methyl 4-(benzyloxy)-1H-indole-2-carboxylate

Base Information

• Chemical Name: methyl 4-(benzyloxy)-1H-indole-2-carboxylate
• CAS No.: 27748-09-0
• Molecular Formula: C17H15 N O3
• Molecular Weight: 281.311
• Hs Code.: 2933990090
• DSSTox Substance ID: DTXSID40406461
• Nikkaji Number: J2.203.169D
• Wikidata: Q82211433
• Mol file: 27748-09-0.mol

Synonyms:27748-09-0;methyl 4-(benzyloxy)-1H-indole-2-carboxylate;methyl 4-phenylmethoxy-1H-indole-2-carboxylate;4-BENZYLOXYINDOLE-2-CARBOXYLIC ACID METHYL ESTER;4-BENZYLOXY-1H-INDOLE-2-CARBOXYLIC ACID METHYL ESTER;methyl 4-benzyloxyindole-2-carboxylate;SCHEMBL6595625;DTXSID40406461;CDDYUJMTTJRWJY-UHFFFAOYSA-N;AKOS000278231;NS-04625;Methyl 4-benzyloxy-1H-indole-2-carboxylate;CS-0301988;methyl4-(benzyloxy)-1H-indole-2-carboxylate;B-2010;EN300-214178;1H-Indole-2-carboxylic acid, 4-(phenylmethoxy)-, methyl ester

Chemical Property of methyl 4-(benzyloxy)-1H-indole-2-carboxylate

Chemical Property:

• Vapor Pressure: 4.31E-09mmHg at 25°C
• Refractive Index: 1.645
• Boiling Point: 472.3°C at 760 mmHg
• Flash Point: 239.5°C
• PSA: 51.32000
• Density: 1.253g/cm³
• LogP: 3.53350
• XLogP3: 3.7
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 5
• Exact Mass: 281.10519334
• Heavy Atom Count: 21
• Complexity: 354

Purity/Quality:

97% ^*data from raw suppliers

4-Benzyloxyindole-2-carboxylicacidmethylester ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC(=O)C1=CC2=C(N1)C=CC=C2OCC3=CC=CC=C3
• General Description: 4-Benzyloxy-1H-indole-2-carboxylic acid methyl ester is a key synthetic intermediate used to produce 4-benzyloxyindole-2-carboxylic acid hydrazide, which serves as the precursor for various pharmacologically active (arylidene)-hydrazides. It enables efficient derivatization under both conventional and microwave-assisted conditions, with the latter significantly improving reaction times and yields. 4-BENZYLOXY-1H-INDOLE-2-CARBOXYLIC ACID METHYL ESTER's structural integrity is confirmed through spectroscopic analysis, supporting its utility in the development of novel bioactive molecules.

Technology Process of methyl 4-(benzyloxy)-1H-indole-2-carboxylate

There total 3 articles about methyl 4-(benzyloxy)-1H-indole-2-carboxylate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 33.0%

(Z)-2-Azido-3-(2-benzyloxy-phenyl)-acrylic acid methyl ester (117175-27-6) → 4-benzyloxyindole-2-carboxylic acid methyl ester (27748-09-0)

Guidance literature:

In xylene; Heating;

DOI:10.1016/S0040-4039(00)80213-0

Reference yield:

benzyl bromide (100-39-0) → 4-benzyloxyindole-2-carboxylic acid methyl ester (27748-09-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) K₂CO₃ / 1.) Me₂CO, heating; 2.) MeOH

2: 33 percent / xylene / Heating

With potassium carbonate; In xylene;

DOI:10.1016/S0040-4039(00)80213-0

Reference yield:

salicylaldehyde (90-02-8) → 4-benzyloxyindole-2-carboxylic acid methyl ester (27748-09-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) K₂CO₃ / 1.) Me₂CO, heating; 2.) MeOH

2: 33 percent / xylene / Heating

With potassium carbonate; In xylene;

DOI:10.1016/S0040-4039(00)80213-0

upstream raw materials:

(Z)-2-Azido-3-(2-benzyloxy-phenyl)-acrylic acid methyl ester

benzyl bromide

salicylaldehyde

Downstream raw materials:

methyl 4-hydroxyindole-2-carboxylate

Refernces

Synthesis, characterization and spectral studies of various newer 4-benzyloxy-1H-indole-2-carboxylic acid (arylidene)-hydrazides

10.1002/jhet.5570420537

This research aims to synthesize and characterize a series of 4-benzyloxy-1H-indole-2-carboxylic acid (arylidene)-hydrazides, which are important synthetic intermediates for creating new pharmacologically active compounds. The study employs both conventional heating methods and microwave irradiation techniques to synthesize these compounds. 4-Benzyloxyindole-2-carboxylic acid methyl ester is the starting material used to synthesize 4-benzyloxyindole-2-carboxylic acid hydrazide (1) through a reaction with hydrazine hydrate. It serves as the core structure for the subsequent synthesis of various (arylidene)-hydrazides. The microwave irradiation method, in particular, shows significant advantages, with reaction times reduced from 6-16 hours to 3-10 minutes and yields increased from 30-55% to 85-90%. The structures of the synthesized compounds are confirmed through spectroscopic techniques such as FTIR, NMR, and MS. The research concludes that microwave-assisted synthesis is an efficient and eco-friendly approach for producing these compounds, and the spectral properties and mass spectral fragmentation patterns of the synthesized hydrazides and hydrazones are thoroughly discussed, highlighting their potential for further pharmaceutical applications.

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