27126-76-7 Usage
Chemical Description
[Hydroxy(tosyloxy)iodo]benzene is a hypervalent iodine reagent used for the synthesis of thiazole-2(3H)-thiones.
Description
[Hydroxy(tosyloxy)iodo]benzene, also known as the Dess-Martin periodinane (DMP), is a versatile synthetic reagent used in various organic synthesis processes. It is a pale yellow crystalline powder that plays a crucial role in phenyliodination and tosylation of a range of organic substrates. Additionally, it is employed in oxidative transformations, including oxidative rearrangements.
Uses
Used in Organic Synthesis:
[Hydroxy(tosyloxy)iodo]benzene is used as a synthetic reagent for phenyliodination and tosylation of a variety of organic substrates, facilitating the formation of new chemical bonds and enhancing the reactivity of these substrates.
Used in Oxidative Transformations:
[Hydroxy(tosyloxy)iodo]benzene is used as an oxidizing agent in oxidative rearrangements, enabling the restructuring of organic molecules to achieve desired products.
Used in Ligand-free Palladium-catalyzed Heck-type Coupling Reactions:
[Hydroxy(tosyloxy)iodo]benzene is used as a reactant in ligand-free palladium-catalyzed Heck-type coupling reactions, which are essential for the formation of carbon-carbon bonds in organic synthesis.
Used in Preparation of Carbodiimides:
It is used as a reactant for the preparation of carbodiimides via dehydrosulfurization of thioureas, which are important intermediates in the synthesis of various pharmaceuticals and agrochemicals.
Used in Preparation of Nitriles:
[Hydroxy(tosyloxy)iodo]benzene is used in the preparation of nitriles by oxidative conversion of alcohols, aldehydes, and amines, which are key building blocks in the synthesis of various organic compounds.
Used in Preparation of Substituted Anilines:
[Hydroxy(tosyloxy)iodo]benzene is used as a reactant in the preparation of substituted anilines via aromatic aldoxime reaction, which are essential for the synthesis of various dyes, pharmaceuticals, and polymers.
Used in Preparation of Tetrahydrofurans:
It is used as a reactant for the preparation of tetrahydrofurans by oxidative cyclization of homoallylic alcohols, which are important structural motifs in natural products and pharmaceuticals.
Used in Synthesis of Isoxazoline N-Oxides:
[Hydroxy(tosyloxy)iodo]benzene is used in the synthesis of isoxazoline N-oxides from β-hydroxyketoximes via oxidative N-O coupling, which are valuable intermediates in the preparation of various biologically active compounds.
Used in Ring Expansion:
[Hydroxy(tosyloxy)iodo]benzene is used in ring expansion reactions, such as in the synthesis of aminopeptidase inhibitors, which are important for the development of new drugs targeting proteolytic enzymes.
Used in Oxidation and Protonation Reactions:
[Hydroxy(tosyloxy)iodo]benzene is used as an oxidizing agent in oxidation and protonation reactions under acidic conditions, which are essential for the synthesis of various organic compounds.
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.
A trivalent hypervalent iodine compound using hypochlorite (by machine translation)
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Paragraph 0064, (2020/02/14)
[A] used in the prior art organic salt, toxic chlorine gas, organic peroxides can be used without the novel trivalent hypervalent iodine compound production. Furthermore, the acyloxy groups other than the trivalent hypervalent iodine compounds having a ligand manufacturing method. (1) Formula [solution](In the formula, R1 Substituted/unsubstituted aromatic group, aliphatic group or the like. N is an integer of 1 or more. ) Represented by the iodine compound, carboxylic acid, carboxylic acid anhydride, a sulfonic acid or sulfonic acid anhydride with at least one organic acid selected from the group consisting of, a hypochlorite mixing, trivalent hypervalent iodine compound. [Drawing] no (by machine translation)
