5649-36-5

Basic information

• Product Name: 1H-Indole, 2,6-dimethyl-
• Synonyms: 1H-Indole, 2,6-dimethyl-;2,6-DiMethyl-1H-Indole
• CAS NO: 5649-36-5
• Molecular Formula: C₁₀H₁₁N
• Molecular Weight: 145.2
• Mol File: 5649-36-5.mol
• Article Data: 11

Chemical Properties

• Melting Point: 82.5°C (estimate)
• Boiling Point: 273.05°C
• Flash Point: 115.1°C
• Appearance: /
• Density: 1.0641 (estimate)
• Vapor Pressure: 0.00943mmHg at 25°C
• Refractive Index: 1.6030 (estimate)
• Storage Temp.: Sealed in dry,Room Temperature
• CAS DataBase Reference: 1H-Indole, 2,6-dimethyl-(CAS DataBase Reference)
• NIST Chemistry Reference: 1H-Indole, 2,6-dimethyl-(5649-36-5)
• EPA Substance Registry System: 1H-Indole, 2,6-dimethyl-(5649-36-5)

Safety Data

• Hazardous Substances Data: 5649-36-5(Hazardous Substances Data)

Usage

General Description

1H-Indole, 2,6-dimethyl- is a naturally occurring organic compound with a chemical structure consisting of a bicyclic structure with a nitrogen atom in the ring. It is commonly found in a variety of plant-based substances, including perfumes, essential oils, and certain food products. The compound is also known for its use in the synthesis of pharmaceuticals and agrochemicals. Additionally, it is associated with various biological activities, such as anti-inflammatory and antimicrobial properties, making it a subject of interest in medicinal and agricultural research. Overall, 1H-Indole, 2,6-dimethyl- has notable applications in both natural products and synthetic chemistry, prompting further investigation into its potential uses and effects.

InChI:InChI=1/C10H11N/c1-7-3-4-9-6-8(2)11-10(9)5-7/h3-6,11H,1-2H3

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Downstream Products

• 480435-96-9 3-(2,6-dimethyl-1H-indol-3-yl)-2,5-dichloro[1,4]benzoquinone 
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Relevant articles and documents

Cobalt-Catalyzed Dearomatization of Indoles via Transfer Hydrogenation to Afford Polycyclic Indolines

A cobalt-catalyzed dearomatization of indoles via transfer hydrogenation with HBpin and H2O has been developed. This reaction offered a straightforward platform to access hexahydropyrido[1,2-a]indoles in high regio- and chemoselectivity. A preliminary reaction mechanism was proposed on the basis of deuterium-labeling experiments, and a cobalt hydride species was involved in the reaction.

Method for preparing indole and derivatives thereof

The invention discloses a method for preparing indole and derivatives of indole. The method for preparing indole and the derivatives of indole is characterized by comprising the following two steps that (1) a catalyst, a ligand and alkali are added in a reaction tube, under the protection of nitrogen, beta-hydroxy ketone or ester is reacted with a mixed solution of o-nitro aryl halides for 3 to 8h in an oil bath pan at the temperature of 90 to 120 DEG C, and then cooled to room temperature after reaction, and extracted, washed, dried and subjected to chromatography to obtain a product of o-nitro alpha-aryl ketone or ester; (2) o-nitro alpha-aryl ketone or ester obtained in the step (1), a reducing agent system and a solvent are added to the reaction tube, and reacted for 3 to 8h at the temperature of 60 to 100 DEG C, and then extracted, washed, dried and subjected to chromatography after being reacted to obtain a target product of indole and the derivatives of indole. Reaction raw materials, the catalyst, the ligand, the alkali and the solvent used in the invention are all industrial commodities, and simple and readily available, wide in sources, cheap in price, and further very stable in performances, and with no need for special storage conditions; in addition, the method for preparing indole and the derivatives of indole disclosed by the invention has the characteristics of low cost, high yield, simple process, less pollution and the like.

Discovery of a First-in-Class, Potent, Selective, and Orally Bioavailable Inhibitor of the p97 AAA ATPase (CB-5083)

The AAA-ATPase p97 plays vital roles in mechanisms of protein homeostasis, including ubiquitin-proteasome system (UPS) mediated protein degradation, endoplasmic reticulum-associated degradation (ERAD), and autophagy. Herein we describe our lead optimization efforts focused on in vitro potency, ADME, and pharmaceutical properties that led to the discovery of a potent, ATP-competitive, D2-selective, and orally bioavailable p97 inhibitor 71, CB-5083. Treatment of tumor cells with 71 leads to significant accumulation of markers associated with inhibition of UPS and ERAD functions, which induces irresolvable proteotoxic stress and cell death. In tumor bearing mice, oral administration of 71 causes rapid accumulation of markers of the unfolded protein response (UPR) and subsequently induces apoptosis leading to sustained antitumor activity in in vivo xenograft models of both solid and hematological tumors. 71 has been taken into phase 1 clinical trials in patients with multiple myeloma and solid tumors.