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1H-Indole, 2-methyl-3-(2-nitro-1-phenylethyl)- is a Michael addition product formed by the conjugate addition of 2-methylindole to β-nitrostyrene. This reaction is efficiently catalyzed under mild conditions by various systems, including silica sulfuric acid, iodine, bis-arylurea/thiourea organocatalysts, and water-soluble copper complexes, yielding the nitroalkylated indole derivative in high yields. The process is notable for its environmental friendliness, short reaction times, and potential for catalyst reuse.

109809-52-1

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109809-52-1 Usage

Check Digit Verification of cas no

The CAS Registry Mumber 109809-52-1 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 1,0,9,8,0 and 9 respectively; the second part has 2 digits, 5 and 2 respectively.
Calculate Digit Verification of CAS Registry Number 109809-52:
(8*1)+(7*0)+(6*9)+(5*8)+(4*0)+(3*9)+(2*5)+(1*2)=141
141 % 10 = 1
So 109809-52-1 is a valid CAS Registry Number.

109809-52-1Downstream Products

109809-52-1Relevant academic research and scientific papers

2-aminopyridinium ions activate nitroalkenes through hydrogen bonding

Takenaka, Norito,Sarangthem, Robindro Singh,Seerla, Sreehari Kumar

, p. 2819 - 2822 (2007)

2-Aminopyridinium ions were found to activate nitroalkenes toward conjugate addition of heteroaromatic compounds with low catalyst loadings and the Diels Alder reaction with the periselectivity opposite to that observed with metal Lewis acids, raising the

Silica sulfuric acid-catalyzed Friedel-Crafts alkylation of indoles with nitro olefins

Hari, G. Sri,Nagaraju,Murthy, M. Marthanda

, p. 100 - 105 (2008)

The 1,4-conjugate addition of indoles to nitro olefins was efficiently carried out using an environmentally benign catalyst, silica sulfuric acid, at ambient temperature. Copyright Taylor & Francis Group, LLC.

H-bonding organocatalysed Friedel-Crafts alkylation of aromatic and heteroaromatic systems with nitroolefins

Dessole, Gabriella,Herrera, Raquel P.,Ricci, Alfredo

, p. 2374 - 2378 (2004)

Catalytic amounts (10 mol%) of bis-arylureas and -thioureas promote the Friedel-Crafts alkylation with nitroolefins of aromatic and heteroaromatic N-containing derivatives. A sizeable improvement of the yields is noticed on running the reactions in the ab

I2-catalyzed Michael addition of indole and pyrrole to nitroolefins

Lin, Chunchi,Hsu, Jianming,Sastry,Fang, Hulin,Tu, Zhijay,Liu, Ju-Tsung,Ching-Fa, Yao

, p. 11751 - 11757 (2005)

An easy and efficient method to generate indolyl nitroalkane 5 and pyrrolyl nitroalkane 7 in high yields using β-nitrostyrene and indole/pyrrole at room temperature in the presence of catalytic amount of iodine is reported. The short reaction times and hi

Water-soluble (salicyladimine)2Cu complex as an efficient and renewable catalyst for Michael addition of indoles to nitroolefins in water

Jiang, Haojie,Zhang, Jie,Xie, Jianwei,Liu, Ping,Xue, Mei

, p. 211 - 216 (2017)

An efficient and environmentally friendly protocol has been demonstrated for water-soluble (salicyladimine)2Cu complex-catalyzed Michael addition of indoles to nitroolefins in water at 30 °C. A variety of substituted indoles and β-nitrostyrenes could be worked well to provide the title products in 81–97% yields. Moreover, the catalyst can be reused directly at least for four times without significantly decreasing activity.

Michael addition of indoles to electron deficient olefins in water catalysed by potassium bisulfate

Kumar, R. Senthil,Perumal, Paramasivan T.

, p. 1383 - 1385 (2006)

The Michael addition of indoles to various election deficient olefins was performed in water using potassium hydrogen sulphate as catalyst at room temperature.

Efficient michael addition of indoles using bismuthyl perchlorate as catalyst

Mohammadpoor-Baltork, Iraj,Reza Memarian, Hamid,Reza Khosropour, Ahmad,Nikoofar, Kobra

, p. 1837 - 1843 (2006)

An efficient method for Michael addition of indoles hasbeen developed using bismuthyl perchlorate (BiOClO4·xH2O) as catalyst. The reaction proceeds to give 3-substituted indoles excellently stirring indoles and Michael acceptors in acetonitrile in the presence of the catalyst at room temperature or in much shorter reaction times under sonication at ambient temperature.{A figure is presented}.

Montmorillonite K10-catalyzed michael addition of indoles to nitroolefins under solvent-free conditions

Chen, Wei-Yi,Li, Xin-Sheng

, p. 2014 - 2021 (2009)

Montmorillonite K10 is a very inexpensive and readily available reagent and efficiently catalyzes the Michael addition of indoles to nitroolefins under solvent-free conditions. Reasonable to excellent yields of the desired products were obtained in most c

Sulfamic acid-catalyzed Michael addition of indoles and pyrrole to electron-deficient nitroolefins under solvent-free condition

An, Li-Tao,Zou, Jian-Ping,Zhang, Li-Li,Zhang, Yong

, p. 4297 - 4300 (2007)

Sulfamic acid (SA) effectively catalyze the Michael addition of indoles and pyrrole to nitroolefins under solvent-free condition to afford the corresponding Michael adducts in good to excellent yields.

Influence of oxophilic behavior of UiO-66(Ce) metal–organic framework with superior catalytic performance in Friedel-Crafts alkylation reaction

Nagarjun, Nagarathinam,Concepcion, Patricia,Dhakshinamoorthy, Amarajothi

, (2020)

In recent years, one of the analogous metal organic frameworks (MOFs) with UiO-66(Zr) topology receiving wider attention is UiO-66(Ce), which exhibits interesting properties and high thermal and chemical stability. Hence, in the present work, UiO-66(Ce) i

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