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377155

Sigma-Aldrich

Chlorobis(cyclooctene)iridium(I)dimer

97%

Synonym(s):

[Ir(coe)2Cl]2, Di-μ-chlorotetrakis(cyclooctene)diiridium

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250 MG
$158.00
1 G
$603.00
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$1,970.00

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250 MG
$158.00
1 G
$603.00
5 G
$1,970.00

About This Item

Empirical Formula (Hill Notation):
C32H56Cl2Ir2
CAS Number:
Molecular Weight:
896.13
MDL number:
UNSPSC Code:
12161600
PubChem Substance ID:
NACRES:
NA.22

$158.00


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Quality Level

assay

97%

form

powder

reaction suitability

core: iridium
reagent type: catalyst

mp

160-165 °C (dec.) (lit.)

SMILES string

Cl[Ir].Cl[Ir].[CH]1[CH]CCCCCC1.[CH]2[CH]CCCCCC2.[CH]3[CH]CCCCCC3.[CH]4[CH]CCCCCC4

InChI

1S/4C8H14.2ClH.2Ir/c4*1-2-4-6-8-7-5-3-1;;;;/h4*1-2H,3-8H2;2*1H;;/q;;;;;;2*+1/p-2/b4*2-1-;;;;

InChI key

WBRREXQCZAFSKS-XFCUKONHSA-L

Application

Catalyst for:
  • Isomerization-hydroboration reactions with nido-carboranyldiphosphine as stabilizing ligand
  • Hydrogen peroxide oxidation of hydroxamic acids and their subsequent hetero Diels-Alder cycloaddition reactions
  • Immobilization of organic functional groups onto solid supports through vinylsilane coupling reactions
  • Alkylation reactions
  • Guerbet reaction
  • Allylic amination reactions in a DNA-diene-iridium(I) hybrid system
  • Asymmetric hydroamination reactions
Chlorobis(cyclooctene)iridium(I)dimer can be used as a catalyst for:
  • Isomerization-hydroboration reactions with nido-carboranyldiphosphine as stabilizing ligand.[1]
  • Hydrogen peroxide oxidation of hydroxamic acids and their subsequent hetero Diels-Alder cycloaddition reactions.[2]
  • Immobilization of organic functional groups onto solid supports through vinylsilane coupling reactions.[3]
  • Alkylation reactions.[4]
  • Guerbet reaction.[5]
  • Allylic amination reactions using a DNA-diene-iridium(I) hybrid system.[6]
  • Asymmetric hydroamination reactions.[7]

pictograms

Exclamation mark

signalword

Warning

Hazard Classifications

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

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves


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An efficient and recyclable catalytic system comprising nano-iridium (0) and a pyridinium salt of nido-carboranyldiphosphine for the synthesis of one-dimensional boronate esters via hydroboration reaction.
Zhu Y, et al.
Organometallics, 31(7), 2589-2596 (2011)
Versatile Pd (II)-Catalyzed C? H Activation/Aryl? Aryl Coupling of Benzoic and Phenyl Acetic Acids.
Koda K, et al.
Chemistry Letters (Jpn), 38(8), 838-839 (2009)
Intermolecular, catalytic asymmetric hydroamination of bicyclic alkenes and dienes in high yield and enantioselectivity.
Zhou J and Hartwig J F
Journal of the American Chemical Society, 130(37), 12220-12221 (2008)
Allylic amination by a DNA?diene?iridium (I) hybrid catalyst.
Fournier P, et al.
Angewandte Chemie (International Edition in English), 48(24), 4426-4429 (2009)
Iridium (I)-catalyzed hydrogen peroxide oxidation of hydroxamic acids and hetero Diels?Alder reaction of the acyl nitroso intermediates with cyclopentadiene.
Iwasa S, et al.
Tetrahedron Letters, 43(35), 6159-6161 (2002)

Articles

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

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    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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  2. 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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