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CAS RN: 12148-71-9 | Product Number: C2662

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

Purity:

Synonyms:

Bis(1,5-cyclooctadiene)di-μ-methoxydiiridium(I)

Product Documents:

Size	Unit Price	Same Day	2-3 Business Days	Other Lead Time	Shipping Information
200MG	$72.00	35	25	It can be shipped in about 2 weeks after ordering	Shipping Simulation
1G	$246.00	≥100	35	It can be shipped in about 2 weeks after ordering	Shipping Simulation

* Please contact our distributors or TCI to order our products. The above prices do not include freight cost, customs, and other charges to the destination.
* The storage conditions are subject to change without notice.

General Information plus

Product Number	C2662
Molecular Formula / Molecular Weight	C₁₈H₃₀Ir₂O₂ = 662.87
Physical State (20 deg.C)	Solid
Storage Temperature	Frozen (<0°C)
Store Under Inert Gas	Store under inert gas
Condition to Avoid	Light Sensitive,Air Sensitive,Moisture Sensitive,Heat Sensitive
Packaging and Container	1G-Glass Bottle with Plastic Insert (View image), 200MG-Glass Bottle with Plastic Insert (View image)
CAS RN	12148-71-9
Reaxys Registry Number	14520157
PubChem Substance ID	160871404
MDL Number	MFCD08459360

Specifications & Properties plus

Safety & Regulations plus

Applications & Literature plus

Application

TCI Practical Example: Hartwig-Miyaura C-H Borylation Using an Iridium Catalyst

Used Chemicals

Procedure: A solution of dtbpy (27 mg, 0.05 mmol), bis(pinacolato)diboron (1.0 g, 4.0 mmol) and [Ir(cod)OMe]₂ (33 mg, 0.025 mmol) in cyclohexane (40 mL) was stirred under nitrogen at room temperature for 10 min. Benzo[1,2-b:4,5-b']dithiophene (380 mg, 2.0 mmol) was added the mixture and stirred 80 ˚C for 18 hours. The reaction mixture was quenched with water and separated both layers, extracted with dichloromethane. The organic phase was dried over anhydrous sodium sulfate and filtered. The solvent was removed under reduced pressure and the crude was washed with methanol (20 mL) to give 1 as a white solid (0.771 g, 87% yield).

Experimenter’s Comments: The reaction mixture was monitored by NMR.
Cyclohexane was bubbled with nitrogen before use.

Analytical Data

Compound 1

¹H NMR (270 MHz, CDCl₃); δ 8.36 (s, 2H), 7.90 (s, 2H), 1.39 (s, 24H).

Lead Reference

Synthesis and Transistor Application of Bis[1]benzothieno[6,7‑d:6′,7′‑d′]benzo[1,2‑b:4,5‑b′]dithiophenes
- S. Nishinaga, H. Mori, Y. Nishihara. J. Org. Chem. 2018, 83, 5506.

Application

Hartwig-Miyaura C-H Borylation

Reference

Room temperature borylation of arenes and heteroarenes using stoichiometric amounts of pinacolborane catalyzed by iridium complexes in an inert solvent
- T. Ishiyama, Y. Nobuta, J. F. Hartwig, N. Miyaura, Chem. Commun. 2003, 2924.

Application

Catalytic Functionalization of Un-activated Primary C―H Bonds

Typical Procedure:
An alcohol or ketone substrate is dissolved in THF and treated with a freshly prepared solution of [Ir(cod)OMe]₂ (0.05 mol%) in THF and then with neat Et₂SiH₂ (1.2 eq.). The resulting solution is stirred at room temperature (23 °C) until complete conversion of the alcohol or ketone. At the completion of the reaction, the corresponding diethyl(hydrido)silyl ether is observed. Then the reaction mixture is placed under high vacuum for 1 h. The concentrated diethyl(hydrido)silyl ether is sequentially treated with freshly prepared solutions of norbornene (1.2 eq.) in THF and [Ir(cod)OMe]₂ (0.5 mol%) in THF, and then with a slurry of Me₄phen (1.25 mol%) in THF. The resulting solution is stirred at room temperature for 1 h and then heated it at 80-120 °C until complete conversion to the corresponding oxasilolane is observed. Then the crude reaction mixture containing the oxasilolane is sequentially treated with MeOH, KHCO₃ (2.5 eq.) and H₂O₂ (30% solution in H₂O, 10 eq.), and the resulting mixture is stirred overnight at 50 °C. The reaction is carefully quenched with aq. NaHSO₃, and the resulting mixture is extracted with EtOAc. The combined organic layer is sequentially washed with 1 M HCl and sat. NaHCO₃, and then dried with MgSO₄. The resulting organic layer is filtered through Celite and concentrated to provide the crude diol, which is either purified directly or after conversion to the corresponding acetate derivative through treatment with Ac₂O and Et₃N.

References

E. M. Simmons, J. F. Hartwig, Nature 2012, 483, 70.

PubMed Literature

Articles/Brochures

C-H Bond Activation Reaction

TCIMAIL

[TCI Practical Example] Hartwig-Miyaura C-H Borylation Using an Iridium Catalyst
[Research Articles] Catalytic Functionalization of Un-activated Primary C-H Bonds

Product Documents (Note: Some products will not have analytical charts available.)

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Product Categories

Chemistry

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Ir (Iridium) Compounds [Chemical Structural Class]

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Metal Compounds [Chemical Structural Class]

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Ir (Iridium) Compounds [Chemical Structural Class]

Appearance	Light yellow to Amber to Dark green powder to crystal
Elemental analysis(Carbon)	31.50 to 34.00 %

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CAS RN: 12148-71-9 | Product Number: C2662