Production Method 1

73-22-3

771-51-7

120-72-9

771-50-6

87-51-4

487-89-8

879-37-8

75833-70-4

103986-22-7

Reaction Conditions

1.1 Reagents: Oxygen Solvents: Water ;  20 min, pH 7.8, 37 °C
1.2 Reagents: Hydrochloric acid Solvents: Water

Reference

Production of indole-3-acetic acid and related indole derivatives from L-tryptophan by Rubrivivax benzoatilyticus JA2

Mujahid, Md.; et al, Applied Microbiology and Biotechnology, 2011, 89(4), 1001-1008

2-(1H-indol-3-yl)acetonitrile Raw materials

• L-Tryptophan

2-(1H-indol-3-yl)acetonitrile Preparation Products

• Indole (120-72-9)
• 1H-indole-3-carboxylic acid (771-50-6)
• 2-(1H-indol-3-yl)acetonitrile (771-51-7)
• 3-Indoleacetic acid (87-51-4)
• Indole-3-carboxaldehyde (487-89-8)
• 2-(1H-indol-3-yl)acetamide (879-37-8)
• 1H,1''H-3,3':3',3''-terindol-2'(1'H)-one (75833-70-4)
• 2-(6-Methoxy-1H-indol-3-yl)acetic Acid (103986-22-7)

• 1. An air-stable organometallic polymer containing titanafluorene moieties obtained by the Sonogashira–Hagihara cross-coupling polycondensation?
  Alvin Tanudjaja,Shinsuke Inagi,Fusao Kitamura,Toshikazu Takata,Ikuyoshi Tomita Dalton Trans., 2021,50, 3037-3043
• 2. An amorphous lanthanum–iridium solid solution with an open structure for efficient water splitting?
  Wei Sun,Chenglong Ma,Xinlong Tian,Jianjun Liao,Ji Yang,Chengjun Ge,Weiwei Huang J. Mater. Chem. A, 2020,8, 12518-12525
• 3. Aggregated-fluorescent detection of PFAS with a simple chip
  Cheng Fang,Jinjian Wu,Zahra Sobhani,Md. Al Amin,Youhong Tang Anal. Methods, 2019,11, 163-170
• 4. An insight into the origin of room-temperature ferromagnetism in SnO2 and Mn-doped SnO2 quantum dots: an experimental and DFT approach?
  Dhamodaran Manikandan,S. Amirthapandian,I. S. Zhidkov,A. I. Kukharenko,S. O. Cholakh,Ramaswamy Murugan Phys. Chem. Chem. Phys., 2018,20, 6500-6514
• 5. An intermolecular C–C coupling reaction of iridium complexes?
  Kathrin Kutlescha,Rhett Kempe New J. Chem., 2010,34, 1954-1960

• Solvents and Organic Chemicals Organic Compounds Organoheterocyclic compounds Indoles and derivatives 3-alkylindoles
• Solvents and Organic Chemicals Organic Compounds Organoheterocyclic compounds Indoles and derivatives Indoles 3-alkylindoles

Professional Introduction to 2-(1H-indol-3-yl)acetonitrile (CAS No. 771-51-7)

2-(1H-indol-3-yl)acetonitrile, a compound with the chemical formula C₁₀H₇N, is a versatile intermediate in organic synthesis and pharmaceutical research. Its CAS number, CAS No. 771-51-7, uniquely identifies it in scientific literature and industrial applications. This heterocyclic compound features an indole moiety linked to an acetonitrile group, making it a valuable building block for the development of novel bioactive molecules.

The indole ring, a prominent structural motif in many natural products and pharmacologically active compounds, contributes significantly to the chemical and biological properties of 2-(1H-indol-3-yl)acetonitrile. Its presence allows for diverse functionalization, enabling researchers to tailor its reactivity for specific synthetic pathways. Recent advancements in medicinal chemistry have highlighted the importance of indole derivatives in drug discovery, particularly in the design of molecules targeting neurological and inflammatory disorders.

In recent years, 2-(1H-indol-3-yl)acetonitrile has garnered attention for its role in synthesizing small-molecule inhibitors. These inhibitors often target enzymes and receptors involved in critical biological processes. For instance, studies have demonstrated its utility in developing compounds that modulate the activity of cyclin-dependent kinases (CDKs), which are implicated in cell cycle regulation and cancer progression. The acetonitrile group in the molecule enhances its solubility and reactivity, facilitating its incorporation into complex synthetic schemes.

The compound's versatility extends to its application in material science, where it serves as a precursor for functional polymers and coatings. Its indole core can be polymerized or cross-linked to create materials with unique electronic and optical properties. Such materials are increasingly relevant in the development of organic electronics, including flexible displays and photovoltaic devices. The growing interest in sustainable chemistry has also prompted investigations into greener synthetic routes for 2-(1H-indol-3-yl)acetonitrile, emphasizing the need for efficient and environmentally friendly methodologies.

From a computational chemistry perspective, 2-(1H-indol-3-yl)acetonitrile has been extensively studied to understand its molecular interactions and binding affinities. Molecular docking simulations have revealed its potential as a scaffold for designing ligands that interact with biological targets such as protein kinases and ion channels. These simulations not only aid in rational drug design but also provide insights into the structural determinants of binding affinity and selectivity.

The synthesis of 2-(1H-indol-3-yl)acetonitrile typically involves multi-step reactions starting from readily available precursors like indole derivatives. Advances in catalytic systems have enabled more efficient and selective transformations, reducing the need for harsh conditions or hazardous reagents. For example, palladium-catalyzed cross-coupling reactions have been employed to introduce the acetonitrile moiety onto the indole ring with high precision. Such methodologies align with the broader trend toward sustainable chemical processes, minimizing waste generation and energy consumption.

In clinical research, derivatives of 2-(1H-indol-3-yl)acetonitrile have shown promise as therapeutic agents. Preclinical studies have explored their efficacy in models of neurodegenerative diseases, where they exhibit protective effects against oxidative stress and inflammation. The indole scaffold's ability to cross the blood-brain barrier makes it an attractive candidate for central nervous system (CNS) drug development. Additionally, its interaction with microglial cells suggests potential applications in modulating neuroinflammatory responses.

The compound's role in synthetic organic chemistry is further underscored by its utility as a precursor for heterocyclic libraries. High-throughput screening methods have been employed to generate diverse analogs of 2-(1H-indol-3-yl)acetonitrile, allowing rapid identification of bioactive molecules. This approach has accelerated the discovery process in drug development pipelines, enabling researchers to identify lead compounds with optimized pharmacokinetic profiles.

Looking ahead, the future of 2-(1H-indol-3-yl)acetonitrile lies in its integration into emerging technologies such as artificial intelligence (AI)-assisted drug design. Machine learning algorithms can predict novel derivatives with enhanced potency and selectivity by analyzing vast datasets of chemical structures and biological responses. Such innovations are poised to transform how new drugs are discovered and developed, making compounds like 2-(1H-indol-3-yl)acetonitrile even more indispensable in modern pharmaceutical research.

• 82199-98-2(1H-Indole-7-acetonitrile)
• 136281-75-9(5-ethyl-1H-Indole-3-acetonitrile)
• 89368-51-4(1H-Indole-3-acetonitrile, 4-ethenyl-)
• 23078-29-7(2-(1H-Indol-3-yl)-2-methylpropanenitrile)
• 39676-14-7(2-(1H-Pyrrolo[3,2-c]pyridin-3-yl)acetonitrile)
• 26405-47-0(5-amino-1H-Indole-3-acetonitrile)
• 134515-11-0(1H-Benz[f]indole-3-acetonitrile)
• 148458-97-3(3-(2-aminoethyl)-1H-Indole-5-acetonitrile)
• 65881-14-3(2-(5-Methyl-1H-indol-3-yl)acetonitrile)
• 136281-76-0(5-propyl-1H-Indole-3-acetonitrile)