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Merck
CN

482285

Rhodium(II) acetate dimer

99.9% trace metals basis

Synonym(s):

Dirhodium tetraacetate, Tetrakis(acetato)dirhodium(II)

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About This Item

Linear Formula:
Rh2(OOCCH3)4
CAS Number:
Molecular Weight:
441.99
NACRES:
NA.23
PubChem Substance ID:
UNSPSC Code:
12352103
EC Number:
240-084-8
MDL number:
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InChI key

SYBXSZMNKDOUCA-UHFFFAOYSA-J

InChI

1S/4C2H4O2.2Rh/c4*1-2(3)4;;/h4*1H3,(H,3,4);;/q;;;;2*+2/p-4

SMILES string

CC(=O)O[Rh]OC(C)=O.CC(=O)O[Rh]OC(C)=O

assay

99.9% trace metals basis

form

powder

reaction suitability

reaction type: C-H Activation, reagent type: catalyst

Quality Level

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General description

Rhodium(II) acetate dimer is a well-defined, air-stable organometallic complex widely recognized for its unique paddlewheel structure and exceptional catalytic properties. As a versatile catalyst, it plays a pivotal role in synthetic chemistry, particularly in C–H activation, carbene transfer, and cyclopropanation reactions. Its solubility in organic solvents and robust reactivity profile make it a valuable tool for homogeneous catalysis, fine chemical synthesis, and pharmaceutical development. Additionally, its use as a precursor in solution-based processes and potential in vapor deposition techniques is being explored for advanced material fabrication.

Application

Catalyst for Rh-mediated C-H activation
Effective catalyst for ylide formation.
Rhodium(II) acetate dimer can be used as:
  • A precursor for solution-based synthesis of rhodium-containing nanomaterials and thin films, for the use in vapor deposition and surface modification for catalysis and electronic applications.
  • A highly selective catalyst for C–H activation and functionalization reactions, enabling direct modification of unactivated C–H bonds for the efficient synthesis of complex molecules, including natural products and pharmaceuticals.
  • A catalyst for metal-carbene and nitrene transfer reactions, facilitating cyclopropanation, C–H amination, and ylide formation with high stereocontrol and functional group tolerance.

pictograms

Exclamation mark

signalword

Warning

hcodes

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)


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Rhodium carbenoid mediated C-H activation of a tertiary methyl group: an enantiospecific approach to the angular triquinanes norsilphiperfolane and norcameroonanes
Srikrishna, A.; et al.
Synlett, 16, 2343-2346 (2011)
A Padwa et al.
The Journal of organic chemistry, 66(7), 2414-2421 (2001-04-03)
Ammonium ylides derived from the Cu(II)-catalyzed decomposition of alpha-diazo carbonyls tethered to tertiary amines underwent a benzylic Stevens [1,2]-rearrangement to give tetrahydroisoquinolines or benzazepines containing fused five-membered rings, a feature found in the cephalotaxus alkaloids. Model studies were also carried
Yu Qian et al.
The Journal of organic chemistry, 75(21), 7483-7486 (2010-10-14)
A new approach to synthesize optically active β-amino-α-hydroxyl acid derivatives via chiral Brønsted acid-Rh(2)(OAc)(4) cocatalyzed three-component reactions of diazo acetates with alcohols and imines is reported. A matched reaction system was identified to give the products in moderate diastereoselectivity and
Jaroslav V Burda et al.
Journal of inorganic biochemistry, 102(1), 53-62 (2007-08-19)
In our study, we have determined the thermodynamic behavior for the replacement reaction of one and two acetyl-ligands from the diaqua-tetrakis(mu-acetylato)dirhodium(II,II) complex by purine DNA bases. The complexes were optimized at the density functional theory (DFT) level with the B3LYP
DNA cleavage by photogenerated Rh(2)(O(2)CCH(3))(4)(H(2)O)(2)(+).
P K Fu et al.
Inorganic chemistry, 40(11), 2476-2477 (2001-05-15)

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