Production Method 1

26340-47-6

80360-14-1

Reaction Conditions

1.1 Reagents: Sodium hydroxide ,  Tetrabutylammonium hydroxide Solvents: Benzene ,  Water

Reference

N-phenyl sulphonation of indoles and the synthesis and reactions of oxepino[3,2-b]indoles and oxepino[3,2-b]azaindoles

Dalton, Lesley, 1983, , ,

Production Method 2

120-72-9

80360-14-1

Reaction Conditions

1.1 Reagents: Butyllithium Solvents: Tetrahydrofuran
1.2 Reagents: Iodine
1.3 Reagents: Lithium diisopropylamide
1.4 -

Reference

Bis-Suzuki reactions of 2,3-dihaloindoles. A convenient synthesis of 2,3-diarylindoles

Liu, Yanbing; et al, Tetrahedron Letters, 2000, 41(45), 8717-8721

Production Method 3

112890-09-2

80360-14-1

Reaction Conditions

1.1 Reagents: Ethane, nitro-, ion(1-), lithium Catalysts: Copper sulfate

Reference

A new carbon-carbon bond-forming reaction in indole chemistry. C-3 arylation and alkylation with phenyl (β-indolyl)iodonium trifluroacetate

Moriarty, Robert M.; et al, Tetrahedron Letters, 1987, 28(27), 3071-4

Production Method 4

129271-98-3

80360-14-1

Reaction Conditions

1.1 Reagents: Iodine ,  Potassium fluoride Solvents: 1,4-Dioxane ;  1 h, 80 °C

Reference

Practical and efficient ipso-iodination of arylboronic acids via KF/I2 system

Tramutola, Francesco ; et al, Tetrahedron Letters, 2015, 56(9), 1122-1123

Production Method 5

36284-95-4

80360-14-1

Reaction Conditions

1.1 Reagents: N-Iodosuccinimide Solvents: Methanol
1.2 Reagents: Sodium hydroxide ,  Tetrabutylammonium bromide Solvents: Toluene

Reference

N-Iodosuccinimide

Virgil, Scott C.; et al, e-EROS Encyclopedia of Reagents for Organic Synthesis, 2001, ,

Production Method 6

40899-71-6

80360-14-1

Reaction Conditions

1.1 Reagents: Pyridine ,  Bis(trifluoroacetoxy)iodobenzene ,  Iodine Solvents: Dichloromethane

Reference

A mild and effective iodination method using iodine in the presence of bis(trifluoroacetoxy)iodobenzene

Benhida, Rachid; et al, Tetrahedron Letters, 1998, 39(38), 6849-6852

Production Method 7

80360-14-1

Reaction Conditions

Reference

Product class 13: indole and its derivatives

Joule, J. A., Science of Synthesis, 2001, 10, 361-652

Production Method 8

15121-84-3

80360-14-1

Reaction Conditions

Reference

Product class 13: indole and its derivatives

Joule, J. A., Science of Synthesis, 2001, 10, 361-652

Production Method 9

80360-14-1

Reaction Conditions

Reference

Product class 13: indole and its derivatives

Joule, J. A., Science of Synthesis, 2001, 10, 361-652

Production Method 10

201486-62-6

80360-14-1

Reaction Conditions

Reference

Product class 13: indole and its derivatives

Joule, J. A., Science of Synthesis, 2001, 10, 361-652

Production Method 11

5339-85-5

80360-14-1

Reaction Conditions

Reference

Product class 13: indole and its derivatives

Joule, J. A., Science of Synthesis, 2001, 10, 361-652

Production Method 12

26340-47-6

80360-14-1

Reaction Conditions

1.1 Reagents: Sodium hydroxide Catalysts: Tetrabutylammonium hydrogen sulfate Solvents: Benzene ,  Water ;  1 h, rt

Reference

A simple iodination protocol via in situ generated ICl using NaI/FeCl3

Mohanakrishnan, Arasambattu K.; et al, Tetrahedron, 2006, 62(14), 3242-3247

Production Method 13

120-72-9

80360-14-1

Reaction Conditions

1.1 Reagents: Potassium hydroxide ,  Iodine Solvents: Water
1.2 Reagents: Sodium hydride

Reference

Development of Highly Stereoselective Asymmetric 6π-Azaelectrocyclization of Conformationally Flexible Linear 1-Azatrienes. From Determination of Multifunctional Chiral Amines, 7-Alkyl cis-1-Amino-2-indanols, to Application as a New Synthetic Strategy: Formal Synthesis of 20-Epiuleine

Tanaka, Katsunori; et al, Journal of Organic Chemistry, 2004, 69(18), 5906-5925

Production Method 14

120-72-9

80360-14-1

Reaction Conditions

1.1 Reagents: Potassium hydroxide ,  Iodine Solvents: Dimethylformamide ;  2 h, rt
1.2 Reagents: Ethyl acetate ,  Sodium thiosulfate Solvents: Water ;  rt
1.3 Reagents: Sodium hydride ,  Water Solvents: Dimethylformamide ;  rt → 0 °C; 20 min, 0 °C; 0 °C; 30 min, 0 °C; 3 h, 0 °C → rt
1.4 Reagents: Ethyl acetate ;  rt

Reference

Direct Synthesis of Benzo[c]carbazoles by Pd-Catalyzed C-H [4 + 2] Annulation of 3-Arylindoles with External 1,3-Dienes

Gerardin, Baptiste; et al, Organic Letters, 2022, 24(44), 8164-8169

Production Method 15

36284-95-4

80360-14-1

Reaction Conditions

1.1 Reagents: N-Iodosuccinimide Solvents: Methanol
1.2 Reagents: Sodium hydroxide Catalysts: Tetrabutylammonium bromide Solvents: Toluene

Reference

N-iodosuccinimide

Virgil, Scott C., e-EROS Encyclopedia of Reagents for Organic Synthesis, 2007, 1, 1-6

Production Method 16

87-52-5

80360-14-1

Reaction Conditions

1.1 Reagents: N-Iodosuccinimide Solvents: Dichloromethane
1.2 Reagents: Sodium hydroxide Catalysts: Tetrabutylammonium bromide Solvents: Toluene ,  Water

Reference

Rapid Route to 3,4-Substituted Indoles via a Directed Ortho Metalation-Retro-Mannich Sequence

Chauder, Brian; et al, Organic Letters, 2002, 4(5), 815-817

Production Method 17

40899-71-6

80360-14-1

Reaction Conditions

1.1 Reagents: Iodine ,  1-[[(4-Methylphenyl)sulfonyl]oxy]-1,2-benziodoxol-3(1H)-one Solvents: Acetonitrile

Reference

Synthetic use of 1-(4-toluenesulfonyloxy)-1,2-benziodoxol-3(1H)-one. Iodination of aromatic rings

Muraki, Takahito; et al, Synlett, 1998, (3), 286-288

Production Method 18

116482-39-4

80360-14-1

Reaction Conditions

Reference

Product class 13: indole and its derivatives

Joule, J. A., Science of Synthesis, 2001, 10, 361-652

Production Method 19

120-72-9

80360-14-1

Reaction Conditions

1.1 Reagents: Potassium hydroxide ,  Iodine Solvents: Dimethylformamide ;  15 min, rt
2.1 Reagents: Sodium hydroxide Catalysts: Tetrabutylammonium bromide Solvents: Tetrahydrofuran ,  Water ;  0 °C; 3 h, rt

Reference

Mono-selective β-C-H arylation of N-methylated amino acids and peptides promoted by the 2-(methylthio)aniline directing group

Kinsinger, Thorsten; et al, Organic & Biomolecular Chemistry, 2019, 17(22), 5595-5600

Production Method 20

120-72-9

80360-14-1

Reaction Conditions

1.1 Reagents: Iodine chloride Solvents: Acetonitrile ;  15 min, 0 °C; 6 h, 0 °C
1.2 Reagents: Ammonium chloride Solvents: Water
2.1 Reagents: Sodium hydroxide Catalysts: Tetrabutylammonium hydrogen sulfate Solvents: Benzene ,  Water ;  1 h, rt

Reference

A simple iodination protocol via in situ generated ICl using NaI/FeCl3

Mohanakrishnan, Arasambattu K.; et al, Tetrahedron, 2006, 62(14), 3242-3247

Production Method 21

80360-14-1

Reaction Conditions

Reference

Product class 13: indole and its derivatives

Joule, J. A., Science of Synthesis, 2001, 10, 361-652

Production Method 22

201486-55-7

80360-14-1

Reaction Conditions

Reference

Product class 13: indole and its derivatives

Joule, J. A., Science of Synthesis, 2001, 10, 361-652

Production Method 23

80360-14-1

Reaction Conditions

Reference

Product class 13: indole and its derivatives

Joule, J. A., Science of Synthesis, 2001, 10, 361-652

Production Method 24

36284-95-4

80360-14-1

Reaction Conditions

1.1 Reagents: N-Iodosuccinimide Solvents: Methanol
2.1 Reagents: Sodium hydroxide Catalysts: Tetrabutylammonium bromide Solvents: Toluene

Reference

N-iodosuccinimide

Virgil, Scott C., e-EROS Encyclopedia of Reagents for Organic Synthesis, 2007, 1, 1-6

Production Method 25

496-15-1

80360-14-1

Reaction Conditions

Reference

Product class 13: indole and its derivatives

Joule, J. A., Science of Synthesis, 2001, 10, 361-652

3-Iodo-1-(phenylsulfonyl)-1H-indole Raw materials

• 2,3-dihydro-1H-indole
• Indole
• 2-Nitrophenethyl alcohol
• [1-(benzenesulfonyl)indol-3-yl]-phenyliodanium,chloride
• 1-(benzenesulfonyl)-1H-indole
• 1-(phenylsulfonyl)-3-indoleboronic acid
• 1H-Indole-1-methanol, α-(4-phenylbutyl)-
• Gramine
• 3-Iodoindole
• 2-Aminophenethyl Alcohol
• N-Methyl-N-(1H-indol-3-yl)methylamine
• (2E)-1-(1H-Indol-1-yl)-3-phenyl-2-propen-1-one
• Benzene, 1-(2-ethoxyethenyl)-2-nitro-, (E)- (9CI)

3-Iodo-1-(phenylsulfonyl)-1H-indole Preparation Products

• 3-Iodo-1-(phenylsulfonyl)-1H-indole (80360-14-1)

• 1. Excellent peroxidase mimicking property of CuO/Pt nanocomposites and their application as an ascorbic acid sensor?
  Xinhuan Wang,Shuangfei Cai,Cui Qi Analyst, 2017,142, 2500-2506
• 2. Fatty acid positional distribution in colostrum and mature milk of women living in Inner Mongolia, North Jiangsu and Guangxi of China?
  Long Deng,Qian Zou,Biao Liu,Wenhui Ye,Chengfei Zhuo,Li Chen,Ze-Yuan Deng,Ya-Wei Fan,Jing Li Food Funct., 2018,9, 4234-4245
• 3. Evolution of cellulose into flexible conductive green electronics: a smart strategy to fabricate sustainable electrodes for supercapacitors
  Tengfei Yu,Yuehan Wu,Wei Li,Bin Li RSC Adv., 2014,4, 34134-34143
• 4. Enabling shape memory and healable effects in a conjugated polymer by incorporating siloxane via dynamic imine bond?
  Yaling Zhang,Chunhui Dai,Shiwei Zhou,Bin Liu Chem. Commun., 2018,54, 10092-10095
• 5. Fate of nitrogen-15 in the subsequent growing season of greenhouse tomato plants (Lycopersicon esculentum Mill) as influenced by alternate partial root-zone irrigation
  Maomao Hou,Fenglin Zhong,Qiu Jin,Enjiang Liu,Jie Feng,Tengyun Wang,Yue Gao RSC Adv., 2017,7, 34392-34400

• Solvents and Organic Chemicals Organic Compounds Benzenoids Benzene and substituted derivatives Benzenesulfonamides

Introduction to 3-Iodo-1-(phenylsulfonyl)-1H-indole (CAS No. 80360-14-1) and Its Significance in Modern Chemical Biology

3-Iodo-1-(phenylsulfonyl)-1H-indole, identified by the chemical identifier CAS No. 80360-14-1, represents a compound of considerable interest in the realm of chemical biology and pharmaceutical research. This heterocyclic molecule, featuring an indole core substituted with an iodo group and a phenylsulfonyl moiety, has garnered attention due to its versatile structural framework and potential applications in drug discovery and molecular imaging. The unique combination of functional groups in this compound imparts distinct chemical properties, making it a valuable scaffold for synthesizing novel bioactive molecules.

The indole ring, a prominent structural motif in numerous pharmacologically active compounds, is known for its role in modulating biological pathways. Its aromaticity and ability to engage in hydrogen bonding make it an ideal platform for designing molecules that interact with biological targets. In 3-Iodo-1-(phenylsulfonyl)-1H-indole, the presence of an iodo substituent at the 3-position enhances electrophilicity, facilitating further functionalization through cross-coupling reactions such as Suzuki or Stille couplings. This attribute is particularly useful in constructing complex molecular architectures.

The phenylsulfonyl group at the 1-position introduces a polar, electron-withdrawing moiety that can influence the electronic properties of the indole ring. This substitution pattern is often employed to enhance binding affinity and metabolic stability, key factors in drug design. The interplay between the iodo group and the phenylsulfonyl group creates a balance of reactivity and stability, making 3-Iodo-1-(phenylsulfonyl)-1H-indole a promising intermediate in synthetic chemistry.

Recent advancements in medicinal chemistry have highlighted the importance of indole derivatives in addressing various therapeutic challenges. For instance, studies have demonstrated that indole-based compounds exhibit potent activity against infectious diseases, cancer, and neurological disorders. The structural features of 3-Iodo-1-(phenylsulfonyl)-1H-indole align well with these pharmacophoric requirements, suggesting its potential utility in developing novel therapeutic agents.

In particular, the iodo substituent serves as a versatile handle for further derivatization. Transition-metal-catalyzed cross-coupling reactions are widely employed to introduce diverse functional groups at specific positions of the indole ring. For example, palladium-catalyzed Suzuki-Miyaura coupling allows for the introduction of aryl or heteroaryl groups, while Stille coupling enables the incorporation of alkyl or alkenyl moieties. These reactions are instrumental in generating libraries of structurally diverse compounds for high-throughput screening.

The phenylsulfonyl group also contributes to the compound's reactivity and functionality. It can participate in nucleophilic aromatic substitution (SNAr) reactions, enabling the introduction of various nucleophiles such as amines or thiols. Additionally, the sulfonyl group can serve as a leaving group in other transformations, such as sulfonamide formation or metalation processes. These attributes make 3-Iodo-1-(phenylsulfonyl)-1H-indole a versatile building block for constructing complex molecules with tailored biological activities.

One notable application of this compound is in the synthesis of probes for molecular imaging techniques. Indole derivatives have been extensively used as contrast agents due to their ability to interact with biological targets and emit detectable signals. The presence of both an iodo group and a phenylsulfonyl moiety allows for further functionalization to enhance imaging properties while maintaining biocompatibility.

Moreover, recent research has explored the use of 3-Iodo-1-(phenylsulfonyl)-1H-indole in developing inhibitors targeting enzyme-mediated pathways relevant to diseases such as cancer and inflammation. The indole core is known to interact with enzymes like kinases and cyclases, which are often dysregulated in pathological conditions. By leveraging the reactivity of the iodo and phenylsulfonyl groups, researchers have designed molecules that disrupt these enzymatic processes without significant off-target effects.

The synthesis of 3-Iodo-1-(phenylsulfonyl)-1H-indole typically involves multi-step organic transformations starting from commercially available precursors. A common synthetic route includes sulfonylation of indole followed by iodination at the 3-position. Optimization of reaction conditions is crucial to achieve high yields and purity while minimizing side products. Advances in catalytic systems have further refined these synthetic protocols, making them more efficient and environmentally friendly.

In conclusion,3-Iodo-1-(phenylsulfonyl)-1H-indole (CAS No. 80360-14-1) is a multifaceted compound with significant potential in chemical biology and pharmaceutical research. Its unique structural features enable diverse functionalization strategies, making it a valuable intermediate for drug discovery and molecular imaging applications. As research continues to uncover new therapeutic targets and methodologies,3-Iodo-1-(phenylsulfonyl)-1H-indole is poised to play an increasingly important role in developing next-generation bioactive molecules.

• 112890-09-2([1-(benzenesulfonyl)indol-3-yl]-phenyliodanium,chloride)
• 8033-69-0(3-Iodo-1-(phenylsulfonyl)indole)
• 170456-80-1(3-Iodo-1-tosylindole)
• 882562-71-2(3-Iodo-1-(phenylsulfonyl)-1H-indole-6-carbonitrile)
• 887115-55-1(3-iodo-1-(phenylsulfonyl)-1H-pyrrolo[2,3-c]pyridine)
• 90481-83-7(1H-INDOLE, 4-BROMO-3-IODO-1-[(4-METHYLPHENYL)SULFONYL]-)
• 582305-43-9(5-Bromo-3-iodo-1-(phenylsulfonyl)indole)
• 102855-25-4(1H-Indole, 4-iodo-1-[(4-methylphenyl)sulfonyl]-)
• 142688-28-6(5-bromo-3-iodo-1-tosyl-1H-indole)
• 882562-73-4(3-Iodo-1-(4-methylbenzenesulfonyl)-1H-pyrrolo[3,2-c]pyridine)