213542-01-9

Basic information

• Product Name: 5-Chloro-3-nitroindole
• Synonyms: 5-Chloro-3-nitroindole;5-chloro-3-nitro-1H-indole
• CAS NO: 213542-01-9
• Molecular Formula: C₈H₅ClN₂O₂
• Molecular Weight: 196.5905
• Mol File: 213542-01-9.mol
• Article Data: 8

Chemical Properties

• Melting Point: 218-220℃
• Boiling Point: 396℃
• Flash Point: 193℃
• Appearance: /
• Density: 1.564
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 5-Chloro-3-nitroindole(CAS DataBase Reference)
• NIST Chemistry Reference: 5-Chloro-3-nitroindole(213542-01-9)
• EPA Substance Registry System: 5-Chloro-3-nitroindole(213542-01-9)

Safety Data

• Hazardous Substances Data: 213542-01-9(Hazardous Substances Data)

Usage

General Description

5-Chloro-3-nitroindole is a chemical compound with the molecular formula C8H5ClN2O2. It is an organic compound that consists of a chloro and nitro group attached to a benzene ring. 5-Chloro-3-nitroindole is commonly used in pharmaceutical research and development, particularly in the synthesis of various biologically active molecules. It has also been studied for its potential applications in the field of organic electronics due to its unique electronic and optical properties. 5-Chloro-3-nitroindole has also been investigated for its potential use as a key building block in the synthesis of complex organic molecules with desired properties.

Upstream product

• 916664-23-8 2-azido 5-chlorobenzaldehyde 
• 6628-86-0 5-chloro-2-nitrobenzaldehyde 
• 1279718-30-7 C₈H₇ClN₄O₃ 
• 17422-32-1 5-chloro-1H-indole 

Downstream Products

• 93704-58-6 N-[2-(5-Chloro-1H-indol-3-ylamino)-phenyl]-acetamide 
• 93704-54-2 N-(5-Chloro-1H-indol-3-yl)-benzene-1,2-diamine 
• 72561-51-4 5-chloro-1H-indol-3-ylamine 

Relevant articles and documents

Synthesis of 1-Substituted Cyclopropylamines via Formal Tertiary Csp3-H Amination of Cyclopropanes

A novel and facile approach to synthesis of 1-substituted cyclopropylamines via phosphine-catalyzed formal tertiary Csp3-H amination of cyclopropanes was described. The indoles, pyrroles, imidazoles, uracils, 2-pyridone, pyrimidin-4(3H)-one, and phthalimide had been proven as good aminating partners. The present protocol features transition-metal-free, excellent regioselectivity, high-atom-economy, and mild reaction conditions and a broad range of substrates. The practicability of this protocol can also be demonstrated with late-stage modification of bioactive molecules, scaled up reaction, and divergent derivatization. Notably, the method has been used in the formal synthesis of the hormone-sensitive lipase (HSL) inhibitor. The mechanistic aspects were elucidated by both experimental and computational studies.

Stereodivergent Synthesis of Tetrahydrofuroindoles through Pd-Catalyzed Asymmetric Dearomative Formal [3+2] Cycloaddition

A stereodivergent synthesis of tetrahydrofuroindoles through palladium-catalyzed asymmetric dearomative formal [3+2] cycloaddition of nitroindoles with epoxybutenes was developed. The polarity of the solvent was found to play a key role in the diastereoselectivity. In toluene, good to excellent yields (70–99 %), diastereoselectivity (87/13->95/5 d.r.), and enantioselectivity (85/15–94/6 e.r.) were obtained, regardless of the properties of the substituents on nitroindoles. In acetonitrile, tetrahydrofuroindoles of a different diastereoisomer were produced with good to excellent yields (75–98 %) and stereoselectivity (78/22–93/7 d.r., 93/7–99/1 e.r.). Mechanistic studies were conducted to illustrate the origin of the diastereodivergency. The kinetic experiments indicate that the rate-determining step of this reaction is different in different solvents. ESI-MS experiments also support the existence of key palladium complex intermediates and the catalytic cycle of the reaction.

Rh2(II)-catalyzed nitro-group migration reactions: Selective synthesis of 3-nitroindoles from β-nitro styryl azides

Rhodium carboxylate complexes (1 mol %) catalyze the migration of electron-withdrawing groups to selectively produce 3-substituted indoles from β-substituted styryl azides. The relative order of migratorial aptitude for this transformation is ester ? amide H sulfonyl benzoyl ? nitro.