nickel(2+) ion bis(triphenylphosphane) dichloride

• ChemBase ID: 302980
• Molecular Formular: C36H30Cl2NiP2
• Molecular Mass: 654.170322
• Monoisotopic Mass: 652.05532248
• SMILES: c1ccc(cc1)P(c1ccccc1)c1ccccc1.c1ccc(cc1)P(c1ccccc1)c1ccccc1.[Cl-].[Cl-].[Ni+2]
• Canonical SMILES: c1ccc(cc1)P(c1ccccc1)c1ccccc1.c1ccc(cc1)P(c1ccccc1)c1ccccc1.[Cl-].[Cl-].[Ni+2]
• InChI: InChI=1S/2C18H15P.2ClH.Ni/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
• InChIKey: ZBRJXVVKPBZPAN-UHFFFAOYSA-L

NAMES AND DATABASE IDS

Names

• IUPAC name: nickel(2+) ion bis(triphenylphosphane) dichloride
• IUPAC Traditional name: nickel(2+) ion bis(triphenylphosphine) dichloride
• Synonyms: Bis(triphenylphosphine)nickel(II) chloride; Bis(triphenylphosphine)dichloronickel(II); Dichlorobis(triphenylphosphine)nickel(II); 双(三苯基膦)二氯化镍(II)

Database IDs

• CAS Number: 14264-16-5
• EC Number: 238-154-8
• MDL Number: MFCD00009592

CALCULATED PROPERTIES

• Polarizability: 32.34495 Å^3
• Polar Surface Area: 0.0 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: false
• H Acceptors: 0
• H Donor: 0
• LogD (pH = 5.5): 5.1066
• LogD (pH = 7.4): 5.1066
• Log P: 5.1066
• Molar Refractivity: 81.6229 cm^3

PROPERTIES

Physical Property

• Apperance: Powder
• Melting Point: ca 225°C dec.

Safety Information

• Storage Warning: Hygroscopic
• RTECS: QR6170000
• European Hazard Symbols: X
• Risk Statements: 22
• Safety Statements: 36
• TSCA Listed: 是
• GHS Pictograms: GHS06
• GHS Hazard statements: H301
• GHS Precautionary statements: P264-P270-P301+P310-P321-P405-P501A

Product Information

• Purity: 98%

REFERENCES

• Catalyst for cross-coupling of organometallic reagents with aryl bromides: Tetrahedron Lett., 1389 (1977), and aryl tert-butyl sulfones: J. Chem. Soc., Perkin 1, 7 (1995), to give unsymmetrical biaryls. Symmetrical coupling of aryl halides can be effected in high yield with a Ni(0) catalyst generated in situ with Zn and triphenylphosphine in DMF, as a mild alternative to the Ullmann reaction: Tetrahedron Lett., 4089 (1977). For the analogous homocoupling of aryl mesylates, see: J. Org. Chem., 60, 176 (1995). The method has been extended to the formation aryl cyanides, providing an alternative to the classical CuCN route, and of diaryl sulfides: J. Org. Chem., 60, 6895 (1995):
  
• Catalyzes the coupling of Grignard reagents with allylic alcohols with displacement of the hydroxyl group: J. Chem. Soc., Chem. Commun., 1604 (1968). This alkene synthesis has been extended to enol ethers and methyl aryl ethers: J. Am. Chem. 101, 2246 (1979). The coupling of dithioacetals with Grignard reagents is also useful: Org. Synth. Coll., 9, 727 (1998), and refs therein.
• In the presence of Zn and pyridine, catalyzes the conjugate addition of alkyl bromides to ɑ?-unsaturated ketones, nitriles and esters: Russ. J. Gen. Chem., 65, 444 (1995).