5416-80-8

Basic information

• Product Name: 2-Methylindole-3-carboxaldehyde
• Synonyms: 2-methyl-1h-indole-3-carboxaldehyd;3-FORMYL-2-METHYLINDOLE;AKOS BBS-00000868;AKOS JY2083591;AKOS 233-93;2-METHYLINDOLE-3-CARBALDEHYDE;2-METHYLINDOLE-3-CARBOXALDEHYDE;2-METHYLINDOLE-3-CARBOXYALDEHYDE
• CAS NO: 5416-80-8
• Molecular Formula: C₁₀H₉NO
• Molecular Weight: 159.18
• EINECS: 226-512-6
• Product Categories: ALDEHYDE;Indoles and derivatives;Indoles;Simple Indoles;Building Blocks;Heterocyclic Building Blocks;Aldehydes;Building Blocks;C10;C10-C12;Carbonyl Compounds;Chemical Synthesis;Heterocyclic Building Blocks;Organic Building Blocks;Heterocycle-Indole series
• Mol File: 5416-80-8.mol
• Article Data: 54

Chemical Properties

• Melting Point: 200-201 °C(lit.)
• Boiling Point: 344.3 °C at 760 mmHg
• Flash Point: 169.9 °C
• Appearance: Brown/Powder
• Density: 1.226 g/cm³
• Vapor Pressure: 6.66E-05mmHg at 25°C
• Refractive Index: 1.698
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• Solubility: soluble in Methanol
• PKA: 16.08±0.30(Predicted)
• CAS DataBase Reference: 2-Methylindole-3-carboxaldehyde(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Methylindole-3-carboxaldehyde(5416-80-8)
• EPA Substance Registry System: 2-Methylindole-3-carboxaldehyde(5416-80-8)

Safety Data

• Hazard Codes: Xi,Xn
• Statements: 36/37/38-22
• Safety Statements: 37/39-26
• WGK Germany: 3
• HazardClass: IRRITANT
• Hazardous Substances Data: 5416-80-8(Hazardous Substances Data)

Usage

Chemical Properties

Brown powder

Uses

Different sources of media describe the Uses of 5416-80-8 differently. You can refer to the following data:
1. Reactant for preparation of:? ;Tryptophan dioxygenase inhibitors pyridyl-ethenyl-indoles as potential anticancer immunomodulators1? ;Fluorescent sensors (BODIPY)2? ;Antimicrobial agents against methicillin-resistant Staphylococcus aureus3? ;G protein-coupled receptor CRTh2 antagonists4? ;Inhibitors of PI3 kinase-α5? ;Antitubercular agents6? ;Anti-inflammatory agents7? ;Mycobacterium tuberculosis protein tyrosine phosphatase B8? ;Glucocorticoid receptor ligands9? ;Agents stimulating neurite outgrowth10
2. Reactant for preparation of:Tryptophan dioxygenase inhibitors pyridyl-ethenyl-indoles as potential anticancer immunomodulatorsFluorescent sensors (BODIPY)Antimicrobial agents against methicillin-resistant Staphylococcus aureusG protein-coupled receptor CRTh2 antagonistsInhibitors of PI3 kinase-αAntitubercular agentsAnti-inflammatory agentsMycobacterium tuberculosis protein tyrosine phosphatase BGlucocorticoid receptor ligandsAgents stimulating neurite outgrowth

Synthesis Reference(s)

Chemical and Pharmaceutical Bulletin, 31, p. 2892, 1983 DOI: 10.1248/cpb.31.2892

General Description

Oxidative activation of 2-methylindole-3-carboxaldehyde via N-heterocyclic carbene organocatalysis generates heterocyclic ortho-quinodimethane as a key intermediate.

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

Upstream product

• 119910-45-1 2-bromo-1H-indole-3-carbaldehyde 
• 594-27-4 tetramethylstannane 
• 66946-71-2 1-formyl-2-methyl-indole 
• 5435-44-9 (E)-3-Ureido-but-2-enoic acid ethyl ester 
• 95-20-5 2-methyl-1H-indole 
• 68-12-2 N,N-dimethyl-formamide 
• 110-45-2 isopentyl formate 
• 67-66-3 chloroform 
• 141-52-6 sodium ethanolate 
• 74-90-8 hydrogen cyanide 
• 60-29-7 diethyl ether 
• 638-49-3 n-pentyl formate 
• 37125-92-1 2-methylgramine 
• 100-97-0 hexamethylenetetramine 

Downstream Products

• 602-04-0 tris(2-methyl-1H-indol-3-yl)methane 
• 180002-79-3 3-Formyl-2-methyl-1-(1-naphthoyl)-1H-indole 
• 51072-83-4 2-methyl-1H-indole-3-carbonitrile 
• 38292-40-9 1,2-dimethyl-1H-indole-3-carbaldehyde 
• 54109-65-8 methyl 1,2-dimethyl-1H-indole-3-carboxylate 
• 150391-68-7 C₂₅H₁₈BrClN₆O 
• 662150-78-9 3-(4,5-diphenyl-1H-imidazol-2-yl)-2-methyl-1H-indole 
• 230283-19-9 N-allyl-2-methyl-indole-3-aldehyde 
• 1912-43-2 2-methyl-3-indoleacetic acid 
• 96821-70-4 (4-o-Tolyl-piperazin-1-yl)-acetic acid [1-(2-methyl-1H-indol-3-yl)-meth-(E)-ylidene]-hydrazide 
• 96821-73-7 (4-p-Tolyl-piperazin-1-yl)-acetic acid [1-(2-methyl-1H-indol-3-yl)-meth-(E)-ylidene]-hydrazide 
• 96821-66-8 (4-Phenyl-piperazin-1-yl)-acetic acid [1-(2-methyl-1H-indol-3-yl)-meth-(E)-ylidene]-hydrazide 
• 92407-85-7 1-(3-Chloro-benzyl)-2-methyl-1H-indole-3-carbaldehyde 
• 80387-68-4 2-methylindole-3-carboxaldehyde 2,6-dimethylphenylhydrazone 

Relevant articles and documents

Naked-eye fluorescent sensor for Cu(II) based on indole conjugate BODIPY dye

Graphical abstract A novel indole mono-styryl BODIPY was synthesised and characterized for the colorimetric recognition of Cu2+. It was also revealed from this study 3 can passively diffuse through cell membrane and stain both bacterial and mammalian cells even in very low concentrations. BODIPY-indole 3 retains inside the cells in cytometry and can be further modified for other applications.

Molecular iodine mediated oxidative cleavage of the C-N bond of aryl and heteroaryl (dimethylamino)methyl groups into aldehydes

The oxidative cleavage of the C-N bond of aryl and heteroaryl (dimethylamino)methyl groups is achieved by employing molecular iodine as a mild oxidizing agent under ambient conditions in the presence of a mild base. The important reaction of C3 formylation of free NH and substituted indoles containing various substituents is accomplished from the corresponding Mannich bases. This methodology can also be extended for the synthesis of aryl and other heteroaryl aldehydes and ketones. Furthermore, the usefulness of the method is successfully demonstrated on a gram scale.

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.

First discovery of pimprinine derivatives and analogs as novel potential herbicidal, insecticidal and nematicidal agents

Pimprinine and streptochlorin are indole natural products produced by many species of organisms, and they are reported to possess a wide range of biological activities, such as anticancer, antiviral, antifungal activity and so on. In this study, three series of pimprinine derivatives or analogs were efficiently synthesized under the optimized methods. Biological assays conducted at Syngenta firstly indicated the pimprinine derivatives or analogs possessed potential herbicidal and insecticidal activity, and this is highlighted by compounds 21g, 21h, 21i, 21j, 21l, 22h, 22i and 23h, they possessed significant biological activity as well as broad spectrum. Meanwhile, compounds with benzothiophene-oxazole core (21h, 22h and 23h), showed effective nematicidal activity in primary screening. Compounds 21g and 21i were identified as the most promising lead structures for further study.