Production Method 1

877-03-2

827-01-0

Reaction Conditions

1.1 Reagents: Cuprous chloride Solvents: N-Methyl-2-pyrrolidone ;  rt → 210 °C; 15 h, 205 - 210 °C

Reference

Highly convenient and large scale synthesis of 5-chloroindole and its 3-substituted analogues

Keetha, Laxminarayana; et al, Journal of the Korean Chemical Society, 2011, 55(2), 240-242

Production Method 2

17422-32-1

827-01-0

Reaction Conditions

1.1 Reagents: Potassium iodide ,  Water Catalysts: Red 21 Solvents: Acetonitrile ;  48 h, rt

Reference

Visible-Light-Promoted Indole C-3 Formylation Using Eosin Y as a Photoredox Catalyst

Zhao, Yin; et al, Synlett, 2022, 33(7), 659-663

Production Method 3

17422-32-1

298-12-4

827-01-0

Reaction Conditions

1.1 Reagents: Ammonium persulfate Solvents: Dimethyl sulfoxide ,  Water ;  2 h, rt
1.2 Reagents: Water ;  rt

Reference

(NH4)2S2O8-Mediated Metal-Free Decarboxylative Formylation/Acylation of α-Oxo/Ketoacids and Its Application to the Synthesis of Indole Alkaloids

Dinesh, Votarikari; et al, Journal of Organic Chemistry, 2022, 87(15), 10359-10365

Production Method 4

17422-32-1

298-12-4

827-01-0

Reaction Conditions

1.1 Solvents: Acetonitrile ,  Water ;  6 h, rt
1.2 Reagents: Water

Reference

Photochemical Decarboxylative Formylation of Indoles with Aqueous Glyoxylic Acid

Dinesh, Votarikari; et al, Synlett, 2023, 34(7), 855-857

Production Method 5

1242737-14-9

827-01-0

Reaction Conditions

1.1 Reagents: Sodium carbonate ,  Boronic acid Catalysts: Tetrakis(triphenylphosphine)palladium Solvents: 1,4-Dioxane ;  reflux
1.2 Reagents: Phosphorus oxychloride ;  0 - 23 °C

Reference

Novel benzofuran-3-one indole inhibitors of PI3 kinase-α and the mammalian target of rapamycin: hit to lead studies

Bursavich, Matthew G.; et al, Bioorganic & Medicinal Chemistry Letters, 2010, 20(8), 2586-2590

Production Method 6

224156-28-9

827-01-0

Reaction Conditions

1.1 -
2.1 Reagents: Phosphorus oxychloride

Reference

The Vilsmeier reaction of fully conjugated carbocycles and heterocycles

Jones, Gurnos; et al, Organic Reactions (Hoboken, 1997, 49,

Production Method 7

17422-32-1

827-01-0

Reaction Conditions

1.1 Reagents: Phosphorus oxychloride Solvents: Dimethylformamide ;  30 min, cooled
1.2 Solvents: Dimethylformamide ;  1 h, 40 °C
1.3 Reagents: Sodium hydroxide Solvents: Water ;  pH 8, cooled

Reference

Synthesis and Antiproliferative Activity of New N-Acylhydrazone Derivatives Containing Benzothiazole and Indole Based Moiety

Liu, Kai; et al, Pharmaceutical Chemistry Journal, 2020, 54(4), 345-352

Production Method 8

17422-32-1

1535-67-7

827-01-0

Reaction Conditions

1.1 Catalysts: Bismuth triflate Solvents: 1,1,1,3,3,3-Hexafluoro-2-propanol ;  5 min, rt
1.2 Solvents: 1,1,1,3,3,3-Hexafluoro-2-propanol ;  12 h, rt
1.3 Reagents: 2-Iodoxybenzoic acid Solvents: Dimethyl sulfoxide ,  Water ;  1 h, rt
1.4 Reagents: Sodium sulfite Solvents: Water ;  rt
1.5 Reagents: Sodium bicarbonate Solvents: Water ;  basified, rt

Reference

Bi(OTf)3 Enabled C-F Bond Cleavage in HFIP: Electrophilic Aromatic Formylation with Difluoro(phenylsulfanyl)methane

Betterley, Nolan M.; et al, Asian Journal of Organic Chemistry, 2018, 7(8), 1642-1647

Production Method 9

17422-32-1

827-01-0

Reaction Conditions

1.1 Reagents: tert-Butyl hydroperoxide ,  Pivalic acid Catalysts: Ruthenium trichloride Solvents: N-Methylacetamide ;  0 °C; 24 h, 25 °C

Reference

Mild and Selective Ru-Catalyzed Formylation and Fe-Catalyzed Acylation of Free (N-H) Indoles Using Anilines as the Carbonyl Source

Wu, Wenliang; et al, Journal of the American Chemical Society, 2011, 133(31), 11924-11927

Production Method 10

17422-32-1

827-01-0

Reaction Conditions

1.1 Reagents: Pivalic acid ,  tert-Butyl peroxybenzoate Catalysts: Tetrabutylammonium iodide Solvents: Dimethyl sulfoxide ;  8 h, 80 °C
1.2 Reagents: Sodium bicarbonate Solvents: Water

Reference

nBu4NI-catalyzed C3-formylation of indoles with N-methylaniline

Li, Lan-Tao; et al, Chemical Communications (Cambridge, 2012, 48(42), 5187-5189

Production Method 11

17422-32-1

827-01-0

Reaction Conditions

1.1 Reagents: Oxygen Catalysts: Iodine Solvents: Dimethylformamide ;  12 h, 100 °C

Reference

Iodine-catalyzed C3-formylation of indoles via C-N bond cleavage of tertiary amines under aerobic conditions

Lu, Lin; et al, Tetrahedron, 2015, 71(22), 3637-3641

Production Method 12

17422-32-1

298-12-4

827-01-0

Reaction Conditions

1.1 Reagents: Sodium perchlorate Catalysts: Aniline ,  Platinum Solvents: Dimethyl sulfoxide ,  Water ;  7 h, rt

Reference

Synthesis of 3-Formylindoles via Electrochemical Decarboxylation of Glyoxylic Acid with an Amine as a Dual Function Organocatalyst

Lin, Dian-Zhao; et al, Organic Letters, 2019, 21(15), 5862-5866

Production Method 13

17422-32-1

827-01-0

Reaction Conditions

1.1 Reagents: Ammonia ,  Oxygen Catalysts: Iron chloride (FeCl3) Solvents: Dimethylformamide ,  Water ;  6 h, 130 °C

Reference

Iron-Catalyzed C3-Formylation of Indoles with Formaldehyde and Aqueous Ammonia under Air

Wang, Qing-Dong; et al, Synlett, 2017, 28(19), 2670-2674

Production Method 14

63665-97-4

827-01-0

Reaction Conditions

1.1 -
2.1 Reagents: Phosphorus oxychloride

Reference

The Vilsmeier reaction of fully conjugated carbocycles and heterocycles

Jones, Gurnos; et al, Organic Reactions (Hoboken, 1997, 49,

Production Method 15

44205-36-9

827-01-0

Reaction Conditions

1.1 -
2.1 -
3.1 Reagents: Phosphorus oxychloride

Reference

The Vilsmeier reaction of fully conjugated carbocycles and heterocycles

Jones, Gurnos; et al, Organic Reactions (Hoboken, 1997, 49,

5-chloro-1H-indole-3-carbaldehyde Raw materials

• 5-Bromo-1H-indole-3-carbaldehyde
• N-(Chloromethylidene)-N-methylmethanaminium
• Dichlorophosphoryloxymethylidene(dimethyl)azanium
• 5-chloro-1H-indole
• 2-oxoacetic acid
• Difluoromethyl Phenyl Sulfide
• 2-BROMO-5-CHLORO-1H-INDOLE
• Phosphorodichloridic acid, chloro(dimethylamino)methyl ester

5-chloro-1H-indole-3-carbaldehyde Preparation Products

• 5-chloro-1H-indole-3-carbaldehyde (827-01-0)

• 1. Fe/S-Catalyzed synthesis of 2-benzoylbenzoxazoles and 2-quinolylbenzoxazoles via redox condensation of o-nitrophenols with acetophenones and methylquinolines?
  Thi Thu Tram Nguyen,Thanh Binh Nguyen Org. Biomol. Chem., 2021,19, 6015-6020
• 2. Emerging investigator series: heterogeneous reactions of sulfur dioxide on mineral dust nanoparticles: from single component to mixed components?
  Tao Wang,Yangyang Liu,Yue Deng,Hongbo Fu,Jianmin Chen Environ. Sci.: Nano, 2018,5, 1821-1833
• 3. Excitation energies from ground-state density-functionals by means of generator coordinates
  A. B. F. da Silva,K. Capelle Phys. Chem. Chem. Phys., 2009,11, 4564-4569
• 4. Excellent mechanical performance and enhanced dielectric properties of OBC/SiO2 elastomeric nanocomposites: effect of dispersion of the SiO2 nanoparticles?
  Xing Zhao,Lu Bai,Rui-Ying Bao,Zheng-Ying Liu,Ming-Bo Yang,Wei Yang RSC Adv., 2017,7, 46297-46305
• 5. 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

• Solvents and Organic Chemicals Organic Compounds Organoheterocyclic compounds Indoles and derivatives Indoles
• Solvents and Organic Chemicals Organic Compounds Aldehyde/Ketone

Recent Advances in the Application of 5-Chloro-1H-Indole-3-Carbaldehyde (CAS: 827-01-0) in Chemical Biology and Pharmaceutical Research

5-Chloro-1H-indole-3-carbaldehyde (CAS: 827-01-0) is a key intermediate in the synthesis of various biologically active compounds, particularly in the development of pharmaceuticals and agrochemicals. Recent studies have highlighted its significance as a versatile building block for the construction of indole-based scaffolds, which are prevalent in many drug molecules. This research brief aims to summarize the latest findings on the synthesis, biological activities, and potential applications of this compound in drug discovery and chemical biology.

In a recent study published in the Journal of Medicinal Chemistry, researchers explored the use of 5-chloro-1H-indole-3-carbaldehyde as a precursor for the synthesis of novel indole derivatives with potent anticancer properties. The study demonstrated that modifications at the 3-position of the indole ring, facilitated by the aldehyde functional group, led to compounds with significant inhibitory activity against various cancer cell lines, including breast and lung cancer. The findings underscore the potential of this compound in the development of targeted cancer therapies.

Another notable application of 5-chloro-1H-indole-3-carbaldehyde is in the field of antimicrobial research. A 2023 study in Bioorganic & Medicinal Chemistry Letters reported the synthesis of indole-based antimicrobial agents using this compound as a starting material. The resulting derivatives exhibited broad-spectrum activity against both Gram-positive and Gram-negative bacteria, with some compounds showing efficacy against drug-resistant strains. This research highlights the compound's utility in addressing the growing challenge of antibiotic resistance.

Beyond its pharmaceutical applications, 5-chloro-1H-indole-3-carbaldehyde has also been investigated for its role in chemical biology. Recent work published in ACS Chemical Biology detailed its use as a probe for studying protein-ligand interactions. The aldehyde group's reactivity allows for facile conjugation to proteins, enabling researchers to explore binding sites and mechanisms of action in biological systems. This approach has provided valuable insights into the design of enzyme inhibitors and other therapeutic agents.

In conclusion, 5-chloro-1H-indole-3-carbaldehyde (CAS: 827-01-0) continues to be a valuable tool in chemical biology and pharmaceutical research. Its versatility as a synthetic intermediate, combined with its potential biological activities, makes it a compound of significant interest for future drug discovery efforts. Ongoing research is expected to further expand its applications, particularly in the development of novel therapeutics for cancer, infectious diseases, and other medical conditions.

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