92-15-9

Basic information

• Product Name: o-Acetoacetaniside
• Synonyms: 1-Acetoacetylamino-2-methoxybenzene;2’-methoxyacetoacetanilide;2-acetoacetanisidide;2-Acetoacetylaminoanisole;2'-Methoxyacetoacetanilide;2-Methoxyacetoacetanilide;2-Methoxyanilid kyseliny acetoctove;2-methoxyanilidkyselinyacetoctove
• CAS NO: 92-15-9
• Molecular Formula: C₁₁H₁₃NO₃
• Molecular Weight: 207.23
• EINECS: 202-131-0
• Product Categories: Intermediates of Dyes and Pigments;Aromatic amine products;Amides;Carbonyl Compounds;Organic Building Blocks
• Mol File: 92-15-9.mol

Chemical Properties

• Melting Point: 85-87 °C(lit.)
• Boiling Point: 346.25°C (rough estimate)
• Flash Point: 179.3 °C
• Appearance: Off-white powder
• Density: 1.1320
• Vapor Density: 7
• Vapor Pressure: 9.32E-06mmHg at 25°C
• Refractive Index: 1.5100 (estimate)
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 11.26±0.46(Predicted)
• CAS DataBase Reference: o-Acetoacetaniside(CAS DataBase Reference)
• NIST Chemistry Reference: o-Acetoacetaniside(92-15-9)
• EPA Substance Registry System: o-Acetoacetaniside(92-15-9)

Safety Data

• Hazard Codes: Xn
• Statements: 22
• WGK Germany: 1
• RTECS: BZ5600000
• Hazardous Substances Data: 92-15-9(Hazardous Substances Data)

Usage

Chemical Properties

Off-white powder

Uses

o-Acetoacetaniside is used a intermediate for the manufacture of organic pigments.

Safety Profile

A skin and eye irritant. When heated to decomposition it emits toxic fumes of NOx, Combustible when exposed to heat or flame or oxidizing materials. To fight fire, use CO2, mist, dry chemicals.

InChI:InChI=1/C11H13NO3/c1-8(13)7-11(14)12-9-5-3-4-6-10(9)15-2/h3-6H,7H2,1-2H3,(H,12,14)

Upstream product

• 674-82-8 4-methyleneoxetan-2-one 
• 90-04-0 2-methoxy-phenylamine 
• 5394-63-8 2,2,6-trimethyl-4H-1,3-dioxin-4-one 
• 105-45-3 acetoacetic acid methyl ester 
• 691-45-2 acetylketene 
• 6358-31-2 2-[(2-methoxy-4-nitrophenyl)azo]-N-(2-methoxyphenyl)-3-oxobutanamide 
• 141-97-9 ethyl acetoacetate 

Downstream Products

• 115081-07-7 2-xanthen-9-yl-acetoacetic acid o-anisidide 
• 42056-95-1 2-(hydroxyimino)-3-oxo-N-(2-methoxyphenyl)butanamide 
• 99840-99-0 3-amino-crotonic acid o-anisidide 
• 100061-20-9 acetoacetic acid-(2-methoxy-5-nitro-anilide) 
• 6375-00-4 3-acetoacetylamino-4-methoxy-benzenesulfonic acid 
• 124227-43-6 6-hydroxy-6-methyl-N,N'-di-(2-methoxyphenyl)-4-oxo-2-phenylcyclohexane-1,3-dicarboxamide 
• 112697-65-1 2-Methyl-[1,8]naphthyridine-3-carboxylic acid (2-methoxy-phenyl)-amide 
• 23433-48-9 3-methyl-2-<2-methoxyphenyl>aminocarbonylquinoxaline 1,4-dioxide 
• 138571-06-9 1,4-dihydro-2,6-dimethyl-3,5-bis<(o-anisylamino)carbonyl>pyridine 
• 123768-05-8 2-Methylquinoline-3-(o-methoxycarboxanilide) 
• 113449-16-4 methyl 2-((2-methoxyphenyl)amino)-2-oxoacetate 
• 1001067-64-6 2-(cyanomethyl)-N-(2-methoxyphenyl)-3-oxobutanamide 
• 6528-34-3 C₁₈H₁₈N₄O₆ 
• 906088-90-2 2-[1,3]dithiolan-2-ylidene-N-(2-methoxy-phenyl)-3-oxo-butyramide 

Relevant articles and documents

Structure-Activity Relationship Studies of Tetrahydroquinolone Free Fatty Acid Receptor 3 Modulators

Free fatty acid receptor 3 (FFA3, previously GPR41) is activated by short-chain fatty acids, mediates health effects of the gut microbiota, and is a therapeutic target for metabolic and inflammatory diseases. The shortage of well-characterized tool compounds has however impeded progress. Herein, we report structure-activity relationship of an allosteric modulator series and characterization of physicochemical and pharmacokinetic properties of selected compounds, including previous and new tools. Two representatives, 57 (TUG-1907) and 63 (TUG-2015), showed improved solubility and preserved potency. Of these, 57, with EC50 = 145 nM and a solubility of 33 μM, showed high clearance in vivo but is a preferred tool in vitro. In contrast, 63, with EC50 = 162 nM and a solubility of 9 μM, showed lower clearance and seems better suited for in vivo studies. Using 57, we demonstrate for the first time that FFA3 activation leads to calcium mobilization in murine dorsal root ganglia.

Effective microwave synthesis of bioactive thieno[2,3-d]pyrimidines

A series of novel 2-Amino-3-cyanothiophenes (2a-2j) were synthesized using heterogeneous base (K2CO3) supported Gewald reaction. Cyclization of 2a-j with formamide and urea in conventional heating as well as microwave irradiation gave thieno[2,3-d]pyrimidines (3a-3j) and thieno[2,3-d]pyrimidin-2(1H)-ones(4a-4j) respectively. The reaction rates were faster and yields were higher in the microwave conditions. The structures of the compounds were confirmed with elemental analysis, mass spectral analysis, FTIR, 1H NMR and 13C NMR techniques. All the synthesized compounds were subjected to antimicrobial activity (MIC) in vitro by broth dilution method and exhibited a moderate antimicrobial activity.

Acetyl aceotphenone amine preparation method of the compound

The invention provides a preparation method of an acetoacetanilide compound. The method comprises the steps of performing diacetylation reaction on aniline compounds and diketene in an organic solvent under anaerobic conditions to obtain the acetoacetanilide compound. The acetoacetanilide compound is prepared under the anaerobic conditions; the acetoacetanilide compound prepared by using the method has a relatively high melting point, thereby being beneficial for applications of the acetoacetanilide compound. In addition, the acetoacetanilide compound prepared by using the method provided by the invention is not easy to agglomerate, and the preparation method of the acetoacetanilide compound, provided by the invention, is relatively low in energy consumption. Experimental results show that the melting point of the acetoacetanilide compound prepared by using the method provided by the invention is 82.5-103 DEG C.

NOVEL COMPOUND WITH ANTIBACTERIAL ACTIVITY

A compound represented by the general formula (I) or a salt thereof having a potent antibacterial activity against bacteria that have acquired resistance to quinolones, and a medicament for prophylactic and/or therapeutic treatment of an infectious disease containing the compound or a salt thereof as an active ingredient, as well as a medicament for prophylactic and/or therapeutic treatment of an infectious disease containing a combination of the compound or a salt thereof, and a quinolone.

COMPOUNDS ACTIVE TOWARDS BROMODOMAINS

Disclosed are compounds towards bromodomains, pharmaceutical compositions containing the compounds and use of the compounds in therapy.

An efficient green protocol for the preparation of acetoacetamides and application of the methodology to a one-pot synthesis of Biginelli dihydropyrimidines. Expansion of dihydropyrimidine topological chemical space

The present study describes the preparation of N-aryl-(15) and N-alkyl-(17) acetoacetamides, in good to excellent yields, using both conventional and microwave heating, by reaction of amine derivatives (14 and 16) with 2,2,6-trimethyl-4H-1,3-dioxin-4-one (TMD, 12) in aqueous medium. The acetoacetamides were used to prepare novel Biginelli dihydropyrimidine derivatives. The introduction of the amino acid derivatives potentially allows for the exploration of new structural complexity and topologically diversifies the chemical space occupied by this versatile chemical scaffold.

Discovery and Optimization of Novel, Selective Histone Methyltransferase SET7 Inhibitors by Pharmacophore- and Docking-Based Virtual Screening

Histone methyltransferases are involved in various biological functions, and these methylation regulating enzymes' abnormal expression or activity has been noted in several human cancers. Within this context, SET domain-containing (lysine methyltransferase) 7 (SET7, also called KMT7, SETD7, SET9) is of increasing significance due to its diverse roles in biological functions and diseases, such as diabetes, cancers, alopecia areata, atherosclerotic vascular disease, HIV, and HCV. In this study, DC-S100, which was discovered by pharmacophore- and docking-based virtual screening, was identified as the hit compound of SET7 inhibitor. Structure-activity relationship (SAR) analysis was performed on analogs of DC-S100 and according to the putative binding mode of DC-S100, structure modifications were made to improve its activity. Of note, compounds DC-S238 and DC-S239, with IC50 values of 4.88 and 4.59 μM, respectively, displayed selectivity for DNMT1, DOT1L, EZH2, NSD1, SETD8, and G9a. Taken together, DC-S238 and DC-S239 can serve as leads for further investigation as SET7 inhibitors and the chemical toolkits for functional biology studies of SET7.

Diaryl-substituted polyethers with acetoacet-anilide fragment in the synthesis of dihydro-pyrimidine-containing podands

The interaction of ortho-aminoaryl polyethers, derivatives of mono-, di-, and triethylene glycol, with acetyl ketene, generated from 2,2,6-trimethyl-4H-1,3-dioxin-4-one produced acetoacetanilide- containing podands. 2,2,6-Trimethyl-4H-1,3-dioxin-4-one reacted with aminoaryl-substituted podands containing a short polyether chain (1-2 atoms) in toluene medium without catalyst. Acetoacetanilide- containing podands with longer polyether chains could be obtained by using triethylamine or acetic acid as catalyst. Acetoacetanilide-containing podands were used in the Biginelli reaction as CH-active components.

Ligand-enabled γ-C-H olefination and carbonylation: Construction of β-quaternary carbon centers

Monoselective γ-C-H olefination and carbonylation of aliphatic acids has been accomplished by using a combination of a quinoline-based ligand and a weakly coordinating amide directing group. The reaction provides a new route for constructing richly functionalized all-carbon quaternary carbon centers at the β-position of aliphatic acids.

Facile synthesis of furoquinoline and effects on radical-induced oxidation of DNA

The aim of this work was to clarify the influences of the position of hydroxyl group and furo[2,3-b] moiety on the antioxidant effectiveness of quinoline. Thus, 4-methyl-2,3-dihydrofuro[2,3-b]quinolin-6-ol (PFQ), 4-methyl-2,3-dihydrofuro[2,3-b]quinolin-8-ol (OFQ), and 4-methyl-2,3- dihydrofuro[2,3-b]quinolin-7-ol (MFQ) were synthesized by a recyclization reaction of 1-acetyl-N-phenylcyclopropanecarboxamide in the presence of SnCl4 as the catalyst. The antioxidant capacities of PFQ, OFQ, and MFQ were evaluated in the experimental system of the oxidation of DNA caused by Cu2+/glutathione (GSH), ?OH, and 2,2′-azobis(2- amidinopropane hydrochloride) (AAPH). OFQ and PFQ were able to protect DNA against Cu2+/GSH- and ?OH-induced oxidation because the furo[2,3-b] moiety was beneficial for stabilizing the produced furoquinoline radical. Moreover, MFQ can decrease the oxidation rate of AAPH-induced oxidation of DNA, while PFQ and OFQ can inhibit AAPH-induced oxidation of DNA for a period. The data obtained from AAPH-induced oxidation of DNA were treated by chemical kinetic method; it was found that PFQ and OFQ can trap 1.3 and 1.5 radicals, respectively. Therefore, the hydroxyl group at different positions changed the mechanism of furoquinoline in protecting DNA against radical-induced oxidation. Graphical Abstract: Effects on Cu2+/glutathione-, ?OH-, and peroxyl radical-induced oxidation of DNA.[Figure not available: see fulltext.]