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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)

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250 MG
€63.30
1 G
€186.00
25 G
€4,410.00

€63.30

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250 MG
€63.30
1 G
€186.00
25 G
€4,410.00

About This Item

Linear Formula:
[Ir(OCH3)(C8H12)]2
CAS Number:
12148-71-9
Molecular Weight:
662.86
MDL number:
MFCD08459360
UNSPSC Code:
12161600
PubChem Substance ID:
329760940
NACRES:
NA.22

€63.30

Please contact Customer Service for Availability
Request a Bulk Order

form

crystals

Quality Level

100

reaction suitability

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

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

Related Categories

Application

A powerful C-H activation catalyst to prepare phenols from arenes[1]
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

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
MKCX5966
MKCX4186
MKCX1044
MKCV9157
MKCW4148

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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)
Catalytic functionalization of unactivated primary C?H bonds directed by an alcohol.
Simmons E, et al.
Nature, 483(7387), 70-70 (2012)
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)
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

Rapid Arylboronic Esters Synthesis by Ir(I)-Catalysis

Arylboronic acids and esters, vital tools in chemical transformations, find extensive use, particularly in the Suzuki-Miyaura cross-coupling reaction.

Questions

1–2 of 2 Questions  

  1. How is shipping temperature determined? And how is it related to the product storage temperature?

    1 answer

    1. Products may be shipped at a different temperature than the recommended long-term storage temperature. If the product quality is sensitive to short-term exposure to conditions other than the recommended long-term storage, it will be shipped on wet or dry-ice. If the product quality is NOT affected by short-term exposure to conditions other than the recommended long-term storage, it will be shipped at ambient temperature. As shipping routes are configured for minimum transit times, shipping at ambient temperature helps control shipping costs for our customers. For more information, please refer to the Storage and Transport Conditions document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/316/622/storage-transport-conditions-mk.pdf

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  2. How can I determine the shelf life / expiration / retest date of this product?

    1 answer

    1. If this product has an expiration or retest date, it will be shown on the Certificate of Analysis (COA, CofA). If there is no retest or expiration date listed on the product's COA, we do not have suitable stability data to determine a shelf life. For these products, the only date on the COA will be the release date; a retest, expiration, or use-by-date will not be displayed.
      For all products, we recommend handling per defined conditions as printed in our product literature and website product descriptions. We recommend that products should be routinely inspected by customers to ensure they perform as expected.
      For products without retest or expiration dates, our standard warranty of 1 year from the date of shipment is applicable.
      For more information, please refer to the Product Dating Information document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/449/386/product-dating-information-mk.pdf

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