828-94-4

Basic information

• Product Name: 5-METHOXY-2,3-DIMETHYL-1H-INDOLE
• Synonyms: 5-METHOXY-2,3-DIMETHYL-1H-INDOLE;2,3-Dimethyl-5-methoxy-1H-indole
• CAS NO: 828-94-4
• Molecular Formula: C₁₁H₁₃NO
• Molecular Weight: 175.22702
• Mol File: 828-94-4.mol
• Article Data: 34

Chemical Properties

• Boiling Point: 325.3 °C at 760 mmHg
• Flash Point: 119.2 °C
• Appearance: /
• Density: 1.106 g/cm³
• Vapor Pressure: 0.00044mmHg at 25°C
• Refractive Index: 1.609
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 5-METHOXY-2,3-DIMETHYL-1H-INDOLE(CAS DataBase Reference)
• NIST Chemistry Reference: 5-METHOXY-2,3-DIMETHYL-1H-INDOLE(828-94-4)
• EPA Substance Registry System: 5-METHOXY-2,3-DIMETHYL-1H-INDOLE(828-94-4)

Safety Data

• Hazardous Substances Data: 828-94-4(Hazardous Substances Data)

Usage

InChI:InChI=1/C11H13NO/c1-7-8(2)12-11-5-4-9(13-3)6-10(7)11/h4-6,12H,1-3H3

Upstream product

• 67748-01-0 3-((4-methoxyphenyl)amino)butan-2-one 
• 20265-97-8 p-anisidine hydrochloride 
• 106103-32-6 5,5-Dimethoxy-3-methyl-3,5-dihydro-2H-indol-3-ol 
• 917-54-4 methyllithium 
• 125438-36-0 3,5,5-Trimethoxy-3-methyl-3,5-dihydro-2H-indole 
• 104-94-9 4-methoxy-aniline 
• 513-85-9 2.3-butanediol 
• 78-93-3 butanone 
• 2028-63-9 but-3-yn-2-ol 
• 380383-75-5 tert-butyl 1-(4-methoxyphenyl)hydrazine-1-carboxylate 
• 19501-58-7 4-methoxyphenylhydrazine hydrochloride 
• 106103-26-8 2,2,2-Trifluoro-N-[2-hydroxy-2-(2-hydroxy-5-methoxy-phenyl)-propyl]-acetamide 
• 1025890-12-3 N-(but-2-ynyl)-4-(methyloxy)aniline 
• 459-64-3 4-methoxybenzenediazonium tetrafluoroborate 

Downstream Products

• 22960-94-7 (4-chlorophenyl)(5-methoxy-2,3-dimethyl-1H-indol-1-yl)methanone 
• 52417-34-2 N-(2-acetyl-4-methoxyphenyl)acetamide 
• 23042-77-5 1-(2-amino-5-methoxy-phenyl)-ethanone 
• 36729-22-3 2,3-dimethyl-1H-indol-5-ol 
• 1350845-72-5 3-benzyl-5-methoxy-2,3-dimethyl-3H-indole 
• 1370410-16-4 (2-iodophenyl)(5-methoxy-2,3-dimethyl-1H-indol-1-yl)methanone 

Relevant articles and documents

Pd(II)-catalyzed intramolecular oxidative Heck dearomative reaction: Approach to thiazole-fused pyrrolidinones with a C2-azaquarternary center

A Pd(ii)-catalyzed intramolecular oxidative Heck dearomative reaction for the construction of thiazole-fused pyrrolidinones with a C2-azaquarternary center and C3-exo-double bond has been achieved for the first time. The reaction exhibited good functional group tolerance and gram-scale capacity.

Acceptorless dehydrogenative condensation: synthesis of indoles and quinolines from diols and anilines

The use of diols and anilines as reagents for the preparation of indoles represents a challenge in organic synthesis. By means of acceptorless dehydrogenative condensation, heterocycles, such as indoles, can be obtained. Herein we present an experimental and theoretical study for this purpose employing heterogeneous catalysts Pt/Al2O3and ZnO in combination with an acid catalyst (p-TSA) and NMP as solvent. Under our optimized conditions, the diol excess has been reduced down to 2 equivalents. This represents a major advance, and allows the use of other diols. 2,3-Butanediol or 1,2-cyclohexanediol has been employed affording 2,3-dimethyl indoles and tetrahydrocarbazoles. In addition, 1,3-propanediol has been employed to prepare quinolines or natural and synthetic julolidines.

One-pot, three-component Fischer indolisation-N-alkylation for rapid synthesis of 1,2,3-trisubstituted indoles

A one-pot, three-component protocol for the synthesis of 1,2,3-trisubstituted indoles has been developed, based upon a Fischer indolisation-indoleN-alkylation sequence. This procedure is very rapid (total reaction time under 30 minutes), operationally straightforward, generally high yielding and draws upon readily available building blocks (aryl hydrazines, ketones, alkyl halides) to generate densely substituted indole products. We have demonstrated the utility of this process in the synthesis of 23 indoles, benzoindoles and tetrahydrocarbazoles bearing varied and useful functionality.