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662283

Bis(tert-butylcarbonyloxy)iodobenzene

Name: Bis(<I>tert</I>-butylcarbonyloxy)iodobenzene
Brand: ALDRICH

97%

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Synonym(s):

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

Empirical Formula (Hill Notation):

C₁₆H₂₃IO₄

CAS Number:

57357-20-7

Molecular Weight:

406.26

MDL number:

MFCD08276835

PubChem Substance ID:

24884583

NACRES:

NA.22

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

Related Categories

C–H Activation Catalysts

Oxidation Reagents

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

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Generation of Mixed Anhydrides via Oxidative Fragmentation of Tertiary Cyclopropanols with Phenyliodine(III) Dicarboxylates.

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

Catalytic intermolecular amination of C-H bonds: method development and mechanistic insights.

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

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