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686891

Sigma-Aldrich

Chiralyst P618

Umicore

Synonym(s):

Pentamethylcyclopentadienylrhodium(III) chloride dimer, Di(μ-chloro)dichlorobis(pentamethylcyclopentadiene)dirhodium(III), 1,3-Cyclopentadiene, 1,2,3,4,5-pentamethyl-, rhodium complex, Bis(dichloro(pentamethylcyclopentadienyl)rhodium), Bis(pentamethylcyclopentadienylrhodium dichloride), Dichloro(pentamethylcyclopentadienyl)rhodium(II) dimer, Tetrachlorobis(pentamethylcyclopentadienyl)dirhodium

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About This Item

Linear Formula:
[Rh(C5Me5)Cl2]2
CAS Number:
12354-85-7
Molecular Weight:
618.08
MDL number:
MFCD00061552
UNSPSC Code:
12352300
PubChem Substance ID:
329761080
NACRES:
NA.22

Quality Level

100

form

powder

reaction suitability

core: rhodium
reaction type: Cross Couplings
reagent type: catalyst
reaction type: C-H Activation

SMILES string

Cl[Rh]Cl.Cl[Rh]Cl.C[C]1[C](C)[C](C)[C](C)[C]1C.C[C]2[C](C)[C](C)[C](C)[C]2C

InChI

1S/2C10H15.4ClH.2Rh/c2*1-6-7(2)9(4)10(5)8(6)3;;;;;;/h2*1-5H3;4*1H;;/q;;;;;;2*+2/p-4

InChI key

QNIVKTTWBMFSBR-UHFFFAOYSA-J

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Application

Umicore Precatalysts for Asymmetric and Cross-Coupling Catalysis

Catalyst for:
  • Oxidative olefination reactions
  • C-C bond cleavage of secondary alcohols
  • Ortho C-H olefination of phenol derivatives
  • Oxidative annulation of pyridines
  • Oxidative ortho-acylation of benzamides with aldehydes via direct functionalization of the sp2 C-H bond
  • Amidation reactions
  • Reductive alkylation reactions
Pentamethylcyclopentadienylrhodium(III) chloride dimer can be used as a catalyst for:
  • The synthesis of multiaryl substituted naphthols via dual C-H bond functionalization of 2-aryloxypyridines.
  • Regioselective C-N bond formation of azo compounds, wherein azide acts as a nitrogen source.
  • Annulation of N-benzoylsulfonamide with isocyanide via C-H bond activation.

Legal Information

Product of Umicore

Additional information available at www.pmc.umicore.com

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H302 + H312 + H332 - H315

Hazard Classifications

Acute Tox. 4 Dermal - Acute Tox. 4 Inhalation - Acute Tox. 4 Oral - Skin Irrit. 2

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

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Rhodium-Catalyzed Synthesis of Multiaryl-substituted Naphthols via a Removable Directing Group
Wang L, et al.
Advanced Synthesis & Catalysis, 359(21), 3818-3825 (2017)
Rhodium-Catalyzed Direct ortho C-N Bond Formation of Aromatic Azo Compounds with Azides
Wang H, et al.
The Journal of Organic Chemistry, 79(7), 3279-3288 (2014)
Rhodium-Catalyzed Annulation of N-Benzoylsulfonamide with Isocyanide through C-H Activation
Zhu C, et al.
Chemistry?A European Journal , 17(45), 12591-12595 (2011)
Rhodium-Catalyzed Synthesis of Multiaryl-substituted Naphthols via a Removable Directing Group
Wang L, et al.
advanced synthesis and catalysis, 359(21), 3818-3825 (2017)

Articles

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