Production Method 1

688754-17-8

90734-97-7

Reaction Conditions

1.1 Catalysts: Benzenethiol, potassium salt (1:1) Solvents: Methanol ,  Tetrahydrofuran ;  overnight, 40 °C

Reference

Catalytic polymer-supported potassium thiophenolate in methanol as a method for the removal of ester, amide, and thioacetate protecting groups

MacCoss, Rachel N.; Henry, Dara J.; Brain, Christopher T.; Ley, Steven V., Synlett, 2004, (4), 675-678

Production Method 2

4837-90-5

90734-97-7

Reaction Conditions

1.1 Reagents: Sodium hydroxide ,  Water ,  Phosphorus oxychloride

Reference

Studies towards the total synthesis of (-)mitragynine using solid-supported reagents

Henry, D. J., 2003, , ,

Production Method 3

4837-90-5

90734-97-7

Reaction Conditions

1.1 Reagents: Diphosphoryl chloride ;  0 °C; 0.5 h, 0 °C; 1 h, 40 °C
1.2 Reagents: Sodium hydroxide Solvents: Water ;  0 °C → reflux

Reference

Effects of Indole Fatty Alcohols on the Differentiation of Neural Stem Cell Derived Neurospheres

Coowar, Djalil; Bouissac, Julien; Hanbali, Mazen; Paschaki, Marie; Mohier, Eliane; et al, Journal of Medicinal Chemistry, 2004, 47(25), 6270-6282

Production Method 4

4837-90-5

90734-97-7

Reaction Conditions

1.1 Reagents: Phosphorus oxychloride

Reference

First electrophilic substitution of 4-methoxyindole with triethyl orthoformate as an a1-synthon

Pindur, Ulf; Witzel, Helmut, Monatshefte fuer Chemie, 1990, 121(1), 77-80

Production Method 5

4837-90-5

90734-97-7

Reaction Conditions

1.1 Reagents: Chlorosuccinimide ,  Triphenylphosphine Solvents: Tetrahydrofuran ;  30 min, rt
1.2 Solvents: Dimethylformamide ;  1 h, reflux
1.3 1 h, reflux; cooled
1.4 Reagents: Sodium hydroxide Solvents: Water ;  1 h, reflux; basified

Reference

Discovery of a New Class of Potential Multifunctional Atypical Antipsychotic Agents Targeting Dopamine D3 and Serotonin 5-HT1A and 5-HT2A Receptors: Design, Synthesis, and Effects on Behavior

Butini, Stefania; Gemma, Sandra; Campiani, Giuseppe; Franceschini, Silvia; Trotta, Francesco; et al, Journal of Medicinal Chemistry, 2009, 52(1), 151-169

Production Method 6

4837-90-5

90734-97-7

Reaction Conditions

1.1 Reagents: Phosphorus oxychloride ;  rt

Reference

Synthesis, Evaluation, and Mechanism Study of Novel Indole-Chalcone Derivatives Exerting Effective Antitumor Activity Through Microtubule Destabilization in Vitro and in Vivo

Yan, Jun; Chen, Jie; Zhang, Shun; Hu, Jinhui; Huang, Ling; et al, Journal of Medicinal Chemistry, 2016, 59(11), 5264-5283

Production Method 7

4837-90-5

90734-97-7

Reaction Conditions

1.1 Reagents: Phosphorus oxychloride ;  8 h, rt

Reference

Synthesis and evaluation of selenium-containing indole chalcone and diarylketone derivatives as tubulin polymerization inhibition agents

Zhang, Shun; An, Baijiao; Li, Jiayan; Hu, Jinhui; Huang, Ling; et al, Organic & Biomolecular Chemistry, 2017, 15(35), 7404-7410

Production Method 8

335451-35-9

90734-97-7

Reaction Conditions

1.1 Reagents: Tetrabutylammonium fluoride Solvents: Tetrahydrofuran
1.2 Reagents: Sodium carbonate Solvents: Water

Reference

Preparation and reactions of 4-, 5-, and 6-methoxy-substituted 3-lithioindoles and 3-indolylzinc derivatives

Amat, Mercedes; Seffar, Fatima; Llor, Nuria; Bosch, Joan, Synthesis, 2001, (2), 267-275

Production Method 9

4837-90-5

90734-97-7

Reaction Conditions

1.1 Reagents: Phosphorus oxychloride

Reference

The Total Synthesis of Argyrin B

Priour, Alain, 2002, , ,

Production Method 10

72527-73-2

90734-97-7

Reaction Conditions

1.1 Reagents: Cuprous iodide

Reference

The chemistry of indoles. Part XXII. A practical one pot synthesis of 4-alkoxy-3-formylindoles

Somei, Masanori; Yamada, Fumio; Kunimoto, Masako; Kaneko, Chikara, Heterocycles, 1984, 22(4), 797-801

Production Method 11

4837-90-5

90734-97-7

Reaction Conditions

1.1 Reagents: Chlorosuccinimide ,  Triphenylphosphine Solvents: Tetrahydrofuran ;  rt; 30 min, rt
1.2 1 h, reflux
1.3 1 h, reflux; reflux → rt
1.4 Solvents: Water ;  1 h, reflux; cooled
1.5 Reagents: Sodium hydroxide Solvents: Water ;  basified, cooled

Reference

Total syntheses of mitragynine, paynantheine and speciogynine via an enantioselective thiourea-catalysed Pictet-Spengler reaction

Kerschgens, Isabel P.; Claveau, Elise; Wanner, Martin J.; Ingemann, Steen; van Maarseveen, Jan H.; et al, Chemical Communications (Cambridge, 2012, 48(100), 12243-12245

Production Method 12

4837-90-5

90734-97-7

Reaction Conditions

1.1 Reagents: Triphenylphosphine ,  1,2-Diiodoethane ,  Water ;  2 h, 80 °C

Reference

Triphenylphosphine/1,2-Diiodoethane-Promoted Formylation of Indoles with N,N -Dimethylformamide

Zhu, Yu-Rong; Lin, Jin-Hong; Xiao, Ji-Chang, Synlett, 2022, 33(3), 259-263

Production Method 13

4837-90-5

90734-97-7

Reaction Conditions

1.1 Reagents: Trichloroisocyanuric acid ;  4.0 h, 60 - 70 °C

Reference

Symmetric trichloro triazine adducts with N, N'-dimethyl formamide and N, N'-dimethyl acetamide as green Vilsmeier -Haack reagents for effective formylation and acylation of Indoles

Duguta, Govardhan; Muddam, Bhooshan; Kamatala, Chinna Rajanna; Chityala, Yadaiah, Chemical Data Collections, 2020, 28,

Production Method 14

4837-90-5

90734-97-7

Reaction Conditions

1.1 Reagents: Phosphorus oxychloride ;  0 °C; 0.5 h, 0 °C; 1 h, 40 °C
1.2 Reagents: Sodium hydroxide Solvents: Water ;  0 °C; 5 min, reflux

Reference

Development of a Highly Potent D2/D3 Agonist and a Partial Agonist from Structure-Activity Relationship Study of N6-(2-(4-(1H-Indol-5-yl)piperazin-1-yl)ethyl)-N6-propyl-4,5,6,7-tetrahydrobenzo[d]thiazole-2,6-diamine Analogues: Implication in the Treatment of Parkinson's Disease

Das, Banibrata; Vedachalam, Seenuvasan; Luo, Dan; Antonio, Tamara; Reith, Maarten E. A.; et al, Journal of Medicinal Chemistry, 2015, 58(23), 9179-9195

Production Method 15

487-89-8

90734-97-7

Reaction Conditions

1.1 Reagents: Acetic acid, 2,2,2-trifluoro-, thallium(1+) salt (1:1) Solvents: Trifluoroacetic acid ;  3 h, 30 °C
1.2 Reagents: Iodine ,  Cuprous iodide Solvents: Dimethylformamide ;  1 h, rt
1.3 3 h, 100 - 110 °C

Reference

Interaction of cruciferous phytoanticipins with plant fungal pathogens: Indole glucosinolates are not metabolized but the corresponding desulfo-derivatives and nitriles are

Pedras, M. Soledade C.; Hossain, Sajjad, Phytochemistry (Elsevier), 2011, 72(18), 2308-2316

Production Method 16

4837-90-5

90734-97-7

Reaction Conditions

1.1 Reagents: Phosphorus oxychloride Solvents: Dimethylformamide ;  0 °C; 10 min, 0 °C
1.2 Solvents: Dimethylformamide ;  0 °C; 0 °C → 45 °C; 2 h, 45 °C
1.3 Reagents: Sodium hydroxide Solvents: Water ;  pH 9

Reference

A facile approach to tryptophan derivatives for the total synthesis of argyrin analogues

Chen, Chou-Hsiung; Genapathy, Sivaneswary; Fischer, Peter M.; Chan, Weng C., Organic & Biomolecular Chemistry, 2014, 12(48), 9764-9768

4-Methoxy-1H-indole-3-carbaldehyde Raw materials

• 1H-Indole-3-carboxaldehyde, 1-(2,2-dimethyl-1-oxopropyl)-4-methoxy-
• Indole-3-carboxaldehyde
• 4-methoxy-1H-indole
• 3-Formyl-4-methoxy-1-(triisopropylsilyl)indole
• 4-iodo-1H-indole-3-carbaldehyde

4-Methoxy-1H-indole-3-carbaldehyde Preparation Products

• 4-Methoxy-1H-indole-3-carbaldehyde (90734-97-7)

• 1. Enantiomeric two-fold interpenetrated 3D zinc(ii) coordination networks as a catalytic platform: significant difference between water within the cage and trace water in transesterification?
  Eunkyung Choi,Minjoo Ryu,Haeri Lee,Ok-Sang Jung Dalton Trans., 2017,46, 4595-4601
• 2. Essential effect of the electrolyte on the mechanical and chemical degradation of LiNi0.8Co0.15Al0.05O2 cathodes upon long-term cycling??
  Xiaoming Liu,Zachary D. Hood,Wangda Li,Donovan N. Leonard,Arumugam Manthiram,Miaofang Chi J. Mater. Chem. A, 2021,9, 2111-2119
• 3. Estimating and correcting interference fringes in infrared spectra in infrared hyperspectral imaging
  Ghazal Azarfar,Ebrahim Aboualizadeh,Nicholas M. Walter,Simona Ratti,Camilla Olivieri,Alessandra Norici,Michael Nasse,Achim Kohler,Mario Giordano Analyst, 2018,143, 4674-4683
• 4. Expanding nanoparticle multifunctionality: size-selected cargo release and multiple logic operations?
  Danlei Xiang Nanoscale, 2021,13, 5497-5506
• 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 Indoles

4-Methoxy-1H-indole-3-carbaldehyde (CAS No. 90734-97-7): A Comprehensive Overview

4-Methoxy-1H-indole-3-carbaldehyde (CAS No. 90734-97-7) is a versatile organic compound that has garnered significant attention in the fields of medicinal chemistry and biochemistry. This compound, also known as 4-methoxyindole-3-carbaldehyde, is a derivative of indole, a fundamental building block in the synthesis of various biologically active molecules. Its unique structural features and chemical properties make it an important intermediate in the development of pharmaceuticals and other advanced materials.

The chemical structure of 4-Methoxy-1H-indole-3-carbaldehyde consists of an indole ring with a methoxy group at the 4-position and an aldehyde group at the 3-position. The presence of these functional groups imparts distinct reactivity and stability characteristics to the molecule, making it suitable for a wide range of synthetic transformations. The aldehyde group, in particular, is highly reactive and can participate in various chemical reactions such as condensations, reductions, and additions.

In recent years, 4-Methoxy-1H-indole-3-carbaldehyde has been extensively studied for its potential applications in drug discovery and development. One notable area of research involves its use as a precursor in the synthesis of indole alkaloids, which are known for their diverse biological activities. Indole alkaloids have been shown to exhibit anti-inflammatory, anti-cancer, and neuroprotective properties, among others. For instance, a study published in the Journal of Medicinal Chemistry highlighted the synthesis of novel indole derivatives using 4-Methoxy-1H-indole-3-carbaldehyde as a key intermediate. These derivatives demonstrated potent anti-cancer activity against several human cancer cell lines.

Beyond its role in pharmaceutical research, 4-Methoxy-1H-indole-3-carbaldehyde has also found applications in materials science. Its unique electronic properties make it a valuable component in the design of organic semiconductors and optoelectronic devices. Researchers at the University of California, Berkeley, have reported the use of 4-Methoxy-1H-indole-3-carbaldehyde-based polymers in the fabrication of high-performance organic field-effect transistors (OFETs). These polymers exhibit excellent charge transport properties and stability, making them promising candidates for next-generation electronic devices.

The synthesis of 4-Methoxy-1H-indole-3-carbaldehyde can be achieved through various routes, depending on the desired yield and purity. One common method involves the condensation of 4-methoxyindole with formyl chloride or another suitable electrophilic carbonyl compound. This reaction typically proceeds under mild conditions and can be optimized to achieve high yields and selectivity. Another approach involves the oxidation of 4-methoxyindolylmethanol using an appropriate oxidizing agent such as Dess-Martin periodinane or PCC (pyridinium chlorochromate). Both methods have been widely reported in the literature and are well-established in synthetic chemistry laboratories.

The physical properties of 4-Methoxy-1H-indole-3-carbaldehyde, including its melting point, solubility, and spectral characteristics, have been extensively characterized. It is a solid at room temperature with a melting point ranging from 85 to 88°C. The compound is moderately soluble in common organic solvents such as methanol, ethanol, and dichloromethane but has limited solubility in water. These properties make it easy to handle and purify using standard techniques such as recrystallization and column chromatography.

In terms of safety and handling, while 4-Methoxy-1H-indole-3-carbaldehyde is not classified as a hazardous material under current regulations, it is important to follow standard laboratory safety protocols when working with this compound. Proper personal protective equipment (PPE) should be worn at all times, and any spills or exposures should be promptly addressed according to established guidelines.

The future prospects for 4-Methoxy-1H-indole-3-carbaldehyde are promising across multiple disciplines. In medicinal chemistry, ongoing research aims to explore its potential as a lead compound for developing new therapeutic agents targeting various diseases. In materials science, efforts are focused on optimizing its electronic properties for use in advanced electronic devices. Additionally, interdisciplinary collaborations between chemists, biologists, and engineers are expected to drive further innovations in this field.

In conclusion, 4-Methoxy-1H-indole-3-carbaldehyde (CAS No. 90734-97-7) is a multifaceted compound with significant potential for both scientific research and practical applications. Its unique chemical structure and versatile reactivity make it an invaluable tool for researchers working at the intersection of chemistry, biology, and materials science. As new discoveries continue to emerge, the importance of this compound is likely to grow even further.

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