4771-50-0

Basic information

• Product Name: 7-METHYLINDOLE-3-CARBOXALDEHYDE
• Synonyms: 7-METHYL-1H-INDOLE-3-CARBALDEHYDE;7-METHYLINDOLE-3-ALDEHYDE;7-METHYLINDOLE-3-CARBOXALDEHYDE;7-METHYLINDOLE-3-CARBOXYALDEHYDE;3-FORMYL-7-METHYLINDOLE;1H-Indole-3-carboxaldehyde, 7-methyl- (9CI);7-Methylindole-3-carboxaldehyde 98%;7-Methyl-3-indolecarboxaldehyde
• CAS NO: 4771-50-0
• Molecular Formula: C₁₀H₉NO
• Molecular Weight: 159.18
• EINECS: -0
• Product Categories: ALDEHYDE;Indoles and derivatives;Indole;Heterocyclic Compounds;Building Blocks;Heterocyclic Building Blocks;Indoles;C10-C12;Aldehydes;Building Blocks;C10;Carbonyl Compounds;Chemical Synthesis;Heterocyclic Building Blocks;Organic Building Blocks
• Mol File: 4771-50-0.mol

Chemical Properties

• Melting Point: 206-208°C
• Boiling Point: 341 °C at 760 mmHg
• Flash Point: 168 °C
• Appearance: /
• Density: 1.226 g/cm³
• Vapor Pressure: 8.31E-05mmHg at 25°C
• Refractive Index: 1.698
• Storage Temp.: −20°C
• PKA: 15.80±0.30(Predicted)
• Sensitive: Air Sensitive
• BRN: 122340
• CAS DataBase Reference: 7-METHYLINDOLE-3-CARBOXALDEHYDE(CAS DataBase Reference)
• NIST Chemistry Reference: 7-METHYLINDOLE-3-CARBOXALDEHYDE(4771-50-0)
• EPA Substance Registry System: 7-METHYLINDOLE-3-CARBOXALDEHYDE(4771-50-0)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36-37
• WGK Germany: 3
• Hazardous Substances Data: 4771-50-0(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
7-METHYLINDOLE-3-CARBOXALDEHYDE is used as a reactant for the preparation of various compounds with therapeutic potential. It serves as a building block for the synthesis of different pharmaceutical agents, including:
1. Tryptophan dioxygenase inhibitors pyridyl-ethenyl-indoles, which are potential anticancer immunomodulators. These compounds can modulate the immune system to enhance the body's response against cancer cells.
2. Antibacterial and antituberculosis agents. These agents can help in the treatment of bacterial infections, including tuberculosis, by targeting specific bacterial enzymes or pathways.
3. Antiandrogens effective against androgen receptor mutants. These compounds can be used in the treatment of prostate cancer and other androgen-dependent conditions by blocking the action of androgens on their receptors.
4. Anti-bovine viral diarrhea virus (BVDV) agents. These agents can help in the prevention and treatment of BVDV infections in cattle, which can lead to significant economic losses in the livestock industry.
5. Receptor subtype 5 antagonists. These compounds can be used in the treatment of various conditions, including neurological disorders, by blocking the action of specific receptors in the body.
6. Glucocorticoid receptor ligands. These compounds can modulate the activity of the glucocorticoid receptor, which plays a crucial role in the regulation of immune responses and stress responses.
7. Necroptosis inhibitors. These compounds can inhibit a form of programmed cell death called necroptosis, which is involved in various pathological conditions, including neurodegenerative diseases and ischemic injuries.
8. Orally efficacious small-molecule activator of the insulin receptor. These compounds can enhance the activity of the insulin receptor, which may be useful in the treatment of diabetes and other conditions related to insulin resistance.

InChI:InChI=1/C10H9NO/c1-7-3-2-4-9-8(6-12)5-11-10(7)9/h2-6,11H,1H3

Upstream product

• 933-67-5 7-methyl-1H-indole 
• 67-66-3 chloroform 
• 68-12-2 N,N-dimethyl-formamide 
• 100-61-8 N-methylaniline 
• 88-72-2 1-methyl-2-nitrobenzene 
• 67-68-5 dimethyl sulfoxide 
• 100-97-0 hexamethylenetetramine 
• 50-00-0 formaldehyd 

Downstream Products

• 14490-05-2 7-methyltryptamine 
• 33468-36-9 7-methyl-L-tryptophan 
• 3456-73-3 7-methyl-DL-tryptophan 

Relevant articles and documents

Access to Polycyclic Indol(en)ines via Base-Catalyzed Intramolecular Dearomatizing 3-Alkenylation of Alkynyl Indoles

Polycyclic indolines and indolenines were synthesized via base-catalyzed intramolecular dearomatizing 3-alkenylation reactions of alkynyl indoles 1 at room temperature. The base enhanced the nucleophilicity of the carbon at the 3-position of the indole moiety, facilitating an exclusive 5-exo-dig cyclization reaction with the alkyne to form spiroindolenines 2. The imine functionality of 2 could undergo in situ nucleophilic addition to form spiroindolines 3 when R was a carbamoyl group or reduction to form spiroindolines 4 when R was H.

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

Despite intensive studies on the synthesis of 3-formylindoles, it is still highly desirable to develop efficient methods for the formylation of indoles, due to the shortcomings of the reported methods, such as inconvenient operations and/or harsh reaction conditions. Here, we describe a Ph3P/ICH2CH2I-promoted formylation of indoles with DMF under mild conditions. A Vilsmeier-type intermediate is readily formed from DMF promoted by the Ph3P/ICH2CH2I system. A onestep formylation process can be applied to various electron-rich indoles, but a hydrolysis needs to be carried out as a second step in the case of electron-deficient indoles. Convenient operations make this protocol attractive.

Preparation method of non-natural L - tryptophan derivative

The invention discloses a preparation method of a non-natural L - tryptophan derivative, which is sequentially subjected to formylation by adopting a cheap and easily available substituted indole compound as a raw material. Cyclization, ring opening, asym

Access to Polycyclic Thienoindolines via Formal [2+2+1] Cyclization of Alkynyl Indoles with S8and K2S

The syntheses of polycyclic thienoindolines bearing a dihydrothiophene or tetrahydrothiophene subunit have not been reported, despite the fact that such compounds may have interesting medicinal properties. Herein, we report a protocol for accessing polycyclic dihydrothiophenes by means of formal [2+2+1] intramolecular dearomatizing cyclization of alkynyl indoles with K2S and S8 as the sources of sulfide. In addition, tetrahydrothienoindolines were stereoselectively synthesized via a one-pot, two-step protocol involving AgNO3-catalyzed alkenyl dearomatization followed by two nucleophilic addition reactions involving K2S.

Access to Polycyclic Sulfonyl Indolines via Fe(II)-Catalyzed or UV-Driven Formal [2 + 2 + 1] Cyclization Reactions of N-((1H-indol-3-yl)methyl)propiolamides with NaHSO3

A variety of structurally novel polycyclic sulfonyl indolines have been synthesized via FeCl2-catalyzed or UV-driven intramolecular formal [2 + 2 + 1] dearomatizing cyclization reactions of N-(1H-indol-3-yl)methyl)propiolamides with NaHSO3 in an aqueous medium. The reactions involve the formation of one C-C bond and two C-S bonds in a single step.

Structure-Guided Synthesis and Mechanistic Studies Reveal Sweetspots on Naphthyl Salicyl Hydrazone Scaffold as Non-Nucleosidic Competitive, Reversible Inhibitors of Human Ribonucleotide Reductase

Ribonucleotide reductase (RR), an established cancer target, is usually inhibited by antimetabolites, which display multiple cross-reactive effects. Recently, we discovered a naphthyl salicyl acyl hydrazone-based inhibitor (NSAH or E-3a) of human RR (hRR) binding at the catalytic site (C-site) and inhibiting hRR reversibly. We herein report the synthesis and biochemical characterization of 25 distinct analogs. We designed each analog through docking to the C-site of hRR based on our 2.7 ? X-ray crystal structure (PDB ID: 5TUS). Broad tolerance to minor structural variations preserving inhibitory potency is observed. E-3f (82% yield) displayed an in vitro IC50 of 5.3 ± 1.8 μM against hRR, making it the most potent in this series. Kinetic assays reveal that E-3a, E-3c, E-3t, and E-3w bind and inhibit hRR through a reversible and competitive mode. Target selectivity toward the R1 subunit of hRR is established, providing a novel way of inhibition of this crucial enzyme.

Synthesis of polycyclic spirooxindoles via an asymmetric catalytic one-pot stepwise Aldol/chloroetherification/aromatization procedure

A general method for the synthesis of chiral pentacyclic spirooxindoles containing a tetrahydropyrano[2,3-b]indole scaffold through a one-pot stepwise sequence from 3-(3-indolomethyl)oxindole, paraformaldehyde and NCS is reported. Furthermore, the pentacyclic spirooxindoles could be transformed to bispirooxindole and other structurally diverse spirocyclic oxindoles.

Method for synthesizing indole -3 - formaldehyde compounds (by machine translation)

The invention relates to a synthetic indole - 3 - formaldehyde compounds, which belongs to the technical field of organic synthesis. The invention will be indole compound, hexamethylene tetramine, crystalline aluminum trichloride, N, N - dimethyl formamide in proportion in 120 °C reaction under the condition of 1 - 20 the H, then filtered, washing, filtering, concentrating, column chromatography purification and other after-treatment technology, make the refined indole - 3 - formaldehyde compound. The invention overcomes the indole - 3 - benzaldehyde compound of preparation need to use not stabilized peroxide, and for a long time under the high temperature reaction of the defect. And the invention uses the advantages of simple equipment, product yield is high, the resulting yield of a target product can be up to 94%. In addition, the invention relates to a low reaction conditions, less catalyst levels, low energy consumption, the post treatment process is simple and easy to use, without the need of using a high dosage of acid or alkali, post-processing the solvent can be recovered and recycled, industrial "three wastes" is discharged little, suitable for large-scale production. (by machine translation)

An environmentally friendly protocol for oxidative halocyclization of tryptamine and tryptophol derivatives

An environmentally friendly and efficient protocol (KX/oxone) for oxidative halocyclization of tryptamine/tryptophol derivatives was developed and demonstrated with 28 examples and concise total synthesis of cyclotryptamine alkaloid protubonines A and B. The distinct advantage of this protocol over all previous methods is that no organic byproduct is generated from a halogenating agent or oxidant, thus greatly reducing the environmental impact of halocyclization and facilitating the post-reaction purification.

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

An efficient iron-catalyzed C3-selective formylation of free (N-H) or N-substituted indoles was developed by employing formaldehyde and aqueous ammonia, with air as the oxidant. This new method gave 3-formylindoles in moderate to excellent yields with fairly short reaction times. Moreover, this procedure for catalytic formylation of indoles can be applied to gram-scale syntheses.