25658-80-4

Basic information

• Product Name: 5-Chloroindoline
• Synonyms: TIMTEC-BB SBB010106;5-CHLOROINDOLINE;5-CHLORO-2,3-DIHYDRO-(1H)-INDOLE
• CAS NO: 25658-80-4
• Molecular Formula: C₈H₈ClN
• Molecular Weight: 153.61
• EINECS: 247-167-8
• Product Categories: Indoline & Oxindole
• Mol File: 25658-80-4.mol
• Article Data: 23

Chemical Properties

• Boiling Point: 93-98°C 0,3mm
• Flash Point: 115.149 °C
• Appearance: /
• Density: 1.214 g/cm³
• Vapor Pressure: 0.00847mmHg at 25°C
• Refractive Index: 1.579
• Storage Temp.: 2-8°C(protect from light)
• PKA: 4.48±0.20(Predicted)
• CAS DataBase Reference: 5-Chloroindoline(CAS DataBase Reference)
• NIST Chemistry Reference: 5-Chloroindoline(25658-80-4)
• EPA Substance Registry System: 5-Chloroindoline(25658-80-4)

Safety Data

• Hazard Codes: Xi,T
• Statements: 25-51
• Safety Statements: 24/25-45
• RIDADR: UN2811
• Hazardous Substances Data: 25658-80-4(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
5-Chloroindoline is used as a building block for the synthesis of pharmaceuticals, serving as a starting material for the development of potential drug candidates. Its unique properties contribute to the creation of new and effective medications.
Used in Agrochemical Industry:
In the agrochemical sector, 5-Chloroindoline is utilized as a component in the synthesis of various agrochemicals, playing a crucial role in the development of products that enhance crop protection and yield.
Used in Dye and Pigment Production:
5-Chloroindoline is employed in the production of dyes and pigments, where its chemical properties are leveraged to create a wide array of colorants for different applications.
Used in Organic Compound Synthesis:
Beyond its applications in specific industries, 5-Chloroindoline is a key intermediate in the synthesis of a broad spectrum of organic compounds, showcasing its versatility and importance in organic chemistry.

InChI:InChI=1/C8H8ClN/c9-7-1-2-8-6(5-7)3-4-10-8/h1-2,5,10H,3-4H2

Upstream product

• 25630-01-7 1-acetyl-5-chloro-indoline 
• 17422-32-1 5-chloro-1H-indole 
• 16078-30-1 1-Acetyl-2,3-dihydro-1H-indole 
• 496-15-1 1-indoline 
• 103-80-0 phenylacetyl chloride 
• 142-61-0 Hexanoyl chloride 
• 78-92-2 iso-butanol 
• 85-42-7 1,2-Cyclohexanedicarboxylic acid-anhydride 
• 24660-31-9 acetaldehyde 4-chlorophenylhydrazone 
• 10241-98-2 5-Chloro-2,3-dihydro-1H-indole-2-carboxylic acid 

Downstream Products

• 96014-90-3 2-(5-chloro-2,3-dihydro-1H-indol-1-yl)benzamide 
• 1612872-72-6 N-(1-acetyl-5-chloroindolin-7-yl)-4-methylbenzenesulfonamide 
• 112398-75-1 5-chloro-1-methyl-1H-indole 
• 666859-58-1 4-[ (5-CHLORO-2, 3-DIHYDRO-1H-INDOL-1-YL) SULFONYL] benzoic acid 
• 116707-71-2 4-chloro-1,2-dihydro-7-(4-phenyl-1-piperazinyl)benzopyrrolo<1,2,3-ef><1,5>benzodiazepine 
• 96014-91-4 2-(5-chloro-2,3-dihydro-7-nitro-1H-indol-1-yl)benzamide 
• 96014-92-5 2-(7-amino-5-chloro-2,3-dihydro-1H-indol-1-yl)benzamide 

Relevant articles and documents

Increased antibacterial properties of indoline-derived phenolic Mannich bases

The search for antibacterial agents for the combat of nosocomial infections is a timely problem, as antibiotic-resistant bacteria continue to thrive. The effect of indoline substituents on the antibacterial properties of aminoalkylphenols was studied, leading to the development of a library of compounds with minimum inhibitory concentrations (MICs) as low as 1.18 μM. Two novel aminoalkylphenols were identified as particularly promising, after MIC and minimum bactericidal concentrations (MBC) determination against a panel of reference strain Gram-positive bacteria, and further confirmed against 40 clinical isolates (Staphylococcus aureus, Staphylococcus epidermidis, Enterococcus faecalis, Enterococcus faecium, and Listeria monocytogenes). The same two aminoalkylphenols displayed low toxicity against two in vivo models (Artemia salina brine shrimp and Saccharomyces cerevisiae). The in vitro cytotoxicity evaluation (on human keratinocytes and human embryonic lung fibroblast cell lines) of the same compounds was also carried out. They demonstrated a particularly toxic effect on the fibroblast cell lines, with IC50 in the 1.7–5.1 μM range, thus narrowing their clinical use. The desired increase in the antibacterial properties of the aminoalkylphenols, particularly indoline-derived phenolic Mannich bases, was reached by introducing an additional nitro group in the indolinyl substituent or by the replacement of a methyl by a bioisosteric trifluoromethyl substituent in the benzyl group introduced through use of boronic acids in the Petasis borono-Mannich reaction. Notably, the introduction of an additional nitro moiety did not confer added toxicity to the aminoalkylphenols.

Dual-Active-Sites Design of Co@C Catalysts for Ultrahigh Selective Hydrogenation of N-Heteroarenes

The dual-active-sites Co@C catalyst provides a general powerful strategy to break the limitation of scaling relation on traditional metal surfaces and thus affords unprecedentedly selective hydrogenation of various N-heteroarenes as well as high activity and stability. A porous carbon shell not only allows H2 diffusion to Co sites for activation but also blocks accessibility of N-heteroarenes, and the hydrogenation of N-heteroarenes is achieved on carbon by the spilled hydrogen from Co sites. In addition, the presence of surface/subsurface carbon at the Co sites shows high anti-sulfur poisoning and anti-oxidant capability. Ideal heterogeneous metal hydrogenation catalysts are featured by simultaneously high activity, selectivity, and stability. Herein, we report a general yet powerful strategy to design and fabricate dual-active-sites Co@C core-shell nanoparticle for boosting selective hydrogenation of various N-heteroarenes. It can break the limitation of scaling relation on traditional metal surfaces, and thus afford unprecedentedly high selectivity, activity, and stability. Combining kinetics analysis and DFT calculations with multiple techniques directly unveil that the critical porous carbon shell with a pore size of 0.53 nm not only allows H2 diffusion to Co sites for activation and blocks accessibility of N-heteroarenes but also catalyzes hydrogenation of N-heteroarenes via hydrogen spillover from Co sites. In addition, the presence of surface/subsurface carbon at the Co sites shows high anti-sulfur poisoning and anti-oxidant capability. This work is valuable for guiding the design and manipulation of cost-effective and robust hydrogenation catalysts. Our research can provide an environmentally friendly approach to afford unprecedentedly selective N-heteroarenes hydrogenation, which will greatly reduce the resource and energy consumption and decrease the amount of waste discharge and water pollution. Therefore, these results could help in achieving the “Clean water and sanitation” goal in the 10 UN Sustainable Development Goals. Meanwhile, the products of N-heteroarenes hydrogenation are the core structural motifs in both fine and bulk chemicals, which will make our life more beautiful. Thus, our research also benefits the “Good health and well-being” goal.

Re-Catalyzed Annulations of Weakly Coordinating N-Carbamoyl Indoles/Indolines with Alkynes via C?H/C?N Bond Cleavage

Described herein are rhenium-catalyzed [3+2] annulations of N-carbamoyl indoles with alkynes via C?H/C?N bond cleavage, which provide rapid access to fused-ring pyrroloindolone derivatives. For the first time, the weakly coordinating O-directing group was successfully employed in rhenium-catalyzed C?H activation reactions, enabled by the unique catalytic trio of Re2(CO)10, Me2Zn and ZnCl2. Mechanistic studies revealed that aminozinc species plays an important role in the reaction. Based on the mechanistic understanding, a more powerful catalytic trio of Re2(CO)10, [MeZnNPh2]2 and Zn(OTf)2 was devised and applied successfully in the [4+2] annulations of indolines and alkynes affording pyrroloquinolinone derivatives.

Design, synthesis and biological evaluation of novel 2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole triazole derivatives as potent TRPV1 antagonists

Reported herein is the design, synthesis, and pharmacologic evaluation of a class of TRPV1 antagonists constructed on 2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole as A-region and triazole as B-region. The SAR analysis indicated that 2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole analogues displayed excellent antagonism of hTRPV1 activation by capsaicin and showed better potency compared to the corresponding dihydroindole analogues. Optimization of this design led to the eventual identification of 2-((1-(2-(trifluoromethyl)phenyl)-1H-1,2,3-triazol-4-yl)methyl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole (6g), a potent TRPV1 antagonist. In vitro, using cells expressing recombinant human TRPV1 channels, 6g displayed potent antagonism activated by capsaicin (IC50 = 0.075 μM) and only partially blocked acid activation of TRPV1. In vivo, 6g exhibited good efficacy in capsaicin-induced and heat-induced pain models and had almost no hyperthermia side-effect. Furthermore, pharmacokinetic studies revealed that compound 6g had a superior oral exposure after oral administration in rats. To understand its binding interactions with the receptor, the docking study of 6g was performed in rTRPV1 model and showed an excellent fit to the binding site. On the basis of its superior profiles, 6g could be considered as the lead candidate for the further development of antinociceptive drugs.

Hydrophobic Metal Halide Perovskites for Visible-Light Photoredox C?C Bond Cleavage and Dehydrogenation Catalysis

Two-dimensional lead and tin halide perovskites were prepared by intercalating the long alkyl group 1-hexadecylammonium (HDA) between the inorganic layers. We observed visible-light absorption, narrow-band photoluminescence, and nanosecond photoexcited lifetimes in these perovskites. Owing to their hydrophobicity and stability even in humid air, we applied these perovskites in the decarboxylation and dehydrogenation of indoline-2-carboxylic acids. (HDA)2PbI4 or (HDA)2SnI4 were investigated as photoredox catalysts for these reactions, and quantitative conversion and high yields were observed with the former.

Sustainable Radical Cascades to Synthesize Difluoroalkylated Pyrrolo[1,2-a]indoles

We disclose herein a photocatalytic difluoroalkylation and cyclization cascade reaction of N-(but-2-enoyl)indoles with broad substrate scopes in up to 90% isolated yield. This method provides sustainable and efficient access to synthesize difluoroalkylated pyrrolo[1,2-a]indoles with a quaternary carbon center under mild conditions.

ALPHA 7 NICOTINIC ACETYLCHOLINE RECEPTOR ALLOSTERIC MODULATORS, THEIR DERIVATIVES AND USES THEREOF

The present application is related to compounds represented by Formula I, which are novel positive allosteric modulators of α7 nAChRs. The application also discloses the treatment of disorders that are responsive to enhancement of acetylcholine action on α7 nAChRs in a mammal by administering an effective amount of a compound of Formula I.

Rh(III)-Catalyzed C7-Thiolation and Selenation of Indolines

The rhodium(III)-catalyzed intermolecular C7-thiolation and selenation of indolines with disulfides and diselenides were developed. This protocol relies on the use of a removable pyrimidyl directing group to access valuable C-7 functionalized indoline scaffolds with ample substrate scope and broad functional group tolerance.

Indoline derivative and application of indoline derivative in medicine

The invention discloses an indoline derivative, or stereisomer, tautomer, nitric oxide, solvate, metabolite, pharmacy-acceptable salt or other prodrugs of the indoline derivative. The indoline derivative is used for resisting 5-HT6 receptors. The invention further relates to a method for preparing the compound and application of the compound in treating or preventing diseases related to 5-HT6 receptors.

Palladium-catalyzed C-7 alkenylation of indolines using molecular oxygen as the sole oxidant

A general and efficient method for the intermolecular direct C-7-selective C-H alkenylation of indolines using palladium(ii) as the catalyst and molecular oxygen as the sole oxidant has been developed. The reaction showed complete regio- and stereoselectivity. All products were E-isomers at the C-7 position, and no Z-isomers or other position substituted products could be detected. The approach also presented an efficient route for the synthesis of C-7 alkenylated indoles.