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1-(3-Methoxybenzyl)-1H-indole-3-carbaldehyde is a chemical compound with the formula C16H15NO2. It is a yellow to light brown crystalline solid that is commonly used in organic synthesis and pharmaceutical research. 1-(3-METHOXYBENZYL)-1H-INDOLE-3-CARBALDEHYDE features an indole ring, a benzyl group with a methoxy substituent, and a carbaldehyde functional group, which makes it versatile for various synthetic applications. Its aromatic and aldehyde groups contribute to its utility in the development of organic compounds and pharmaceuticals, while its unique structure offers potential for selective interactions with biological targets, establishing it as a valuable building block in medicinal chemistry.

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  • 261637-72-3 Structure
  • Basic information

    1. Product Name: 1-(3-METHOXYBENZYL)-1H-INDOLE-3-CARBALDEHYDE
    2. Synonyms: 1-(3-METHOXYBENZYL)-1H-INDOLE-3-CARBALDEHYDE;1-(3-methoxybenzyl)-1H-indole-3-carbaldehyde(SALTDATA: FREE);1-(3-methoxybenzyl)indole-3-carbaldehyde;1-[(3-methoxyphenyl)methyl]-3-indolecarboxaldehyde;1-[(3-methoxyphenyl)methyl]indole-3-carbaldehyde;IVK/4021695
    3. CAS NO:261637-72-3
    4. Molecular Formula: C17H15NO2
    5. Molecular Weight: 265.31
    6. EINECS: N/A
    7. Product Categories: N/A
    8. Mol File: 261637-72-3.mol
  • Chemical Properties

    1. Melting Point: N/A
    2. Boiling Point: 473.8°C at 760 mmHg
    3. Flash Point: 240.4°C
    4. Appearance: /
    5. Density: 1.13g/cm3
    6. Vapor Pressure: 3.81E-09mmHg at 25°C
    7. Refractive Index: 1.591
    8. Storage Temp.: N/A
    9. Solubility: N/A
    10. CAS DataBase Reference: 1-(3-METHOXYBENZYL)-1H-INDOLE-3-CARBALDEHYDE(CAS DataBase Reference)
    11. NIST Chemistry Reference: 1-(3-METHOXYBENZYL)-1H-INDOLE-3-CARBALDEHYDE(261637-72-3)
    12. EPA Substance Registry System: 1-(3-METHOXYBENZYL)-1H-INDOLE-3-CARBALDEHYDE(261637-72-3)
  • Safety Data

    1. Hazard Codes: N/A
    2. Statements: N/A
    3. Safety Statements: N/A
    4. WGK Germany:
    5. RTECS:
    6. HazardClass: N/A
    7. PackingGroup: N/A
    8. Hazardous Substances Data: 261637-72-3(Hazardous Substances Data)

261637-72-3 Usage

Uses

Used in Organic Synthesis:
1-(3-Methoxybenzyl)-1H-indole-3-carbaldehyde is used as a key intermediate in organic synthesis for the production of various organic compounds. Its aromatic and aldehyde groups facilitate the formation of new chemical bonds and reactions, making it a versatile component in the synthesis of complex organic molecules.
Used in Pharmaceutical Research:
In the pharmaceutical industry, 1-(3-Methoxybenzyl)-1H-indole-3-carbaldehyde is used as a building block for the development of new pharmaceuticals. Its unique structure allows for selective interactions with biological targets, which can be exploited to design drugs with specific therapeutic effects.
Used in Medicinal Chemistry:
1-(3-Methoxybenzyl)-1H-indole-3-carbaldehyde is utilized in medicinal chemistry as a valuable component for the creation of novel drug candidates. Its potential for selective binding to biological targets makes it an attractive starting point for the design and optimization of new therapeutic agents.

Check Digit Verification of cas no

The CAS Registry Mumber 261637-72-3 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 2,6,1,6,3 and 7 respectively; the second part has 2 digits, 7 and 2 respectively.
Calculate Digit Verification of CAS Registry Number 261637-72:
(8*2)+(7*6)+(6*1)+(5*6)+(4*3)+(3*7)+(2*7)+(1*2)=143
143 % 10 = 3
So 261637-72-3 is a valid CAS Registry Number.
InChI:InChI=1/C17H15NO2/c1-20-15-6-4-5-13(9-15)10-18-11-14(12-19)16-7-2-3-8-17(16)18/h2-9,11-12H,10H2,1H3

261637-72-3SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 16, 2017

Revision Date: Aug 16, 2017

1.Identification

1.1 GHS Product identifier

Product name 1-[(3-methoxyphenyl)methyl]indole-3-carbaldehyde

1.2 Other means of identification

Product number -
Other names -

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

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More Details:261637-72-3 SDS

261637-72-3Downstream Products

261637-72-3Relevant articles and documents

Synthesis, antimycobacterial and anticancer activity of novel indole-based thiosemicarbazones

Mashayekhi, Vida,Haj Mohammad Ebrahim Tehrani, Kamaleddin,Azerang, Parisa,Sardari, Soroush,Kobarfard, Farzad

, (2021/09/08)

Based on the structural elements of bioactive indole-based compounds, a series of novel 1-substituted indole-3-carboxaldehyde thiosemicarbazones were synthesized as potential antimycobacterial and anticancer agents. The derivatives were prepared via a two

Design, synthesis and biological evaluation of matrine derivatives as potential anticancer agents

Li, Zheng,Luo, Mengyang,Cai, Bin,Wu, Lichuan,Huang, Mengtian,Haroon-Ur-Rashid,Jiang, Jun,Wang, Lisheng

supporting information, p. 677 - 683 (2018/02/06)

Using matrine (1) as the lead compound, a series of new 14-(N-substituted-2-pyrrolemethylene) matrine and 14-(N-substituted-indolemethylene) matrine derivatives was designed and synthesized for their potential application as anticancer agents. The structure of these compounds was characterized by 1H NMR, 13C NMR and ESI-MS spectral analyses. The target compounds were evaluated for their in vitro cytotoxicity against three human cancer cell lines (SMMC-7721, A549 and CNE2). The results revealed that compound A6 and B21 displayed the most significant anticancer activity against three cancer cell lines with IC50 values in range of 3.42–8.05 μM, which showed better activity than the parent compound (Matrine) and positive control Cisplatin. Furthermore, the Annexin V-FITC/PI dual staining assay revealed that compound A6 and B21 could significantly induce the apoptosis of SMMC-7721 and CNE2 cells in a dose-dependent manner. The cell cycle analysis also revealed that compound A6 could cause cell cycle arrest of SMMC-7721 and CNE2 cells at G2/M phase.

B-ring modified aurones as promising allosteric inhibitors of hepatitis C virus RNA-dependent RNA polymerase

Meguellati, Amel,Ahmed-Belkacem, Abdelhakim,Yi, Wei,Haudecoeur, Romain,Crouillère, Marie,Brillet, Rozenn,Pawlotsky, Jean-Michel,Boumendjel, Ahcène,Peuchmaur, Marine

, p. 579 - 592 (2014/06/09)

Following our recent report showing the potential of naturally occurring aurones (2-benzylidenebenzofuran-3(2H)-ones) as anti-hepatitis C virus (HCV) agents, efforts were continued in order to refine the structural requirements for the inhibitory effect on HCV RNA-dependent RNA polymerase (RdRp). In this study, we targeted the B-ring moiety of aurones with the aim to improve structural features associated with higher inhibition of the targeted polymerase. In vitro evaluation of the RdRp inhibitory activity of the 37 newly synthesized compounds pointed out that the replacement of the B-ring with an N-substituted indole moiety induced the highest inhibitory effect. Of these, compounds 31, 40 and 41 were found to be the most active (IC50 = 2.3-2.4 μM). Docking experiments performed with the most active compounds revealed that the allosteric thumb pocket I of RdRp is the binding pocket for aurone analogues.

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