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

General Description

5-Chloroindoline is an organic chemical compound with the molecular formula C8H6ClN. It is a chlorinated derivative of indoline and is commonly used as a building block in the synthesis of pharmaceuticals, agrochemicals, and other organic compounds. 5-Chloroindoline has a wide range of applications in the field of medicinal chemistry, where it is used as a starting material for the synthesis of potential drug candidates. It is also used in the production of dyes and pigments, as well as in the synthesis of various other organic compounds. 5-Chloroindoline possesses unique chemical and physical properties that make it a valuable and versatile building block in the field of 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

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

Downstream Products

• 92083-53-9 α-(5-chloro-1-indolinyl)-m-tolunitrile 
• 126149-64-2 5-chloro-7-(2-fluorobenzoyl)indoline 
• 666859-58-1 4-[ (5-CHLORO-2, 3-DIHYDRO-1H-INDOL-1-YL) SULFONYL] benzoic acid 
• 96014-90-3 2-(5-chloro-2,3-dihydro-1H-indol-1-yl)benzamide 
• 71971-45-4 5-chloro-1-(2-nitro-phenyl)-2,3-dihydro-indole 
• 1207113-97-0 C₂₀H₁₅ClF₆N₂O₂ 
• 1620581-34-1 2-(5-((5-chloroindolin-1-yl)sulfonyl)-2-methoxyphenyl)-2-isobutyl-4-methylpentanenitrile 
• 17422-32-1 5-chloro-1H-indole 
• 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 
• 92083-54-0 3-(5-chloro-1-indolinylmethyl)benzenemethanamine 
• 92083-26-6 3-(5-chloro-2,3-dihydro-1H-indol-1-yl)-benzenemethanamine 
• 126149-67-5 9-chloro-1-(2-fluoro-phenyl)-6,7-dihydro-[1,4]diazepino[6,7,1-hi]indole-3,4-dione 3-oxime 

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.

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.

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.