10075-48-6

Basic information

• Product Name: 5-BROMO-3-METHYLINDOLE
• Synonyms: 5-BROMO-3-METHYLINDOLE;5-Bromo-3-methyl-1H-indole;1H-Indole, 5-broMo-3-Methyl-;3-Methyl-5-bromoindole;5-Bromoskatole;NSC 79234;5-broMo-3-Methyl-indol-
• CAS NO: 10075-48-6
• Molecular Formula: C₉H₈BrN
• Molecular Weight: 210.07
• Product Categories: Halogenated;Indole;Organohalides
• Mol File: 10075-48-6.mol
• Article Data: 30

Chemical Properties

• Melting Point: 78-82°C
• Boiling Point: 325.1 °C at 760 mmHg
• Flash Point: 150.4 °C
• Appearance: /
• Density: 1.563
• Vapor Pressure: 0.000446mmHg at 25°C
• Refractive Index: 1.684
• Storage Temp.: 2-8°C
• PKA: 16.34±0.30(Predicted)
• CAS DataBase Reference: 5-BROMO-3-METHYLINDOLE(CAS DataBase Reference)
• NIST Chemistry Reference: 5-BROMO-3-METHYLINDOLE(10075-48-6)
• EPA Substance Registry System: 5-BROMO-3-METHYLINDOLE(10075-48-6)

Safety Data

• Hazard Codes: Xi,Xn
• Statements: 22-37/38-41
• Safety Statements: 26-39
• WGK Germany: 3
• HazardClass: IRRITANT
• Hazardous Substances Data: 10075-48-6(Hazardous Substances Data)

Usage

General Description

5-Bromo-3-methylindole is a chemical compound with the molecular formula C9H8BrN. It is a derivative of indole, which is a heterocyclic aromatic organic compound. 5-Bromo-3-methylindole is commonly used as a building block in the synthesis of various pharmaceuticals and fine chemicals. It is also used in the preparation of chemical intermediates for the production of dyes, pigments, and other organic compounds. The compound is known for its mild aromatic odor and is typically stored and handled under carefully controlled conditions to prevent exposure to moisture and air. Overall, 5-Bromo-3-methylindole is a versatile and important chemical in the pharmaceutical and chemical industries.

InChI:InChI=1/C9H8BrN/c1-6-5-11-9-3-2-7(10)4-8(6)9/h2-5,11H,1H3

Upstream product

• 586-78-7 para-nitrophenyl bromide 
• 125914-22-9 2-(5-bromo-2-nitrophenyl)acetonitrile 
• 589-21-9 (4-bromophenyl)hydrazine 
• 87-48-9 5-Bromo-1H-indole-2,3-dione 
• 622-88-8 4-bromophenylhydrazine hydrochloride 
• 10075-50-0 5-bromo-1H-indole 
• 877-03-2 5-bromo-1H-indole-3-carboxaldehyde 
• 70070-22-3 5-bromo-3-methyl-1H-indole-2-carboxylic acid ethyl ester 
• 67-56-1 methanol 
• 92557-51-2 5-Bromo-indole-3-carbinol 

Downstream Products

• 151417-95-7 1-benzenesulfonyl-5-bromo-3-methylindole 
• 847549-13-7 [2-(3-methyl-1H-indol-5-yl)-ethyl]-carbamic acid benzyl ester 
• 851524-90-8 3-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole 
• 222306-39-0 5-bromo-1-ethyl-2-[(4-fluorophenyl)(hydroxy)methyl]-3-methyl-1H-indole 
• 222306-38-9 5-bromo-1-ethyl-2-(4-fluorobenzoyl)-3-methyl-1H-indole 
• 6548-09-0 5-bromo-DL-tryptophan 
• 151417-96-8 1-benzenesulfonyl-5-bromo-3-bromomethylindole 
• 151417-97-9 2-Acetylamino-2-(1-benzenesulfonyl-5-bromo-1H-indol-3-ylmethyl)-malonic acid diethyl ester 
• 10075-49-7 N-methyl-3-methyl-5-bromoindole 
• 1609470-56-5 C₁₇H₁₄BrF₂NO₂S 
• 1640122-66-2 N-acetyl-3-(4-methoxyphenyl)-3-methyl-5-bromoindoline 
• 1640122-86-6 3-(N-acetyl-5-bromo-3-methylindolin-3-yl)-1-tosylindole 
• 1431726-29-2 C₁₈H₁₇BrN₂O₂S 
• 1428236-53-6 C₂₀H₁₈BrNO₃ 

Relevant articles and documents

Palladium-catalyzed C-H ethoxycarbonyldifluoromethylation of electron-rich heteroarenes

The first Pd-catalyzed C-H ethoxycarbonyldifluoromethylation with BrCF2CO2Et has been developed. The use of a bidentate phosphine ligand (Xantphos) is critical for the reaction to occur. A variety of electron-rich heteroarenes, including indoles, furans, thiophenes, and pyrroles, can be ethoxycarbonyldifluoromethylated in moderate to excellent yields. The reactions take place at the C-H bonds adjacent to the heteroatoms with high regioselectivity. This method provides a new protocol for the introduction of difuoroalkyl groups into electron-rich heteroarenes.

Synthesis of Pyrido[2,3-b]indole Derivatives via Rhodium-Catalyzed Cyclization of Indoles and 1-Sulfonyl-1,2,3-triazoles

Acyloxy-substituted α,β-unsaturated imines generated in situ from triazoles can act as aza-[4 C] synthons and be trapped by indoles in a stepwise [4 + 2] cycloaddition reaction, thus providing rapid access to valuable pyrido[2,3-b]indoles in high yields. Attractive features of this reaction system include operational simplicity, readily available substrates, construction of sterically demanding quaternary centers, and convenient derivatization using triflate. (Figure presented.).

Organocatalytic Formal (3 + 2) Cycloaddition toward Chiral Pyrrolo[1,2- a]indoles via Dynamic Kinetic Resolution of Allene Intermediates

We report the chiral phosphoric acid catalyzed formal (3 + 2) cycloaddition of 3-substituted 1H-indoles and propargylic alcohols containing a functional directing group (p-NHAc or p-OH). This work represents a straightforward method to synthesize chiral pyrrolo[1,2-a]indole bearing a tetrasubstituted carbon stereocenter. The reaction proceeds smoothly with a wide array of substrate tolerance to deliver various chiral pyrrolo[1,2-a]indoles in up to 93percent yield and 98percent ee. The utility of this method is highlighted by the diverse transformations of the products into various indole derivatives.

Rhenium(I)-Catalyzed C-Methylation of Ketones, Indoles, and Arylacetonitriles Using Methanol

A ReCl(CO)5/MeC(CH2PPh2)3 (L2) system was developed for the C-methylation reactions utilizing methanol and base, following the borrowing hydrogen strategy. Diverse ketones, indoles, and arylacetonitriles underwent mono-and dimethylation selectively up to 99% yield. Remarkably, tandem multiple methylations were also achieved by employing this catalytic system.

Selective Oxidative Cleavage of 3-Methylindoles with Primary Amines Affording Quinazolinones

A selective functionalization of C-C-C bonds toward N-C-O bonds is realized by an n-Bu4NI-catalyzed reaction of 3-methylindoles with primary amines using TBHP as the unique oxidant. The systematic process involves oxygenation, nitrogenation, ring-opening, and recyclization, affording a broad range of quinazolinones in good to excellent yields.