4382-53-0

Basic information

• Product Name: 5-BENZYLOXYINDOLE-3-ACETIC ACID
• Synonyms: RARECHEM AL BO 1284;TIMTEC-BB SBB003017;5-BENZYLOXYINDOLE-3-ACETIC ACID;5-Benzyloxy-3-indoleaceticacid;5-BzlO-IAA;5-BENZYLOXYINDOLE-3-ACETIC ACID (5BOxIAA);2-[5-(benzyloxy)-1H-indol-3-yl]acetic acid;2-[5-(phenylmethoxy)-1H-indol-3-yl]acetic acid
• CAS NO: 4382-53-0
• Molecular Formula: C₁₇H₁₅NO₃
• Molecular Weight: 281.31
• Product Categories: Indoles and derivatives;Heterocyclic Compounds;Building Blocks;Heterocyclic Building Blocks;Indoles
• Mol File: 4382-53-0.mol
• Article Data: 4

Chemical Properties

• Melting Point: 147-149 °C(Solv: ethanol, 50% (64-17-5))
• Boiling Point: 533.199 °C at 760 mmHg
• Flash Point: 276.269 °C
• Appearance: off-white to tan/crystalline
• Density: 1.314 g/cm³
• Vapor Pressure: 3.37E-12mmHg at 25°C
• Refractive Index: 1.679
• Storage Temp.: 2-8°C
• PKA: 4.51±0.30(Predicted)
• CAS DataBase Reference: 5-BENZYLOXYINDOLE-3-ACETIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: 5-BENZYLOXYINDOLE-3-ACETIC ACID(4382-53-0)
• EPA Substance Registry System: 5-BENZYLOXYINDOLE-3-ACETIC ACID(4382-53-0)

Safety Data

• Hazard Codes: Xi
• Statements: 36/38
• Safety Statements: 26
• WGK Germany: 3
• Hazardous Substances Data: 4382-53-0(Hazardous Substances Data)

Usage

Description

5-Benzyloxyindole-3-acetic acid is an organic compound with the molecular formula C17H15NO3. It is a derivative of indole-3-acetic acid, featuring a benzyloxy group attached to the 5th position of the indole ring. 5-BENZYLOXYINDOLE-3-ACETIC ACID is of interest in various fields due to its potential applications and properties.

Uses

Used in Pharmaceutical Industry:
5-Benzyloxyindole-3-acetic acid is used as a reactant for the preparation of inhibitors of Gli1-mediated transcription, which are considered potential anticancer agents. These inhibitors can play a crucial role in the development of new cancer treatments by targeting specific cellular pathways involved in tumor growth and progression.
Used in Chemical Synthesis:
In the field of chemical synthesis, 5-Benzyloxyindole-3-acetic acid serves as a starting material for the creation of synthetic analogs of spider toxins. These analogs can be used for various purposes, including the development of new drugs and therapies, as well as for research purposes to better understand the mechanisms of action of these toxins.
Used in Research and Development:
5-Benzyloxyindole-3-acetic acid is used as a compound for biological study, specifically for molecular recognition of indole derivatives by polymers imprinted with indole-3-acetic acid. This application is important for the development of advanced materials and sensors, as well as for understanding the interactions between molecules and their biological targets.

InChI:InChI=1/C17H15NO3/c19-17(20)8-13-10-18-16-7-6-14(9-15(13)16)21-11-12-4-2-1-3-5-12/h1-7,9-10,18H,8,11H2,(H,19,20)

Upstream product

• 109039-36-3 4-(4-benzyloxy-phenylhydrazono)-butyric acid 
• 2436-15-9 NSC 73391 
• 1453-97-0 5-benzyloxygramine 
• 1215-59-4 5-benzyloxy-1H-indole 
• 22424-61-9 2-[5-(benzyloxy)-1H-indol-3-yl]-2-oxoacetyl chloride 
• 101601-00-7 (5-benzyloxy-indol-3-yl)-glyoxylic acid 
• 6640-09-1 5-benzyloxy-1H-indole-2-carboxylic acid 
• 92438-11-4 5-Benzyloxy-2,ω-dinitro-styrol 
• 22424-59-5 (5-benzyloxy-2-nitro-phenyl)-pyruvic acid 
• 773837-37-9 sodium cyanide 

Downstream Products

• 54-16-0 5-Hydroxyindole-3-acetic acid 
• 41339-61-1 5-benzyloxy-3-(2-hydroxyethyl)indole 
• 145118-11-2 4-Nitrophenyl <(5-Benzyloxy)-1H-indol-3-yl>acetate 
• 5599-44-0 methyl (5-benzyloxy-1H-indol-3-yl)acetate 
• 145118-21-4 N-Acetyl-N'-acetyl>-L-alanyl>hexane-1,6-diamine 
• 145118-20-3 N-acetyl>-L-alanyl>-N'-<(tert-butyloxy)carbonyl>hexane-1,6-diamine 
• 145118-33-8 N-2,N⁶-Bis<(benzyloxy)carbonyl>-L-lysyl-N'-acetyl>-L-alanyl>hexane-1,6-diamine 
• 22311-12-2 N-<β-(5'-Benzyloxy-3'-indolyl)-ethyl>-4-(1-hydroxymethyl-propyl)-pyridiniumbromid 
• 132148-51-7 5-(benzyloxy)-3-(2-bromoethyl)-1H-indole 
• 15218-25-4 (+/-)-10-methoxycorynantheidol 
• 132148-55-1 2-(9-Benzyloxy-1,4,6,7,12,12b-hexahydro-indolo[2,3-a]quinolizin-2-yl)-butan-1-ol 
• 132148-62-0 2-(9-Benzyloxy-3-ethyl-1,4,6,7,12,12b-hexahydro-indolo[2,3-a]quinolizin-2-yl)-ethanol 
• 132148-54-0 1-[2-(5-Benzyloxy-1H-indol-3-yl)-ethyl]-4-(1-hydroxymethyl-propyl)-1,2,3,6-tetrahydro-pyridine-2-carbonitrile 
• 132148-56-2 Acetic acid 2-(9-benzyloxy-1,4,6,7,12,12b-hexahydro-indolo[2,3-a]quinolizin-2-yl)-butyl ester 

Relevant articles and documents

SEPIAPTERIN REDUCTASE INHIBITORS FOR THE TREATMENT OF PAIN

Disclosed herein are small molecule heterocyclic inhibitors of sepiapterin reductase (SPR), and pro-drugs and pharmaceutically acceptable salts thereof. The Also featured are pharmaceutical compositions of the compounds and uses of these compounds for the treatment or prevention of pain (e.g., inflammatory pain, nociceptive pain, functional pain, and neuropathic pain)

Aromatic bromination versus oxidation of indolylmalonates by bromine

The reactions of 5-substituted indolylmalonates (2a-e), carrying an electron-withdrawing group at the N(1) position, with bromine in CCl4 or AcOH are reported. These substrates undergo oxidation in competition with the well-known aromatic bromination. Under the two sets of conditions, with parent indolylmalonate (2a), chemospecific oxidation is observed, whereas with 5-hydroxyindolylmalonate (2c), bromination at the 4- and 6-position is the dominating reaction. Investigation of the products composition of several 5-substituted indolylmalonates revealed the following trend: with a 5-substituted electron-withdrawing group like fluorine, the indolylmalonate undergoes oxidation rather than bromination. In contrast, with a 5-substituted electron-donating group, like a hydroxyl group, the ring bromination occurs preferentially over the oxidation. When the 5-substituent is an alkoxyl group, a significant amount of brominated-oxidized products is obtained. Monitoring the oxidation reaction by mass spectrometry allowed the characterization of the 2-bromoindolylidenemalonate intermediate. A bromonium ion is considered as possible pathway in the formation of this intermediate. The conformation of unsymmetrical methoxyl and benzyloxyl substituents was determined from 1H NMR spectra, single-crystal X-ray diffraction and ab initio calculations.