40432-84-6

Basic information

• Product Name: 5-BROMOINDOLE-3-ACETIC ACID
• Synonyms: 5-BROMOINDOLE-3-ACETIC ACID (5BrIAA);5-Bromoindole-3-acetic acid,99%;5-Bromoindole-3-acetic acid ,93%;2-(5-broMo-1H-indol-3-yl)acetic acid;5-BroMoindole-3-acetic acid, 99% 1GR;1H-Indole-3-acetic acid, 5-bromo-;5-BROMOINDOLE-3-ACETIC ACID;(5-BROMO-1H-INDOL-3-YL)-ACETIC ACID
• CAS NO: 40432-84-6
• Molecular Formula: C₁₀H₈BrNO₂
• Molecular Weight: 254.08
• EINECS: 254-917-8
• Product Categories: Building Blocks;C10;C7 to C10;Chemical Synthesis;Halogenated Heterocycles;Heterocyclic Building Blocks;Indoles and derivatives;Halogenated Heterocycles;Heterocyclic Building Blocks;Indoles;IndolesBuilding Blocks
• Mol File: 40432-84-6.mol
• Article Data: 6

Chemical Properties

• Melting Point: 143-145 °C(lit.)
• Boiling Point: 465.961 °C at 760 mmHg
• Flash Point: 235.605 °C
• Appearance: Off-white to beige/Crystalline Powder
• Density: 1.6254 (rough estimate)
• Vapor Pressure: 1.75E-09mmHg at 25°C
• Refractive Index: 1.6320 (estimate)
• Storage Temp.: Refrigerator (+4°C)
• PKA: 4.36±0.30(Predicted)
• CAS DataBase Reference: 5-BROMOINDOLE-3-ACETIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: 5-BROMOINDOLE-3-ACETIC ACID(40432-84-6)
• EPA Substance Registry System: 5-BROMOINDOLE-3-ACETIC ACID(40432-84-6)

Safety Data

• Hazard Codes: Xn
• Statements: 20/21/22-36/37/38
• Safety Statements: 24/25-36-26-22
• WGK Germany: 3
• Hazardous Substances Data: 40432-84-6(Hazardous Substances Data)

Usage

Description

5-Bromoindole-3-acetic acid is an organic compound that serves as a key building block in the development of novel auxin mimic herbicides. It possesses unique chemical properties that make it a valuable component in the synthesis of bioactive molecules with potential applications in agriculture and weed control.

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

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

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 
• 32774-29-1 2-(5-Bromo-1H-indol-3-yl)ethanol 
• 117235-22-0 methyl 2-(5-bromo-1H-indole-3-yl)acetate 
• 936252-32-3 2-(3-(5-bromo-1-(p-toluenesulfonyl)indolyl)ethyloxy)adenosine 
• 1027571-59-0 2-(5-bromo-1-tosyl-1H-indol-3-yl)ethyl 4-methylbenzenesulfonate 
• 936252-56-1 5-bromo-3-(2-iodoethyl)-1-(p-toluenesulfonyl)indole 
• 936252-77-6 2-(3''-(5''-bromo-1''-(p-toluenesulfonyl)indolyl)ethyloxy)-6-chloro-3',4',5'-triacetyladenosine 
• 924635-01-8 benzyl 5-bromo-3-(3-chloro-2-oxopropyl)-1H-indole-1-carboxylate 
• 196081-79-5 2-(5-bromo-1H-indol-3-yl)acetamide 
• 1134099-84-5 1-(4-benzylpiperidin-1-yl)-2-(5-bromo-1H-indol-3-yl)ethanone 
• 1244769-23-0 1-(4-methylpiperazin-1-yl)-2-(1-octyl-5-m-tolyl-1H-indol-3-yl)ethanone 
• 1244769-20-7 N,N-diethyl-2-(1-octyl-5-m-tolyl-1H-indol-3-yl)acetamide 

Relevant articles and documents

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.

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.

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.