λ1-rhodium(1+) ion bis(methanidylidyneoxidanium) (2Z)-4-oxopent-2-en-2-olate

• ChemBase ID: 303332
• Molecular Formular: C7H7O4Rh
• Molecular Mass: 258.03358
• Monoisotopic Mass: 257.9399377
• SMILES: C/C(=C/C(=O)C)/[O-].[C-]#[O+].[C-]#[O+].[Rh+]
• Canonical SMILES: [O-]/C(=C\C(=O)C)/C.[O+]#[C-].[O+]#[C-].[Rh+]
• InChI: InChI=1S/C5H8O2.2CO.Rh/c1-4(6)3-5(2)7;2*1-2;/h3,6H,1-2H3;;;/q;;;+1/p-1/b4-3-
• InChIKey: BZCAWKOPWNIDOC-FGSKAQBVSA-M

NAMES AND DATABASE IDS

Names

• IUPAC name: λ^1-rhodium(1+) ion bis(methanidylidyneoxidanium) (2Z)-4-oxopent-2-en-2-olate
• IUPAC Traditional name: λ^1-rhodium(1+) ion bis(carbon monoxide) (2Z)-4-oxopent-2-en-2-olate
• Synonyms: (Acetylacetonato)dicarbonylrhodium(I); Acetylacetonatorhodium(I) dicarbonyl; Dicarbonyl(2,4-pentanedionato)rhodium(I); 二羰基乙酰丙酮铑(I)

Database IDs

• CAS Number: 14874-82-9
• EC Number: 238-947-9
• MDL Number: MFCD00009884

CALCULATED PROPERTIES

• Acid pKa: 9.890059
• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 0.34448203
• LogD (pH = 7.4): 0.34309724
• Log P: 0.3444997
• Molar Refractivity: 39.1896 cm^3
• Polarizability: 10.113493 Å^3
• Polar Surface Area: 40.13 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Soluble in acetone
• Apperance: Crystalline
• Melting Point: 144-147°C subl.

Safety Information

• European Hazard Symbols: Flammable (F); Toxic (T)
• UN Number: UN2926
• Hazard Class: 4.1
• Packing Group: II
• Risk Statements: 11-25-36-43-53
• Safety Statements: 20-24-26-37-45-60
• TSCA Listed: 否
• GHS Pictograms: GHS02; GHS06
• GHS Hazard statements: H301-H319-H317-H228-H412
• GHS Precautionary statements: P210-P241-P301+P310-P305+P351+P338-P405-P501A

Product Information

• Purity: 99%

REFERENCES

• Miyaura has utilized this complex, in combination with a chelating phosphine ligand, for the conjugate addition of arylboronic acids to enones, to give saturated ketones: Organometallics, 16, 4339 (1997). Addition of aryl- and alkenylboronic acids to aldehydes to give secondary alcohols can also be brought about under similar conditions: Angew. Chem. Int. Ed., 37, 3279 (1998):
  
• Catalyst for hydroformylation of alkenes with CO/H₂ at atmospheric pressure to give enals: Angew. Chem. Int. Ed., 34, 1760 (1995).
• An extension of these reactions to the addition of potassium alkenyl- and aryltrifluoroborates to aldehydes and enones has also been reported: Org. Lett., 1, 1683 (1999).