316181-82-5

Basic information

• Product Name: 3-Acetyl-6-bromoindole
• Synonyms: 3-Acetyl-6-bromoindole;1-(6-BROMO-1H-INDOL-3-YL)ETHANONE;1-(6-broMo-1H-indol-3-yl)ethan-1-one
• CAS NO: 316181-82-5
• Molecular Formula: C₁₀H₈BrNO
• Molecular Weight: 238.08062
• Product Categories: Indole
• Mol File: 316181-82-5.mol

Chemical Properties

• Boiling Point: 388.995 °C at 760 mmHg
• Flash Point: 189.058 °C
• Appearance: /
• Density: 1.592 g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.676
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 3-Acetyl-6-bromoindole(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Acetyl-6-bromoindole(316181-82-5)
• EPA Substance Registry System: 3-Acetyl-6-bromoindole(316181-82-5)

Safety Data

• Hazardous Substances Data: 316181-82-5(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Synthesis:
3-Acetyl-6-bromoindole is used as a key intermediate in the development of new drugs and therapeutic agents. Its unique structure allows for the creation of a variety of pharmaceutical compounds, contributing to advancements in medicinal chemistry.
Used in Organic Synthesis:
In the realm of organic synthesis, 3-Acetyl-6-bromoindole serves as a valuable building block for the production of various organic molecules. Its presence in the synthesis process enhances the diversity and complexity of the resulting organic compounds, broadening the scope of chemical research and applications.

InChI:InChI=1/C10H8BrNO/c1-6(13)9-5-12-10-4-7(11)2-3-8(9)10/h2-5,12H,1H3

Upstream product

• 52415-29-9 6-bromo-1H-indole 
• 75-36-5 acetyl chloride 
• 108-24-7 acetic anhydride 

Downstream Products

• 224434-85-9 1-(6-bromo-1-tosyl-1H-indol-3-yl)ethan-1-one 
• 290333-09-4 1-[1-[(4-methylphenyl)sulfonyl]-6-bromo-1H-indol-3-yl]-3-(dimethylamino)-2-propen-1-one 
• 1311395-23-9 4-(6-bromo-1H-indol-3-yl)-5-(4-acetylphenyl)pyrimidin-2-amine 
• 1311395-27-3 4-[2-amino-4-(6-bromo-1H-indol-3-yl)pyrimidin-5-yl]benzamide 
• 1311395-31-9 4-(6-bromo-1H-indol-3-yl)-5-(4-trifluoromethylphenyl)pyrimidin-2-amine 
• 1311395-35-3 4-(6-bromo-1H-indol-3-yl)-5-(3-methoxyphenyl)pyrimidin-2-amine 

Relevant articles and documents

A radical addition and cyclization relay promoted by Mn(OAc)3?2H2O: Synthesis of 1,2-oxaphospholoindoles and mechanistic study

Novel and efficient Mn(OAc)3?2H2O promoted radical addition-[4 + 1] cyclization relay of 3-indolymethanols and phosphites was disclosed, which afforded 1,2-oxaphospholoindole derivatives in moderate to good yields. Based on the experimental and computational studies, a mechanism involving radical addition and intramolecular cyclization cascade was proposed.

Cascade Reaction to Selectively Synthesize Multifunctional Indole Derivatives by IrIII-Catalyzed C?H Activation

An effective and condition-controlled way to synthesize with high selectivity a variety of functionalized indoles with potent biological properties has been developed. Notably, 2,4-dialkynyl indole products were obtained by direct double C?H bond alkynylation, whereas alkynyl at the C4 position could convert to carbonyl to generate 2-alkynyl-3,4-diacetyl indoles fast and effectively. Additionally, a one-pot relay catalytic reaction led to 2,5-di-alkynyl-3,4-diacetyl indoles when using a carbonyl group as the directing group and by controlling the type and quantity of additives. A possible mechanism was proposed based on many studies including deuterium-exchange experiments, the necessary conditions of product conversion, and the effect of water on the reaction.

REV-ERB AGONISTS FOR THE TREATMENT OF TH17-MEDIATED INFLAMMATORY DISORDERS

The present disclosure provides compounds of Formula IA and Formula IB and their pharmaceutical compositions as selective agonists of REV-ERB-α: where R1, R2, R3, R4, R5, RX1, RX2, nA, nB, X, Y, and Z are described herein. The compounds are useful in various methods and uses, such as in the treatment of diseases including hyperglycemia, dyslipidemia, atherosclerosis, and autoimmune and inflammatory disorders or diseases, and as cancer therapeutics, such as for the treatment of glioblastoma, hepatocellular carcinoma, and colorectal cancer, and for immune-oncology purposes.

Ketone-Directed Cobalt(III)-Catalyzed Regioselective C2 Amidation of Indoles

An efficient cobalt(III)-catalyzed method for the direct C-H amidation of unprotected indoles for 2-amino indole scaffold construction has been developed. With dioxazolone as the amidating reagent, a variety of 2-amino indole derivatives were achieved in moderate to excellent yields using an organic acid as the additive and a ketone as the directing group.

Preparation and application of pyrimidinedionoindole and pyridinonoindole compounds

The invention relates to a preparation method of a compound containing a pyrimidine-2, 4-diono[5, 4-b]indole skeleton or a pyridine-2-ono[3, 2-d]indole skeleton, and further relates to medical application of the compound serving as a BET Bromo structural domain inhibitor.

Weak Coordination Enabled Switchable C4-Alkenylation and Alkylation of Indoles with Allyl Alcohols

A weak carbonyl coordination facilitated tunable reactivity between alkenylation and alkylation of indoles at the C4 C-H site is presented using readily accessible allylic alcohols in the presence of Rh catalysis by switching the additives or directing group. Exclusive site selectivity, functional group tolerance, and late-stage modifications are the important practical features.

Second-Generation Meridianin Analogues Inhibit the Formation of Mycobacterium smegmatis Biofilms and Sensitize Polymyxin-Resistant Gram-Negative Bacteria to Colistin

Drug-resistant bacteria are rapidly becoming a significant problem across the globe. One element that factors into this crisis is the role played by bacterial biofilms in the recalcitrance of some infections to the effects of conventional antibiotics. Bacteria within a biofilm are highly tolerant of both antibiotic treatment and host immune responses. Biofilms are implicated in many chronic infections, including tuberculosis, in which they can act as bacterial reservoirs, requiring an arduous antibiotic regimen to eradicate the infection. A separate, compounding problem is that antibiotics once seen as last-resort drugs, such as the polymyxin colistin, are now seeing more frequent usage as resistance to front-line drugs in Gram-negative bacteria becomes more prevalent. The increased use of such antibiotics inevitably leads to an increased frequency of resistance. Drugs that inhibit biofilms and/or act as adjuvants to overcome resistance to existing antibiotics will potentially be an important component of future approaches to antibacterial treatment. We have previously demonstrated that analogues of the meridianin natural product family possess adjuvant and antibiofilm activities. In this study, we explore structural variation of the lead molecule from previous studies, and identify compounds showing both improved biofilm inhibition potency and synergy with colistin.

Weak Coordination-Guided Regioselective Direct Redox-Neutral C4 Allylation of Indoles with Morita-Baylis-Hillman Adducts

A weak carbonyl coordination-guided regioselective C4 allylation of indoles is demonstrated using the versatile Morita-Baylis-Hillman adduct in the presence of Rh catalysts in a redox-neutral fashion. The substrate scope, functional group diversity, oxidant free character, mechanistic aspects, and synthetic utilities are important practical features.

PHARMACEUTICAL COMPOUNDS FOR TREATMENT OF MEDICAL DISORDERS

Complement Factor D inhibitors, pharmaceutical compositions, and uses thereof, as well as processes for their manufacture are provided. The compounds provided include Formula I, Formula II, Formula III, and Formula IV or a pharmaceutically acceptable salt, prodrug, isotopic analog, N-oxide, or isolated isomer thereof, optionally in a pharmaceutically acceptable composition. The inhibitors described herein target Factor D and inhibit or regulate the complement cascade.

Meridianin D Analogues Display Antibiofilm Activity against MRSA and Increase Colistin Efficacy in Gram-Negative Bacteria

In the last 30 years, development of new classes of antibiotics has slowed, increasing the necessity for new options to treat multidrug resistant bacterial infections. Development of antibiotic adjuvants that increase the effectiveness of currently available antibiotics is a promising alternative approach to classical antibiotic development. Reports of the ability of the natural product meridianin D to modulate bacterial behavior have been rare. Herein, we describe the ability of meridianin D to inhibit biofilm formation of methicillin-resistant Staphylococcus aureus (MRSA) and to increase the potency of colistin against colistin-resistant and sensitive Gram-negative bacteria. Analogues were identified that are capable of inhibiting and dispersing MRSA biofilms and lowering the colistin MIC to below the CLSI breakpoint against Acinetobacter baumannii, Klebsiella pneumoniae, and Escherichia coli.