5599-44-0

Basic information

• Product Name: METHYL 5-BENZYLOXYINDOLE-3-ACETATE
• Synonyms: 5-BENZYLOXYINDOLE-3-ACETIC ACID METHYL ESTER;METHYL 5-BENZYLOXYINDOLE-3-ACETATE;5-Benzyloxyindole-3-acetic methyl ester;5-Benzyloxyindole-3-acetic acid methyl ester, Methyl 5-benzyloxyindole-3-acetate, 98%;5-BzlO-IAA-OMe
• CAS NO: 5599-44-0
• Molecular Formula: C₁₈H₁₇NO₃
• Molecular Weight: 295.33
• Mol File: 5599-44-0.mol
• Article Data: 4

Chemical Properties

• Melting Point: 72-74 °C
• Boiling Point: 480.8 °C at 760 mmHg
• Flash Point: 244.6 °C
• Appearance: white to off-white crystalline powder
• Density: 1.233 g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.634
• PKA: 16.29±0.30(Predicted)
• CAS DataBase Reference: METHYL 5-BENZYLOXYINDOLE-3-ACETATE(CAS DataBase Reference)
• NIST Chemistry Reference: METHYL 5-BENZYLOXYINDOLE-3-ACETATE(5599-44-0)
• EPA Substance Registry System: METHYL 5-BENZYLOXYINDOLE-3-ACETATE(5599-44-0)

Safety Data

• Hazardous Substances Data: 5599-44-0(Hazardous Substances Data)

Usage

Description

METHYL 5-BENZYLOXYINDOLE-3-ACETATE is a chemical compound with the molecular formula C20H19NO3. It is a derivative of indole, a heterocyclic organic compound commonly found in many natural products. METHYL 5-BENZYLOXYINDOLE-3-ACETATE is characterized by a methyl ester group attached to the indole ring, as well as a benzyloxy group at the 5-position. The 3-acetate side chain adds additional chemical functionality to the molecule. Its unique structure and reactivity make it a valuable building block for the preparation of more complex compounds with potential biological activities or industrial uses.

Uses

Used in Pharmaceutical and Medicinal Chemistry:
METHYL 5-BENZYLOXYINDOLE-3-ACETATE is used as an intermediate in the synthesis of pharmaceutical compounds for various therapeutic applications. Its unique structure and reactivity allow for the development of new drugs with potential biological activities.
Used in Organic Synthesis Processes:
METHYL 5-BENZYLOXYINDOLE-3-ACETATE is used as a building block in organic synthesis processes to create more complex compounds with potential industrial and commercial applications. Its versatility in chemical reactions makes it a valuable component in the synthesis of various organic compounds.

InChI:InChI=1/C18H17NO3/c1-21-18(20)9-14-11-19-17-8-7-15(10-16(14)17)22-12-13-5-3-2-4-6-13/h2-8,10-11,19H,9,12H2,1H3

Upstream product

• 4382-53-0 2-(5-benzyloxy-1H-indol-3-yl)acetic acid 
• 2436-15-9 NSC 73391 
• 67-56-1 methanol 

Downstream Products

• 5599-45-1 (5-benzyloxy-indol-3-yl)-acetic acid methylamide 
• 5599-67-7 [2-(5-benzyloxy-indol-3-yl)-ethyl]-methyl-amine 
• 497258-33-0 dimethyl 2-(5-benzyloxy-1-carbomethoxy-1H-indol-3-yl)malonate 
• 112273-39-9 (5-benzyloxy-indol-3-yl)-acetic acid hydrazide 
• 858232-78-7 (5-benzyloxy-indol-3-yl)-acetic acid-(2-amino-ethylamide) 

Relevant articles and documents

SUBSTITUTED 5-HYDROXYINDOLE COMPOUNDS AS MODULATORS OF ALPHA-1 ANTITRYPSIN

Novel compounds, compositions, and methods of using and preparing the same, which may be useful for treating alpha-1 antitrypsin deficiency (AATD).

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.