bis(chloroiridium); bis(cycloocta-1,5-diene)

• ChemBase ID: 140615
• Molecular Formular: C16H24Cl2Ir2
• Molecular Mass: 671.70176
• Monoisotopic Mass: 672.05135813
• SMILES: C1C=CCCC=CC1.C1C=CCCC=CC1.Cl[Ir].Cl[Ir]
• Canonical SMILES: C1CC=CCCC=C1.C1CC=CCCC=C1.[Ir]Cl.[Ir]Cl
• InChI: InChI=1S/2C8H12.2ClH.2Ir/c2*1-2-4-6-8-7-5-3-1;;;;/h2*1-2,7-8H,3-6H2;2*1H;;/q;;;;2*+1/p-2
• InChIKey: ZFOUDQNHNLDNLD-UHFFFAOYSA-L

NAMES AND DATABASE IDS

Names

• IUPAC name: bis(chloroiridium); bis(cycloocta-1,5-diene)
• IUPAC Traditional name: bis(1,5-cyclooctadiene); bis(chloroiridium)
• Synonyms: [Ir(1,5-cod)Cl]2; [Ir(cod)Cl]2; 1,5-Cyclooctadiene-iridium(I) chloride dimer; Chloro(1,5-cyclooctadiene)iridium(I) dimer; Di-μ-chlorobis[(1,2,5,6-η)-1,5-cyclooctadiene]diiridium; Iridium(I) chloride 1,5-cyclooctadiene complex dimer; Bis(1,5-cyclooctadiene)diiridium(I) dichloride; Bis(1,5-cyclooctadiene)diiridium(I) dichloride; Chloro(1,5-cyclooctadiene)iridium(I) dimer; 1,5-环辛二烯氯化铱(I)二聚体; 二-μ-氯双[(1,2,5,6-η)-1,5-环辛二烯]二铱; 氯代-1,5-环戊二烯铱二聚体; 氯化铱(I) 1,5-环辛二烯络合物二聚体; 双(1,5-环辛二烯)氯化铱(I)二聚体; (1,5-环辛二烯)二氯化铱(I)二聚体

Database IDs

• CAS Number: 12112-67-3
• EC Number: 235-170-7
• MDL Number: MFCD00012414
• PubChem SID: 24856629

CALCULATED PROPERTIES

• H Acceptors: 0
• H Donor: 0
• LogD (pH = 5.5): 2.832706
• LogD (pH = 7.4): 2.832706
• Log P: 2.832706
• Molar Refractivity: 39.0412 cm^3
• Polarizability: 14.319889 Å^3
• Polar Surface Area: 0.0 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Soluble in chloroform, toluene. Slightly soluble in acetone, alcohol.
• Apperance: Crystalline powder
• Melting Point: 190°C dec.; 205 °C (dec.)(lit.)

Safety Information

• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26
• TSCA Listed: 否
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves

Product Information

• Purity: 97%; Ir 57.2%
• Empirical Formula (Hill Notation): C16H24Cl2Ir2

DETAILS

Sigma Aldrich - 275131

Application
Metal precursor for asymmetric allylic substitutions.1
Packaging
100, 500 mg in glass bottle

Sigma Aldrich - 683094

Packaging
2 g in glass bottle
500 mg in glass bottle
Legal Information
Product of Umicore
Application
Umicore Precatalysts for Asymmetric and Cross-Coupling CatalysisMetal precursor for asymmetric allylic substitutions.1

REFERENCES

• Catalyst precursor for asymmetric hydrogenation: Angew. Chem. Int. Ed., 37, 2897 (1998).
• Effective catalyst for the reaction of alcohols with vinyl acetate to give vinyl ethers: J. Am. Chem. Soc., 124, 1590 (2002).
• With catalytic amounts of dppp (1,3-Bis(diphenylphosphino)propane, A12931) and Cs₂CO₃, a transfer hydrogenation system with 2-propanol as the H source can reduce both olefinic double bonds and carbonyl groups; for ɑ?-unsaturated ketones, selective reduction to saturated ketones can be achieved: J. Org. Chem., 66, 4710 (2001).
• In the presence of a phosphite, catalyzes displacements by carbon nucleophiles at the more substituted position in allylic systems: Angew Chem. Int. Ed., 36, 263 (1997); J. Am. Chem. Soc., 120, 8647 (1998).
• Catalyst for Miyaura and Hartwig's direct boronylation of arenes with Bis(pinacolato)diboron, L16088: J. Am. Chem. Soc., 124, 390 (2002):