24662-37-1

Basic information

• Product Name: 3-CYANO-1-METHYLINDOLE
• Synonyms: 3-CYANO-1-METHYLINDOLE;1-methyl-1H-indole-3-carbonitrile;1H-Indole-3-carbonitrile,1-methyl-(9CI);1-methyl-indole-3-carbonitrile;1-methyl-1H-indole-3-carbonitrile(SALTDATA: FREE)
• CAS NO: 24662-37-1
• Molecular Formula: C₁₀H₈N₂
• Molecular Weight: 156.18
• Product Categories: INDOLE;pharmacetical
• Mol File: 24662-37-1.mol
• Article Data: 5

Chemical Properties

• Melting Point: 55-56℃
• Boiling Point: 327.8°C at 760 mmHg
• Flash Point: 152°C
• Appearance: /
• Density: 1.09g/cm³
• Vapor Pressure: 0.000198mmHg at 25°C
• Refractive Index: 1.603
• CAS DataBase Reference: 3-CYANO-1-METHYLINDOLE(CAS DataBase Reference)
• NIST Chemistry Reference: 3-CYANO-1-METHYLINDOLE(24662-37-1)
• EPA Substance Registry System: 3-CYANO-1-METHYLINDOLE(24662-37-1)

Safety Data

• Hazard Codes: T
• Statements: 25-36
• Safety Statements: 26-45
• RIDADR: UN 2811 6.1 / PGIII
• WGK Germany: 3
• Hazardous Substances Data: 24662-37-1(Hazardous Substances Data)

Usage

InChI:InChI=1/C10H8N2/c1-12-7-8(6-11)9-4-2-3-5-10(9)12/h2-5,7H,1H3

Upstream product

• 603-76-9 1-methylindole 
• 557-21-1 zinc(II) cyanide 
• 683229-61-0 1-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole 
• 68-12-2 N,N-dimethyl-formamide 
• 390799-61-8 1-methylindole-3-carboxamidine E-oxime 

Downstream Products

• 390799-61-8 1-methylindole-3-carboxamidine E-oxime 
• 490039-77-5 2-iodo-1-methyl-1H-indole-3-carbonitrile 
• 1284312-37-3 3-(4'-fluorophenyl)-5-(N-methyl-3'-indolyl)-1,2,4-triazole 
• 1284312-38-4 3-(4'-trifluoromethylphenyl)-5-(N-methyl-3'-indolyl)-1,2,4-triazole 
• 1284312-39-5 3-(3',4'-dimethoxyphenyl)-5-(N-methyl-3'-indolyl)-1,2,4-triazole 
• 1284312-42-0 3-(4'-benzyloxy-3'-methoxyphenyl)-5-(N-methyl-3'-indolyl)-1,2,4-triazole 
• 1284312-40-8 3-(3',5'-dimethoxyphenyl)-5-(N-methyl-3'-indolyl)-1,2,4-triazole 
• 1284312-35-1 3-phenyl-5-(N-methyl-3'-indolyl)-1,2,4-triazole 
• 1284312-43-1 3-(3',4',5'-trimethoxyphenyl)-5-(N-methyl-3'-indolyl)-1,2,4-triazole 
• 1284312-36-2 3-(4'-chlorophenyl)-5-(N-methyl-3'-indolyl)-1,2,4-triazole 
• 82414-31-1 1-methyl-1H-indole-3-carboxylic acid phenylamide 
• 317832-08-9 3-(diphenylphosphinyl)-N-methylindole 
• 1237776-27-0 3-cyano-1-methyl-2-(1-phenylethyl)indole 
• 730237-52-2 1-methyl-1H-indole-3-carboxamidine 

Relevant articles and documents

Chemistry informer libraries: A chemoinformatics enabled approach to evaluate and advance synthetic methods

Major new advances in synthetic chemistry methods are typically reported using simple, non-standardized reaction substrates, and reaction failures are rarely documented. This makes the evaluation and choice of a synthetic method difficult. We report a standardized complex molecule diagnostic approach using collections of relevant drug-like molecules which we call chemistry informer libraries. With this approach, all chemistry results, successes and failures, can be documented to compare and evolve synthetic methods. To aid in the visualization of chemistry results in drug-like physicochemical space we have used an informatics methodology termed principal component analysis. We have validated this method using palladium- and copper-catalyzed reactions, including Suzuki-Miyaura, cyanation and Buchwald-Hartwig amination.

Direct transformation of N, N -dimethylformamide to -CN: Pd-catalyzed cyanation of heteroarenes via C-H functionalization

This paper describes the direct cyanation of indoles and benzofurans employing N,N-dimethylformamide (DMF) as both reagent and solvent. Isotopic labeling experiments indicated that both the N and the C of the cyano group derived from DMF. This transformation offers an alternative method for preparing aryl nitriles, though it is currently limited in scope to indoles and benzofurans.

Iminoxyl radicals and stable products from the one-electron oxidation of 1-methylindole-3-carbaldehyde oximes

The radical intermediates and the stable products formed on one-electron oxidation of 1-methylindole-3-carbaldehyde oxime 2a were compared with those of 1-methylindole-3-carboxamidine oxime 4a in aqueous solution. The dibromide radical anion generated radiolytically by pulse radiolysis reacted with both 2a and 4a >C=NOH to yield the radical cations [>C=NOH]·+, which exist in prototropic equilibria with the neutral iminoxyl radicals [>C=NO]· (pKa = 3.53 ? 0.03 and 5.01 ± 0.01 at ionic strength 0.05 M, respectively). This was confirmed by the observed primary salt-effect which accelerated the decay of the radical cations but not the iminoxyl radicals. Methylation of the N-hydroxyimino function in both 2a and 4a precluded deprotonation of the corresponding radical cations [>C=NOCH3]·+. At low concentrations of 2a and high dose rates the 2a radicals [>C=NO]· decayed bimolecularly via unstable dimers to the aldehyde >C=O, with higher concentrations and lower dose rates favouring the chain-catalysed isomerisation of the N-hydroxyimino moiety. Radicals from 4a decay bimolecularly to form unstable dimers which degrade to produce an amide, nitrile and carboxylic acid. The observed differences in the oxidation chemistry of 2a and 4a probably reflect the enhanced stabilisation of iminoxyl radicals through α-amino substitution.