66416-72-6

Usage

Uses

Used in Pharmaceutical Industry:
4-Bromo-2-iodoaniline is used as a chemical intermediate for the preparation of quinolone derivatives, which are important in the development of antibiotics and other pharmaceutical compounds. These derivatives exhibit broad-spectrum antimicrobial activity and are used to treat a variety of bacterial infections.
Used in Chemical Synthesis:
4-Bromo-2-iodoaniline is also used in the synthesis of a resin-bound sulfonamide, which serves as a starting material for the preparation of 2,3,5-trisubstituted indoles. These indole derivatives are valuable in the synthesis of various organic compounds and have potential applications in the development of pharmaceuticals, agrochemicals, and other specialty chemicals.

InChI:InChI=1/C6H5BrIN/c7-4-1-2-6(9)5(8)3-4/h1-3H,9H2

Upstream product

• 106-40-1 4-bromo-aniline 
• 615-43-0 2-iodophenylamine 
• 62-53-3 aniline 

Downstream Products

• 89280-77-3 4-bromo-2,6-diiodoaniline 
• 562080-91-5 N-(4-bromo-2-iodophenyl)acetamide 
• 112671-47-3 ethyl (4-bromo-2-iodophenyl)carbamate 
• 5304-21-2 6-bromo-2-methylbenzothiazole 
• 71205-21-5 methyl (E)-3-(2-amino-5-bromophenyl)prop-2-enoate 
• 543740-87-0 2-[(2-amino-5-bromophenyl)ethynyl]-4,6-dibromophenylamine 
• 7254-19-5 5-bromo-2-indolecarboxylic acid 
• 665033-14-7 4-bromo-2-(phenylethynyl)aniline 
• 869486-64-6 N-(4-bromo-2-iodophenyl)methylamine 
• 83515-06-4 5-bromo-2-phenylindole 
• 878133-05-2 N-(4-bromo-2-iodophenyl)-2,2,2-trifluoroacetamide 
• 210345-56-5 5-bromo-1H-indole-2-carboxylic acid methyl ester 

Relevant academic research and scientific papers

CYCLOPROPYL DIHYDROQUINOLINE SULFONAMIDE COMPOUNDS

The present invention provides a compound of Formula (I): an enantiomer, diastereoisomer, atropisomer thereof, a mixture thereof, or a pharmaceutically acceptable salt thereof, that inhibits voltage-gated sodium channels, in particular NaV1.7. The compoun

Modular counter-Fischer?indole synthesis through radical-enolate coupling

A single-electron transfer mediated modular indole formation reaction from a 2-iodoaniline derivative and a ketone has been developed. This transition-metal-free reaction shows a broad substrate scope and unconventional regioselectivity trends. Moreover, important functional groups for further transformation are tolerated under the reaction conditions. Density functional theory studies reveal that the reaction proceeds by metal coordination, which converts a disfavored 5-endo-trig cyclization to an accessible 7-endo-trig process.

Cu(II)-Promoted Cascade Synthesis of Fused Imidazo-Pyridine-Carbonitriles

A Cu(II)-promoted synthesis of an aza-fused N-heterocycle having a benz-imidazopyridine scaffold is developed via an addition-cyclization reaction followed by an Ullmann-type C-N coupling between o-iodoanilines and γ-ketodinitriles. This protocol features a broad substrate scope, giving products in 32-84% yields. The compounds show excellent photoluminescence properties having two absorption maxima in the region between 270-280 and 338-350 nm and emission maxima in the range of 502-533 nm. The HOMO-LUMO energy gap of 3.49-3.57 eV was determined using Gaussian 09 at the B3LYP/6-31G (d, p) basis set level. We also demonstrated a few postsynthetic modifications.

CYCLOBUTYL DIHYDROQUINOLINE SULFONAMIDE COMPOUNDS

The present invention provides a cyclobutyl dihydroquinoline sulfonamide compound of Formula (I), an enantiomer, diastereoisomer, atropisomer thereof, a mixture thereof, or a pharmaceutically acceptable salt thereof, that inhibits voltage-gated sodium channels, in particular Nav1.7. The compounds are useful for the treatment of diseases associated with the activity of sodium channels such as pain disorders, cough, and itch. Also provided are pharmaceutical compositions containing the compounds of the present invention. Also further provided is an atropi-selective preparation of said compounds of Formula (I), and intermediate thereof.

A novel DMSO-assisted regioselective iodination of aniline analogues

A metal- and oxidant-free electrophilic iodination of aniline analogues was achieved in high to excellent yields at room temperature in MTBE with 0 or 3.5 equivalents of DMSO. Examined substituents include N-alkyl, N,N-dialkyl, N-morpholinyl and N-piperazinyl as well as methyl, Br, CN and CO2CH3 aryl ring substitutions.

AN IMPROVED ONE POT, ONE STEP PROCESS FOR THE HALOGENATION OF AROMATICS USING SOLID ACID CATALYSTS

The present invention disclosed an improved one pot, one step process for halogenation of compound of formula (II) to afford corresponding halogenated compound of formula (I) having improved yield and increased selectivity under very mild conditions.

Sodium sulfate-hydrogen peroxide-sodium chloride adduct: selective protocol for the oxidative bromination, iodination and temperature dependent oxidation of sulfides to sulfoxides and sulfones

The regioselective bromination and iodination of unprotected aromatic primary amines using enclathrated hydrogen peroxide as an oxidant under mild conditions has been developed, in which potassium bromide (KBr) and potassium iodide (KI) were used as brominating and iodinating agents, respectively. The adduct shows not only regioselectivity for para- or ortho-isomers but also a remarkable chemoselectivity for monobromination. Selective oxidation of sulfides to sulfoxides and sulfones has also been studied and good to excellent yields of the desired products were obtained. Acetic acid was found to be the solvent of choice for these reactions. This simple method represents an ecologically benign and alternative pathway for the oxidative halogenation of anilines and the oxidation of sulfides to sulfoxides and sulfones.

Intramolecular Hydroamination of Selenoalkynes to 2-Selenylindoles in the Absence of Catalyst

In this work, a series of 2-chalcogenylindoles was synthesized by an efficient methodology, starting from chalcogenoalkynes, including a previously unreported tellurium indole derivative. For the first time, these 2-substituted chalcogenylindoles were obtained in the absence of metal catalyst or base, under thermal conditions only. In addition, the results described herein represent a methodology with inverse regioselectivity for the chalcogen functionalization of indoles.

Total synthesis of kealiiquinone: the regio-controlled strategy for accessing its 1-methyl-4-arylbenzimidazolone core

A practical, concise and straightforward total synthesis of kealiiquinone 1, a naphtho[2,3-d]imidazole alkaloid obtained from the Micronesian marine sponge Leucetta sp. was accomplished. The squaric acid chemistry to construct the 1,4-quinoid ring and the regioselective N-methylation through a benzo[c][1,2,5]selenadiazolium heterocycle are the key features in this report. The full details of the representative approaches involving the different attempted synthetic strategies are also presented. Finally a successful total synthesis of this complex secondary metabolite is described.

PtCl4-catalyzed cyclization of N-acetyl-2-alkynylanilines: A mild and efficient synthesis of N-acetyl-2-substituted indoles

An efficient synthesis of N-acetyl-2-substituted indole derivatives via direct intramolecular hydroamination of N-acetyl-2-alkynylaniline derivatives was developed. The reaction could be applied to a wide range of substrates employing only 1–2 mol% of PtCl4 as the catalyst to furnish the desired indole products in moderate to excellent yields. The current protocol is efficient, reliable and scalable, and could serve as an important tool for convenient and rapid access to this important class of N-heterocyclic skeleton from readily available substrates.