16078-30-1

Basic information

• Product Name: 1-ACETYLINDOLINE
• Synonyms: 1-acetyl-2,3-dihydro-1h-indol;1-acetyl-indolin;1-(2,3-DIHYDRO-1H-INDOL-1-YL)ETHAN-1-ONE;1-(2,3-DIHYDRO-INDOL-1-YL)-ETHANONE;1-ACETYL-2,3-DIHYDROINDOLE;1-ACETYLINDOLINE;N-ACETYL INDOLINE;Acetylindoline,N-
• CAS NO: 16078-30-1
• Molecular Formula: C₁₀H₁₁NO
• Molecular Weight: 161.20044
• Product Categories: ACETYLGROUP;Indoles and derivatives;Indoline & Oxindole;Building Blocks;Heterocyclic Building Blocks;Indoles;Building Blocks;C10;Chemical Synthesis;Heterocyclic Building Blocks
• Mol File: 16078-30-1.mol

Chemical Properties

• Melting Point: 102-104 °C(lit.)
• Boiling Point: 355.1 °C at 760 mmHg
• Flash Point: 174.5 °C
• Appearance: Off-white crystals
• Density: 1.144 g/cm³
• Vapor Pressure: 3.2E-05mmHg at 25°C
• Refractive Index: 1.575
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 1.13±0.20(Predicted)
• CAS DataBase Reference: 1-ACETYLINDOLINE(CAS DataBase Reference)
• NIST Chemistry Reference: 1-ACETYLINDOLINE(16078-30-1)
• EPA Substance Registry System: 1-ACETYLINDOLINE(16078-30-1)

Safety Data

• Safety Statements: 22-24/25
• WGK Germany: 3
• RTECS: NM1892500
• Hazardous Substances Data: 16078-30-1(Hazardous Substances Data)

Usage

Uses

1. Used in Pharmaceutical Industry:
1-Acetylindoline is used as a reactant for the preparation of triazolothiadiazepine dioxide derivatives, which are potentially valuable in the development of new pharmaceutical compounds.
2. Used in Chemical Synthesis:
1-Acetylindoline is used as a reactant for the preparation of halo-substituted aromatic amides, which are important building blocks in the synthesis of various organic compounds.
3. Used in Medicinal Chemistry:
1-Acetylindoline is used as a reactant for the preparation of [[(phenyl)piperazinyl]alkyl]indolyl]ethanone and [[[(phenoxyethyl)piperazinyl]alkyl]indolyl]ethanone derivatives, which are known as α1-adrenoreceptor antagonists. These compounds have potential applications in the treatment of various medical conditions, such as hypertension and benign prostatic hyperplasia.
4. Used in Antimicrobial Agents:
1-Acetylindoline is used as a reactant for the synthesis of naphthalenedione derivatives, which exhibit antimycobacterial activity. These compounds can be used in the development of new drugs to combat tuberculosis and other mycobacterial infections.
5. Used in Organic Chemistry:
1-Acetylindoline is used as a reactant for regioselective ortho Suzuki-Miyaura coupling reactions, which are important for the formation of carbon-carbon bonds in the synthesis of complex organic molecules. This application is relevant in various fields, including pharmaceuticals, materials science, and agrochemicals.

Synthesis Reference(s)

Tetrahedron, 52, p. 7525, 1996 DOI: 10.1016/0040-4020(96)00266-9Tetrahedron Letters, 24, p. 561, 1983 DOI: 10.1016/S0040-4039(00)81464-1

InChI:InChI=1/C10H11NO/c1-8(12)11-7-6-9-4-2-3-5-10(9)11/h2-5H,6-7H2,1H3

Upstream product

• 496-15-1 1-indoline 
• 99293-86-4 N-acetylindolin-3-ol 
• 16800-68-3 1-acetyl-2,3-dihydro-1H-indol-3-one 
• 16800-67-2 N,O-diacetylindoxyl 
• 90869-54-8 acetic acid-[2-(2-chloro-ethyl)-anilide] 
• 69258-86-2 2-(2-acetylaminophenyl)ethyl alcohol 
• 120-72-9 indole 
• 64-19-7 acetic acid 
• 108-24-7 acetic anhydride 
• 104682-95-3 1-acetyl-2,3-dihydro-7-iodoindole 
• 292638-85-8 acrylic acid methyl ester 
• 86296-00-6 N-methoxy-N-<2-(o-bromophenyl)ethyl>amine 
• 75-36-5 acetyl chloride 
• 186581-53-3 diazomethane 

Downstream Products

• 16078-35-6 1-(1-acetylindolin-5-yl)ethanone 
• 105907-13-9 1-(1-acetyl-indolin-7-yl)-2-chloro-ethanone 
• 76139-03-2 2-chloro-1-(1-acetyl-2,3-dihydroindole-5-yl)ethanone 
• 22190-38-1 5-bromo-N-acetylindoline 
• 33632-27-8 1-(5-nitro-2,3-dihydroindol-1-yl)ethanone 
• 576-15-8 N-acetylindole 
• 153247-93-9 1-acetylindoline-5-carboxylic acid 
• 16078-34-5 5-Acetyl-2,3-dihydro-1H-indole 
• 147265-76-7 6-Acetyl-2,3-dihydro-1H-indole 
• 104019-19-4 7-acetylindoline 
• 114144-24-0 1-acetyl-2,3-dihydro-7-bromoindole 
• 4993-96-8 1-(5-aminoindolin-1-yl)ethanone 
• 52206-05-0 1-acetyl-2,3-dihydro-1H-indole-5-sulfonyl chloride 
• 4770-36-9 1-acetyl-2,3-dihydro-7-hydroxyindole 

Relevant articles and documents

Mild Rh(III)-catalyzed C7-allylation of indolines with allylic carbonates

The rhodium(III)-catalyzed direct allylation of indolines with allylic carbonates at room temperature is described. These transformations provide the facile and efficient construction of C7-allylated indolic scaffold.

Exploration of the diketoacid integrase inhibitor chemotype leading to the discovery of the anilide-ketoacids chemotype

Integrase is one of three enzymes expressed by HIV and represents a validated target for therapy. A previous study of the diketoacid-based chemotype suggested that there are two aryl-binding domains on integrase. In this study, modifications to the indole-based diketoacid chemotype are explored. It is demonstrated that the indole group can be replaced with secondary but not tertiary (e.g., N-methyl) aniline-based amides without sacrificing in vitro inhibitory activity. The difference in activity between the secondary and tertiary amides is most likely due to the opposite conformational preferences of the amide bonds, s-trans for the secondary-amide and s-cis for the tertiary-amide. However, it was found that the conformational preference of the tertiary amide can be reversed by incorporating the amide nitrogen atom into an indoline heterocycle, resulting in very potent integrase inhibitors.

A rapid and clean synthetic approach to cyclic peptides: Via micro-flow peptide chain elongation and photochemical cyclization: Synthesis of a cyclic RGD peptide

A cyclic RGD peptide was efficiently synthesized based on micro-flow, triphosgene-mediated peptide chain elongation and micro-flow photochemical macrolactamization. Our approach enabled a rapid (amidation for peptide chain elongation 5 s, macrolactamization 5 min) and clean (only one column chromatographic separation) synthesis of a cyclic peptide.

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.

Cobalt Catalyzed Hydroarylation of Michael Acceptors with Indolines Directed by a Weakly Coordinating Functional Group

A cobalt(III) catalyzed hydroarylation of Michael acceptors using indolines, selectively at the C-7 position, has been reported. For the selective C-7 functionalization of indoline, we have used a weakly coordinating amide carbonyl group. During the process of optimization, we have also discovered the unusual cocatalytic activity of zinc triflate in the C-H functionalization reaction. Hydroarylation of unprotected maleimide using indolines was a challenging substrate and never accomplished before, we were able to achieve this with our methodology in good yields.

Oxidative palladium(II)-catalyzed C-7 alkenylation of indolines

A mild procedure for C-7-selective C-H alkenylation of various indolines under oxidative palladium(II) catalysis is reported. A fully substituted urea, formed by carbamoylation of the indoline nitrogen atom, functions as a directing group. Both α,β-unsaturated acceptors and styrenes participate in this direct C-H functionalization. With a free NH group at the urea terminus, the nitrogen atom subsequently cyclizes in a 1,4-fashion to yield a six-membered ring.

Method for promoting acylation of amine or alcohol by carbon dioxide

The invention relates to a method for promoting acylation of amine or alcohol by carbon dioxide, which comprises the following steps of: mixing an amine compound, carboxylate or thiocarboxylate compound and a reaction solvent under the action of carbon dioxide, and reacting to obtain an amide compound, or under the action of carbon dioxide, mixing the alcohol compound, the thiocarboxylate compound and the reaction solvent [gamma]-valerolactone, and reacting to obtain the ester compound. According to the invention, under the promotion action of carbon dioxide, carboxylate or thiocarboxylate is used as an acylation reagent, and amine and alcohol are converted into amide and ester compounds in the absence of a transition metal catalyst, so that acylation reagents such as acyl chloride or anhydride with irritation and corrosivity are avoided; and the method has the advantages of simple operation, mild reaction conditions, high tolerance of substrate functional groups, strong applicability and high yield, and provides an efficient, reliable and economical preparation method for synthesis of amide and ester compounds.

Preparation and catalytic evaluation of a palladium catalyst deposited over modified clinoptilolite (Pd&at;MCP) for chemoselective N-formylation and N-acylation of amines

Novel palladium nanoparticles stabilized by clinoptilolite as a natural inexpensive zeolite prepared and used for N-formylation and N-acylation of amines at room temperature at environmentally benign reaction conditions in good to excellent yields. Pd (II) was immobilized on the surface of clinoptilolite via facile multi-step amine functionalization to obtain a sustainable, recoverable, and highly active nano-catalyst. The structural and morphological characterizations of the catalyst carried out using XRD, FT-IR, BET and TEM techniques. Moreover, the catalyst is easily recovered using simple filtration and reused for 7 consecutive runs without any loss in activity.

The Relation Between Position and Chemical Composition of Bis-Indole Substituents Determines Their Interactions with G-Quadruplex DNA

G-quadruplex (G4) DNA structures are linked to fundamental biological processes and human diseases, which has triggered the development of compounds that affect these DNA structures. However, more knowledge is needed about how small molecules interact with G4 DNA structures. This study describes the development of a new class of bis-indoles (3,3-diindolyl-methyl derivatives) and detailed studies of how they interact with G4 DNA using orthogonal assays, biophysical techniques, and computational studies. This revealed compounds that strongly bind and stabilize G4 DNA structures, and detailed binding interactions which for example, show that charge variance can play a key role in G4 DNA binding. Furthermore, the structure–activity relationships generated opened the possibilities to replace or introduce new substituents on the core structure, which is of key importance to optimize compound properties or introduce probes to further expand the possibilities of these compounds as tailored research tools to study G4 biology.

Efficient synthesis process of medical intermediate 5-bromoindole

The invention discloses an efficient synthesis process of a medical intermediate 5-bromoindole, comprising the following steps of: using an indole compound as a raw material, carrying out low-pressureliquid-phase hydrogenation to destroy five-membered ring conjugation of indole to obtain an indoline compound; enabling the indoline compound to react with an acylation reagent, and protecting nitrogen, so as to obtain an N-acyl indoline compound; carrying out bromination on the N-acyl indoline compound to obtain a 5-bromo-N-acyl indoline compound; carrying out deacylation protection on the 5-bromo-N-acyl indoline compound to obtain a 5-bromoindoline compound; and carrying out oxidative dehydrogenation on the 5-bromoindoline compound by using oxygen or air under the action of a cuprous catalyst and nitric oxide to obtain the target compound 5-bromoindole. The steps involved in the process are convenient to operate, the conditions are mild, and environmental pollution is reduced; finally,the prepared product is high in yield, high in purity and low in energy consumption.