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3-IODO-BENZO[B]THIOHENE, also known as 3-iodobenzo[b]thiophene, is a heterocyclic aromatic compound with the molecular formula C8H5IS. It features a benzene ring fused to a thiophene ring, with an iodine substituent at the 3-position. This unique structure makes it a versatile building block in various fields.

36748-88-6

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36748-88-6 Usage

Uses

Used in Pharmaceutical Industry:
3-IODO-BENZO[B]THIOHENE is used as a key intermediate in the synthesis of pharmaceuticals for its ability to contribute to the development of new drugs with potential therapeutic properties.
Used in Agrochemical Industry:
In the agrochemical sector, 3-IODO-BENZO[B]THIOHENE is utilized as a building block for the creation of novel agrochemicals, potentially enhancing crop protection and yield.
Used in Materials Science:
3-IODO-BENZO[B]THIOHENE is employed as a component in the development of advanced materials, leveraging its unique chemical structure to improve material properties.
Used in Electronics Industry:
3-IODO-BENZO[B]THIOHENE is used as a precursor in the production of electronic materials, such as organic semiconductors and conducting polymers, due to its electronic properties and potential to enhance device performance.
Used in Chemical Research:
As an important intermediate, 3-IODO-BENZO[B]THIOHENE is utilized in various chemical reactions and transformations, contributing to the advancement of chemical science and the discovery of new compounds.

Check Digit Verification of cas no

The CAS Registry Mumber 36748-88-6 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 3,6,7,4 and 8 respectively; the second part has 2 digits, 8 and 8 respectively.
Calculate Digit Verification of CAS Registry Number 36748-88:
(7*3)+(6*6)+(5*7)+(4*4)+(3*8)+(2*8)+(1*8)=156
156 % 10 = 6
So 36748-88-6 is a valid CAS Registry Number.

36748-88-6SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 16, 2017

Revision Date: Aug 16, 2017

1.Identification

1.1 GHS Product identifier

Product name 3-iodo-1-benzothiophene

1.2 Other means of identification

Product number -
Other names 3-iodobenzothiophene

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:36748-88-6 SDS

36748-88-6Relevant articles and documents

Oxone-mediated halocyclization/demethylation of 2-alkynylthioanisoles with sodium halides towards 3-halobenzo[b]thiophenes

Chen, Xinyu,Zhang, Zhebing,Sun, Tao,Cai, Haokun,Gao, Yuzhen,Cai, Tao,Shang, Tianbo,Luo, Yanjuan,Yu, Guoqi,Shen, Hualiang,Wu, Guofeng,Hei, Yanlin,Li, Enmin,Fan, Gang

supporting information, (2022/01/14)

An efficient and practical protocol for the Oxone-mediated halocyclization/demethylation of 2-alkynylthioanisoles towards valuable 3-halobenzo[b]thiophenes is described. Structurally diverse 3-halobenzothiophenes were obtained in good to excellent yields

Nucleophilic C-H Etherification of Heteroarenes Enabled by Base-Catalyzed Halogen Transfer

Puleo, Thomas R.,Klaus, Danielle R.,Bandar, Jeffrey S.

supporting information, p. 12480 - 12486 (2021/08/24)

We report a general protocol for the direct C-H etherification of N-heteroarenes. Potassium tert-butoxide catalyzes halogen transfer from 2-halothiophenes to N-heteroarenes to form N-heteroaryl halide intermediates that undergo tandem base-promoted alcohol substitution. Thus, the simple inclusion of inexpensive 2-halothiophenes enables regioselective oxidative coupling of alcohols with 1,3-azoles, pyridines, diazines, and polyazines under basic reaction conditions.

Orthogonal Stability and Reactivity of Aryl Germanes Enables Rapid and Selective (Multi)Halogenations

Deckers, Kristina,Fricke, Christoph,Schoenebeck, Franziska

supporting information, p. 18717 - 18722 (2020/08/25)

While halogenation is of key importance in synthesis and radioimaging, the currently available repertoire is largely designed to introduce a single halogen per molecule. This report makes the selective introduction of several different halogens accessible. Showcased here is the privileged stability of nontoxic aryl germanes under harsh fluorination conditions (that allow selective fluorination in their presence), while displaying superior reactivity and functional-group tolerance in electrophilic iodinations and brominations, outcompeting silanes or boronic esters under rapid and additive-free conditions. Mechanistic experiments and computational studies suggest a concerted electrophilic aromatic substitution as the underlying mechanism.

Photocatalytic Oxidative Iodination of Electron-Rich Arenes

Narobe, Rok,Düsel, Simon J. S.,Iskra, Jernej,K?nig, Burkhard

supporting information, p. 3998 - 4004 (2019/07/17)

A visible-light-mediated oxidative iodination of electron-rich arenes has been developed. 2.5 mol% of unsubstituted anthraquinone as photocatalyst were used in combination with elementary iodine, trifluoroacetic acid and oxygen as the terminal oxidant. The iodination proceeds upon irradiation in non- or weakly-electron donating solvents (DCM, DCE and benzene) wherein a spectral window in strongly coloured iodine solutions can be observed at around 400 nm. The method provides good to excellent yields (up to 98%) and shows excellent regioselectivity and good functional group tolerance (triple bonds, ketone, ester, amide). Moreover, the photo-iodination was also upscaled to a 5 mmol scale (1.1 g). Mechanistic investigations by intermediate trapping and competition experiments indicate a photocatalytic arene oxidation and the subsequent reaction with iodine as a likely mechanistic pathway. (Figure presented.).

Metal-Free, Oxidant-Free, and Controllable Graphene Oxide Catalyzed Direct Iodination of Arenes and Ketones

Zhang, Jingyu,Li, Shiguang,Deng, Guo-Jun,Gong, Hang

, p. 376 - 380 (2017/12/07)

A direct, metal-free, and oxidant-free method for the graphene oxide (GO)-catalyzed iodination of arenes and ketones with iodine in a neutral medium was explored. This iodination protocol was performed by using a simple technique to avoid the use of external metal catalysts and oxidants and harsh acidic/basic reaction conditions. In addition, by this method the degree of iodination could be controlled, and the reaction was scalable and compatible with air. This strategy opens a new field for GO-catalyzed chemistry and provides an avenue for the convenient direct iodination of arenes and ketones.

Metathesis-active ligands enable a catalytic functional group metathesis between aroyl chlorides and aryl iodides

Lee, Yong Ho,Morandi, Bill

, p. 1016 - 1022 (2018/09/06)

Current methods for functional group interconversion have, for the most part, relied on relatively strong driving forces which often require highly reactive reagents to generate irreversibly a desired product in high yield and selectivity. These approaches generally prevent the use of the same catalytic strategy to perform the reverse reaction. Here we describe a catalytic functional group metathesis approach to interconvert, under CO-free conditions, two synthetically important classes of electrophiles that are often employed in the preparation of pharmaceuticals and agrochemicals—aroyl chlorides (ArCOCl) and aryl iodides (ArI). Our reaction design relies on the implementation of a key reversible ligand C–P bond cleavage event, which enables a non-innocent, metathesis-active phosphine ligand to mediate a rapid aryl group transfer between the two different electrophiles. Beyond enabling a practical and safer approach to the interconversion of ArCOCl and ArI, this type of ligand non-innocence provides a blueprint for the development of a broad range of functional group metathesis reactions employing synthetically relevant aryl electrophiles.

Transition-Metal-Free Decarboxylative Iodination: New Routes for Decarboxylative Oxidative Cross-Couplings

Perry, Gregory J. P.,Quibell, Jacob M.,Panigrahi, Adyasha,Larrosa, Igor

supporting information, p. 11527 - 11536 (2017/08/30)

Constructing products of high synthetic value from inexpensive and abundant starting materials is of great importance. Aryl iodides are essential building blocks for the synthesis of functional molecules, and efficient methods for their synthesis from chemical feedstocks are highly sought after. Here we report a low-cost decarboxylative iodination that occurs simply from readily available benzoic acids and I2. The reaction is scalable and the scope and robustness of the reaction is thoroughly examined. Mechanistic studies suggest that this reaction does not proceed via a radical mechanism, which is in contrast to classical Hunsdiecker-type decarboxylative halogenations. In addition, DFT studies allow comparisons to be made between our procedure and current transition-metal-catalyzed decarboxylations. The utility of this procedure is demonstrated in its application to oxidative cross-couplings of aromatics via decarboxylative/C-H or double decarboxylative activations that use I2 as the terminal oxidant. This strategy allows the preparation of biaryls previously inaccessible via decarboxylative methods and holds other advantages over existing decarboxylative oxidative couplings, as stoichiometric transition metals are avoided.

Green synthesis of benzo[b]thiophenes via iron(III) mediated 5-endo-dig iodocyclization of 2-alkynylthioanisoles

Kesharwani, Tanay,Kornman, Cory T.,Tonnaer, Amanda L.,Royappa, Andrew D.

supporting information, p. 411 - 414 (2016/01/12)

A reaction of iron(III) chloride with sodium iodide was used to generate iodine for an innovative take on electrophilic cyclization. With ethanol as solvent, the reaction was observed to provide ideal conditions for iodocyclization of 2-alkynylthioanisole

Synthesis of optically active homotryptophan and its oxygen and sulfur analogues

Goswami, Koushik,Paul, Sibasish,Bugde, Sandesh T.,Sinha, Surajit

, p. 280 - 286 (2012/01/05)

d-Homotryptophan and its sulfur analogue have been synthesized by Sonogashira coupling between 3-iodoheteroarenes and ethynyloxazolidine followed by reduction of triple bond and oxidation of alcohol to acid. l-Homotryptophan and its oxygen analogue have b

Iodine/Palladium approaches to the synthesis of polyheterocyclic compounds

Mehta, Saurabh,Larock, Richard C.

supporting information; experimental part, p. 1652 - 1658 (2010/05/01)

Chemical Equation Represented A simple, straightforward strategy for the synthesis of polyheterocyclic compounds (PHCs) is reported, which involves iterative cycles of palladium-catalyzed Sonogashira coupling, followed by iodocyclization using I2 or ICI. A variety of heterocyclic units, including benzofurans, benzothiophenes, indoles, and isocoumarins, can be efficiently incorporated under mild reaction conditions. In addition, variations of this strategy afford a variety of linked and fused PHCs.

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