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Chloro(1,5-cyclooctadiene)rhodium(I) Dimer
(CAS RN:12092-47-6 Product Number:B1045)

Structure

Chloro(1,5-cyclooctadiene)rhodium(I) Dimer
Synonym Bis(1,5-cyclooctadiene)dirhodium(I) Dichloride
Synonym 1,5-Cyclooctadiene Rhodium(I) Chloride Dimer
Synonym [Rh(COD)Cl]2

General Information

Product Number B1045

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Purity/Analysis Method >98.0%(T)
Storage Temperature
M.F. / M.W. C16H24Cl2Rh2=493.08
CAS RN 12092-47-6
Related CAS RN
MDL Number MFCD00012415
Packaging and Container
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Specification

Appearance Light yellow to Brown powder to crystal
Purity(Argentmetric Titration) min. 98.0 %

References

Reaxys-RN 14860700
PubChem SID 87563994
EC Number 235-157-6

GHS

Pictogram
Signal Word Warning
Hazard Statements
  • H315
  • :Causes skin irritation.
  • H319
  • :Causes serious eye irritation.
Precautionary Statements
  • P264
  • :Wash hands and face thoroughly after handling.
  • P280
  • :Wear protective gloves, eye protection.
  • P302+P352+P332+P313+P362+P364
  • :IF ON SKIN: Wash with plenty of water. If skin irritation occurs: Get medical advice or attention. Take off contaminated clothing and wash it before reuse.
  • P305+P351+P338+P337+P313
  • :IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. If eye irritation persists: Get medical advice or attention.

Transport Information

HS Number 2843909000

Application

Rh-catalyzed endo- and Enantioselective Hydroacylation of o-Allylbenzaldehydes

B1045,D4501

Typical Procedure:
In a nitrogen-filled dry box, the appropriate o-allylbenzaldehyde (0.20 mmol, 1.0 eq.), [Rh(COD)Cl]2 (2.5 mg, 0.0050 mmol, 0.025 eq.), (R)-DTBM-SEGPHOS® (11.8 mg, 0.010 mmol, 0.050 eq.), NaBARF (8.9 mg, 0.010 mmol, 0.050 eq.), and anhydrous 1,4-dioxane (1 mL) are added to a 1-dram vial. The vial is sealed with a PFTE/silicone-lined septum cap and removed from the dry box. The reaction mixture is heated to 100 °C and allowed to stir at this temperature until the reaction is judged to be complete by TLC analysis. The mixture is cooled to room temperature, filtered through a pad of silica gel (eluting with EtOAc), and concentrated under reduced pressure. The crude reaction mixture is purified by flash column silica gel chromatography (hexane/EtOAc or hexane/Et2O) to yield the corresponding products.

References

Rhodium-Catalyzed Cross-coupling of Organoboron Compounds with Vinyl Acetate

Typical procedure: Under nitrogen atmosphere, a mixture of an arylboron compounds (0.50 mmol), [RhCl(cod)]2 (6.2 mg, 13 μmol), DPPB (11.7 mg, 28 μmol), and K3PO4 (320 mg, 1.5 mmol) is diluted with toluene (2.0 mL). Alkenyl acetate (1.1 or 2.5 mmol) and tert-amyl alcohol (0.55-1.5 mmol) are added into the resulting suspension at room temperature. The mixture is stirred at 100℃ for 24 h and then diluted with hexane (2.0 mL) or EtOAc (2.0 mL). After the filtration through a Celite pad, solvent is removed from the filtrate under reduced pressure. The residue is purified with a flash column chromatography (EtOAc-hexane) to give the desired product.

References

1,2-Addition of Chiral Secondary and Tertiary Alkyl Trifluoroborate

Typical procedure: A dry Schlenk tube flask is charged with the potassium trifluoroborate salt (0.45 mmol), [RhCl(cod)]2 (2.5 mol%, 3.6 mg) and the aldehyde (0.3 mmol). After cycles of vacuum and nitrogen (3 cycles), deoxygenated 1,4-dioxane (1.4 mL) and deoxygenated H2O (240 μL) are added. The reaction mixture is stirred at 60-100ºC and the progress of the reaction is checked by TLC. The mixture is cooled to room temperature, saturated NH4Cl solution is added, and then the mixture is extracted with EtOAc. The combined organic layers are dried over MgSO4. Concentration and purification through silica gel column chromatography gives the products.

References

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