29110-74-5

Basic information

• Product Name: 3-CHLORO-1H-INDAZOLE
• Synonyms: TIMTEC-BB SBB004051;3-CHLOROINDAZOLE;3-CHLORO-1H-INDAZOLE;3-CHLORO-1H-INDAZOLE 99%;3-Chloro-1H-indazole,99%;1H-Indazole, 3-chloro-;3-Chloroindazole 97%;3-chloro-2H-indazole
• CAS NO: 29110-74-5
• Molecular Formula: C₇H₅ClN₂
• Molecular Weight: 152.58
• EINECS: 249-444-9
• Product Categories: pharmacetical;IndazolesBuilding Blocks;Halogenated Heterocycles;Heterocyclic Building Blocks;Indazoles;Building Blocks;Chemical Synthesis;Halogenated Heterocycles;Heterocyclic Building Blocks
• Mol File: 29110-74-5.mol

Chemical Properties

• Melting Point: 149 °C (subl.)(lit.)
• Boiling Point: 250.67°C (rough estimate)
• Flash Point: 59.4 °C
• Appearance: Almost white to light beige/Fluffy Powder
• Density: 1.2763 (rough estimate)
• Vapor Pressure: 3.03mmHg at 25°C
• Refractive Index: 1.5500 (estimate)
• Storage Temp.: Inert atmosphere,Room Temperature
• PKA: 11.93±0.40(Predicted)
• CAS DataBase Reference: 3-CHLORO-1H-INDAZOLE(CAS DataBase Reference)
• NIST Chemistry Reference: 3-CHLORO-1H-INDAZOLE(29110-74-5)
• EPA Substance Registry System: 3-CHLORO-1H-INDAZOLE(29110-74-5)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37/39
• WGK Germany: 3
• Hazardous Substances Data: 29110-74-5(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
3-Chloro-1H-Indazole is used as a key intermediate in the synthesis of various pharmaceutical compounds. Its electron-withdrawing nature and structural features contribute to its utility in the development of new drugs with potential therapeutic applications.
Used in Chemical Research:
In the field of chemical research, 3-Chloro-1H-Indazole serves as a valuable building block for the creation of novel indazole-based molecules. Its reactivity and structural properties make it an attractive candidate for further exploration and modification in the pursuit of new chemical entities with specific biological activities.
Used in the Preparation of 3-Chloro-1-(4′-Methylphenyl)-Indazole:
Specifically, 3-Chloro-1H-Indazole has been utilized in the preparation of 3-chloro-1-(4′-methylphenyl)-indazole, which is an important compound in its own right. This derivative may have potential applications in various fields, such as pharmaceuticals, materials science, or chemical research, depending on its properties and reactivity.

InChI:InChI=1/C7H5ClN2/c8-7-5-3-1-2-4-6(5)9-10-7/h1-4H,(H,9,10)

Upstream product

• 2596-89-6 3-Diazo-3H-indazol 
• 4498-67-3 1H-Indazole-3-carboxylic acid 
• 271-44-3 benzimidazole 
• 33906-30-8 2-hydrazinobenzoic acid hydrochloride 
• 7647-01-0 hydrogenchloride 
• 7364-25-2 1H-indazol-3-ol 
• 10025-87-3 trichlorophosphate 

Downstream Products

• 1006707-92-1 3-chloro-1-phenyl-1H-indazole 
• 271-42-1 2H-indazole 
• 271-44-3 benzimidazole 
• 75844-69-8 t-butyl piperidinecarboxylate 
• 79099-07-3 N-tert-butyloxycarbonylpiperidin-4-one 
• 85838-94-4 N-Boc-1,2,3,6-tetrahydropyridine 

Relevant articles and documents

Decarboxylative Bromination of Heteroarenes: Initial Mechanistic Insights

After an initial report from our laboratory describing metal-free decarboxylative halogenation of various azaheteroarenes, we set out to investigate the possible mechanism by which this chemistry occurs. Evidence from this mechanistic investigation sugges

Oxidative Photochlorination of Electron-Rich Arenes via in situ Bromination

Electron-rich arenes are oxidatively photochlorinated in the presence of catalytic amounts of bromide ions, visible light, and 4CzIPN as organic photoredox catalyst. The substrates are brominated in situ in a first photoredox-catalyzed oxidation step, followed by a photocatalyzed ipso-chlorination, yielding the target compounds in high ortho/para regioselectivity. Dioxygen serves as a green and convenient terminal oxidant. The use of aqueous hydrochloric acid as the chloride source reduces the amount of saline by-products.

Visible-light photocatalytic activation of N-chlorosuccinimide by organic dyes for the chlorination of arenes and heteroarenes

A variety of arenes and heteroarenes are chlorinated in moderate to excellent yields using N-chlorosuccinimide (NCS) under visible-light activated conditions. A screening of known organic dye photocatalysts resulted in the identification of methylene green as the most efficient catalyst to use with NCS. According to mechanistic studies described within, the reaction is speculated to proceed via a single electron oxidation of NCS utilizing methylene green under visible-light photoredox pathway. The photo-oxidation of NCS amplifies the electrophilicity of the chlorine atom of the NCS, thus leading to enhanced reactivity as a chlorinating reagent with aromatic substrates.

A practical lewis base catalyzed electrophilic chlorination of arenes and heterocycles

A mild phosphine sulfide catalyzed electrophilic halogenation of arenes and heterocycles that utilizes inexpensive and readily available N-halosuccinimides is disclosed. This methodology is shown to efficiently chlorinate diverse aromatics, including simple arenes such as anthracene, and heterocycles such as indoles, pyrrolopyrimidines, and imidazoles. Arenes with Lewis acidic moieties also proved amenable, underscoring the mild nature of this chemistry. Lewis base catalysis was also found to improve several diverse aromatic brominations and iodinations.

Heterocyclic substituted 2-methyl-benzimidazole antiviral agents

The present invention concerns antiviral compounds, their methods of preparation and their compositions, and use in the treatment of viral infections. More particularly, the invention provides heterocyclic substituted 2-methylbenzimidazole derivatives for the treatment of respiratory syncytial virus infection.

An efficient method for the N-debenzylation of aromatic heterocycles

The treatment of N-benzylated heterocycles with potassium tert-butoxide/DMSO and oxygen at room temperature cleanly affords N-debenzylated products in high yield. This procedure can be utilized on a variety of functionalized nitrogen-containing heterocycles such as imidazoles, benzimidazoles, pyrazoles, indazoles, carbazoles, and indoles.