441715-93-1

Basic information

• Product Name: 6-FLUORO-1-METHYL-1H-INDOLE-3-CARBALDEHYDE
• Synonyms: 6-FLUORO-1-METHYL-1H-INDOLE-3-CARBALDEHYDE;TIMTEC-BB SBB010607;Albb-005048;6-fluoro-1-methyl-1H-indole-3-carbaldehyde(SALTDATA: FREE);6-fluoro-1-Methyl-1H-indole;1H-indole-3-carboxaldehyde, 6-fluoro-1-methyl-;6-Fluoro-1-methyl-1H-indol-3-carbaldehyde
• CAS NO: 441715-93-1
• Molecular Formula: C₁₀H₈FNO
• Molecular Weight: 177.18
• Mol File: 441715-93-1.mol

Chemical Properties

• Boiling Point: 322.3°C at 760 mmHg
• Flash Point: 148.7°C
• Appearance: /
• Density: 1.2g/cm³
• Vapor Pressure: 0.000281mmHg at 25°C
• Refractive Index: 1.568
• Storage Temp.: 2-8°C(protect from light)
• CAS DataBase Reference: 6-FLUORO-1-METHYL-1H-INDOLE-3-CARBALDEHYDE(CAS DataBase Reference)
• NIST Chemistry Reference: 6-FLUORO-1-METHYL-1H-INDOLE-3-CARBALDEHYDE(441715-93-1)
• EPA Substance Registry System: 6-FLUORO-1-METHYL-1H-INDOLE-3-CARBALDEHYDE(441715-93-1)

Safety Data

• Hazard Codes: Xi
• Statements: 41
• Safety Statements: 26-39
• HazardClass: IRRITANT
• Hazardous Substances Data: 441715-93-1(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
6-Fluoro-1-methyl-1H-indole-3-carbaldehyde is used as a building block for the synthesis of novel organic compounds with enhanced properties. Its unique structure and potential biological activities make it a valuable component in the development of new pharmaceuticals, potentially contributing to the creation of innovative treatments and therapies.
Used in Agrochemical Industry:
Similarly, in the agrochemical industry, 6-Fluoro-1-methyl-1H-indole-3-carbaldehyde may serve as a key intermediate in the synthesis of new compounds with applications in pest control, crop protection, or other agricultural areas. Its unique properties could lead to the development of more effective and environmentally friendly agrochemicals.
Used in Organic Chemistry Research:
6-Fluoro-1-methyl-1H-indole-3-carbaldehyde is used as a subject of study in organic chemistry to explore its reactivity, synthesis pathways, and potential to form new compounds. Understanding its behavior in various chemical reactions can lead to advancements in synthetic methods and the discovery of new chemical entities.
Used in Drug Discovery:
In the field of drug discovery, 6-Fluoro-1-methyl-1H-indole-3-carbaldehyde is utilized for its potential to contribute to the development of new pharmaceutical agents. Its unique structure may offer advantages in terms of selectivity, potency, or other drug-like properties, making it an interesting target for medicinal chemistry efforts.

InChI:InChI=1/C10H8FNO/c1-12-5-7(6-13)9-3-2-8(11)4-10(9)12/h2-6H,1H3

Upstream product

• 2795-41-7 6-fluoro-1H-indole-3-carbaldehyde 
• 74-88-4 methyl iodide 
• 399-51-9 6-fluoro-1H-indole 
• 441715-92-0 6-fluoro-1-methyl-1H-indole 
• 110-18-9 N,N,N,N,-tetramethylethylenediamine 
• 67-68-5 dimethyl sulfoxide 
• 50-00-0 formaldehyd 
• 68-12-2 N,N-dimethyl-formamide 

Downstream Products

• 441715-26-0 6-fluoro-1-methyl-1H-indole-3-carboxylic acid 
• 441715-96-4 C₃₁H₃₃F₂N₃O₅ 
• 441712-71-6 trans-4-[1-[[2-(6-fluoro-1-methyl-3-indolyl)-6-benzoxazolyl]acetyl]-(4S)-fluoro-(2S)-pyrrolidinylmethoxy]cyclohexanecarboxylic acid 
• 1609064-40-5 N-(2-(6-fluoro-1-methyl-1H-indol-3-yl)ethyl)-4-methylbenzenesulfonamide 
• 1623771-12-9 (E)-1-(6-fluoro-1-methyl-1H-indol-3-yl)-N-(4-methoxyphenyl)methanimine 
• 1623771-19-6 6-fluoro-1-methyl-2-(1-phenylpropyl)-1H-indole-3-carbaldehyde 

Relevant articles and documents

Cobalt-Catalyzed Enantioselective C–H Arylation of Indoles

Atropoisomeric (hetero)biaryls are scaffolds with increasing importance in the pharmaceutical and agrochemical industries. Although it is the most obvious disconnection to construct such compounds, the direct enantioselective C–H arylation through the concomitant induction of the chiral information remains extremely challenging and uncommon. Herein, the unprecedented earth-abundant 3d-metal-catalyzed atroposelective direct arylation is reported, furnishing rare atropoisomeric C2-arylated indoles. Kinetic studies and DFT computation revealed an uncommon mechanism for this asymmetric transformation, with the oxidative addition being the rate- and enantio-determining step. Excellent stereoselectivities were reached (up to 96% ee), while using an unusual N-heterocyclic carbene ligand bearing an essential remote substituent. Attractive dispersion interactions along with positive C–H-π interactions exerted by the ligand were identified as key factors to guarantee the excellent enantioselection.

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.

Electrochemically Enabled C3-Formylation and -Acylation of Indoles with Aldehydes

Reported herein is an effective strategy for oxidative cross-coupling of indoles with various aldehydes. The strategy is based on a two-step transformation via a well-known Mannich-type reaction and a C-N bond cleavage for carbonyl introduction. The key step - the C-N bond cleavage of the Mannich product - was enabled by electrochemistry. This strategy (with over 40 examples) ensures excellent functional-group tolerance as well as late-stage functionalization of pharmaceutical molecules.

Indole-substituted hydrazide derivatives and uses thereof

The invention discloses indole-substituted hydrazide derivatives and a use thereof, concretely relates to novel indole-substituted hydrazide derivatives and a medicinal composition including the abovecompounds, a use of the derivatives and the medicinal composition in the protection of nerve cells, and also relates to a method for preparing the compounds and the medicinal composition, and a use of the compounds and the medicinal composition in the preparation of drugs for treating diseases associated with glutamate excitotoxicity and oxidative stress damage or free radicals, or neurodegenerative diseases, especially the Alzheimer disease.

Visible Light-Driven C-3 Functionalization of Indoles over Conjugated Microporous Polymers

Metal-free and heterogeneous organic photocatalysts provide an environmentally friendly alternative to traditional metal-based catalysts. This paper reports a series of carbazole-based conjugated microporous polymers (CMPs) with tunable redox potentials and explores their photocatalytic performance with regard to C-3 formylation and thiocyanation of indoles. Conjugated polymers were synthesized through FeCl3 mediated Friedel-Crafts reactions, and their redox potentials were well regulated by simply altering the nature of the core (i.e., 1,4-dibenzyl, 1,3,5-tribenzyl, or 1,3,5-triazin-2,4,6-triyl). The resulting CMPs exhibited high surface areas, visible light absorptions, and tunable semiconductor-range band gaps. With the highest oxidative capability, CMP-CSU6 derived from 1,3,5-tri(9H-carbazol-9-yl)benzene showed the highest efficiency for C-3 formylation and thiocyanation of indoles at room temperature. Notably, the as-made catalysts can be easily recovered with good retention of photocatalytic activity and reused at least five times, suggesting good recyclability. These results are significant for constructing high-performance porous polymer catalysts with tunable photoredox potentials targeting an efficient material design for catalysis.

CuCl2/TBHP-mediated direct chlorooxidation of indoles

CuCl2/TBHP-mediated direct chlorooxidation of indole derivatives under simple aerobic conditions was reported, leading to facile preparations of a range of 3,3-disubstituted 3-chlorooxindoles in good yields and selectivities.

I2-mediated C3-formylation of indoles by tertiary amine and H2O

An I2-promoted 3-formylation of free (N-H) and N-substituted indoles with tetramethylethylenediamine (TMEDA) and H2O as the carbonyl source is achieved, providing 3-formylindole in moderate to excellent yields with good functional gr

Aerobic transition-metal-free visible-light photoredox indole C-3 formylation reaction

An aerobic visible-light-promoted indole C-3 formylation reaction catalyzed by Rose Bengal has been developed. This transition-metal-free process employs molecular oxygen as the terminal oxidant and uses TMEDA as the one-carbon source through C-N bond cleavage. The reaction is compatible with a variety of functional groups.

The ammonium-promoted formylation of indoles by DMSO and H2O

DMSO and H2O is an efficient combination in the NH 4OAc-promoted formylation of indole, where DMSO serves as a C1 carbon source. The mechanism study reveals that the procedure involves a usual and unusual Pummerer reaction.

The copper-catalyzed C-3-formylation of indole C-H bonds using tertiary amines and molecular oxygen

A copper-catalyzed formylation reaction has been developed by employing oxygen (O2) as the clean oxidant. The C-H bonds of indoles were C-3-formylated by tetramethylethylenediamine (TMEDA) and water (H2O; in situ formed and external added water) as the carbonyl source in moderate to good yields with good functional group tolerance. Thus, it represents a facile procedure leading to 3-formylindoles. Copyright