27126-76-7 Usage
Chemical Description
[Hydroxy(tosyloxy)iodo]benzene is a hypervalent iodine reagent used for the synthesis of thiazole-2(3H)-thiones.
Chemical Properties
Pale yellow crystalline powder
Uses
Different sources of media describe the Uses of 27126-76-7 differently. You can refer to the following data:
1. Versatile synthetic reagent in phenyliodination and/or tosylation of a range of organic substrates; in oxidative transformations including oxidative rearrangements.
2. Reactant for:Ligand-free palladium-catalyzed Heck-type coupling reactionsPreparation of carbodiimides via dehydrosulfurization of thioureasPreparation of nitriles by oxidative conversion of alcohols, aldehydes, and aminesPreparation of substituted anilines via aromatic aldoxime reactionPreparation of tetrahydrofurans by oxidative cyclization of homoallylic alcoholsPreparation of isoxazoline N-Oxides from ?-hydroxyketoximes via oxidative N-O couplingRing expansion in synthesis of aminopeptidase inhibitorsOxidation and protonation reactions in acidic conditions
Purification Methods
Possible impurities are tosic acid (removed by washing with Me2CO) and acetic acid (removed by washing with Et2O). It is purified by dissolving in the minimum volume of MeOH, adding Et2O to cloud point and setting aside for the prisms to separate [Koser & Wettach J Org Chem 42 1476 1977, NMR: Koser et al. J Org Chem 41 3609 1976]. It has also been crystallised from CH2Cl2 (needles, m 140-142o) [Neiland & Karele J Org Chem, USSR (Engl Transl) 6 889 1970].
Check Digit Verification of cas no
The CAS Registry Mumber 27126-76-7 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 2,7,1,2 and 6 respectively; the second part has 2 digits, 7 and 6 respectively.
Calculate Digit Verification of CAS Registry Number 27126-76:
(7*2)+(6*7)+(5*1)+(4*2)+(3*6)+(2*7)+(1*6)=107
107 % 10 = 7
So 27126-76-7 is a valid CAS Registry Number.
InChI:InChI=1/C13H13IO4S/c1-11-7-9-13(10-8-11)19(16,17)18-14(15)12-5-3-2-4-6-12/h2-10,15H,1H3
27126-76-7Relevant articles and documents
Koser et al.
, p. 3609 (1976)
Application of [hydroxy(tosyloxy)iodo]benzene in the wittig-ring expansion sequence for the synthesis of β-benzocycloalkenones from α-benzocycloalkenones
Justik, Michael W.,Koser, Gerald F.
, p. 217 - 225 (2005)
The conversion of α-benzocycloalkenones to homologous β-benzocycloalkenones containing six, seven and eight-membered rings is reported. This was accomplished via a Wittig olefination-oxidative rearrangement sequence using [hydroxy(tosyloxy)iodo]-benzene (HTIB) is the oxidant, that enables the synthesis of regioisomeric pairs of methyl-substituted β-benzocycloalkenones. The incorporation of carbon-13 at C-1 of the β-tetralone nucleus was also demonstrated. The Wittig-HTIB approach is a useful alternative to analogous sequences in which Tl(NO3) 3·3H2O or the Prevost combination (AgNO 3/I2) are employed in the oxidation step.
Synthesis of Diverse Aryliodine(III) Reagents by Anodic Oxidation?
Zu, Bing,Ke, Jie,Guo, Yonghong,He, Chuan
supporting information, p. 627 - 632 (2021/02/12)
An anodic oxidation enabled synthesis of hypervalent iodine(III) reagents from aryl iodides is demonstrated. Under mild electrochemical conditions, a range of aryliodine(III) reagents including iodosylarenes, (difunctionaliodo)arenes, benziodoxoles and diaryliodonium salts can be efficiently synthesized and derivatized in good to excellent yields with high selectivity. As only electrons serve as the oxidation reagents, this method offers a more straightforward and sustainable manner avoiding the use of expensive or hazardous chemical oxidants.
SYNTHESIS OF HYPERVALENT IODINE REAGENTS WITH DIOXYGEN
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Paragraph 0085-0086, (2019/01/15)
Methods of synthesis of hypervalent iodine reagents and methods for oxidation of organic compounds are disclosed.
