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19012-03-4

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19012-03-4 Usage

Chemical Properties

light yellow to orange or brown crystalline powder

Uses

Different sources of media describe the Uses of 19012-03-4 differently. You can refer to the following data:
1. Reactant for preparation of nitroolefins and β-nitroalcohols via microwave- or ultrasound-assisted Henry reactions Reactant for synthesis of quinolinones via three-component Ugi reaction Reactant for synthesis of α-ketoamides as inhibitors of Dengue virus protease with antiviral activity in cell-culture Reactant for preparation of thiazolopyrimidinones as inhibitors of Bcl-2 proteins Reactant for preparation of vinylindoles via Peterson olefination or olefination with Nysted reagent Reactant for preparation of indolyl alkenes from microwave-enhanced Knoevenagel condensation as antibacterial agents.
2. 1-Methylindole-3-carboxaldehyde is used as a reactant for preparation of nitroolefins and β-nitroalcohols via microwave- or ultrasound-assisted Henry reactions, reactant for synthesis of quinolinones via three-component Ugi reaction, reactant for synthesis of α-ketoamides as inhibitors of Dengue virus protease with antiviral activity in cell-culture, reactant for preparation of thiazolopyrimidinones as inhibitors of Bcl-2 proteins, reactant for preparation of vinylindoles via Peterson olefination or olefination with Nysted reagent, reactant for preparation of indolyl alkenes from microwave-enhanced Knoevenagel condensation as antibacterial agents 1-Methylindole-3-carboxaldehyde may be used in the synthesis of (Z)-3-(1-methyl-1H-indol-3-yl)-2-(thiophen-3-yl)acrylonitrile, via base-catalyzed condensation with thiophene-3-acetonitrile. It was also used in the preparation of monomer, required for the synthesis of poly(3-vinyl-1-methylindole).

Synthesis Reference(s)

Tetrahedron, 49, p. 4015, 1993 DOI: 10.1016/S0040-4020(01)89915-4Synthesis, p. 396, 1987 DOI: 10.1055/s-1987-27960

General Description

1-Methylindole-3-carboxaldehyde is a heterocyclic indole aldehyde. 1-Methylindole-3-carboxaldehyde on condensation with 2-hydroxybenzohydrazide yields Schiff base.

Check Digit Verification of cas no

The CAS Registry Mumber 19012-03-4 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 1,9,0,1 and 2 respectively; the second part has 2 digits, 0 and 3 respectively.
Calculate Digit Verification of CAS Registry Number 19012-03:
(7*1)+(6*9)+(5*0)+(4*1)+(3*2)+(2*0)+(1*3)=74
74 % 10 = 4
So 19012-03-4 is a valid CAS Registry Number.
InChI:InChI=1/C10H9NO/c1-11-6-8(7-12)9-4-2-3-5-10(9)11/h2-7H,1H3

19012-03-4 Well-known Company Product Price

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  • (Code)Product description
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  • Alfa Aesar

  • (L02212)  1-Methylindole-3-carboxaldehyde, 98+%   

  • 19012-03-4

  • 1g

  • 238.0CNY

  • Detail
  • Alfa Aesar

  • (L02212)  1-Methylindole-3-carboxaldehyde, 98+%   

  • 19012-03-4

  • 5g

  • 837.0CNY

  • Detail
  • Alfa Aesar

  • (L02212)  1-Methylindole-3-carboxaldehyde, 98+%   

  • 19012-03-4

  • 25g

  • 3834.0CNY

  • Detail
  • Aldrich

  • (357987)  1-Methylindole-3-carboxaldehyde  97%

  • 19012-03-4

  • 357987-5G

  • 1,026.09CNY

  • Detail
  • Aldrich

  • (357987)  1-Methylindole-3-carboxaldehyde  97%

  • 19012-03-4

  • 357987-25G

  • 4,086.81CNY

  • Detail

19012-03-4SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 19, 2017

Revision Date: Aug 19, 2017

1.Identification

1.1 GHS Product identifier

Product name 1-methylindole-3-carbaldehyde

1.2 Other means of identification

Product number -
Other names 3-formyl N-methyl indole

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

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:19012-03-4 SDS

19012-03-4Relevant articles and documents

Light- and redox-gated molecular brakes consisting of a pentiptycene rotor and an indole pad

Kao, Chen-Yi,Lee, I-Tsun,Prabhakar, Ch.,Yang, Jye-Shane

, p. 507 - 516 (2014)

Two photochemically and electrochemically active alkenes 3Me and 3An containing pentiptycene and indole groups have been synthesized and investigated as light and/or redox-gated molecular brakes. The pentiptycene group functions as the four-bladed rotor, the indole group as the brake pad, and the vinylene group as the switch module. The E configuration corresponds to the brake-off state, in which the rotation of the rotor is free with a rotation rate of 108-109 at ambient temperature according to DFT calculations. The Z configuration corresponds to the brake-on state, in which the rotation rate is decreased to 101-102, depending on the N-substituent of indole, according to line-shape analysis of variable temperature 13C NMR spectra. The overall braking effect reaches a factor of 106-108. While the combined photochemical E → Z and electrochemical Z → E switching has a higher capacity than the two-way photochemical switching in the case of 3Me, the switching capacity are comparable for the two methods in 3An. The results also show that photochemical E-Z isomerization is much more reliable than the electrochemical counterpart, as the stability of the redox intermediates plays a critical role in determining the robustness of the molecular brakes via electrochemical switching. The photochemical and/or electrochemical switching between the E and Z isomers of two alkenes substituted with both pentiptycene and indole groups results in a change of the rotation rate as large as 106-108 fold for the pentiptycene group about the pentiptycene-vinylene C-C bond, corresponding to a new generation of light- and redox-gated molecular brakes.

Synthesis of a photostable energy-transfer pair for dNA traffic lights

Bohl?nder, Peggy R.,Wagenknecht, Hans-Achim

, p. 7547 - 7551 (2014)

A new cyano-substituted thiazole red derivative as a red emitter and a novel green fluorescent donor dye of the cyanine styryl type were synthesized in good yields. Characterization of their optical properties revealed excellent photostabilities and large apparent Stokes' shifts. Both dyes can be incorporated into oligonucleotides through postsynthetic click -type chemistry and combined in a diagonal arrangement in double-stranded DNA. As a result, both dyes combine to an energy-transfer pair in DNA that shows remarkable optical properties such as significant emission wavelength shift from green to red upon hybridization owing to high energy-transfer efficiency between the two dyes and remarkable emission red/green color contrast ratio. The combination of these dyes as an energy-transfer pair according to our concept of DNA traffic lights has high potential for applications in molecular imaging.

Intramolecular alkylations of aromatic compounds, XXII: Synthesis of cis-1,6,10-trimethyl-1,2,3,4,5,6,7,8,9,10-decahydroindolo(4,3-fg)quinoline, a new approach to the ergolen framework

Reimann,Hargasser

, p. 823 - 826 (1988)

-

Synthesis of Analogues of Indole Alkaloids from Sea Sponges – Aplysinopsins by the Reaction of Amines with (4Z)-4-[(1H-indol-3-yl)-methylene]-1,3-oxazol-5(4H)-ones

Suzdalev, Konstantin F.,Babakova, Maria N.

, p. 1200 - 1206 (2016)

A new two-step approach toward the synthesis of aplysinopsin analogues 5-(1-R-1H-indol-3-ylmethylene)-2-aryl-3,5-dihydroimidazol-4-ones consisting in obtaining and reaction of 4-(1-R-1H-indol-3-ylmethilene)-2-Ar-4H-oxazol-5-ones with amines was developed. The configuration of starting compounds and final products was determined by13С and1H-nmr spectroscopy.

Amphiphilic Cyanine-Platinum Conjugates as Fluorescent Nanodrugs

Sun, Tingting,Li, Zhensheng,Xie, Zhigang,Jing, Xiabin

, p. 221 - 225 (2016)

Two fluorescent nanomedicines based on small molecular cyanine-platinum conjugates have been prepared via a nanoprecipitation method and characterized by transmission electron microscopy (TEM) as well as dynamic light scattering (DLS). The conjugates exhibited an enhanced fluorescence in their nanoparticle formulation compared to that in solution. The nanomedicines could be endocytosed by cancer cells as revealed by confocal laser scanning microscopy (CLSM) and showed high cellular proliferation inhibition. Fluorescent platinum nanomedicines prepared directly from small molecules could be an alternative strategy for developing new drugs with simultaneous cellular imaging and cancer therapy functions.

Yb(OTf)3catalyzed [1,3]-rearrangement of 3-alkenyl oxindoles

He, Lingchen,Hu, Xin-Gen,Jiang, Jun,Li, Juan,Li, Xinhua,Liu, Hongxin,Song, Chao,Wan, Junlin,Wu, Chaofei,Xiao, Hong-Ping

supporting information, p. 122 - 126 (2021/12/29)

A Yb(OTf)3catalyzed [1,3]-rearrangement of 3-alkenyl oxindoles was achieved, affording a variety of multifunctional 3-ylideneoxindoles with good yields andZ/Eselectivities (64%-89% yield, 78?:?22->99?:?1Z/E). Importantly, an operationally simple, one-pot sequential catalytic synthesis of 3-ylideneoxindoles was also developed. Additionally, a cross [1,3]-rearrangement experiment and nonracemic transformation were also carried out, which indicated a concerted rearrangement mechanism of this methodology.

Design, synthesis and biological evaluation of N-substituted indole-thiazolidinedione analogues as potential pancreatic lipase inhibitors

George, Ginson,Auti, Prashant S.,Paul, Atish T.

, p. 49 - 59 (2021/05/04)

Pancreatic Lipase (PL) is a key enzyme responsible for the digestion of 50%–70% of dietary triglycerides, hence its inhibition is considered as a viable approach for the management of obesity. A series of indole-TZD hybrid analogues were synthesized, characterized and evaluated for their PL inhibitory activity. Knoevenagel condensation of various substituted indole-3-carboxaldehyde with substituted thiazolidinediones resulted in the formation of titled analogues. Analogues 6d and 6e exerted potent PL inhibitory activity (IC50-6.19 and 8.96?μM, respectively). Further, these analogues exerted a competitive mode of PL inhibition. Moreover, molecular modelling studies were in agreement with the in vitro results (Pearson's r?=.8682, p?.05). The fluorescence spectroscopic analysis further supported the strong binding affinity of these analogues with PL. A molecular dynamics study (20?ns) indicated that these analogues were stable in a dynamic environment. Thus, the present study highlighted the potential role of indole-thiazolidinedione hybrid analogues as potential PL inhibitors and further optimization might result in the development of new PL inhibitory lead candidates.

Synthesis, in silico studies, and evaluation of syn and anti isomers of n-substituted indole-3-carbaldehyde oxime derivatives as urease inhibitors against helicobacter pylori

Gunaratna, Medha J.,Kalatuwawege, Ishani P.,Udukala, Dinusha N.

, (2021/11/27)

Gastrointestinal tract infection caused by Helicobacter pylori is a common virulent disease found worldwide, and the infection rate is much higher in developing countries than in developed ones. In the pathogenesis of H. pylori in the gastrointestinal tract, the secretion of the urease enzyme plays a major role. Therefore, inhibition of urease is a better approach against H. pylori infection. In the present study, a series of syn and anti isomers of N-substituted indole-3-carbaldehyde oxime derivatives was synthesized via Schiff base reaction of appropriate carbaldehyde derivatives with hydroxylamine hydrochloride. The in vitro urease inhibitory activities of those derivatives were evaluated against that of Macrotyloma uniflorum urease using the modified Berthelot reaction. Out of the tested compounds, compound 8 (IC50 = 0.0516 ± 0.0035 mM) and compound 9 (IC50 = 0.0345 ± 0.0008 mM) were identified as the derivatives with potent urease inhibitory activity with compared to thiourea (IC50 = 0.2387 ± 0.0048 mM). Additionally, in silico studies for all oxime compounds were performed to investigate the binding interactions with the active site of the urease enzyme compared to thiourea. Furthermore, the drug-likeness of the synthesized oxime compounds was also predicted.

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