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

Chemical Properties

OFF-WHITE TO BEIGE CRYSTALLINE POWDER

Uses

5-Bromoindole-3-acetic Acid can be used as reactant/reagent for design and synthesis and evaluation of novel auxin mimic herbicides for weed control activity.

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 
• 1134099-84-5 1-(4-benzylpiperidin-1-yl)-2-(5-bromo-1H-indol-3-yl)ethanone 
• 142273-20-9 kenpaullone 
• 168649-23-8 5-(2-phenyl)-indole-3-acetic acid 
• 885068-03-1 (5-{6-[2-(2-fluoro-4-trifluoromethyl-phenyl)-ethylamino]-2-methoxy-pyrimidin-4-yl}-1H-indol-3-yl)-acetic acid 

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.