885278-80-8

Basic information

• Product Name: 2,3-DIHYDRO-1H-INDOLE-4-CARBONITRILE HYDROCHLORIDE
• Synonyms: 2,3-DIHYDRO-1H-INDOLE-4-CARBONITRILE HYDROCHLORIDE;1H-Indole-4-carbonitrile,2,3-dihydro-;Indoline-4-carbonitrile
• CAS NO: 885278-80-8
• Molecular Formula: C9H9ClN2
• Molecular Weight: 180.63416
• Mol File: 885278-80-8.mol
• Article Data: 7

Chemical Properties

• Boiling Point: 304.5±31.0 °C(Predicted)
• Appearance: /
• Density: 1.18±0.1 g/cm3(Predicted)
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 3.80±0.20(Predicted)
• CAS DataBase Reference: 2,3-DIHYDRO-1H-INDOLE-4-CARBONITRILE HYDROCHLORIDE(CAS DataBase Reference)
• NIST Chemistry Reference: 2,3-DIHYDRO-1H-INDOLE-4-CARBONITRILE HYDROCHLORIDE(885278-80-8)
• EPA Substance Registry System: 2,3-DIHYDRO-1H-INDOLE-4-CARBONITRILE HYDROCHLORIDE(885278-80-8)

Safety Data

• Hazardous Substances Data: 885278-80-8(Hazardous Substances Data)

Usage

General Description

2,3-Dihydro-1H-indole-4-carbonitrile hydrochloride is a chemical compound with the molecular formula C9H8ClN3. It is a white to off-white solid that is soluble in water and organic solvents. 2,3-DIHYDRO-1H-INDOLE-4-CARBONITRILE HYDROCHLORIDE is primarily used as an intermediate in the synthesis of pharmaceuticals and agrochemicals. It is also used in research and development as a building block for the creation of new compounds. In addition, it has potential applications in the field of medicinal chemistry for the development of new drugs. However, it is important to handle and store this chemical with care, as it may pose health hazards if not used and handled properly.

Upstream product

• 41910-64-9 4-chloroindoline 
• 57-13-6 urea 
• 16136-52-0 4-cyanoindole 
• 1578263-85-0 C₁₁H₇F₃N₂O 
• 1578263-84-9 C₁₀H₇BrF₃NO 
• 86626-38-2 4-bromo-2,3-dihydro-1H-indole 
• 52488-36-5 4-bromo-1H-indole 
• 557-21-1 zinc(II) cyanide 

Downstream Products

• 1578263-48-5 C₁₉H₁₈N₂O₃ 
• 1578263-49-6 1-(3-(4-fluorophenoxy)-2(S)-hydroxy-2-methylpropanoyl)indoline-4-carbonitrile 
• 1578263-50-9 C₁₉H₁₇FN₂O₃ 
• 1578263-51-0 C₁₉H₁₇FN₂O₃ 
• 1578263-52-1 C₁₉H₁₇ClN₂O₃ 
• 1578263-53-2 C₁₉H₁₇ClN₂O₃ 
• 1578263-54-3 C₁₉H₁₇ClN₂O₃ 
• 1578263-55-4 C₁₉H₁₇BrN₂O₃ 
• 1578263-56-5 C₂₀H₁₇F₃N₂O₃ 
• 1578263-57-6 C₂₀H₂₀N₂O₄ 
• 1578263-58-7 C₂₁H₂₀N₂O₅ 
• 1578263-59-8 C₂₂H₁₉N₃O₄ 
• 1578263-60-1 C₂₀H₁₇N₃O₃ 
• 1578263-61-2 C₂₀H₁₇F₃N₂O₃ 

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.

Gold-catalyzed C5-alkylation of indolines and sequential oxidative aromatization: Access to C5-functionalized indoles

A novel protocol for the synthesis of C5-alkylated indole derivatives via a gold-catalyzed reaction of indolines with diazo compounds and subsequent oxidative aromatization has been developed. C-H bond functionalization selectively occurs at the C5-position of indolines without a directing group. The experimental operation is simple and the whole process can be manipulated in one-pot.

1-(2-hydroxy-2-methyl-3-phenoxypropanoyl)indoline-4-carbonitrile derivatives as potent and tissue selective androgen receptor modulators

We present a novel series of selective androgen receptor modulators (SARMs) which shows excellent biological activity and physical properties. 1-(2-Hydroxy-2-methyl-3-phenoxypropanoyl)-indoline-4-carbonitriles showed potent binding to the androgen receptor (AR) and activated AR-mediated transcription in vitro. Representative compounds demonstrated diminished activity in promoting the intramolecular interaction between the AR carboxyl (C) and amino (N) termini. This N/C-termini interaction is a biomarker assay for the undesired androgenic responses in vivo. In orchidectomized rats, daily administration of a lead compound from this series showed anabolic activity by increasing levator ani muscle weight. Importantly, minimal androgenic effects (increased tissue weights) were observed in the prostate and seminal vesicles, along with minimal repression of circulating luteinizing hormone (LH) levels and no change in the lipid and triglyceride levels. This lead compound completed a two week rat toxicology study, and was well tolerated at doses up to 100 mg/kg/day, the highest dose tested, for 14 consecutive days.