Production Method 1

771-51-7

879-37-8

Reaction Conditions

1.1 Catalysts: Nitrile hydratase

Reference

Synthesis of various aromatic amide derivatives using nitrile hydratase of Rhodococcus rhodochrous J1

Mauger, Jacques; et al, Tetrahedron, 1989, 45(5), 1347-54

Production Method 2

61-54-1

879-37-8

Reaction Conditions

1.1 Reagents: Potassium tert-butoxide Catalysts: Stereoisomer of dibromo[(1,2,5,6-η)-1,5-cyclooctadiene][6-phenyl-7-(phenylmethyl… Solvents: tert-Butanol ;  24 h, 70 °C

Reference

Aerobic oxidation of primary amines to amides catalyzed by an annulated mesoionic carbene (MIC) stabilized Ru complex

Yadav, Suman; et al, Catalysis Science & Technology, 2021, 11(21), 7018-7028

Production Method 3

87-51-4

879-37-8

Reaction Conditions

1.1 Reagents: 1,1′-Carbonyldiimidazole Solvents: Tetrahydrofuran ;  1.5 h, rt
1.2 Reagents: Ammonia Solvents: Water ;  18 h, rt

Reference

Development of [18F]Maleimide-Based Glycogen Synthase Kinase-3β Ligands for Positron Emission Tomography Imaging

Hu, Kongzhen; et al, ACS Medicinal Chemistry Letters, 2017, 8(3), 287-292

Production Method 4

120-72-9

3638-64-0

879-37-8

Reaction Conditions

1.1 Reagents: Phosphorus trichloride ;  5 min, 50 - 55 °C
1.2 3 h, 50 - 55 °C
1.3 Reagents: Ammonia Solvents: Water ;  pH 8, cooled

Reference

Direct reductive coupling of indoles to nitrostyrenes en route to (indol-3-yl)acetamides

Aksenov, Alexander V.; et al, RSC Advances, 2016, 6(96), 93881-93886

Production Method 5

50720-05-3

879-37-8

Reaction Conditions

1.1 Reagents: Ammonium hydroxide Solvents: Tetrahydrofuran ;  0 °C; 1 h, 0 °C → rt

Reference

Design, synthesis and anti-AD effects of dual inhibitor targeting glutaminyl cyclase/GSK-3β

Xie, Yazhou; et al, European Journal of Medicinal Chemistry, 2023, 248,

Production Method 6

73-22-3

879-37-8

Reaction Conditions

1.1 Reagents: Glucose ,  Disodium NADH ,  Glucose dehydrogenase Catalysts: Tryptophan 2-monooxygenase ,  Riboflavin reductase (NADPH) ;  48 h, 30 °C

Reference

Versatile and facile one-pot biosynthesis for amides and carboxylic acids in E. coli by engineering auxin pathways of plant microbiomes

Menon, Navya; et al, ACS Catalysis, 2022, 12(4), 2309-2319

Production Method 7

73-22-3

879-37-8

120-72-9

771-50-6

771-51-7

87-51-4

487-89-8

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

Production Method 8

771-51-7

879-37-8

Reaction Conditions

1.1 Reagents: Water Catalysts: Ruthenium, tetracarbonyl-μ-hydrotrihydro-μ-hydroxy-μ3-hydroxy-μ4-oxotetrakis(tri… ;  18 h, 80 - 95 °C

Reference

Kinetic, Spectroscopic, and X-Ray Crystallographic Evidence for the Cooperative Mechanism of the Hydration of Nitriles Catalyzed by a Tetranuclear Ruthenium-μ-oxo-μ-hydroxo Complex

Yi, Chae S.; et al, Organometallics, 2008, 27(9), 2030-2035

Production Method 9

87-51-4

879-37-8

Reaction Conditions

1.1 Reagents: Oxalyl chloride Catalysts: Dimethylformamide Solvents: Dichloromethane ;  cooled; 4 h, rt
1.2 Reagents: Ammonia Solvents: Water ;  cooled; 3 h, cooled

Reference

Synthesis, single crystal X-ray analysis and vibrational spectral studies of 3,4-di(1H-indol-3-yl)-1H-pyrrole-2,5-dione

Guo, Qian; et al, Journal of Molecular Structure, 2023, 1281,

Production Method 10

879-37-8

Reaction Conditions

Reference

Synthesis and properties of azoles and their derivatives. 32. Synthesis and some reactions of hydrochlorides of indolylcarboxylic acid iminoesters

Kelarev, V. I.; et al, Khimiya Geterotsiklicheskikh Soedinenii, 1980, (5), 645-50

Production Method 11

120-72-9

56-45-1

879-37-8

Reaction Conditions

1.1 Catalysts: Tryptophan synthase ;  48 h, 30 °C
1.2 Reagents: Glucose ,  Disodium NADH ,  Glucose dehydrogenase Catalysts: Tryptophan 2-monooxygenase ,  Riboflavin reductase (NADPH) ;  48 h, 30 °C

Reference

Versatile and facile one-pot biosynthesis for amides and carboxylic acids in E. coli by engineering auxin pathways of plant microbiomes

Menon, Navya; et al, ACS Catalysis, 2022, 12(4), 2309-2319

Production Method 12

50720-05-3

879-37-8

Reaction Conditions

1.1 Reagents: Ammonia Solvents: Water ;  cooled; 3 h, rt

Reference

Synthesis, single crystal X-ray analysis and vibrational spectral studies of 3,4-di(1H-indol-3-yl)-1H-pyrrole-2,5-dione

Guo, Qian; et al, Journal of Molecular Structure, 2023, 1281,

Production Method 13

73-22-3

879-37-8

Reaction Conditions

1.1 Catalysts: Indole-3-acetic acid synthetase Solvents: Water ;  6 h, pH 8, 37 °C
1.2 Reagents: Hydrochloric acid Solvents: Water ;  pH 2

Reference

Tryptophan-dependent indole-3-acetic acid biosynthesis by 'IAA-synthase' proceeds via indole-3-acetamide

Pollmann, Stephan; et al, Phytochemistry (Elsevier), 2009, 70(4), 523-531

Production Method 14

771-51-7

879-37-8

Reaction Conditions

1.1 Reagents: Hydrochloric acid
2.1 -

Reference

Synthesis and properties of azoles and their derivatives. 32. Synthesis and some reactions of hydrochlorides of indolylcarboxylic acid iminoesters

Kelarev, V. I.; et al, Khimiya Geterotsiklicheskikh Soedinenii, 1980, (5), 645-50

Production Method 15

4770-03-0

879-37-8

80485-89-8

Reaction Conditions

1.1 Reagents: Formic acid ,  Hydrogen Catalysts: Palladium Solvents: Methanol ;  3 h, -10 °C; 1 h, -10 °C → 10 °C

Reference

The first isocyanide of plant origin expands functional group diversity in cruciferous phytoalexins: synthesis, structure and bioactivity of isocyalexin A

Pedras, M. Soledade C.; et al, Organic & Biomolecular Chemistry, 2012, 10(18), 3613-3616

Production Method 16

54-12-6

879-37-8

87-51-4

Reaction Conditions

1.1 Reagents: Sulfur Solvents: Pyridine

Reference

Oxidative degradation of a-substituted carboxylic acids

Feichtinger, Hans, Chemische Berichte, 1962, 95, 2238-42

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

• Indole
• 2-(1H-indol-3-yl)acetonitrile
• tryptophan
• L-Serine
• 1H-Indole-3-acetyl chloride
• 3-Nitro-1H-indole
• L-Tryptophan
• 3-Indoleacetic acid
• 1-Nitroethene (~ 1 mole/L in Toluene)
• Tryptamine

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

• Indole (120-72-9)
• 1H-indole-3-carboxylic acid (771-50-6)
• 2-(1H-indol-3-yl)acetonitrile (771-51-7)
• N-1H-Indol-3-ylformamide (80485-89-8)
• 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. Fe3O4 nanosphere@microporous organic networks: enhanced anode performances in lithium ion batteries through carbonization?
  Byungho Lim,Jaewon Jin,Jin Yoo,Seung Yong Han,Kyeongyeol Kim,Sungah Kang,Nojin Park,Sang Moon Lee,Hae Jin Kim,Seung Uk Son Chem. Commun., 2014,50, 7723-7726
• 2. Embedding heteroatoms: an effective approach to create porphyrin-based functional materials
  Norihito Fukui,Keisuke Fujimoto,Hideki Yorimitsu,Atsuhiro Osuka Dalton Trans., 2017,46, 13322-13341
• 3. Excellent humidity sensor based on ultrathin HKUST-1 nanosheets?
  Qiaoe Wang,Meiling Lian,Xiaowen Zhu,Xu Chen RSC Adv., 2021,11, 192-197
• 4. Dissociative electron attachment to HGaF4 Lewis–Br?nsted superacid
  Marcin Czapla,Jack Simons Phys. Chem. Chem. Phys., 2018,20, 21739-21745
• 5. Fe3O4/Au/Fe3O4 nanoflowers exhibiting tunable saturation magnetization and enhanced bioconjugation
  Feng Shi,Kunping Yan,Mingli Peng,Xiao Cheng,Yanling Luo,Xuemei Chen,V. A. L. Roy,Zuankai Wang Nanoscale, 2012,4, 747-751

• 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

2-(1H-indol-3-yl)acetamide (CAS No. 879-37-8): A Comprehensive Overview

2-(1H-indol-3-yl)acetamide, also known by its CAS number 879-37-8, is a chemical compound that has garnered significant attention in the fields of organic chemistry, pharmacology, and materials science. This compound is characterized by its indole-based structure, which is a heterocyclic aromatic system with a nitrogen atom at position 1. The indole moiety is a fundamental building block in many natural products and bioactive molecules, making 2-(1H-indol-3-yl)acetamide a valuable compound for both academic and industrial research.

The structure of 2-(1H-indol-3-yl)acetamide consists of an indole ring substituted with an acetamide group at the 3-position. This substitution pattern is critical for its biological activity and chemical reactivity. The indole ring's aromaticity and the electron-donating properties of the acetamide group contribute to its unique electronic characteristics, which are exploited in various applications. Recent studies have highlighted the potential of this compound in drug discovery, particularly in targeting specific enzymes and receptors involved in diseases such as cancer and neurodegenerative disorders.

In terms of synthesis, 2-(1H-indol-3-yl)acetamide can be prepared through several routes, including Friedl?nder synthesis, which involves the condensation of an o-amino aryl aldehyde with a ketone or aldehyde. The choice of synthetic method depends on the desired scale, purity, and cost-effectiveness. Researchers have also explored green chemistry approaches to synthesize this compound, emphasizing sustainability and reducing environmental impact.

The biological activity of 2-(1H-indol-3-yl)acetamide has been extensively studied. It has shown promising results as a potential anticancer agent by inhibiting key enzymes such as histone deacetylases (HDACs). HDAC inhibitors are known to induce cell cycle arrest and apoptosis in cancer cells, making them valuable targets for chemotherapy. Recent clinical trials have demonstrated the efficacy of similar compounds in reducing tumor growth and improving patient outcomes.

Beyond its pharmacological applications, 2-(1H-indol-3-yl)acetamide has also found use in materials science. Its ability to form self-assembled monolayers (SAMs) on various surfaces makes it a candidate for applications in nanotechnology and surface modification. SAMs are crucial for creating functional surfaces with tailored properties, such as improved biocompatibility or enhanced catalytic activity.

In conclusion, 2-(1H-indol-3-yl)acetamide, with its CAS number 879-37-8, is a versatile compound with diverse applications across multiple disciplines. Its indole-based structure provides a foundation for exploring new drug candidates and advanced materials. As research continues to uncover its potential, this compound is poised to play an increasingly important role in both academic and industrial settings.

• 103404-85-9(5-HYDROXYINDOLE-3-ACETAMIDE)
• 1204700-53-7(1H-Indole-d5-3-acetamide)
• 332062-08-5(Fmoc-S-3-amino-4,4-diphenyl-butyric acid)
• 1270529-38-8(1,2,3,4,5,6-Hexahydro-[2,3]bipyridinyl-6-ol)
• 2680771-01-9(4-cyclopentyl-3-{(prop-2-en-1-yloxy)carbonylamino}butanoic acid)
• 2098070-20-1(2-(3-(Pyridin-3-yl)-1H-pyrazol-1-yl)acetimidamide)
• 1444113-98-7(N-(3-cyanothiolan-3-yl)-2-[(2,2,2-trifluoroethyl)sulfanyl]pyridine-4-carboxamide)
• 941977-17-9(N'-(3-chloro-2-methylphenyl)-N-2-(dimethylamino)-2-(naphthalen-1-yl)ethylethanediamide)
• 2138166-62-6(2,2-Difluoro-3-[methyl(2-methylbutyl)amino]propanoic acid)
• 89640-58-4(2-Iodo-4-nitrophenylhydrazine)