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662283

Sigma-Aldrich

Bis(tert-butylcarbonyloxy)iodobenzene

97%

Synonym(s):

(Di-tert-butylcarbonyloxyiodo)benzol, 2,2-Dimethylpropanoic acid, phenyliodine complex, Bis(2,2-dimethylpropanoato-O)phenyliodide, Di-(Pivaloyloxy)iodobenzene

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About This Item

Empirical Formula (Hill Notation):
C16H23IO4
CAS Number:
57357-20-7
Molecular Weight:
406.26
MDL number:
MFCD08276835
UNSPSC Code:
12352002
PubChem Substance ID:
24884583
NACRES:
NA.22

Quality Level

100

Assay

97%

form

solid

reaction suitability

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

mp

104-109 °C

SMILES string

CC(C)(C)C(=O)O[I](OC(=O)C(C)(C)C)c1ccccc1

InChI

1S/C16H23IO4/c1-15(2,3)13(18)20-17(12-10-8-7-9-11-12)21-14(19)16(4,5)6/h7-11H,1-6H3

InChI key

DZKPLZUSZXYHFB-UHFFFAOYSA-N

Application

Rh2(esp)2: An Exceptionally Efficient and Selective Catalyst for C-H Amination

Reagent for:
  • Preparation of α,β-unsaturated-γ-lactams via Rh-catalyzed C-H amination of allene carbamates, then Ru-catalyzed cyclocarbonylation
  • Palladium-catalyzed diamination
  • Preparation of functionalized bicyclic heterocyclic compounds by rhodium-catalyzed allene amidation and cyclization
  • Preparation of piperidine and pyrrolidine derivatives via copper-catalyzed intramolecular aminoacetoxylation of aminoolefins
  • C-H acyloxylation of arenes

  • Hypervalent iodine oxidant
Hypervalent iodine reagent used with the Rh2(esp)2 catalyst (662623) in the amination of C-H bonds.

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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Dzmitry M Zubrytski et al.
Molecules (Basel, Switzerland), 26(1) (2021-01-06)
Oxidative fragmentation of tertiary cyclopropanols with phenyliodine(III) dicarboxylates in aprotic solvents (dichloromethane, chloroform, toluene) produces mixed anhydrides. The fragmentation reaction is especially facile with phenyliodine(III) reagents bearing electron-withdrawing carboxylate ligands (trifluoroacetyl, 2,4,6-trichlorobenzoyl, 3-nitrobenzoyl), and affords 95-98% yields of the corresponding
Kristin Williams Fiori et al.
Journal of the American Chemical Society, 129(3), 562-568 (2007-01-18)
Reaction methodology for intermolecular C-H amination of benzylic and 3 degrees C-H bonds is described. This process uses the starting alkane as the limiting reagent, gives optically pure tetrasubstituted amines through stereospecific insertion into enantiomeric 3 degrees centers, displays high

Articles

Rh2(esp)2 Catalyst

New! Rh2(esp)2, and exceptionally efficient and selective catalyst for C-H amination.

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