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1-Chloro-1,3-dihydro-3,3-dimethyl-1,2-benziodoxole is a crystalline, air-stable, yellow chloroiodane compound that serves as a versatile reactant and starting material in organic synthesis. It exhibits good solubility in polar organic solvents, such as dichloromethane or ethyl acetate, and is used in the preparation of various hypervalent iodine compounds.
Used in Pharmaceutical Industry:
1-Chloro-1,3-dihydro-3,3-dimethyl-1,2-benziodoxole is used as a reactant in the one-pot preparation of hypervalent iodine(III)-CF3 reagent for electrophilic trifluoromethylation reactions. This process is crucial for the synthesis of pharmaceutical compounds, as trifluoromethylation can enhance the biological activity and pharmacokinetic properties of drug molecules.
Used in Organic Synthesis:
1-Chloro-3,3-dimethylbenziodoxole is used as a starting material for the production of other hypervalent iodine compounds, which are essential in various organic synthesis processes. These hypervalent iodine compounds can act as oxidants, catalysts, or reagents, facilitating a wide range of chemical transformations.
Used as a Mild Chlorinating Reagent:
Due to its reactivity and stability, 1-Chloro-1,3-dihydro-3,3-dimethyl-1,2-benziodoxole can also be employed as a mild chlorinating reagent in organic synthesis. This application allows for the selective introduction of chlorine atoms into target molecules, which can be crucial for the development of new chemical entities and materials.

69352-04-1

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69352-04-1 Usage

Check Digit Verification of cas no

The CAS Registry Mumber 69352-04-1 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 6,9,3,5 and 2 respectively; the second part has 2 digits, 0 and 4 respectively.
Calculate Digit Verification of CAS Registry Number 69352-04:
(7*6)+(6*9)+(5*3)+(4*5)+(3*2)+(2*0)+(1*4)=141
141 % 10 = 1
So 69352-04-1 is a valid CAS Registry Number.

69352-04-1SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 13, 2017

Revision Date: Aug 13, 2017

1.Identification

1.1 GHS Product identifier

Product name 1-chloro-3,3-dimethyl-1λ<sup>3</sup>,2-benziodoxole

1.2 Other means of identification

Product number -
Other names 1-chloro-3,3-dimethyl-1H-1,2-benziodoxole

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:69352-04-1 SDS

69352-04-1Relevant articles and documents

Iron-Catalyzed Enantioselective Radical Carboazidation and Diazidation of α,β-Unsaturated Carbonyl Compounds

Liu, Wen,Pu, Maoping,He, Jun,Zhang, Tinghui,Dong, Shunxi,Liu, Xiaohua,Wu, Yun-Dong,Feng, Xiaoming

supporting information, p. 11856 - 11863 (2021/08/16)

Azidation of alkenes is an efficient protocol to synthesize organic azides which are important structural motifs in organic synthesis. Enantioselective radical azidation, as a useful strategy to install a C-N3 bond, remains challenging due to the inherently instability and unique structure of radicals. Here, we disclose an efficient enantioselective radical carboazidation and diazidation of α,β-unsaturated ketones and amides catalyzed by chiral N,N′-dioxide/Fe(OTf)2 complexes. An array of substituted alkenes was transformed to the corresponding α-azido carbonyl derivatives in good to excellent enantioselectivities, benefiting the preparation of chiral α-amino ketones, vicinal amino alcohols, and vicinal diamines. Control experiments and mechanistic studies proved the radical pathway in the reaction process. The DFT calculations showed that the azido transferred to the radical intermediate via an intramolecular five-membered transition state with the internal nitrogen of the Fe-N3 species.

One-Pot Synthesis of Primary and Secondary Aliphatic Amines via Mild and Selective sp3 C?H Imination

Comito, Robert J.,Ghosh, Subrata K.,Hu, Mengnan

supporting information, p. 17601 - 17608 (2021/11/03)

The direct replacement of sp3 C?H bonds with simple amine units (?NH2) remains synthetically challenging, although primary aliphatic amines are ubiquitous in medicinal chemistry and natural product synthesis. We report a mild and selective protocol for preparing primary and secondary aliphatic amines in a single pot, based on intermolecular sp3 C?H imination. The first C?H imination of diverse alkanes, this method shows useful site-selectivity within substrates bearing multiple sp3 C?H bonds. Furthermore, this reaction tolerates polar functional groups relevant for complex molecule synthesis, highlighted in the synthesis of amine pharmaceuticals and amination of natural products. We characterize a unique C?H imination mechanism based on radical rebound to an iminyl radical, supported by kinetic isotope effects, stereoablation, resubmission, and computational modeling. This work constitutes a selective method for complex amine synthesis and a new mechanistic platform for C?H amination.

Oxidative cyanation of 2-oxindoles: formal total synthesis of (±)-gliocladin C

Bisai, Alakesh,Das, Mrinal Kanti,De, Subhadip,Maity, Arindam,Naskar, Malay,Roy, Avishek

supporting information, p. 1679 - 1684 (2020/03/05)

Efficient oxidative direct cyanations of 3-alkyl/aryl 2-oxindoles using Cyano-1,2-BenziodoXol-3(1H)-one (CBX) (2a) have been reported under 'transition metal-free' conditions to synthesize a wide variety of 3-cyano 3-alkyl/aryl 2-oxindoles sharing an all-carbon quaternary center under additive-free conditions. The application of this process is shown by the formal total synthesis of (±)-gliocladin C (11c) in a few steps.

Radical C?H-Amination of Heteroarenes using Dual Initiation by Visible Light and Iodine

Lucchetti, Nicola,Tkacheva, Anastasia,Fantasia, Serena,Mu?iz, Kilian

supporting information, p. 3889 - 3893 (2018/09/21)

A novel light-induced C?H amination of heteroarenes can be accomplished with preformed iodine(III) reagents as the combined oxidant and nitrogen source. The reaction requires the use of a small amount of molecular iodine, which under photochemical activation generates in situ an iodine(I) reagent as the initiator of the radical amination reaction. A total of 32 examples exemplify the broad scope of the transformation. (Figure presented.).

Determining the predominant tautomeric structure of iodine-based group-transfer reagents by 17O NMR spectroscopy

Santschi, Nico,Pitts, Cody Ross,Jelier, Benson J.,Verel, René

, p. 2289 - 2294 (2018/09/14)

Cyclic benziodoxole systems have become a premier scaffold for the design of electrophilic transfer reagents. A particularly intriguing aspect is the fundamental II–IIII tautomerism about the hypervalent bond, which has led in certain cases to a surprising re-evaluation of the classic hypervalent structure. Thus, through a combination of 17O NMR spectroscopy at natural abundance with DFT calculations, we establish a convenient method to provide solution-phase structural insights for this class of ubiquitous reagents. In particular, we confirm that Shen’s revised, electrophilic SCF3-transfer reagent also adopts an "acyclic" thioperoxide tautomeric form in solution. After calibration, the approach described herein likely provides a more general and direct method to distinguish between cyclic and acyclic structural features based on a single experimental 17O NMR spectrum and a computationally-derived isotropic shift value. Furthermore, we apply this structural elucidation technique to predict the constitution of an electrophilic iodine-based cyano-transfer reagent as an NC–I–O motif and study the acid-mediated activation of Togni's trifluoromethylation reagent.

Metal-Free Oxidative Cross Coupling of Indoles with Electron-Rich (Hetero)arenes

Caramenti, Paola,Nandi, Raj Kumar,Waser, Jerome

supporting information, p. 10049 - 10053 (2018/07/29)

A new method for the synthesis of bi-heteroaryls is reported, based on the umpolung of indoles with benziodoxol(on)e hypervalent iodine reagents (IndoleBX). The oxidative coupling of IndoleBX with an equimolar amount of electron-rich benzenes, indoles, pyrroles, and thiophenes proceeded under mild transition-metal-free conditions. Functionalized non-symmetrical bi-indolyl heterocycles were accessed efficiently. Introduction of a new type of C2-substituted indole benziodoxole reagents further allowed extending the scope of the reaction to NH unprotected and C3-alkylated indoles. The obtained bi-heterocycles are important building blocks in synthetic and medicinal chemistry, and could be easily transformed into more complex heterocyclic systems.

Divergent Access to (1,1) and (1,2)-Azidolactones from Alkenes using Hypervalent Iodine Reagents

Alazet, Sébastien,Le Vaillant, Franck,Nicolai, Stefano,Courant, Thibaut,Waser, Jerome

supporting information, p. 9501 - 9504 (2017/07/22)

A versatile synthesis of azidolactones through azidation and cyclization of carboxylic acids onto alkenes has been developed. Based on either photoredox or palladium catalysis, (1,1) and (1,2) azido lactones can be selectively synthesized. The choice of catalyst and benziodoxol(on)e reagent serving as azide source was essential to initiate either a radical or Lewis acid mediated process with divergent outcome. These transformations were carried out under mild conditions using a low catalyst loading and gave access to a large scope of azido lactones.

Synthesis and Structure of Hypervalent Iodine(III) Reagents Containing Phthalimidate and Application to Oxidative Amination Reactions

Kiyokawa, Kensuke,Kosaka, Tomoki,Kojima, Takumi,Minakata, Satoshi

, p. 13719 - 13723 (2015/11/11)

A new class of hypervalent iodine reagents containing phthalimidate was synthesized, and structurally characterized by X-ray analysis. The benziodoxole-based reagent displays satisfactory solubility in common organic solvents and is reasonably stable in solution as well as in the solid state. The reagent was used for the oxidative amination of the C(sp3)-H bond of N,N-dimethylanilines. In addition, the reagent was also applicable to oxidative amination with rearrangement of trialkylamines as well as enamines that were prepared in situ from secondary amines and aldehydes.

Enantioselective Synthesis of Homoallylic Azides and Nitriles via Palladium-Catalyzed Decarboxylative Allylation

Vita, Maria Victoria,Caramenti, Paola,Waser, Jerome

supporting information, p. 5832 - 5835 (2015/12/11)

Azides and nitriles are important building blocks for the synthesis of nitrogen-containing bioactive compounds. The first example of enantioselective palladium-catalyzed decarboxylative allylation of α-azido and cyano β-ketoesters is reported. Indanone derivatives were obtained in 50-88% yield/77-97% ee and 46-98% yield/78-93% ee for azide and nitrile substituents, respectively. The required starting materials were synthesized in one step from ketoesters via electrophilic azidation and cyanation using benziodoxole hypervalent iodine reagents. The products could be easily converted into useful nitrogen-containing building blocks, such as triazoles, amides, or α- and β- amino ketones.

Ethynylbenziodoxolones (EBX) as reagents for the ethynylation of stabilized enolates

Fernandez Gonzalez, Davinia,Brand, Jonathan P.,Mondiere, Regis,Waser, Jerome

supporting information, p. 1631 - 1639 (2013/07/05)

Herein, we report a detailed study on the electrophilic alkynylation of cyclic keto esters and amides with ethynylbenziodoxolone (EBX) reagents. The structure and stability of this class of reagents is first described more in details. Differential scannin

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