685062

Sigma-Aldrich

(1,5-Cyclooctadiene)(methoxy)iridium(I) dimer

Synonym(s):
[Ir(OMe)(1,5-cod)]2, Bis(1,5-cyclooctadiene)di-μ-methoxydiiridium(I)
Linear Formula:
[Ir(OCH3)(C8H12)]2
CAS Number:
Molecular Weight:
662.86
MDL number:
PubChem Substance ID:
NACRES:
NA.22

reaction suitability

core: iridium
reagent type: catalyst
reaction type: C-H Activation

Quality Level

mp

154-179 °C (D)

storage temp.

−20°C

SMILES string

C[O+]1[Ir-]2[O+](C)[Ir-]12.C3CC=CCCC=C3.C4CC=CCCC=C4

InChI

1S/2C8H12.2CH3O.2Ir/c2*1-2-4-6-8-7-5-3-1;2*1-2;;/h2*1-2,7-8H,3-6H2;2*1H3;;/q;;2*+1;2*-1/b2*2-1-,8-7-;;;;

InChI key

BGWIAAATAAWGOI-MIXQCLKLSA-N

Application

Catalyst for:
  • Preparation of heteroaryl fused indole ring systems as inhibitors of HCV NS5B polymerase
  • Borylation/Suzuki-Miyaura coupling
  • Metalation-Suzuki cross-coupling procedure for the synthesis of biaryls and heterobiaryls
  • Tetraborylation reactions
  • Highly regio- and enantioselective asymmetric hydroboration
  • Ortho-silylation of aryl ketone, benzaldehyde, and benzyl alcohol derivatives via C-H activation
A powerful C-H activation catalyst to prepare phenols from arenes

Packaging

250 mg in glass bottle
1, 25 g in glass bottle

Pictograms

Exclamation mark

Signal Word

Warning

Hazard Statements

Precautionary Statements

Target Organs

Respiratory system

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

RIDADR

NONH for all modes of transport

WGK Germany

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificate of Analysis
Certificate of Origin
Ir?Catalyzed Borylation of C H Bonds in N?Containing Heterocycles: Regioselectivity in the Synthesis of Heteroaryl Boronate Esters.
Mkhalid I, et al.
Angewandte Chemie (International Edition in English), 45(3), 489-491 (2006)
Catalytic functionalization of unactivated primary C?H bonds directed by an alcohol.
Simmons E, et al.
Nature, 483(7387), 70-70 (2012)
Direct C?H borylation and C?H arylation of pyrrolo [2, 3-d] pyrimidines: synthesis of 6, 8-disubstituted 7-deazapurines.
Klecka M, et al.
Organic & Biomolecular Chemistry, 7(5), 866-868 (2009)
A general strategy for the perfluoroalkylation of arenes and arylbromides by using arylboronate esters and [(phen) CuRF].
Litvinas N, et al.
Angewandte Chemie (International Edition in English), 51(2), 536-539 (2012)
Robert E Maleczka et al.
Journal of the American Chemical Society, 125(26), 7792-7793 (2003-06-26)
An efficient one-pot C-H activation/borylation/oxidation protocol for the preparation of phenols is described. This method is particularly attractive for the generation of meta-substituted phenols bearing ortho-/para-directing groups, as such substrates are difficult to access by other phenol syntheses.
Articles
Arylboronic acids and esters are invaluable tools for the chemical community. These powerful reagents are used for a variety of transformations, most notably the Suzuki-Miyaura cross-coupling reaction.
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