703-80-0

Basic information

• Product Name: 3-Acetylindole
• Synonyms: TIMTEC-BB SBB003977;IFLAB-BB F1727-0313;1-(1H-INDOL-3-YL)ETHANONE;3-ACETYL-2,3-BENZOPYRROLE;3-ACETYL-1-BENZAZOLE;3-ACETYLINDOLE;3-INDOLYL METHYL KETONE;AKOS BBS-00004490
• CAS NO: 703-80-0
• Molecular Formula: C₁₀H₉NO
• Molecular Weight: 159.18
• EINECS: 211-875-5
• Product Categories: ACETYLGROUP;Indoles and derivatives;IndoleDerivative;Pyrroles & Indoles;Indole;Heterocyclic Compounds;Indoles;Simple Indoles;Pyrroles & Indoles;Building Blocks;C10;Chemical Synthesis;Heterocyclic Building Blocks
• Mol File: 703-80-0.mol
• Article Data: 98

Chemical Properties

• Melting Point: 188-192 °C(lit.)
• Boiling Point: 284.68°C (rough estimate)
• Flash Point: 163.7 °C
• Appearance: Yellow to light brown/Powder
• Density: 1.1202 (rough estimate)
• Vapor Pressure: 0.000132mmHg at 25°C
• Refractive Index: 1.6070 (estimate)
• Storage Temp.: Store below +30°C.
• Solubility: DMSO; Dichloromethane; Methanol
• PKA: 15.38±0.30(Predicted)
• BRN: 122579
• CAS DataBase Reference: 3-Acetylindole(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Acetylindole(703-80-0)
• EPA Substance Registry System: 3-Acetylindole(703-80-0)

Safety Data

• Safety Statements: 22-24/25
• WGK Germany: 3
• RTECS: OB4520000
• HazardClass: IRRITANT
• Hazardous Substances Data: 703-80-0(Hazardous Substances Data)

Usage

Chemical Properties

yellow to light brown powder

Uses

Different sources of media describe the Uses of 703-80-0 differently. You can refer to the following data:
1. Reactant for preparation of:? ;Indole derivatives as antitumor agents1? ;Endothelin-1 antagonists2? ;Oncrasin-1 derivatives as inhibitors of the C-terminal domain of RNA polymerase II with antitumor activities3? ;Inhibitors of hepatitis C NS3/4A serine protease4? ;Antibacterial agens against MDR Staphylococcus aureus strains5? ;Antimalarial agents6? ;Anti-bovine viral diarrhea virus (BVDV) agents7? ;HIV-1 integrase inhibitors8? ;Inhibitors of NF-κB transcription regulation related to TNF-α cytokine release9
2. Reactant for preparation of:Indole derivatives as antitumor agentsEndothelin-1 antagonistsOncrasin-1 derivatives as inhibitors of the C-terminal domain of RNA polymerase II with antitumor activitiesInhibitors of hepatitis C NS3/4A serine proteaseAntibacterial agens against MDR Staphylococcus aureus strainsAntimalarial agentsAnti-bovine viral diarrhea virus (BVDV) agentsHIV-1 integrase inhibitorsInhibitors of NF-κB transcription regulation related to TNF-α cytokine release
3. 3-Acetylindole can be used as anti-fungal agents.

Purification Methods

Recrystallise the indole from MeOH or *C6H6 containing a little EtOH. The phenylureido derivative has m 154o. [Baker J Chem Soc 461 1946, Beilstein 21/8 V 297.]

InChI:InChI=1/C10H9NO/c1-7(12)9-6-11-10-5-3-2-4-8(9)10/h2-6,11H,1H3

Upstream product

• 91-22-5 quinoline 
• 99055-69-3 1-indol-3-yl-ethanone-hydrazone 
• 64-19-7 acetic acid 
• 99532-45-3 3-acetyl-1-benzenesulfonylindole 
• 98258-81-2 3-(2-chloroacetyl)-1-methoxyindole 
• 141-78-6 ethyl acetate 
• 120-72-9 indole 
• 141-82-2 malonic acid 
• 110-15-6 succinic acid 
• 127-17-3 2-oxo-propionic acid 
• 4151-33-1 Pyruvic acid potassium salt 
• 62570-16-5 N-benzoyl-α-(3-indolyl)-1,2-dihydroquinoline 
• 99409-00-4 Ethoxy(3-indolyl)methylcarbenium-tetrafluoroborat 
• 105399-10-8 3-acetylindole-2-carboxylic acid 

Downstream Products

• 771-50-6 1H-indole-3-carboxylic acid 
• 38470-64-3 (2E)-1-(1H-indol-3-yl)-3-phenylprop-2-en-1-one 
• 72527-77-6 3-acetyl-4-iodoindole 
• 716305-02-1 3-(4-hydroxy-phenyl)-1-(1H-indol-3-yl)-propenone 
• 74364-11-7 3-methoxy-2-methyl-1-phenyl-9H-carbazole 
• 124604-63-3 C₂₄H₂₄N₂O₃ 
• 124604-56-4 1,6-dioxo-6a-(3,3-diphenyl-2-propenyl)-2,3,3a,4,5,6,6a,7a-octahydropyrido<3,2,1-jk>carbazole 
• 124604-67-7 (3aS,11bR,11cR)-11b-(3,3-Diphenyl-allyl)-1-trimethylsilanyloxy-3,3a,4,5,11b,11c-hexahydro-pyrido[3,2,1-jk]carbazol-6-one 
• 125569-83-7 9-(tert-butoxycarbonyl)-2-cyclohexyl-1-hydroxy-3-(triisopropylsiloxy)carbazole 
• 1269423-90-6 {4-[(1E)-3-(1H-indol-3-yl)-3-oxoprop-1-en-1-yl]phenoxy}acetic acid 
• 716305-03-2 1-[5-(4-hydroxy-3-methoxy-phenyl)-3-(1H-indol-3-yl)-4,5-dihydro-pyrazol-1-yl]-ethanone 
• 716305-06-5 1-[5-(4-dimethylamino-phenyl)-3-(1H-indol-3-yl)-4,5-dihydro-pyrazol-1-yl]-ethanone 
• 716305-07-6 1-[3-(1H-indol-3-yl)-5-(4-methoxy-phenyl)-4,5-dihydro-pyrazol-1-yl]-ethanone 
• 716305-04-3 3-[1-Acetyl-5-(p-hydroxyphenyl)-2-pyrazolin-3-yl] indole 

Relevant articles and documents

Synthesis, biological evaluation and molecular modeling of imidazo[1,2-a]pyridine derivatives as potent antitubulin agents

Two series of novel 5,7-diarylimidazo[1,2-a]pyridine-8-carbonitrile derivatives (3a–3q and 7a–7n) were designed by modification of CA-4 pharmacophore to develop colchicine targeted antitubulin agents. All compounds were efficiently synthesized and evaluated for their cytotoxicity against five selected cancer cell lines (HT-29, H460, A549, MKN-45 and SMMC-7721) which got an insight in structure and activity relationships (SARs). Several molecules (7e, 7f, 7h–7j and 7m) were disclosed to exhibit promising antiproliferative activity with IC50 values in double-digit nanomolar degree. Optimization toward these compounds led to the discovery of a promising lead 7e, which showed noteworthy potency with IC50 value ranging from 0.01 to 3.2?μM superior to CA-4 and Crolibulin. Importantly, immunofluorescence staining and colchcine competitive binding assay revealed that microtubule dynamics was disrupted by 7e by binding at the colchicine site of tubulin. Moreover, molecular docking studies suggested the binding of this mimic at colchcine-binding site is similar to Crolibulin, as was in conformity with the observed SARs for these compounds.

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.

KOH-mediated stereoselective alkylation of 3-bromooxindoles for the synthesis of 3,3′-disubstituted oxindoles with two contiguous all carbon quaternary centres

The stereoselective synthesis of 3,3′-disubstituted oxindoles having all-carbon quaternary stereocenters has been achieved using KOH as a base with an excellent diastereomeric ratio (98?:?2). The practicability of the present methodology has been validated with the synthesis of a series of substrates in good to excellent yields. The aesthetic simplicity, accessibility, and eco-friendly base (KOH) have prompted the broader application of the present methodology in organic synthesis.