2519-61-1

Basic information

• Product Name: 4-Chloroindole-3-acetic acid
• Synonyms: 4-CHLORO-3-INDOLEACETIC ACID;4-CHLORO-IAA;4-CHLOROINDOLE-3-ACETIC ACID;4-CHLOROINDOLE-3-ACETIC ACID 98% (HPLC);(4-Chloro-1H-indol-3-yl)acetic acid;4-CHLOROINDOLE-3-ACETIC ACID (4ClIAA);2-(4-chloro-1H-indol-3-yl)acetic acid;2-(4-chloro-1H-indol-3-yl)ethanoic acid
• CAS NO: 2519-61-1
• Molecular Formula: C₁₀H₈ClNO₂
• Molecular Weight: 209.63
• EINECS: 1312995-182-4
• Product Categories: Agro-Products;Aromatics;Indole Derivatives
• Mol File: 2519-61-1.mol
• Article Data: 8

Chemical Properties

• Melting Point: approximate 188℃
• Boiling Point: 445.6 °C at 760 mmHg
• Flash Point: 223.3 °C
• Appearance: /Solid
• Density: 1.484 g/cm³
• Vapor Pressure: 1.01E-08mmHg at 25°C
• Refractive Index: 1.698
• Storage Temp.: −20°C
• Solubility: DMSO (Slightly), Ethyl Acetate (Slightly), Methanol
• PKA: 4.28±0.30(Predicted)
• CAS DataBase Reference: 4-Chloroindole-3-acetic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Chloroindole-3-acetic acid(2519-61-1)
• EPA Substance Registry System: 4-Chloroindole-3-acetic acid(2519-61-1)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 16-26-36
• Hazardous Substances Data: 2519-61-1(Hazardous Substances Data)

Usage

Chemical Properties

Off-White Solid

Uses

5,6-Dichloroindole-3-acetic acid and 4-Chloroindole-3-acetic acid are potent candidates for new rooting promoters without estrogenic activity. Plant growth stimulators.

InChI:InChI=1/C10H8ClNO2/c11-7-2-1-3-8-10(7)6(5-12-8)4-9(13)14/h1-3,5,12H,4H2,(H,13,14)

Upstream product

• 25235-85-2 4-chloro-1H-indole 
• 107-14-2 chloroacetonitrile 
• 40247-57-2 4-chloro-3-dimethylaminomethylindole 
• 151-50-8 potassium cyanide 
• 83-42-1 6-chloro-2-nitrotoluene 
• 118191-06-3 2-chloro-6-nitrobenzaldehyde N,N-dimethylenamine 
• 89245-40-9 1-methoxycarbonyl-4-nitro-3-indoleacetonitrile 
• 89245-39-6 4-amino-1-methoxycarbonyl-3-indoleacetonitrile 
• 7150-46-1 4-nitrogramine 
• 4770-06-3 4-nitroindole-3-acetonitrile 
• 4769-97-5 4-nitro-1H-indoIe 
• 149746-07-6 ethyl 4-chloro-1H-indol-3-yl(methylthio)acetate 
• 32991-06-3 3-chloro-trans-2-[β-(dimethylamino)vinyl]-nitrobenzene 
• 63352-98-7 4-chloro-3-diethylaminomethylindole 

Downstream Products

• 19077-78-2 Methyl 4-chloro-3-indoleacetate 
• 196881-05-7 ethyl 4-chloroindole-3-acetate 

Relevant articles and documents

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A 4 - chloro indole - 3 - acetic acid

The invention discloses a 4-chloroindole-3-acetic acid preparing method. The method specifically comprises the steps of 1, conducting condensation reaction of a compound i and DMFDMA at the temperature of 80-120 DEG C in anhydrous DMF solvent, so that a compound ii is generated; 2, dissolving the compound ii in solvent formed by mixing THF with alcohol, adding Raney nickel and adding hydrazine hydrate dropwise for reaction at the temperature of 15-30 DEG C in an inert atmosphere, and obtaining a compound iii after reaction ends completely; 3, dissolving the compound iii in solvent, adding inorganic strong base and a phase transfer catalyst, adding a compound iv dropwise at the temperature of 20-35 DEG C for substitution reaction, conducting heating for backflow after the compound iv is added, and obtaining a compound v after reaction ends completely; 4, hydrolyzing the compound v to obtain the target product 4-chloroindole-3-acetic acid. According to the preparing method, no highly-toxic product is adopted as raw materials, and the whole reaction process is safe.

Halogenated indole-3-acetic acids as oxidatively activated prodrugs with potential for targeted cancer therapy

Substituted indole-3-acetic acid (IAA) derivatives, plant auxins with potential for use as prodrugs in enzyme-prodrug directed cancer therapies, were oxidised with horseradish peroxidase (HRP) and toxicity against V79 Chinese hamster lung fibroblasts was determined. Rate constants for oxidation by HRP compound I were also measured. Halogenated IAAs were found to be the most cytotoxic, with typical surviving fractions of -3 after incubation for 2 h with 100 μM prodrug and HRP.