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

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

Uses

Used in Pharmaceutical Research and Development:
5-Chloro-3-nitroindole is utilized as a key intermediate in the synthesis of various biologically active molecules. Its presence in the molecular structure can influence the pharmacological activity and selectivity of the resulting compounds, making it a valuable component in drug discovery and design processes.
Used in Organic Electronics:
Due to its distinctive electronic and optical characteristics, 5-Chloro-3-nitroindole is explored for applications in the field of organic electronics. It may contribute to the development of novel electronic devices and materials, such as organic light-emitting diodes (OLEDs) or organic photovoltaics, where its properties can enhance performance or introduce new functionalities.
Used in the Synthesis of Complex Organic Molecules:
5-Chloro-3-nitroindole serves as a fundamental building block in the creation of complex organic molecules with tailored properties. Its reactivity and structural features make it suitable for use in organic synthesis, allowing chemists to construct molecules with specific characteristics for various applications, including but not limited to pharmaceuticals, materials science, and specialty chemicals.

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.

Phosphine-catalyzed dearomative [3+2] annulation of 3-nitroindoles and allenoates

The efficient phosphine-catalyzed dearomative [3+2] annulation of 3-nitroindoles with allenoates has been successfully developed, providing a facile access to cyclopenta[b]indolines with good to excellent yields and high diastereoselectivities. This strategy features mild reaction conditions, high functional group tolerance, and scalability. Additionally, the 2-nitrobenzofuran and 2-nitrobenzothiophene were good dearomative [3+2] annulation partners.

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.

HISTONE DEMETHYLASE INHIBITORS

The present invention relates generally to compositions and methods for treating cancer and neoplastic disease. Provided herein are substituted 3-aminopyridine derivative compounds, substituted 3-aminopyridazine derivative compounds, and pharmaceutical compositions comprising said compounds. The subject compounds and compositions are useful for inhibition histone demethylase. Furthermore, the subject compounds and compositions are useful for the treatment of cancer, such as prostate cancer, breast cancer, bladder cancer, lung cancer and/or melanoma and the like.

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.

Design, synthesis, and biological evaluation of substituted-N-(thieno[2,3-b]pyridin-3-yl)-guanidines, N-(1H-pyrrolo[2,3-b]pyridin-3-yl)-guanidines, and N-(1H-indol-3-yl)-guanidines

Sulfonylureas stimulate insulin secretion independent of the blood glucose concentration and therefore cause hypoglycemia in type 2 diabetic patients. Over the last years, a number of aryl-imidazoline derivatives have been identified that stimulate insulin secretion in a glucose-dependent manner. In the present study, we have developed three series of substituted N-(thieno[2,3-b]pyridin-3-yl)-guanidine (2a-l), N-(1H-pyrrolo[2,3-b]pyridin-3-yl)-guanidine (3a-l), and N-(1H-indol-3-yl)-guanidine (4a-l) as new class of antidiabetic agents. In vitro glucose-dependent insulinotropic activity of test compounds 2a-l, 3a-l, and 4a-l was evaluated using RIN5F (Rat Insulinoma cell) based assay. All the test compounds showed concentration-dependent insulin secretion, only in presence of glucose load (16.7 mmol). Some of the test compounds (2c, 3c, and 4c) from each series were found to be equipotent to BL 11282 (standard aryl-imidazoline), which indicated that the guanidine group acts as a bioisostere of imidazoline ring system.

ATP-citrate lyase as a target for hypolipidemic intervention. 2. Synthesis and evaluation of (3R*,5S*)-ω-substituted-3-carboxy-3,5- dihydroxyalkanoic acids and their γ-lactone prodrugs as inhibitors of the enzyme in vitro and in vivo

A series of (3R*,5S*)-ω-substituted-3-carboxy-3,5-dihydroxyalkanoic acids have been synthesized and evaluated as inhibitors of the recombinant human form of ATP-citrate lyase. The best of these have K(i)'s in the 200- 1000 nM range. As the corresponding thermodynamically favored γ-lactone prodrugs, a number of compounds are able to inhibit cholesterol and fatty acid synthesis in HepG2 cells and reduce plasma triglyceride levels in vivo. The best of these, compound 77, is able to induce clear hypocholesterolemic and hypotriglyceridaemic responses when administered orally to rat and dog. These results provide evidence to support the hypothesis that compounds which inhibit ATP-citrate lyase have the potential to be a novel class of hypolipidemic agent, which possess combined hypocholesterolemic and hypotriglyceridemic activities.

Synthesis of Substituted Indolobenzodiazepine Derivatives

Various substituted-7,12-dihydroindolobenzodiazepines (4a-e) have been prepared from the corresponding 3-aminoindoles (1a-e) through Ullmann reaction with o-chloroaniline, acylation of the resulting 3-(o-aminophenylamino)indoles (2a-e) and cyclization of amides (3a-e) with POCl3.Similar systems have also been synthesized from ethyl 3-bromoindole-2-carboxylates (6a-e).The bromo esters react with o-phenylenediamine to give ethyl 3-(o-aminophenylamino)indole-2-carboxylates (7a-e) which undergo cyclization in the presence of PPA to yield 5,6,7,12-tetrahydroindolobenzodiazepin-6-ones (8a-e).