27816-53-1

Basic information

• Product Name: 1,5-dimethyl-1H-indole
• Synonyms: 1H-Indole, 1,5-dimethyl-
• CAS NO: 27816-53-1
• Molecular Formula: C₁₀H₁₁N
• Molecular Weight: 145.201
• Mol File: 27816-53-1.mol
• Article Data: 50

Chemical Properties

• Boiling Point: 262.7°C at 760 mmHg
• Flash Point: 112.7°C
• Density: 0.99g/cm³
• Vapor Pressure: 0.0175mmHg at 25°C
• Refractive Index: 1.561
• CAS DataBase Reference: 1,5-dimethyl-1H-indole(CAS DataBase Reference)
• NIST Chemistry Reference: 1,5-dimethyl-1H-indole(27816-53-1)
• EPA Substance Registry System: 1,5-dimethyl-1H-indole(27816-53-1)

Safety Data

• Hazardous Substances Data: 27816-53-1(Hazardous Substances Data)

Usage

General Description

1,5-dimethyl-1H-indole, also known as 1,5-dimethylindole, is a chemical compound with the molecular formula C10H11N. It is a substituted indole derivative, which is a bicyclic heterocyclic organic compound that is ubiquitous in nature. 1,5-dimethyl-1H-indole is commonly used as a building block in the synthesis of pharmaceuticals, agrochemicals, and dyes. It has been found to exhibit potential antiviral, anti-inflammatory, and anticancer activities in various studies. The compound is also known for its distinct odor, and it is used in the production of perfumes and fragrances. 1,5-dimethyl-1H-indole must be handled and stored with appropriate care, as it is considered hazardous to human health and the environment.

Upstream product

• 614-96-0 5-methyl-1H-indole 
• 616-38-6 carbonic acid dimethyl ester 
• 10075-52-2 5-bromo-1-methyl-H-indole 
• 917-54-4 methyllithium 
• 431-47-0 trifluoroacetic acid-methyl ester 
• 837392-62-8 1-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole 
• 74-88-4 methyl iodide 
• 512-56-1 trimethyl phosphite 
• 623-08-5 N-methyl-p-toluidine 
• 107-21-1 ethylene glycol 
• 60397-77-5 N-(2,4-dimethylphenyl)formamide 
• 608-05-9 5-methyl-indole-2,3-dione 
• 181651-24-1 N-methyl-N-(4-methylphenyl)ethenesulfinamide 
• 108093-89-6 formic acid-(2,4,N-trimethyl-anilide) 

Downstream Products

• 112194-38-4 (3R,6R)-3-[(R)-1-(1,5-Dimethylindol-3-yl)ethyl]-6-(pyridin-2-ylmethyl)piperazine-2,5-dione 
• 959682-84-9 1,3-bis(1,5-dimethyl-1H-indole-3-yl)propane-1,3-dione 
• 112398-46-6 (η6-5-methyl-N-methylindole)(η5-cyclopentadienyl)ruthenium hexafluorophosphate 
• 132554-35-9 N-methyl-2-phenyl-5-methylindole 
• 1334225-09-0 octan-2-yl 1,5-dimethyl-1H-indole-3-carboxylate 
• 1014697-38-1 benzyl 1,5-dimethyl-1H-indole-3-carboxylate 
• 1334224-96-2 butyl 1,5-dimethyl-1H-indole-3-carboxylate 
• 1315257-98-7 N-(3-chloro-1,5-dimethyl-1H-indol-2-yl)-N,4-dimethylbenzenesulfonamide 
• 1315257-84-1 N-(1,5-dimethyl-1H-indol-2-yl)-N,4-dimethylbenzenesulfonamide 
• 1351557-08-8 6,9-dimethyl-11-phenyl-6H-indolo[2,3-b]quinoline 
• 335032-69-4 5-methyl-N-methylindole-3-carbaldehyde 
• 128200-46-4 1,5-dimethyl-1H-indole-3-carbonitrile 
• 1461703-57-0 C₁₈H₁₇NO₂ 
• 1646144-87-7 C₂₀H₂₁NO₂ 

Relevant articles and documents

Regioselective 2-alkylation of indoles with α-bromo esters catalyzed by Pd/P,P=O system

A palladium-catalyzed 2-alkylation of indoles with α-bromo esters is developed by employing a P,P=O ligand. The method features excellent regioselectivities, mild reaction conditions, and good functional group compatibility. The employment of the P,P=O ligand as well as 4? molecular sieves were crucial for the success of the transformation. Mechanistic studies indicate the reaction proceed through a radical pathway.

Salicylaldehyde-Promoted Cobalt-Catalyzed C-H/N-H Annulation of Indolyl Amides with Alkynes: Direct Synthesis of a 5-HT3 Receptor Antagonist Analogue

A cobalt-catalyzed annulation of the C(sp2)-H/N-H bond of indoloamides with alkynes assisted by 8-aminoquinoline is reported for the synthesis of six-membered indololactams. The use of salicylaldehyde as the ligand is crucial for this transformation. The protocol has a broad scope for both alkynes and indoles. Preparing an active Co complex illustrates that salicylaldehyde plays a key role in the C-H activation step. The synthetic applications are proven by the gram-scale reaction and one-step construction of the multicyclic 5-HT3 receptor antagonist.

Isothiourea-Catalyzed Enantioselective Synthesis of Tetrahydro-α-carbolinones

An isothiourea-catalyzed enantioselective annulation protocol using indolin-2-imines with a series of α,β-unsaturated p-nitrophenyl esters for the synthesis of tetrahydro-α-carbolinones was developed. Using 5 mol % of the isothiourea HyperBTM as the Lewis base catalyst, this process allows the enantioselective preparation of a range of C(4)-substituted tetrahydro-α-carbolinones in good to excellent yield and with high enantioselectivity (20 examples, 32-99% yield and up to 99:1 er).