62368-29-0

Basic information

• Product Name: 1-ACETYL-6-AMINOINDOLINE
• Synonyms: 1-(6-Aminoindolin-1-yl)ethanone;1-Acetyl-6-amino-2,3-dihydro-1H-indole, 1-Acetyl-2,3-dihydro-1H-indol-6-amine;Ethanone, 1-(6-aMino-2,3-dihydro-1H-indol-1-yl)-;1-(6-Amino-2,3-dihydro-indol-1-yl)ethanone;1-Acetyl-6-amino-2,3-dihydroindole;6-Amino-N-acetylindoline;NSC 87623;1-(6-amino-1-indolinyl)ethanone
• CAS NO: 62368-29-0
• Molecular Formula: C₁₀H₁₂N₂O
• Molecular Weight: 176.22
• Product Categories: Building Blocks;Heterocyclic Compounds;Building Blocks;Heterocyclic Building Blocks;Indoles
• Mol File: 62368-29-0.mol

Chemical Properties

• Melting Point: 182 °C
• Boiling Point: 453.2 °C at 760 mmHg
• Flash Point: 227.9 °C
• Appearance: yellow to tan/powder
• Density: 1.231 g/cm³
• Vapor Pressure: 2.11E-08mmHg at 25°C
• Refractive Index: 1.628
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 1-ACETYL-6-AMINOINDOLINE(CAS DataBase Reference)
• NIST Chemistry Reference: 1-ACETYL-6-AMINOINDOLINE(62368-29-0)
• EPA Substance Registry System: 1-ACETYL-6-AMINOINDOLINE(62368-29-0)

Safety Data

• Hazard Codes: Xn,Xi
• Statements: 22
• WGK Germany: 3
• Hazardous Substances Data: 62368-29-0(Hazardous Substances Data)

Usage

Uses

1-Acetyl-6-aminoindoline is used as a reactant for the preparation of:
Transient receptor potential cation channel V1 (TRPV1) antagonists: These are compounds that block the TRPV1 ion channel, which is involved in pain sensation, body temperature regulation, and other physiological processes. The synthesis of such antagonists using 1-Acetyl-6-aminoindoline can contribute to the development of potential therapeutic agents for pain management and other related conditions.
Inhibitors of the human immunodeficiency virus (HIV) envelope glycoprotein gp120 binding to the cluster of differentiation 4 (CD4) receptor: By inhibiting the interaction between gp120 and CD4, these compounds can potentially be used in the development of antiretroviral drugs to combat HIV infection.
Antiproliferative agents: These are substances that inhibit cell proliferation, which can be useful in the development of cancer treatments and other conditions where uncontrolled cell growth is a concern.
Serotonin 5-HT2C/2B receptor antagonists: These compounds block the serotonin receptors 5-HT2C and 5-HT2B, which can be relevant in the treatment of various psychiatric and neurological disorders, such as depression, anxiety, and schizophrenia.
Additionally, 1-Acetyl-6-aminoindoline is used as a reactant in the synthesis of anilines, phenols, and heterocycles with aryl iodides. This application highlights its versatility in organic chemistry and its potential use in the development of a wide range of chemical compounds and materials.
Used in Pharmaceutical Industry:
1-Acetyl-6-aminoindoline is used as a key intermediate for the synthesis of various pharmaceutical compounds, including those with potential applications in pain management, HIV treatment, cancer therapy, and the treatment of psychiatric and neurological disorders.
Used in Chemical Synthesis:
1-Acetyl-6-aminoindoline is used as a versatile building block in the synthesis of anilines, phenols, and heterocycles with aryl iodides, contributing to the development of a diverse range of chemical compounds and materials.

InChI:InChI=1/C10H12N2O/c1-7(13)12-5-4-8-2-3-9(11)6-10(8)12/h2-3,6H,4-5,11H2,1H3

Upstream product

• 22949-08-2 1-acetyl-6-nitro-2,3-dihydroindole 
• 19727-83-4 6-nitroindoline 
• 496-15-1 1-indoline 
• 4769-96-4 6-nitroindole 
• 108-24-7 acetic anhydride 

Downstream Products

• 115666-43-8 1-acetyl-2,3-dihydro-6-iodoindole 
• 4770-34-7 1-acetyl-6-hydroxy-2,3-dihydroindole 
• 396682-63-6 1-[6-(1-benzyl-piperidin-4-ylamino)-2,3-dihydro-indol-1-yl]-ethanone 
• 848951-74-6 1-[6-(1-phenethyl-piperidin-4-ylamino)-2,3-dihydro-1ndol-1yl]-ethanone 
• 849355-51-7 methyl N-(1-acetylindolin-6-yl)-2-sulfamoyl benzoate 
• 872876-52-3 (R)-N-carbobenzyloxy-6'-iodotryptophan 
• 872877-29-7 (S)-N-carbobenzyloxy-6'-iodotryptophan 
• 872876-93-2 (R)-N-carbobenzyloxy-6'-iodotryptophan tert-butyl ester 
• 872877-20-8 (R)-6-(4,4,5,5-tetramethyl[1,3,2]dioxaborolan-2-yl)-N-carbobenzyloxytryptophan 
• 872877-18-4 (R)-6-(4,4,5,5-tetramethyl[1,3,2]dioxaborolan-2-yl)-N-carbobenzyloxy-6'-iodotryptophan tert-butyl ester 
• 872876-83-0 (R,R)-(6'-iodo-N-carbobenzyloxytryptophyl)-3',5'-dichloro-4'-hydroxyphenylglycine tert-butyl ester 
• 872876-95-4 (R,R)-3-{6-[3-(N-tert-butoxycarbonyl-2-methoxycarbonylmethylamino)-5-iodo-6-methoxyphenyl]indol-3-yl}-2-carbobenzyloxyaminopropionic acid tert-butyl ester 
• 115666-47-2 6-iodo-1 H-indole 
• 115666-46-1 6-iodo-2,3-dihydro-1H-indole 

Relevant articles and documents

Synthesis of Pyranocyclopentaindolines Representing the Western Sections of Janthitrem B, JBIR-137, and Shearinine G

The synthesis of the ABCD tetracyclic partial structures of the fungal indole diterpenes janthitrem B, JBIR-137, and shearinine G is reported. The route starts from 5-formylated indoline that is coupled to a dihydropyran moiety, followed by Prins cyclization. A diene was obtained that was oxygenated in a divergent manner. The hydroxylated tetracyclic western half of janthitrem B was obtained in eight steps and 10 % overall yield. We also share our experience with alternative approaches passing via alkynylated precursors. This includes the gold-catalyzed cycloisomerization of a 6-ethynyl-5-prenylindoline.

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New antiproliferative benzoindolinothiazepines derivatives

New benzoindolinothiazepines containing a piperazine moiety are described as potent antiproliferative agents against PC3 human prostatic cell lines. This activity could be explained by an accumulation of cells in G1 phase.

Synthesis of substituted benzoindolinothiazepines using 5- And 6-nitroindolines

The synthesis of benzoindolothiazepine compounds was investigated using Friedel-Crafts reactions conditions from indolines. The amine function of indolinic identity was protected to avoid an alkylation of this function by methyl iodide. It was observed that the treatment of the desired amines with commercially available methyl chlorosulfanoylbenzonate resulted in the formation of sulfonamide compounds. It was also observed that the cyclization of the carboxylic acid under Friedel-Crafts conditions resulted in the formation of the desired tetracycles.

Photo-induced rearrangement of 1-ethoxy-2-phenylindole

Photoirradiation of 1-ethoxy-2-phenylindole in methanol afforded 3- and 6-ethoxy-2-phenylindoles. The structural determination of the latter is carried out by direct comparison of its spectral data with those of the authentic 4-, 5-, 6-, and 7-ethoxy-2-phenylindoles, whose syntheses are also included.