152213-66-6

Basic information

• Product Name: 1H-Indole-3-aceticacid,6-bromo-(9CI)
• Synonyms: 1H-Indole-3-aceticacid,6-bromo-(9CI);2-(6-broMo-1H-indol-3-yl)acetic acid;(6-broMo-1H-indol-3-yl)acetic acid;6-broMo-1H-indole-3-acetic acid;6-Bromoindole-3-acetic acid
• CAS NO: 152213-66-6
• Molecular Formula: C₁₀H₈BrNO₂
• Molecular Weight: 254.08002
• Product Categories: INDOLE
• Mol File: 152213-66-6.mol

Chemical Properties

• Appearance: /
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• CAS DataBase Reference: 1H-Indole-3-aceticacid,6-bromo-(9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: 1H-Indole-3-aceticacid,6-bromo-(9CI)(152213-66-6)
• EPA Substance Registry System: 1H-Indole-3-aceticacid,6-bromo-(9CI)(152213-66-6)

Safety Data

• Hazardous Substances Data: 152213-66-6(Hazardous Substances Data)

Usage

Uses

Used in Agricultural Research:
1H-Indole-3-aceticacid,6-bromo-(9CI) is used as a research chemical for studying the effects of auxins on various plant processes. It helps in understanding the role of auxins in regulating cell elongation, root initiation, and fruit development.
Used in Horticulture Applications:
1H-Indole-3-aceticacid,6-bromo-(9CI) is used as a growth regulator in horticulture to influence plant growth and productivity. Its potential applications include promoting root growth, enhancing fruit development, and improving overall plant health.
Used in Plant Growth Regulation:
1H-Indole-3-aceticacid,6-bromo-(9CI) is used as a plant growth regulator to control and manipulate various aspects of plant growth, such as stem elongation, root development, and fruit ripening. This allows for better management of plant growth in agricultural and horticultural settings.

Upstream product

• 152213-61-1 2-(6-bromo-1H-indol-3-yl)acetonitrile 
• 59609-63-1 6-Bromogramine 
• 927676-51-5 2-(6-bromo-1H-indol-3-yl)-2-oxoacetic acid 
• 10075-50-0 5-bromo-1H-indole 
• 830-93-3 N-[(5-bromo-1H-indol-3-yl)methyl]-N,N-dimethylamine 
• 778-82-5 ethyl 3-indoleacetate 
• 52415-29-9 6-bromo-1H-indole 
• 73857-25-7 dimethyl 2-(1-(methoxycarbonyl)-1H-indole-3-yl)malonate 

Downstream Products

• 1239701-35-9 C₆₈H₈₄BrN₇O₁₃SSi₂ 
• 152213-63-3 (6-bromo-1H-indol-3-yl)acetic acid methyl ester 

Relevant articles and documents

Formal synthesis of (-)-flustramine B and its absolute configuration assignment by vibrational circular dichroism exciton chirality

Abstract A formal synthesis of the natural product (-)-flustramine B (3) is described, together with an easy and reliable approach for the absolute configuration assignment of a series of (3R,14S)- and (3S,14S)-oxindolylacetylphenyloxazolidinones 4, 6, 13

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.

Phidianidine A and Synthetic Analogues as Naturally Inspired Marine Antifoulants

Stationary and slow-moving marine organisms regularly employ a natural product chemical defense to prevent being colonized by marine micro- and macroorganisms. While these natural antifoulants can be structurally diverse, they often display highly conserved chemistries and physicochemical properties, suggesting a natural marine antifouling pharmacophore. In our current report, we investigate the marine natural product phidianidine A, which displays several chemical properties found in highly potent marine antifoulants. Phidianidine A and synthetic analogues were screened against the settlement and metamorphosis of Amphibalanus improvisus cyprids, and several of the compounds displayed inhibitory activities at low micromolar concentrations with IC50 values down to 0.7 μg/mL observed. The settlement study highlights that phidianidine A is a potent natural antifoulant and that the scaffold can be tuned to generate simpler and improved synthetic analogues. The bioactivity is closely linked to the size of the compound and to its basicity. The study also illustrates that active analogues can be prepared in the absence of the natural constrained 1,2,4-oxadiazole ring. A synthetic lead analogue of phidianidine A was incorporated in a coating and included in antifouling field trials, where it was shown that the coating induced potent inhibition of marine bacteria and microalgae settlement.

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.

The Fragment-Based Development of a Benzofuran Hit as a New Class of Escherichia coli DsbA Inhibitors

A fragment-based drug discovery approach was taken to target the thiol-disulfide oxidoreductase enzyme DsbA from Escherichia coli (EcDsbA). This enzyme is critical for the correct folding of virulence factors in many pathogenic Gram-negative bacteria, and small molecule inhibitors can potentially be developed as anti-virulence compounds. Biophysical screening of a library of fragments identified several classes of fragments with affinity to EcDsbA. One hit with high mM affinity, 2-(6-bromobenzofuran-3-yl)acetic acid (6), was chemically elaborated at several positions around the scaffold. X-ray crystal structures of the elaborated analogues showed binding in the hydrophobic binding groove adjacent to the catalytic disulfide bond of EcDsbA. Binding affinity was calculated based on NMR studies and compounds 25 and 28 were identified as the highest affinity binders with dissociation constants (KD) of 326 ± 25 and 341 ± 57 μM respectively. This work suggests the potential to develop benzofuran fragments into a novel class of EcDsbA inhibitors.

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.

Indole acetic acid acyl guanidines as beta-secretase inhibitors

There is provided a series of substituted acyl guanidines of Formula (I) or a stereoisomer; or a pharmaceutically acceptable salt thereof, wherein R1, R2, R3, R4, R5, R6, R7, and

Total synthesis of (±)-chartelline C

The first total synthesis of (±)-chartelline C in a concise 10-step sequence is reported. Highlights of the completion of this decades-old puzzle include (1) chemo- and position-selective installation of the heteroaromatic halogens, (2) halogen-sparing mo

Indole-3-acetic acid derivatives

Compounds of formula (I), or physiologically functional derivatives thereof, wherein: R1, R2, R3 and R′3 are independently selected from H or lower alkyl; and R4, R5, R6 and R7 are independently selected from H, electron withdrawing groups (such as F, Cl, Br, I, OCF3, carboxyl groups, acetal groups, electron deficient aryl groups), lower alkyl groups, lower alkoxy groups, aryl groups or aryloxy groups, wherein at least one of R4, R5, R6 and R7 is selected from an electron withdrawing group, may be used in methods of therapy, particular in treating neoplastic diseases in methods of GDEPT, ADPET, PDEPT and PDT.

Use of indole-3-acetic acid derivatives in medicine

Compounds of formula (I), or physiologically functional derivatives thereof, wherein: R1, R2, R3 and R′3 are independently selected from II or lower alkyl; and R4, R5, R6 and R7 are independently selected from H, electron withdrawing groups (such as F, Cl, Br, I, OCF3, carboxyl groups, acetal groups, electron deficient aryl groups), lower alkyl groups lower alkoxy groups, aryl groups or aryloxy groups, wherein it least one of R4, R5, R6, and R7 is selected from an electron withdrawing group, may be used in methods of therapy, particular in treating neoplastic diseases in methods of GDEPT, ADPET, PDEPT and PDT