372089-59-3

Basic information

• Product Name: 6-BROMO-1H-INDOLE-2-CARBOXYLIC ACID METHYL ESTER
• Synonyms: Methyl 6-bromo-1H-indole-2-carboxylate≥ 99% (HPLC);6-BROMO-1H-INDOLE-2-CARBOXYLIC ACID METHYL ESTER;AKOS JY2083110;Methyl 6-Bromo-1H-Indole-2-Carboxylate;1H-Indole-2-carboxylic acid, 6-broMo-, Methyl ester
• CAS NO: 372089-59-3
• Molecular Formula: C10H8BrNO2
• Molecular Weight: 254.08
• Mol File: 372089-59-3.mol

Chemical Properties

• Boiling Point: 386.2°C at 760 mmHg
• Flash Point: 187.3°C
• Appearance: /
• Density: 1.629g/cm³
• Vapor Pressure: 3.61E-06mmHg at 25°C
• Refractive Index: 1.666
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility: Soluble in acetone.
• PKA: 14.04±0.30(Predicted)
• CAS DataBase Reference: 6-BROMO-1H-INDOLE-2-CARBOXYLIC ACID METHYL ESTER(CAS DataBase Reference)
• NIST Chemistry Reference: 6-BROMO-1H-INDOLE-2-CARBOXYLIC ACID METHYL ESTER(372089-59-3)
• EPA Substance Registry System: 6-BROMO-1H-INDOLE-2-CARBOXYLIC ACID METHYL ESTER(372089-59-3)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 372089-59-3(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
6-BROMO-1H-INDOLE-2-CARBOXYLIC ACID METHYL ESTER is used as a key intermediate for the synthesis of various organic compounds. Its unique structure allows for further functionalization and modification, making it a valuable building block in the creation of complex organic molecules.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 6-BROMO-1H-INDOLE-2-CARBOXYLIC ACID METHYL ESTER is used as a starting material for the development of new drugs. Its indole core and functional groups can be utilized to design and synthesize bioactive molecules with potential therapeutic applications.
Used in Agrochemicals:
6-BROMO-1H-INDOLE-2-CARBOXYLIC ACID METHYL ESTER is used as a precursor in the synthesis of agrochemicals, such as pesticides and herbicides. Its reactivity and structural features make it suitable for the development of effective compounds that can protect crops from pests and diseases.
Used in Dye Industry:
In the dye industry, 6-BROMO-1H-INDOLE-2-CARBOXYLIC ACID METHYL ESTER is used as a raw material for the production of dyes and pigments. Its indole-based structure can be modified to create a wide range of colors and shades, making it a valuable component in the formulation of various dyes.

InChI:InChI=1/C10H8BrNO2/c1-14-10(13)9-4-6-2-3-7(11)5-8(6)12-9/h2-5,12H,1H3

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Relevant articles and documents

Evaluation of Heterocyclic Carboxamides as Potential Efflux Pump Inhibitors in Pseudomonas aeruginosa

The ability to rescue the activity of antimicrobials that are no longer effective against bacterial pathogens such as Pseudomonas aeruginosa is an attractive strategy to combat antimicrobial drug resistance. Herein, novel efflux pump inhibitors (EPIs) demonstrating strong potentiation in combination with levofloxacin against wild-type P. aeruginosa ATCC 27853 are presented. A structure activity relationship of aryl substituted heterocyclic carboxamides containing a pentane diamine side chain is described. Out of several classes of fused heterocyclic carboxamides, aryl indole carboxamide compound 6j (TXA01182) at 6.25 μg/mL showed 8-fold potentiation of levofloxacin. TXA01182 was found to have equally synergistic activities with other antimicrobial classes (monobactam, fluoroquinolones, sulfonamide and tetracyclines) against P. aeruginosa. Several biophysical and genetic studies rule out membrane disruption and support efflux inhibition as the mechanism of action (MOA) of TXA01182. TXA01182 was determined to lower the frequency of resistance (FoR) of the partner antimicrobials and enhance the killing kinetics of levofloxacin. Furthermore, TXA01182 demonstrated a synergistic effect with levofloxacin against several multidrug resistant P. aeruginosa clinical isolates.

Synthesis of Indoles by Reductive Cyclization of Nitro Compounds Using Formate Esters as CO Surrogates

Alkyl and aryl formate esters were evaluated as CO sources in the Pd- and Pd/Ru-catalyzed reductive cyclization of 2-nitrostyrenes to give indoles. Whereas the use of alkyl formates requires the presence of a ruthenium catalyst such as Ru3(CO)12, the reaction with phenyl formate can be performed by using a Pd/phenanthroline complex alone. Phenyl formate was found to be the most effective CO source and the desired products were obtained in excellent yields, often higher than those previously reported using pressurized CO. The reaction tolerates many functional groups, including sensitive ones like a free aldehydic group or a pendant pyrrole. Detailed experiments and kinetic studies allow to conclude that the activation of phenyl formate is base-catalyzed and that the metal doesn't play a role in the decarbonylation step. The reactions can be performed in a single thick-walled glass tube with as little as 0.2 mol-% palladium catalyst and even on a 2 g scale. The same protocol can be extended to other nitro compounds, affording different heterocycles.

THIENO[3,2-B] PYRROLE[3,2-D]PYRIDAZINONE DERIVATIVES AND THEIR USE AS PKM2 DERIVATIVES FOR THE TREATMENT OF CANCER, OBESITY AND DIABETES RELATED DISORDERS

Described herein are compounds that regulate pyruvate kinase activity, pharmaceutical compositions and methods of use thereof. These compounds are represented by Formula (I) wherein R2, L1-L2, U1-U7, m, ring A, and Q are as defined herein.

A Bu4N[Fe(CO)3(NO)]-Catalyzed Hemetsberger–Knittel Indole Synthesis

The nucleophilic Fe complex Bu4N[Fe(CO)3(NO)] (TBA[Fe]) catalyzes the direct intramolecular amination of aryl vinyl azides to give the corresponding indole derivatives in good to excellent yields.

RHO-ASSOCIATED PROTEIN KINASE INHIBITOR, PHARMACEUTICAL COMPOSITION COMPRISING THE SAME, AS WELL AS PREPARATION METHOD AND USE THEREOF

The present invention relates to a Rho-associated protein kinase inhibitor of Formula (I), a pharmaceutical composition comprising the same, a preparation method thereof, and use thereof for the prevention or treatment of a disease mediated by the Rho-associated protein kinase (ROCK).

RHO-ASSOCIATED PROTEIN KINASE INHIBITOR, PHARMACEUTICAL COMPOSITION COMPRISING THE SAME, AS WELL AS PREPARATION METHOD AND USE THEREOF

The present invention relates to a Rho-associated protein kinase inhibitor of Formula (I), a pharmaceutical composition comprising the same, a preparation method thereof, and use thereof for the prevention or treatment of a disease mediated by the Rho-associated protein kinase (ROCK).

HETEROCYCLIC COMPOUNDS AS PAD INHIBITORS

Heterocyclic compounds of Formula (I), (II), and (III) are described herein along with their polymorphs, stereoisomers, prodrugs, solvates, co-crystals, intermediates, pharmaceutically acceptable salts, and metabolites thereof. The compounds described herein, their polymorphs, stereoisomers, prodrugs, solvates, co-crystals, intermediates, pharmaceutically acceptable salts, and metabolites thereof are PAD4 inhibitors and may be useful in the treatment of various disorders, for example rheumatoid arthritis, vasculitis, systemic lupus erythematosis, cutaneous lupus erythematosis, ulcerative colitis, cancer, cystic fibrosis, asthma, multiple sclerosis and psoriasis.

THERAPEUTIC COMPOUNDS AND METHODS TO TREAT INFECTION

Disclosed herein are compounds of formula (I), or a salt thereof and compositions comprising compounds of formula I that exhibit antibacterial activities, when tested alone and/or in combination with a bacterial efflux pump inhibitor. Also disclosed are methods of treating or preventing a bacterial infection in an animal comprising administering to the animal a compound of formula I alone or in combination with the administration of a bacterial efflux pump inhibitor.

Synthesis of N-Heterocycles by Reductive Cyclization of Nitro Compounds using Formate Esters as Carbon Monoxide Surrogates

A series of alkyl and aryl formate esters were evaluated as CO sources in the Pd- and Pd/Ru-catalyzed reductive cyclization of substituted nitro compounds to afford heterocycles, especially indoles. Phenyl formate was found to be the most effective, and it allowed the desired products to be obtained in excellent yields, often higher than those previously reported with pressurized CO. Through detailed experiments and kinetic studies, we were able to discern between metal-catalyzed and base-mediated activation of phenyl formate and confirmed that just the base was effective in catalyzing its decarbonylation.

INDOLE DERIVATIVES AS EFFLUX PUMP INHIBITORS

Disclosed herein are compounds of formula (I): and salts thereof. Also disclosed are compositions comprising compounds of formula I and compounds of formula I for use in treating or preventing bacterial infections.