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N-(4-iodophenyl)-4-methylbenzenesulfonamide, also known as IMS, is a chemical compound with the molecular formula C13H12INO2S. It is a sulfonamide derivative that contains both an iodophenyl and a methylbenzene group. IMS is characterized by its unique structure and reactivity, making it a valuable intermediate in organic synthesis and a versatile compound in the field of medicinal chemistry and drug development.

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  • 158268-30-5 Structure
  • Basic information

    1. Product Name: N-(4-iodophenyl)-4-methylbenzenesulfonamide
    2. Synonyms:
    3. CAS NO:158268-30-5
    4. Molecular Formula: C13H12INO2S
    5. Molecular Weight: 373.2094
    6. EINECS: N/A
    7. Product Categories: N/A
    8. Mol File: 158268-30-5.mol
  • Chemical Properties

    1. Melting Point: N/A
    2. Boiling Point: 446.5°C at 760 mmHg
    3. Flash Point: 223.8°C
    4. Appearance: N/A
    5. Density: 1.72g/cm3
    6. Vapor Pressure: 3.62E-08mmHg at 25°C
    7. Refractive Index: 1.674
    8. Storage Temp.: N/A
    9. Solubility: N/A
    10. CAS DataBase Reference: N-(4-iodophenyl)-4-methylbenzenesulfonamide(CAS DataBase Reference)
    11. NIST Chemistry Reference: N-(4-iodophenyl)-4-methylbenzenesulfonamide(158268-30-5)
    12. EPA Substance Registry System: N-(4-iodophenyl)-4-methylbenzenesulfonamide(158268-30-5)
  • Safety Data

    1. Hazard Codes: N/A
    2. Statements: N/A
    3. Safety Statements: N/A
    4. WGK Germany:
    5. RTECS:
    6. HazardClass: N/A
    7. PackingGroup: N/A
    8. Hazardous Substances Data: 158268-30-5(Hazardous Substances Data)

158268-30-5 Usage

Uses

Used in Pharmaceutical Industry:
N-(4-iodophenyl)-4-methylbenzenesulfonamide is used as a building block for the synthesis of various biologically active compounds, such as potential anticancer agents and antimicrobial drugs. Its unique structure and reactivity contribute to the development of new and effective pharmaceuticals.
Used in Medicinal Chemistry Research:
IMS is used as a reagent in medicinal chemistry research and drug discovery due to its ability to modify and block specific biological targets. This makes it a valuable tool for exploring novel therapeutic approaches and advancing the understanding of disease mechanisms.
Used in Organic Synthesis:
N-(4-iodophenyl)-4-methylbenzenesulfonamide is used as an intermediate in organic synthesis, allowing for the creation of a wide range of chemical compounds with diverse applications. Its versatility in this field is attributed to its unique structure and reactivity, facilitating the synthesis of complex molecules and contributing to the advancement of chemical science.

Check Digit Verification of cas no

The CAS Registry Mumber 158268-30-5 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 1,5,8,2,6 and 8 respectively; the second part has 2 digits, 3 and 0 respectively.
Calculate Digit Verification of CAS Registry Number 158268-30:
(8*1)+(7*5)+(6*8)+(5*2)+(4*6)+(3*8)+(2*3)+(1*0)=155
155 % 10 = 5
So 158268-30-5 is a valid CAS Registry Number.

158268-30-5SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 15, 2017

Revision Date: Aug 15, 2017

1.Identification

1.1 GHS Product identifier

Product name N-(4-iodophenyl)-4-methylbenzenesulfonamide

1.2 Other means of identification

Product number -
Other names N-tosyl-4-iodoaniline

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:158268-30-5 SDS

158268-30-5Relevant articles and documents

Palladium-catalyzed alkylation-hydride reduction sequence: Synthesis of meta-substituted arenes

Wilhelm, Thorsten,Lautens, Mark

, p. 4053 - 4056 (2005)

(Chemical Equation Presented) A new three-component, palladium-catalyzed domino reaction which gives access to meta-substituted arenes using aryl iodides and primary alkyl halides is reported. Various functional groups are tolerated on both the aryl iodide and alkyl halide. In addition, isotopic labeling studies provide insight into the mechanism of this Catellani-type reaction.

Fully automated multi-step solution phase synthesis using polymer supported reagents: preparation of histone deacetylase inhibitors.

Vickerstaffe, Emma,Warrington, Brian H,Ladlow, Mark,Ley, Steven V

, p. 2419 - 2422 (2003)

The first fully automated multi-step polymer assisted solution phase (PASP) synthesis is described. An array of histone deacetylase (HDAc) inhibitors was prepared by an unattended 4-5 step sequence incorporating in-line 'catch and release' purification.

Synthesis, Characterization, and Reactivity of an Ethynyl Benziodoxolone (EBX)-Acetonitrile Complex

Yudasaka, Masaharu,Shimbo, Daisuke,Maruyama, Toshifumi,Tada, Norihiro,Itoh, Akichika

supporting information, p. 1098 - 1102 (2019/05/16)

The synthesis of a crystalline ethynyl-1,2-benziodoxol-3(1H)-one (EBX)-acetonitrile complex is described. EBX has been widely used as an active species for a variety of reactions; however, its high instability has so far prevented its isolation. The EBX-acetonitrile is self-assembled into a double-layered honeycomb structure through weak hypervalent iodine secondary interactions and hydrogen bonding. The N-ethynylation of a variety of sulfonamides using the EBX-acetonitrile complex as a substrate under mild conditions is also described.

Disulfide-Catalyzed Iodination of Electron-Rich Aromatic Compounds

Iida, Keisuke,Ishida, Shunsuke,Watanabe, Takamichi,Arai, Takayoshi

, (2019/06/13)

Herein, a disulfide-catalyzed electrophilic iodination of aromatic compounds using 1,3-diiodo-5,5-dimethylhydantoin (DIH) has been developed. The disulfide activates DIH as a Lewis base to promote the iodination reaction in acetonitrile under mild conditions. This system is applicable to a wide range of electron-rich aromatic compounds, including acetanilide, anisole, imidazole, and pyrazole derivatives.

Disulfide-Catalyzed Iodination of Electron-Rich Aromatic Compounds

Iida, Keisuke,Ishida, Shunsuke,Watanabe, Takamichi,Arai, Takayoshi

, p. 7411 - 7417 (2019/06/18)

Herein, a disulfide-catalyzed electrophilic iodination of aromatic compounds using 1,3-diiodo-5,5-dimethylhydantoin (DIH) has been developed. The disulfide activates DIH as a Lewis base to promote the iodination reaction in acetonitrile under mild conditions. This system is applicable to a wide range of electron-rich aromatic compounds, including acetanilide, anisole, imidazole, and pyrazole derivatives.

Triple Mode of Alkylation with Ethyl Bromodifluoroacetate: N, or O-Difluoromethylation, N-Ethylation and S-(ethoxycarbonyl)difluoromethylation

Polley, Arghya,Bairy, Gurupada,Das, Pritha,Jana, Ranjan

supporting information, p. 4161 - 4167 (2018/09/21)

In this report, we have explored a triple mode of chemical reactivity of ethyl bromodifluoroacetate. Typically, bromodifluoroacetic acid has been used as a difluorocarbene precursor for difluoromethylation of soft nucleophiles. Here we have disclosed nucleophilicity and base dependent divergent chemical reactivity of ethyl bromodifluoroacetate. It furnishes lithium hydroxide and cesium carbonate promoted difluoromethylation of tosyl-protected aniline and electron-deficient phenols respectively. Interestingly, switching the base from lithium hydroxide to 4-N,N-dimethylamino pyridine (DMAP) tosyl-protected anilines afforded the corresponding N-ethylation product. Whereas, highly nucleophilic thiophenols furnished the corresponding S-carboethoxydifluoromethylation product via a rapid SN2 attack to the bromine atom prior to the ester hydrolysis. This mechanistic divergence was established through several control experiments. It was revealed that difluoromethylation reaction proceeds through a tandem in situ ester hydrolysis/decarboxylative-debrominative difluorocarbene formation and subsequent trapping by the soft nucleophile-NHTs or electron-deficient phenolic ?OH groups. In the presence of DMAP the hydrolysis of the ester is perturbed instead a nucleophilic attack at the ethyl moiety provides the N-ethylation product. Hence, besides the development of a practical base-promoted N-difluoromethylation of amines and electron-deficient phenols, divergent reactivity pattern of inexpensive and user-friendly ethyl bromodifluoroacetate has been explored. (Figure presented.).

Multicomponent Oxidative Trifluoromethylation of Alkynes with Photoredox Catalysis: Synthesis of α-Trifluoromethyl Ketones

Malpani, Yashwardhan R.,Biswas, Bishyajit Kumar,Han, Hong Sik,Jung, Young-Sik,Han, Soo Bong

supporting information, p. 1693 - 1697 (2018/04/16)

The direct oxidative addition of CF3 and H2O to alkynes was achieved with photoredox catalysis to obtain α-trifluoromethyl ketones via rapid enol-keto tautomerization. The reaction exhibits high functional group tolerance and regioselectivity. Heterocycles of various sizes containing CF3 were synthesized from the α-CF3-substituted diketones obtained through the protocol, thereby demonstrating the versatile applicability of the method. Mechanistic studies of the reaction with isotopes provided insight into the reaction pathway.

NaI-Catalyzed Oxidative Amination of Aromatic Sodium Sulfinates: Synergetic Effect of Ethylene Dibromide and Air as Oxidants

Fu, Ying,Li, Quan-Zhou,Xu, Qin-Shan,Hügel, Helmut,Li, Ming-Peng,Du, Zhengyin

supporting information, p. 6966 - 6970 (2018/11/23)

A novel NaI-catalyzed oxidative amination of sodium sulfinates, employing both ethylene dibromide (EDB) and air as the oxidants, is described. EDB was first demonstrated to be a promising mild organic oxidant that in air, converted NaI into molecular iodine to promote the cross-coupling reactions of aromatic sodium sulfinates with amines to produce arylsulfonamides. Mechanistic studies indicated that a radical pathway might be involved in the reaction process.

Synthesis of: N -arylsulfonamides via Fe-promoted reaction of sulfonyl halides with nitroarenes in an aqueous medium

Jiang, Jun,Zeng, Sheng,Chen, De,Cheng, Chaozhihui,Deng, Wei,Xiang, Jiannan

supporting information, p. 5016 - 5020 (2018/07/25)

A fascinating Fe-promoted protocol for the synthesis of N-arylsulfonamides has been developed. Starting from commercially available nitroarenes and sulfonyl chlorides, moderate to excellent yields of the corresponding N-arylsulfonamides can be obtained. In particular, Fe dust serves as the sole reductant in the transformation and it can be easily performed on a large scale.

Oxidant-dependent Cu-catalyzed alkynylation and aminomethylation: C-H versus C-C cleavage in TMEDA

Shen, Qi,Zhang, Lei,Zhou, Yu-Ren,Li, Jian-Xin

supporting information, p. 6725 - 6728 (2013/11/19)

Oxidant-dependent Cu-catalyzed alkynylation and aminomethylation reactions have been achieved under facile and mild conditions. TMEDA coupled with various terminal alkynes via C-H bond cleavage in good yields using atmospheric oxygen as an oxidant. Switching from air to TBHP afforded aminomethylation products of terminal alkynes through C-C bond cleavage of TMEDA. The protocol provided a novel strategy to prepare bi/tridentate N-ligand.

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