52562-50-2

Basic information

• Product Name: 5-METHYLINDOLE-3-CARBOXALDEHYDE
• Synonyms: CBI-BB ZERO/005313;AKOS JY2082657;5-METHYLINDOLE-3-ALDEHYDE;5-METHYLINDOLE-3-CARBALDEHYDE;5-METHYLINDOLE-3-CARBOXALDEHYDE;5-METHYLINDOLE-3-CARBOXYALDEHYDE;5-METHYL-1H-INDOLE-3-CARBALDEHYDE;1H-Indole-3-carboxaldehyde, 5-methyl- (9CI)
• CAS NO: 52562-50-2
• Molecular Formula: C₁₀H₉NO
• Molecular Weight: 159.18
• Product Categories: ALDEHYDE;Indoles and derivatives;Indole;Heterocyclic Compounds;Building Blocks;Heterocyclic Building Blocks;Indoles
• Mol File: 52562-50-2.mol
• Article Data: 39

Chemical Properties

• Melting Point: 148-151 °C(lit.)
• Boiling Point: 348.2 °C at 760 mmHg
• Flash Point: 172.3 °C
• Appearance: /
• Density: 1.226 g/cm³
• Vapor Pressure: 5.12E-05mmHg at 25°C
• Refractive Index: 1.698
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• PKA: 15.68±0.30(Predicted)
• CAS DataBase Reference: 5-METHYLINDOLE-3-CARBOXALDEHYDE(CAS DataBase Reference)
• NIST Chemistry Reference: 5-METHYLINDOLE-3-CARBOXALDEHYDE(52562-50-2)
• EPA Substance Registry System: 5-METHYLINDOLE-3-CARBOXALDEHYDE(52562-50-2)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• HazardClass: IRRITANT
• Hazardous Substances Data: 52562-50-2(Hazardous Substances Data)

Usage

Description

5-METHYLINDOLE-3-CARBOXALDEHYDE, also known as 5-Methyl-1H-indole-3-carbaldehyde, is an organic compound with the chemical formula C9H9NO. It is a useful reagent in the synthesis of various organic compounds, particularly in the preparation of N-alkylated indoleand pyrrole-3-carbaldehydes. Its unique structure and properties make it a valuable component in various applications across different industries.

Uses

Used in Chemical Synthesis:
5-METHYLINDOLE-3-CARBOXALDEHYDE is used as a reagent for the regioand enantioselective preparation of N-alkylated indoleand pyrrole-3-carbaldehydes. Its ability to selectively form desired products with specific stereochemistry makes it a valuable tool in the synthesis of complex organic molecules.
Used in Coordination Chemistry:
5-METHYLINDOLE-3-CARBOXALDEHYDE is used in the synthesis of novel flexible tripodal ligands derived from 3-methylindole. These ligands can form mononuclear complexes with various metal ions, such as Zn(II), Cu(II), Ni(II), Hg(II), and Pd(II). These complexes have potential applications in various fields, including catalysis, sensing, and materials science.
Used in Pharmaceutical Industry:
5-METHYLINDOLE-3-CARBOXALDEHYDE can be used as a building block or intermediate in the synthesis of pharmaceutical compounds. Its unique structure and reactivity make it a promising candidate for the development of new drugs with novel therapeutic properties.
Used in Materials Science:
The metal complexes formed using 5-METHYLINDOLE-3-CARBOXALDEHYDE as a ligand can be used in the development of advanced materials with specific properties, such as conductivity, magnetism, or luminescence. These materials can find applications in various fields, including electronics, sensors, and energy storage.

InChI:InChI=1/C10H9NO/c1-7-2-3-10-9(4-7)8(6-12)5-11-10/h2-6,11H,1H3

Upstream product

• 30218-58-7 N,N-dimethyl-1-(5-methyl-1H-indol-3-yl)methanamine 
• 614-96-0 5-methyl-1H-indole 
• 298-12-4 Glyoxilic acid 
• 50-00-0 formaldehyd 
• 100-97-0 hexamethylenetetramine 
• 110-18-9 N,N,N,N,-tetramethylethylenediamine 
• 109-94-4 formic acid ethyl ester 
• 68-12-2 N,N-dimethyl-formamide 
• 67-66-3 chloroform 
• 100-61-8 N-methylaniline 

Downstream Products

• 194490-13-6 5-methyl-1H-indole-3-carbonitrile 
• 1134334-45-4 C₁₇H₁₅NO 
• 614-96-0 5-methyl-1H-indole 
• 1428969-23-6 2-((3-methoxyphenyl)amino)-1-(5-methyl-1H-indol-3-yl)-2-phenylethanone 
• 914348-94-0 tert-butyl 3-formyl-5-methyl-1H-indole-1-carboxylate 
• 1569644-53-6 (E)-tert-butyl 3-(3-(2-(3-fluorobenzoyl)-1-isopropylhydrazinyl)-3-oxoprop-1-enyl)-5-methyl-1H-indole-1-carboxylate 
• 1569645-84-6 (E)-3-(1-(tert-butoxycarbonyl)-5-methyl-1H-indol-3-yl)acrylic acid 
• 1521625-26-2 N-butyl-5-methylindole-3-carboxaldehyde 
• 608-05-9 5-methyl-indole-2,3-dione 
• 5599-50-8 3,6-Dimethyl-9H-carbazole 
• 1428236-47-8 C₂₁H₂₁NO₃ 
• 1415234-09-1 C₁₈H₁₂Cl₂N₂ 
• 1398574-84-9 C₁₇H₁₄FNO 
• 1376447-10-7 (E)-3-(1-(3-fluorobenzyl)-5-methyl-1H-indol-3-yl)acrylic acid 

Relevant articles and documents

Triphenylphosphine/1,2-Diiodoethane-Promoted Formylation of Indoles with N, N -Dimethylformamide

Despite intensive studies on the synthesis of 3-formylindoles, it is still highly desirable to develop efficient methods for the formylation of indoles, due to the shortcomings of the reported methods, such as inconvenient operations and/or harsh reaction conditions. Here, we describe a Ph3P/ICH2CH2I-promoted formylation of indoles with DMF under mild conditions. A Vilsmeier-type intermediate is readily formed from DMF promoted by the Ph3P/ICH2CH2I system. A onestep formylation process can be applied to various electron-rich indoles, but a hydrolysis needs to be carried out as a second step in the case of electron-deficient indoles. Convenient operations make this protocol attractive.

Design and Synthesis of Pyrano[3,2-b]indolones Showing Antimycobacterial Activity

Latent Mycobacterium tuberculosis infection presents one of the largest challenges for tuberculosis control and novel antimycobacterial drug development. A series of pyrano[3,2-b]indolone-based compounds was designed and synthesized via an original eight-step scheme. The synthesized compounds were evaluated for their in vitro activity against M. tuberculosis strains H37Rv and streptomycin-starved 18b (SS18b), representing models for replicating and nonreplicating mycobacteria, respectively. Compound 10a exhibited good activity with MIC99 values of 0.3 and 0.4 μg/mL against H37Rv and SS18b, respectively, as well as low toxicity, acceptable intracellular activity, and satisfactory metabolic stability and was selected as the lead compound for further studies. An analysis of 10a-resistant M. bovis mutants disclosed a cross-resistance with pretomanid and altered relative amounts of different forms of cofactor F420 in these strains. Complementation experiments showed that F420-dependent glucose-6-phosphate dehydrogenase and the synthesis of mature F420 were important for 10a activity. Overall these studies revealed 10a to be a prodrug that is activated by an unknown F420-dependent enzyme in mycobacteria.

Asymmetric Total Synthesis of Sarpagine and Koumine Alkaloids

We report here a concise, collective, and asymmetric total synthesis of sarpagine alkaloids and biogenetically related koumine alkaloids, which structurally feature a rigid cage scaffold, with L-tryptophan as the starting material. Two key bridged skeleton-forming reactions, namely tandem sequential oxidative cyclopropanol ring-opening cyclization and ketone α-allenylation, ensure concurrent assembly of the caged sarpagine scaffold and installation of requisite derivative handles. With a common caged intermediate as the branch point, by taking advantage of ketone and allene groups therein, total synthesis of five sarpagine alkaloids (affinisine, normacusine B, trinervine, Na-methyl-16-epipericyclivine, and vellosimine) with various substituents and three koumine alkaloids (koumine, koumimine, and N-demethylkoumine) with more complex cage scaffolds has been accomplished.