21296-94-6

Basic information

• Product Name: 2,3-DIMETHYL-5-NITROINDOLE
• Synonyms: RARECHEM AH BS 0099;2,3-DIMETHYL-5-NITROINDOLE;2,3-DIMETHYL-5-NITROINDOLE 97%;Einecs 244-321-6;Nsc 84204
• CAS NO: 21296-94-6
• Molecular Formula: C₁₀H₁₀N₂O₂
• Molecular Weight: 190.2
• EINECS: 244-321-6
• Mol File: 21296-94-6.mol

Chemical Properties

• Melting Point: 184-186°C
• Boiling Point: 377.2°Cat760mmHg
• Flash Point: 181.9°C
• Appearance: /
• Density: 1.3g/cm³
• Vapor Pressure: 1.49E-05mmHg at 25°C
• Refractive Index: 1.671
• PKA: 16.12±0.30(Predicted)
• BRN: 162798
• CAS DataBase Reference: 2,3-DIMETHYL-5-NITROINDOLE(CAS DataBase Reference)
• NIST Chemistry Reference: 2,3-DIMETHYL-5-NITROINDOLE(21296-94-6)
• EPA Substance Registry System: 2,3-DIMETHYL-5-NITROINDOLE(21296-94-6)

Safety Data

• Hazard Codes: Xi
• Safety Statements: 22-24/25
• Hazardous Substances Data: 21296-94-6(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
2,3-DIMETHYL-5-NITROINDOLE is used as a synthetic building block for the development of new pharmaceuticals and organic compounds. Its unique structure and properties contribute to the creation of novel drug candidates, potentially leading to advancements in medicinal chemistry.
Used in Research and Development:
In the realm of scientific research, 2,3-DIMETHYL-5-NITROINDOLE serves as a crucial component in the exploration and development of new drugs and materials. Its application in research facilitates the discovery of innovative therapeutic agents and contributes to the expansion of the chemical knowledge base.

InChI:InChI=1/C10H10N2O2/c1-6-7(2)11-10-4-3-8(12(13)14)5-9(6)10/h3-5,11H,1-2H3

Upstream product

• 91-55-4 2,3-dimethylindole 
• 1017-79-4 butan-2-one-(4-nitro-phenylhydrazone) 
• 636-99-7 4-nitrophenylhydrazine hydrochloride 
• 78-93-3 butanone 
• 100-16-3 4-nitrophenylhydrazone 
• 100-01-6 4-nitro-aniline 

Downstream Products

• 16712-58-6 5-amino-2,3-dimethylindole 
• 1333397-47-9 C₁₇H₁₈N₂ 
• 1374754-54-7 1,2,3-trimethyl-7,9-diphenyl-3H-pyrrolo[3,2-f]quinoline 
• 1374754-55-8 4-(1,2,3-trimethyl-9-phenyl-3H-pyrrolo[3,2-f]quinolin-7-yl)phenyl fluoride 
• 1374754-56-9 4-(1,2,3-trimethyl-9-phenyl-3H-pyrrolo[3,2-f]quinolin-7-yl)phenyl chloride 
• 1374754-57-0 4-(1,2,3-trimethyl-9-phenyl-3H-pyrrolo[3,2-f]quinolin-7-yl)phenyl bromide 
• 1374754-58-1 1,2,3-trimethyl-7-(4-methylphenyl)-9-phenyl-3H-pyrrolo[3,2-f]quinoline 
• 1374754-59-2 7-(4-methoxyphenyl)-1,2,3-trimethyl-9-phenyl-3H-pyrrolo[3,2-f]quinoline 
• 1374754-60-5 7-mesityl-1,2,3-trimethyl-9-phenyl-3H-pyrrolo[3,2-f]quinoline 
• 1374754-62-7 3-ethyl-1,2-dimethyl-7,9-diphenyl-3H-pyrrolo[3,2-f]quinoline 
• 1374754-63-8 3-benzyl-1,2-dimethyl-7,9-diphenyl-3H-pyrrolo[3,2-f]quinoline 
• 1374754-75-2 9-(4-methoxyphenyl)-1,2,3-trimethyl-7-phenyl-3H-pyrrolo[3,2-f]quinoline 
• 1374754-76-3 4-(4-methoxyphenyl)-7,8,9-trimethyl-2-phenyl-7H-pyrrolo[2,3-h]quinoline 
• 1374754-78-5 8,9-dimethyl-4-(4-methylphenyl)-2-phenyl-7H-pyrrolo[2,3-h]quinoline 

Relevant articles and documents

Palladium-Catalyzed Amination/Dearomatization Reaction of Indoles and Benzofurans

This report describes a palladium-catalyzed dearomatization and amination tandem reaction of 2,3-disubstituted indoles and benzofurans via the Catellani strategy. This reaction provides a new method for the construction of amino-substituted indoline-fused cyclic and benzofuran spiro compounds in good yields. The reaction has broad functional group compatibility and substrate scope.

One-pot synthesis of pyrrolo[3,2-f]-and pyrrolo[2,3-h]quinoline derivatives: Observation of an unexpected mechanistic pathway

One-pot synthesis of pyrrolo[3,2-f]- and pyrrolo[2,3-h]quinolines were obtained starting from substituted 5-aminoindoles, benzaldehydes, and phenylacetylenes in the presence of La(OTf)3 as a catalyst in good yields. The indole moiety in 5-aminoindole is believed to be mainly responsible for the observation of unexpected mechanistic pathway to the formation of pyrrolo[2,3-h]quinoline. Georg Thieme Verlag Stuttgart · New York.

2,3-Dialkyl(dimethylamino)indoles: Interaction with 5HT1, 5HT2, and rat stomach fundal serotonin receptors

2,3-Dialkyl(dimethylamino)indoles, synthesized via the Fisher indole synthesis, were found to weakly bind to 5HT1 and 5HT2 sites in brain cortical membranes (IC50 greater than 1 μM at both sites for all compounds). These (dimethylamino)indoles were relatively potent antagonists of the serotonin receptor in the rat stomach fundus. At higher concentrations, several of the compounds were weak agonists at this receptor. For direct comparison with data obtained in the isolated rat fundus, antagonism of serotonin-induced contractions at 5HT2 receptors in the rat jugular vein was also examined. Several of the compounds showed good selectivity for the fundus receptor relative to the 5HT2 receptor; together with minimal affinity for 5HT1 and 5HT2 binding sites in brain cortical membranes, these results support the idea that the serotonin receptor in the stomach fundus is distinct from 5HT1 and 5HT2 binding sites.