Production Method 1

58901-12-5

95-20-5

Reaction Conditions

1.1 Reagents: Triphenylphosphine ,  Stannous chloride Catalysts: Ruthenium trichloride Solvents: 1,4-Dioxane ,  Water
1.2 Reagents: Hydrochloric acid
1.3 Solvents: Chloroform

Reference

Ruthenium-catalyzed heteroannulation of anilines with alkanolammonium chlorides leading to indoles

Cho, C. S.; Kim, J. H.; Kim, T.-J.; Shim, S. C., Tetrahedron, 2001, 57(16), 3321-3329

Production Method 2

6872-06-6

95-20-5

Reaction Conditions

1.1 Catalysts: 2765219-06-3 Solvents: Acetonitrile ;  24 h, rt

Reference

Photocatalytic Aerobic Dehydrogenation of N-Heterocycles with Ir(III) Photosensitizers Bearing the 2(2'-Pyridyl)benzimidazole Scaffold

Echevarria, Igor; Vaquero, Monica ; Manzano, Blanca R. ; Jalon, Felix A.; Quesada, Roberto; et al, Inorganic Chemistry, 2022, 61(16), 6193-6208

Production Method 3

6126-53-0

95-20-5

Reaction Conditions

1.1 Reagents: Ethylene ,  Potassium carbonate ,  Ammonium acetate Catalysts: Palladium Solvents: 1,4-Dioxane ;  rt; rt → 110 °C; 3 h, 110 °C

Reference

Synthesis of Substituted Anilines from Cyclohexanones Using Pd/C-Ethylene System and Its Application to Indole Synthesis

Maeda, Katsumi; Matsubara, Ryosuke ; Hayashi, Masahiko, Organic Letters, 2021, 23(5), 1530-1534

Production Method 4

6872-06-6

95-20-5

Reaction Conditions

1.1 Catalysts: 2177262-59-6 Solvents: p-Xylene ;  48 h, 140 °C

Reference

Osmium Catalysts for Acceptorless and Base-Free Dehydrogenation of Alcohols and Amines: Unusual Coordination Modes of a BPI Anion

Buil, Maria L.; Esteruelas, Miguel A. ; Gay, M. Pilar ; Gomez-Gallego, Mar; Nicasio, Antonio I.; et al, Organometallics, 2018, 37(4), 603-617

Production Method 5

6872-06-6

95-20-5

Reaction Conditions

1.1 Catalysts: (PB-7-11-22333)-Trihydro(2,4-pentanedionato-κO2,κO4)bis[tris(1-methylethyl)phosp… Solvents: p-Xylene ;  48 h, 140 °C

Reference

Osmium hydride acetylacetonate complexes and their application in acceptorless dehydrogenative coupling of alcohols and amines and for the dehydrogenation of cyclic amines

Esteruelas, Miguel A. ; Lezaun, Virginia; Martinez, Antonio; Olivan, Montserrat; Onate, Enrique, Organometallics, 2017, 36(15), 2996-3004

Production Method 6

53855-47-3

95-20-5

Reaction Conditions

1.1 Reagents: Hydrochloric acid Solvents: Ethanol ,  Water

Reference

The chemistry of indoles

Mills, Keith, 1966, , ,

Production Method 7

6872-06-6

95-20-5

Reaction Conditions

1.1 Catalysts: Hafnium, hexakis[μ5-[[4,4′-([2,2′-bipyridine]-5,5′-diyl-κN1,κN1′)bis[benzoato-κO… Solvents: Acetonitrile ,  2,2,2-Trifluoroethanol ;  12 h, rt

Reference

Metal-Organic Layers Hierarchically Integrate Three Synergistic Active Sites for Tandem Catalysis

Quan, Yangjian; Lan, Guangxu; Shi, Wenjie; Xu, Ziwan; Fan, Yingjie; et al, Angewandte Chemie, 2021, 60(6), 3115-3120

Production Method 8

6872-06-6

95-20-5

Reaction Conditions

1.1 Catalysts: 2306758-00-7 Solvents: Methanol ;  4 - 12 h, rt

Reference

Efficient acceptorless photo-dehydrogenation of alcohols and N-heterocycles with binuclear platinum(II) diphosphite complexes

Zhong, Jian-Ji; To, Wai-Pong; Liu, Yungen; Lu, Wei; Che, Chi-Ming, Chemical Science, 2019, 10(18), 4883-4889

Production Method 9

65826-91-7

95-20-5

Reaction Conditions

1.1 Reagents: Potassium carbonate Catalysts: Iridium, di-μ-chlorodichlorobis[(1,2,3,4,5-η)-1,2,3,4,5-pentamethyl-2,4-cyclopen… Solvents: Toluene

Reference

Oxidative Cyclization of Amino Alcohols Catalyzed by a Cp*Ir Complex. Synthesis of Indoles, 1,2,3,4-Tetrahydroquinolines, and 2,3,4,5-Tetrahydro-1-benzazepine

Fujita, Kenichi; Yamamoto, Kazunari; Yamaguchi, Ryohei, Organic Letters, 2002, 4(16), 2691-2694

Production Method 10

73930-99-1

95-20-5

Reaction Conditions

1.1 Reagents: Carbon monoxide Catalysts: Triphenylphosphine ,  Palladium diacetate Solvents: Dimethylformamide ;  72 h, 6 atm, 120 °C

Reference

A base-modulated chemoselective synthesis of 3-cyanoindoles or 4-cyanoquinolines using a palladium-catalyzed N-heterocyclization

Banini, Serge R.; Turner, Michael R.; Cummings, Matthew M.; Soederberg, Bjoern C. G., Tetrahedron, 2011, 67(20), 3603-3611

Production Method 11

173436-68-5

95-20-5

Reaction Conditions

1.1 Reagents: Potassium hydroxide Solvents: Methanol ;  4 h, reflux

Reference

Indomethacin Analogues that Enhance Doxorubicin Cytotoxicity in Multidrug Resistant Cells without Cox Inhibitory Activity

Arisawa, Mitsuhiro; Kasaya, Yayoi; Obata, Tohru; Sasaki, Takuma; Ito, Mika; et al, ACS Medicinal Chemistry Letters, 2011, 2(5), 353-357

Production Method 12

6872-06-6

95-20-5

Reaction Conditions

1.1 Catalysts: Tetracarbonyl-μ-hydro[(1,2,3,4,5-η)-1-hydroxylato-2,3,4,5-tetraphenyl-2,4-cyclop… Solvents: Mesitylene ;  24 h, 165 °C

Reference

Acceptorless and base-free dehydrogenation of alcohols and amines using ruthenium-hydride complexes

Muthaiah, Senthilkumar; Hong, Soon Hyeok, Advanced Synthesis & Catalysis, 2012, 354(16), 3045-3053

Production Method 13

6872-06-6

95-20-5

Reaction Conditions

1.1 Catalysts: Palladium

Reference

Indoles. II. The acid-catalyzed rearrangement of N-(2-alkenyl)anilines

Bader, Alfred R.; Bridgewater, Roden J.; Freeman, Paul R., Journal of the American Chemical Society, 1961, 83, 3319-23

Production Method 14

6872-06-6

95-20-5

Reaction Conditions

1.1 Catalysts: 2756592-03-5 Solvents: Dimethylacetamide ;  32 h, rt

Reference

Imidazole-linked porphyrin-based conjugated microporous polymers for metal-free photocatalytic oxidative dehydrogenation of N-heterocycles

Chen, Yaju; Jiang, Jun, Sustainable Energy & Fuels, 2021, 5(24), 6478-6487

Production Method 15

19005-93-7

95-20-5

Reaction Conditions

1.1 Reagents: Hydrogen Catalysts: Palladium Solvents: Ethanol ;  rt; 24 h, 100 °C

Reference

Recyclable Pd/C catalyzed one-step reduction of carbonyls to hydrocarbons under simple conditions without extra base

Zhou, Xiao-Yu ; Chen, Xia, Tetrahedron Letters, 2020, 61(5),

Production Method 16

120-72-9

95-20-5

Reaction Conditions

1.1 Reagents: Sodium hydride Solvents: Tetrahydrofuran ,  Water ;  15 min, 0 °C; 1 h, rt; rt → 0 °C; 30 min, rt
1.2 Reagents: Sodium carbonate Solvents: Water ;  0 °C

Reference

Ga(DS)3-catalyzed double hydroarylation of acetylenic esters with indoles for the synthesis of bisindolyl propanoates

An, Li-Tao; Cai, Jing-Jing; Pan, Xiang-Qiang; Chen, Tang-Ming; Zou, Jian-Ping; et al, Tetrahedron Letters, 2015, 56(26), 3996-3998

Production Method 17

6872-06-6

95-20-5

Reaction Conditions

1.1 Catalysts: Cadmium sulfide ,  Cadmium selenide ,  Nickel dichloride Solvents: Acetonitrile ,  Water ;  12 h, rt

Reference

Efficient acceptorless dehydrogenation of hydrogen-rich N-heterocycles photocatalyzed by Ni(OH)2@CdSe/CdS quantum dots

Liu, Yanpeng; Yu, Tianjun; Zeng, Yi; Chen, Jinping; Yang, Guoqiang; et al, Catalysis Science & Technology, 2021, 11(11), 3810-3817

Production Method 18

6872-06-6

95-20-5

Reaction Conditions

1.1 Catalysts: Di-μ-chlorobis[(1,2,5,6-η)-1,5-cyclooctadiene]diiridium ,  1,2-Bis(diphenylphosphino)benzene (crosslinked, polystyrene-bound) Solvents: p-Xylene ;  5 min, rt
1.2 20 h, 130 °C

Reference

Ir-Catalyzed Reversible Acceptorless Dehydrogenation/Hydrogenation of N-Substituted and Unsubstituted Heterocycles Enabled by a Polymer-Cross-Linking Bisphosphine

Zhang, Deliang; Iwai, Tomohiro; Sawamura, Masaya, Organic Letters, 2020, 22(13), 5240-5245

Production Method 19

6872-06-6

95-20-5

Reaction Conditions

1.1 Catalysts: Cobalt(1+), [2-(dicyclohexylphosphino-κP)-N-[2-(dicyclohexylphosphino-κP)ethyl]e… Solvents: p-Xylene ;  4 d, rt → 150 °C

Reference

Acceptorless, Reversible Dehydrogenation and Hydrogenation of N-Heterocycles with a Cobalt Pincer Catalyst

Xu, Ruibo; Chakraborty, Sumit; Yuan, Hongmei; Jones, William D., ACS Catalysis, 2015, 5(11), 6350-6354

Production Method 20

6872-06-6

95-20-5

Reaction Conditions

1.1 Catalysts: Carbon Solvents: 2-Methyl-2-butanol ;  24 h, 10 bar, 150 °C

Reference

Metal- and Additive-Free Aerobic Dehydrogenation of N-Heterocycles and Hydrocarbons by N-Doped Carbon

Shang, Sensen; Li, Yingguang; Lv, Ying; Dai, Wen, Asian Journal of Organic Chemistry, 2022, 11(7),

Production Method 21

6872-06-6

15009-91-3

95-20-5

Reaction Conditions

1.1C:Ni(NO3)2 (nickel-nitrogen-doped graphene shell), S:H2O, rt; rt → 145°C; 18 h, 145°C, 0.35 MPa

Reference

Superhydrophobic nickel/carbon core-shell nanocomposites for the hydrogen transfer reactions of nitrobenzene and N-heterocycles

By Pang, Shaofeng et al, Green Chemistry, 2020, 22(6), 1996-2010

2-Methylindole Raw materials

• Indole
• Indole-2-carbaldehyde
• 1-(2-Aminophenyl)propan-2-ol
• 2-Propanol,1,1',1''-nitrilotris-, hydrochloride (9CI)
• Benzene, 1-nitro-2-(1-propenyl)-
• 1H-Indole, 2-methyl-1-[(4-methylphenyl)sulfonyl]-
• 2-Methylindoline
• Pyridine, 2-nitro-
• Ethyl 2-methyl-1H-indole-3-carboxylate
• Cyclohexanone, 2-(2-oxopropyl)-

2-Methylindole Preparation Products

• 2-Methylindole (95-20-5)

• 1. Distinct correlation between (CN2)x units and pores: a low-cost method for predesigned wide range control of micropore size of porous carbon?
  Xiaotong Feng,Lei Bian,Jie Ma,Lei Zhou,Xiayan Wang,Guangsheng Guo,Qiaosheng Pu Chem. Commun., 2019,55, 3963-3966
• 2. Emulsion soft templating of carbide-derived carbon nanospheres with controllable porosity for capacitive electrochemical energy storage?
  M. Zeiger,N. J?ckel,P. Strubel,L. Borchardt,R. Reinhold,W. Nickel,J. Eckert,V. Presser,S. Kaskel J. Mater. Chem. A, 2015,3, 17983-17990
• 3. Emerging investigator series: bacteriophages as nano engineering tools for quality monitoring and pathogen detection in water and wastewater
  Fereshteh Bayat Environ. Sci.: Nano, 2021,8, 367-389
• 4. Dissociation of aryl sulfonyl phthalimide radical anions: relevance to the biological activity of arylsulfonyl amides?
  Abdelaziz Houmam,Emad M. Hamed Chem. Commun., 2012,48, 11328-11330
• 5. EWOD-driven droplet microfluidic device integrated with optoelectronic tweezers as an automated platform for cellular isolation and analysis?
  Gaurav J. Shah,Eric P.-Y. Chiou,Ming C. Wu,Chang-Jin “CJ” Kim Lab Chip, 2009,9, 1732-1739

• Solvents and Organic Chemicals Organic Compounds Organoheterocyclic compounds Indoles and derivatives Indoles

Exploring the Versatile Applications and Properties of 2-Methylindole (CAS No. 95-20-5)

2-Methylindole, also known as 2-MI or methylketole, is a heterocyclic organic compound with the molecular formula C9H9N. This compound belongs to the indole family, which is widely recognized for its significance in pharmaceuticals, fragrances, and agrochemicals. With the CAS number 95-20-5, 2-Methylindole has garnered attention in both academic research and industrial applications due to its unique chemical properties and versatile utility.

The physical and chemical properties of 2-Methylindole make it a valuable intermediate in organic synthesis. It appears as a white to pale yellow crystalline solid with a melting point ranging between 57-60°C. The compound is sparingly soluble in water but dissolves well in organic solvents such as ethanol, ether, and benzene. Its aromatic structure, featuring a fused benzene and pyrrole ring, contributes to its reactivity, enabling it to participate in various chemical transformations, including electrophilic substitution and condensation reactions.

One of the most prominent applications of 2-Methylindole is in the fragrance industry. The compound imparts a floral, slightly animalic odor, making it a key ingredient in perfumery. It is often used to create synthetic musk and floral accords, enhancing the complexity and longevity of fragrances. Additionally, 2-Methylindole serves as a precursor in the synthesis of pharmaceutical intermediates, particularly in the development of compounds with potential therapeutic effects.

In recent years, the demand for 2-Methylindole has surged due to its role in the synthesis of biologically active molecules. Researchers are exploring its derivatives for their potential in drug discovery, particularly in the fields of anti-inflammatory and antimicrobial agents. The compound's ability to act as a building block for more complex structures has made it a subject of interest in medicinal chemistry. For instance, indole derivatives are being investigated for their efficacy in treating neurological disorders and metabolic diseases.

The agrochemical industry also benefits from the use of 2-Methylindole. It is employed in the synthesis of plant growth regulators and pesticides, contributing to improved crop yields and pest management. The compound's role in green chemistry is another area of exploration, as scientists seek sustainable methods for its production and application. With the growing emphasis on environmentally friendly practices, 2-Methylindole is being studied for its potential in biodegradable formulations.

From a market perspective, the global demand for 2-Methylindole is driven by its diverse applications. The pharmaceutical sector remains a significant consumer, followed by the fragrance and flavor industry. Emerging economies are witnessing increased production and consumption of 2-Methylindole, reflecting the compound's expanding role in various industries. Manufacturers are focusing on optimizing synthesis routes to enhance yield and purity, ensuring compliance with stringent regulatory standards.

For those seeking high-quality 2-Methylindole, it is essential to source the compound from reputable suppliers who adhere to Good Manufacturing Practices (GMP). Purity and consistency are critical factors, especially for applications in pharmaceuticals and fragrances. Analytical techniques such as HPLC and GC-MS are commonly employed to verify the quality of 2-Methylindole, ensuring it meets the required specifications.

In conclusion, 2-Methylindole (CAS No. 95-20-5) is a multifaceted compound with significant applications across multiple industries. Its unique chemical properties, coupled with its role in fragrance, pharmaceuticals, and agrochemicals, underscore its importance in modern chemistry. As research continues to uncover new potentials for 2-Methylindole, its relevance in scientific and industrial domains is expected to grow, making it a compound of enduring interest.

• 1196-79-8(2,5-Dimethyl-1H-indole)
• 85-06-3(3-Methylbenzo[f]quinoline)
• 61351-98-2(1,8-Phenanthroline, 2-methyl-)
• 52105-16-5(4,7-Phenanthroline, 3-methyl-)
• 605-88-9(Benzo[h]quinoline,2-methyl-)
• 88813-63-2(Benzoquinoline, methyl- (9CI))
• 27323-28-0(1H-Indole, methyl-)
• 131705-88-9(2-methyl-1H-Pyrrolo[2,3-f]quinoline)
• 27601-00-9(Quinoline, methyl-)
• 56479-11-9(Magnesium, bromo(2-methyl-1H-indol-1-yl)-)