemica™
NiCl₂(dppf)
NiCl₂(dppf) | CAS 67292-34-6 | ≥98%
| Pack size | Excl. VAT | Incl. VAT | Add to cart |
|---|---|---|---|
| 5 g | €74,20 | ||
| 10 g | €98,20 | ||
| 25 g | €129,20 | ||
| 100 g | €198,20 |
Taxes and fees, e.g. VAT, included in the price. Shipping calculated at checkout.Free shipping on EU, UK and EFTA orders above €250, and above €400 to the rest of the world.
Technical Specifications
| CAS Number | 67292-34-6 |
| MDL Number | MFCD00270284 |
| SMILES | C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C[CH]C=C3.C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=C[CH]3.Cl[Ni]Cl.[Fe] |
| InChI | InChI=1S/2C17H14P.2ClH.Fe.Ni/c2*1-3-9-15(10-4-1)18(17-13-7-8-14-17)16-11-5-2-6-12-16;;;;/h2*1-14H;2*1H;;/q;;;;;+2/p-2 |
| InChIKey | NSSWUOVWGSDARH-UHFFFAOYSA-L |
| PubChem CID | 16213132 |
| Molecular Formula | C₃₄H₂₈Cl₂FeNiP₂ |
| Molecular Weight | 683.98 g/mol |
| Melting Point | 285 °C (dec.) |
| Purity | ≥98% |
| Physical Form | Green to dark green powder |
| HS Code | 2931.90 |
| Shelf Life | Retest period: 36 months from date of manufacture |
| Storage Conditions | Store in a cool, dry place in a tightly sealed container under inert gas. |
Product Description & Scientific Applications
NiCl₂(dppf), [1,1′-bis(diphenylphosphino)ferrocene]dichloronickel(II), is a nickel(II) complex of the bidentate phosphine dppf, one of the first ligands used successfully in nickel-catalysed cross-coupling. It is a precatalyst: in the reaction mixture it is reduced to nickel(0) by zinc or manganese powder or by n-butyllithium, and some couplings of aryl chlorides need no added reductant.
Suzuki–Miyaura coupling. NiCl₂(dppf) couples arylboronic acids with aryl mesylates, arenesulfonates and aryl chlorides. Electron-rich and electron-poor aryl chlorides react; nitrile, aldehyde, ketone, ester, amide and amine groups are tolerated, nitro groups are not. Some heteroaryl chlorides also react.
Nickel-catalysed Suzuki–Miyaura coupling: X = Cl, OMs (mesylate) or OSO₂Ar (arenesulfonate); Ar and Ar′ are aryl groups. Zinc is used with mesylates and arenesulfonates, n-butyllithium with aryl chlorides; aryl chlorides can also react without an added reductant.
Kumada and Negishi coupling. NiCl₂(dppf) catalyses cross-coupling with Grignard and organozinc reagents. With aryl Grignard reagents it couples aryl mesylates, and with alkyl Grignard reagents it couples benzylic ethers. In naphthalenes that carry both a benzylic ether and a methoxy group, NiCl₂(dppf) reacts at the benzylic C–O bond, whereas NiCl₂(PCy₃)₂ reacts at the methoxy group.
C–N coupling. NiCl₂(dppf) catalyses the N-arylation of diarylamines, including carbazoles, phenothiazines and phenoxazines, with aryl halides to give triarylamines.
N-Arylation of a diarylamine; X = halide.
Carboxylation with CO₂. With manganese powder as the reductant and some added dppf, NiCl₂(dppf) converts naphthyl pivalates and carbon dioxide into naphthoic acids.
Shipping Destinations
- EU & UK: Priority delivery, 2–5 business days.
- United States (DDP): 3–7 business days, duties and taxes prepaid.
- EFTA Countries (DDP): 3–7 business days, duties and taxes prepaid.
- Worldwide: 7–14 business days, selected locations.
Safety Information
| GHS Pictograms |
|
| Signal Word | Danger |
| Hazard Class | Not regulated for transport |
| Transport Category | Not classified as dangerous goods for transport (ADR/IATA/IMDG) |
| H-Statements | H317 - H334 - H350 |
| P-Statements | P201 - P202 - P261 - P272 - P280 - P284 - P302+P352 - P304+P340 - P308+P313 - P333+P313 - P342+P311 - P362+P364 - P405 - P501 |
Documentation
| Safety Data Sheet | Download PDF |
![Chemical structure of NiCl₂(dppf) ([1,1′-bis(diphenylphosphino)ferrocene]dichloronickel(II), C₃₄H₂₈Cl₂FeNiP₂), CAS 67292-34-6, ≥98% — nickel(II) precatalyst, reduced in situ (for example with zinc or n-butyllithium) to the active nickel(0) catalyst. Used for Suzuki–Miyaura coupling of arylboronic acids with aryl chlorides and aryl sulfonates such as mesylates and tosylates, and for couplings with Grignard and organozinc reagents. Supplied by NorrChemica with DDP shipping. CoA and SDS provided.](http://www.norrchemica.com/cdn/shop/files/NiCl2_dppf.png?v=1792522475&width=1445)