10553-14-7

Basic information

• Product Name: 7-NITROINDOLE-3-CARBOXALDEHYDE
• Synonyms: 7-NITRO-1H-INDOLE-3-CARBALDEHYDE;7-NITROINDOLE-3-ALDEHYDE;7-NITROINDOLE-3-CARBOXALDEHYDE;7-NITROINDOLE-3-CARBOXYALDEHYDE;7-Nitroindole-3-carboxaldehyde 98%;Zinc02572407;7-Nitro-1H-indole-3-carboxaldehyde 95+%;3-Carboxy-7-nitro-1H-indole
• CAS NO: 10553-14-7
• Molecular Formula: C₉H₆N₂O₃
• Molecular Weight: 190.16
• Product Categories: Indole
• Mol File: 10553-14-7.mol
• Article Data: 8

Chemical Properties

• Boiling Point: 441.47 °C at 760 mmHg
• Flash Point: 220.794 °C
• Appearance: /Solid
• Density: 1.517 g/cm³
• Vapor Pressure: 5.43E-08mmHg at 25°C
• Refractive Index: 1.764
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• PKA: 12.47±0.30(Predicted)
• CAS DataBase Reference: 7-NITROINDOLE-3-CARBOXALDEHYDE(CAS DataBase Reference)
• NIST Chemistry Reference: 7-NITROINDOLE-3-CARBOXALDEHYDE(10553-14-7)
• EPA Substance Registry System: 7-NITROINDOLE-3-CARBOXALDEHYDE(10553-14-7)

Safety Data

• Hazard Codes: Xi
• Hazardous Substances Data: 10553-14-7(Hazardous Substances Data)

Usage

General Description

7-NITROINDOLE-3-CARBOXALDEHYDE is a chemical compound that belongs to the class of nitroindole derivatives. It is a yellow crystalline solid with the molecular formula C9H6N2O3. 7-NITROINDOLE-3-CARBOXALDEHYDE is commonly used as a starting material for the synthesis of various organic compounds and pharmaceuticals. 7-NITROINDOLE-3-CARBOXALDEHYDE has been extensively studied for its potential applications in the field of medicinal chemistry, particularly for its antimicrobial and anti-inflammatory properties. Additionally, it has been investigated for its potential as a fluorescent probe in bioimaging studies. Due to its diverse range of applications, this compound is of interest to researchers in various scientific disciplines.

InChI:InChI=1/C9H6N2O3/c12-5-6-4-10-9-7(6)2-1-3-8(9)11(13)14/h1-5,10H

Upstream product

• 6960-42-5 7-nitro-1H-indole 
• 68-12-2 N,N-dimethyl-formamide 
• 50-00-0 formaldehyd 
• 100-97-0 hexamethylenetetramine 

Downstream Products

• 165669-11-4 7-amino-1H-indole-3-carbonitrile 
• 165669-10-3 3-cyano-7-nitroindole 
• 247186-94-3 4-amino-N-(3-cyano-1H-indol-7-yl)-benzenesulfonamide 
• 247186-93-2 N-(3-cyano-7-indolyl)-4-nitrobenzenesulfonamide 
• 247186-91-0 4-(3-cyano-1H-indol-7-ylsulfamoyl)-benzoic acid 
• 1423754-13-5 C₁₇H₁₃N₃O₆S 
• 1423754-19-1 (S)-2-((R)-2-nitro-1-(7-nitro-1-tosyl-1H-indol-3-yl)ethyl)pentanal 
• 1214362-44-3 7-aminoindole-3-carbaldehyde 

Relevant articles and documents

Method for synthesizing indole -3 - formaldehyde compounds (by machine translation)

The invention relates to a synthetic indole - 3 - formaldehyde compounds, which belongs to the technical field of organic synthesis. The invention will be indole compound, hexamethylene tetramine, crystalline aluminum trichloride, N, N - dimethyl formamide in proportion in 120 °C reaction under the condition of 1 - 20 the H, then filtered, washing, filtering, concentrating, column chromatography purification and other after-treatment technology, make the refined indole - 3 - formaldehyde compound. The invention overcomes the indole - 3 - benzaldehyde compound of preparation need to use not stabilized peroxide, and for a long time under the high temperature reaction of the defect. And the invention uses the advantages of simple equipment, product yield is high, the resulting yield of a target product can be up to 94%. In addition, the invention relates to a low reaction conditions, less catalyst levels, low energy consumption, the post treatment process is simple and easy to use, without the need of using a high dosage of acid or alkali, post-processing the solvent can be recovered and recycled, industrial "three wastes" is discharged little, suitable for large-scale production. (by machine translation)

Iron-Catalyzed C3-Formylation of Indoles with Formaldehyde and Aqueous Ammonia under Air

An efficient iron-catalyzed C3-selective formylation of free (N-H) or N-substituted indoles was developed by employing formaldehyde and aqueous ammonia, with air as the oxidant. This new method gave 3-formylindoles in moderate to excellent yields with fairly short reaction times. Moreover, this procedure for catalytic formylation of indoles can be applied to gram-scale syntheses.

Organocatalytic asymmetric Michael addition of aliphatic aldehydes to indolylnitroalkenes: Access to contiguous stereogenic tryptamine precursors

Because of the importance of the indole framework and the versatile transformation of nitro and formyl groups, the efficient synthesis of optically pure 2-alkyl-3-(1H-indol-3-yl)-4-nitrobutanals, one type of tryptamine precursors are of great interest for pharmaceutical and biological research. Herein, the Michael addition of aliphatic aldehydes to indolylnitroalkenes has been developed using (S)-diphenylprolinol trimethylsilyl ether as an organocatalyst, which provides the desired optically pure syn 2-alkyl-3-(1H-indol-3-yl)-4-nitrobutanal derivatives in up to 98% yield with up to >99:1 dr and >99% ee. To show the synthetic usefulness of this methodology, optically active 2-alkyl-4-nitro-3-(1-tosyl-1H-indol-3-yl)butan-1- ol and tryptamine derivatives are readily obtained by stepwise systematic transformations.