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Usage

Uses

Used in Agricultural Industry:
5-Bromoindole-3-acetic acid is used as a reactant/reagent for the design and synthesis of innovative auxin mimic herbicides. These herbicides are specifically engineered to target and control weed growth, providing an effective solution for farmers and agricultural professionals seeking to protect their crops and maintain healthy, productive fields.
Additionally, the evaluation of these novel auxin mimic herbicides allows for the continuous improvement and optimization of their weed control activity, ensuring that they remain effective and environmentally responsible options for modern agriculture.

InChI:InChI=1/C10H8BrNO2/c11-7-1-2-9-8(4-7)6(5-12-9)3-10(13)14/h1-2,4-5,12H,3H2,(H,13,14)/p-1

Upstream product

• 774-14-1 (5-bromo-1H-indol-3-yl)-acetonitrile 
• 830-93-3 N-[(5-bromo-1H-indol-3-yl)methyl]-N,N-dimethylamine 
• 156695-44-2 2-(5-bromo-1H-indol-3-yl)-2-oxoacetic acid 
• 63843-81-2 2-(5-bromo-1H-indol-3-yl)-2-oxoacetyl chloride 
• 10075-50-0 5-bromo-1H-indole 

Downstream Products

• 87-51-4 indole-3-acetic acid 
• 82462-44-0 <5-n-(3)H>indol-3-ylacetic acid 
• 168649-23-8 5-(2-phenyl)-indole-3-acetic acid 
• 117235-22-0 methyl 2-(5-bromo-1H-indole-3-yl)acetate 
• 142273-20-9 kenpaullone 
• 885068-03-1 (5-{6-[2-(2-fluoro-4-trifluoromethyl-phenyl)-ethylamino]-2-methoxy-pyrimidin-4-yl}-1H-indol-3-yl)-acetic acid 
• 1144102-65-7 2-(5-bromo-1H-indol-3-yl)-1-phenylethan-1-one 

Relevant academic research and scientific papers

PLANT GROWTH REGULATOR

Providing an auxin derivative that can exert its intended effect more efficiently, while reducing any unintended effects. A compound represented by the General Formula (1) having a specific substituent at the 5- and/or 6-position of the auxin indole ring.

Asymmetric Dearomatizing Fluoroamidation of Indole Derivatives with Dianionic Phase-Transfer Catalyst

Asymmetric dearomatizing fluorocyclization of indole derivatives was investigated using a dicarboxylate phase-transfer catalyst. This reaction proceeds under mild reaction conditions to provide fluoropyrroloindoline derivatives in a highly enantioselective manner. Various substitution patterns on the indole ring are well tolerated. To facilitate the reaction and ensure reproducibility, the addition of water is essential, and its possible role is discussed.

New synthetic approach to paullones and characterization of their SIRT1 inhibitory activity

A series of 7,12-dihydroindolo[3,2-d][1]benzazepine-6(5H)-ones (paullones) substituted at C9/C10 (Br) and C2 (Me, CF3, CO2Me) have been synthesized by a one-pot Suzuki-Miyaura cross-coupling of an o-aminoarylboronic acid and methyl 2-iodoindoleacetate followed by intramolecular amide formation. Other approaches to the paullone scaffold based on Pd-catalyzed C-H activation were unsuccessful. In vitro enzymatic assay with recombinant human SIRT-1 indicated a strong inhibitory profile for the series, in particular the analogue with a methoxycarbonyl group at C2 and a bromine at C9. These compounds are, in general, inducers of granulocyte differentiation of the U937 acute leukemia cell line and cause a marked increase in pre-G1 of the cell cycle.

Enantioselective copper-catalyzed construction of aryl pyrroloindolines via an arylation-cyclization cascade

An enantioselective arylation-cyclization cascade has been accomplished using a combination of diaryliodonium salts and asymmetric copper catalysis. These mild catalytic conditions provide a new strategy for the enantioselective construction of pyrroloindolines, an important alkaloid structural motif that is commonly found among biologically active natural products.

A convenient method for the synthesis of indole-3-acetic acids

Starting from the corresponding indoles, indole-3-acetic acids were synthesized through indole-3-glyoxylic acids, followed by hydrazone formation with p-toluenesulfonhydrazide, then reduction of the hydrazones with sodium borohydride.

Substituent Effects on the Spectral, Acid-Base, and Redox Properties of Indolyl Radicals: A Pulse Radiolysis Study

Spectral and acid-base properties and reduction potentials of various substituted indolyl radicals were studied by pulse radiolysis in aqueous solutions at 20 deg C.Except for the 5-methoxyindolyl and 5-carboxyindolyl radicals, the spectra of the substituted indolyl radicals resemble the previously published 320- and 520-nm spectra of the neutral and 330- and 580-nm spectra of the cation indolyl and tryptophan radicals.The substitution of indolyl radical cation by electron-attracting groups (positive ?+) results in a blue shift of the 580-nm band by ca. 30 nm,, whereas the spectra of methylindolyl (?+ = -0.31) are similar to those of unsubstituted indolyl radicals.The 430- and 455-nm bands appearing in the spectra of the 5-carboxyindolyl and 5-methoxyindolyl radical cations, respectively, indicate even stronger interaction of the unpaired electron with the 5-substituent.The radical cations of various indole-3-acetic acids decarboxylate at pH values below their pKa to produce allyl radicals.The 5-bromoindolyl radical undergoes solvolysis to 5-hydroxyindolyl radical in acidic and alkaline media.The dissociation constants and reduction potentials of the substituted indolyl radicals correlate with the Brown substituent constants: pKr = 4.14 - 2.13Σ?+, correlation coefficient 0.987, and E0/0.059 = 22.29 + 3.5Σ?+, correlation coefficient 0.980.The ρ values from these correlations (-2.13 and 3.5) are similar to that of the Hammett correlation of the dissociation constants of the protonated indole nitrogen in various substituted indoles, ρ = -2.49, but smaller than the ρ value of the dependence on the substituent of the reduction potentials of phenoxyl radicals, ρ = 5.4.