2415-87-4

Basic information

• Product Name: 3'-chloroacetoacetanilide
• Synonyms: N-(3-chlorophenyl)-3-keto-butyramide;N-(3-Chlorophenyl)-3-oxobutyramide;N-(3-Chlorophenyl)
• CAS NO: 2415-87-4
• Molecular Formula: C₁₀H₁₀ClNO₂
• Molecular Weight: 211.65
• EINECS: 219-328-2
• Mol File: 2415-87-4.mol

Chemical Properties

• Melting Point: 101.0 to 105.0 °C
• Boiling Point: 397.0±27.0 °C(Predicted)
• Appearance: /
• Density: 1.285±0.06 g/cm3(Predicted)
• PKA: 10.99±0.46(Predicted)
• CAS DataBase Reference: 3'-chloroacetoacetanilide(CAS DataBase Reference)
• NIST Chemistry Reference: 3'-chloroacetoacetanilide(2415-87-4)
• EPA Substance Registry System: 3'-chloroacetoacetanilide(2415-87-4)

Safety Data

• Hazardous Substances Data: 2415-87-4(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
3'-chloroacetoacetanilide is used as an intermediate in the synthesis of various pharmaceuticals for its versatile reactivity and synthetic potential. It plays a crucial role in the development of new drugs and medicines.
Used in Agrochemical Industry:
3'-chloroacetoacetanilide is used as an intermediate in the synthesis of various agrochemicals, contributing to the development of effective pesticides and other agricultural chemicals.
Used in Dye and Pigment Industry:
3'-chloroacetoacetanilide is used as a precursor for the preparation of dyes, pigments, and other organic compounds, enabling the creation of a wide range of colors and properties in various applications.
Used in Organic Synthesis:
3'-chloroacetoacetanilide is utilized as a valuable building block in organic synthesis, allowing chemists to create a variety of complex organic molecules for research and industrial purposes.
However, it is important to handle 3'-chloroacetoacetanilide with caution due to its potential health hazards and environmental impact. Proper safety measures should be taken during its production, use, and disposal to minimize any adverse effects.

Upstream product

• 105-45-3 acetoacetic acid methyl ester 
• 108-42-9 3-chloro-aniline 
• 141-97-9 ethyl acetoacetate 
• 674-82-8 4-methyleneoxetan-2-one 

Downstream Products

• 463342-78-1 (1Z)-2-[(3-chlorophenyl)amino]-2-oxo-N-phenylethanehydrazonoyl chloride 
• 463342-80-5 (1Z)-N-(2-chlorophenyl)-2-[(3-chlorophenyl)amino]-2-oxoethanehydrazonoyl chloride 
• 463342-82-7 (1Z)-N-(3-chlorophenyl)-2-[(3-chlorophenyl)amino]-2-oxoethanehydrazonoyl chloride 
• 1434475-82-7 (Z)-3-((3-chlorophenyl)amino)-1-phenylprop-2-en-1-one 
• 146140-57-0 2-(bis(methylthio)methylene)-N-(3-chlorophenyl)-3-oxobutanamide 
• 421576-00-3 N-(3-chlorophenyl)-4-(3,4-dimethoxyphenyl)-6-methyl-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxamide 
• 332373-17-8 N-(3-chlorophenyl)-4-(3-chlorophenyl)-6-methyl-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxamide 
• 332373-19-0 N,4-bis(3-chlorophenyl)-6-methyl-2-thioxo-1,2,3,4-tetrahydropyrimidine-5-carboxamide 

Relevant articles and documents

Ru-NHC-Catalyzed Asymmetric Hydrogenation of 2-Quinolones to Chiral 3,4-Dihydro-2-Quinolones

Direct enantioselective hydrogenation of unsaturated compounds to generate chiral three-dimensional motifs is one of the most straightforward and important approaches in synthetic chemistry. We realized the Ru(II)-NHC-catalyzed asymmetric hydrogenation of 2-quinolones under mild reaction conditions. Alkyl-, aryl- and halogen-substituted optically active dihydro-2-quinolones were obtained in high yields with moderate to excellent enantioselectivities. The reaction provides an efficient and atom-economic pathway to construct simple chiral 3,4-dihydro-2-quinolones. The desired products could be further reduced to tetrahydroquinolines and octahydroquinolones.

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.

Design, Multicomponent Synthesis and Characterization of Diversely Substituted Pyrazolo[1,5-a] Pyrimidine Derivatives

The synthesis of various heterocyclic compounds using acetoacetanilide[AAA], we have demonstrated that acetoactanilide are versatile intermediate for the synthesis of pyrazolopyrimidine derivatives. Thus, to explore further, we sought that the reaction of various acetoactanilide, an appropriate aldehyde and 5-amino-N-cyclohexyl-3-(methylthio)-1H-pyrazole-4-carboxamide in the presence of base in isopropyl alcohol could be an effective strategy to furnish the novel pyrazolopyrimidine derivatives. Here we describe the novel synthetic methodology for the fused pyrazolopyrimidines.

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.

Targeting dormant tuberculosis bacilli: Results for molecules with a novel pyrimidone scaffold

Our inability to completely control TB has been due in part to the presence of dormant mycobacteria. This also renders drug regimens ineffective and is the prime cause of the appearance of drug-resistant strains. In continuation of our efforts to develop novel antitubercular agents that especially target dormant mycobacteria, a set of 55 new compounds belonging to the pyrimidone class were designed on the basis of CoMFA and CoMSIA studies, and these were synthesized and subsequently tested against both the dormant and virulent BCG strain of M. tuberculosis. Some novel compounds have been identified which selectively inhibit the dormant tuberculosis bacilli with significantly low IC50 values. This study reports the second molecule after TMC-207, having the ability to inhibit tuberculosis bacilli exclusively in its dormant phase. The synthesis was accomplished by a modified multicomponent Biginelli reaction. A classification model was generated using the binary QSAR approach - recursive partitioning (RP) to identify structural characteristics related to the activity. Physicochemical, structural, topological, connectivity indices, and E-state key descriptors were used for generation of the decision tree. The decision tree could provide insights into structure-activity relationships that will guide the design of more potent inhibitors. This paper reports the second molecule after TMC-207, with the ability to inhibit tuberculosis bacilli in its dormant phase. The paper reports molecules with a novel Pyrimidone Scaffold, the synthesis of which was accomplished with a modified multi-component Biginelli reaction. A classification model was generated using recursive partitioning (RP) technique to identify structural characteristics of the molecules with their varying activities.

Synthesis and pharmacological screening of some 1,4-dihydropyridine and their derivatives for anticonvulsant activity

A new series of 1,4-dihydropyridine and their derivatives have been synthesized and the structures of the compounds have been confirmed by IR and NMR. The title compounds are evaluated for anticonvulsant activity by maximal electroshock method. Some of these compounds have been found to exhibit excellent anticonvulsant activity.

Unexpected formation of new bicyclic γ-lactams by dimerization of α-chloroacetoacetanilides

Novel and unusual dimerization reaction of α-chloroacetoacetanilide under basic reaction condition to give structurally unique 6-oxa-3-azabicyclo[3.1.0]hexane was described.

Synthesis and characterization of N-acylaniline derivatives as potential chemical hybridizing agents (CHAs) for wheat (Triticum aestivum L.)

Induction of male sterility by deployment of chemical hybridizing agents (CHAs) are important in heterosis breeding of self-pollinated crops like wheat, wherein the male and female organs are in the same flower. Taking a lead from the earlier work on rice, a total of 25 N-acylanilines comprising of malonanilates, acetoacetanilides, and acetanilides (including halogenated acetanilides) were synthesized and screened as CHAs on three genotypes of wheat, viz., PBW 343, HD 2046, and HD 2733 at 1500 ppm in the winter of 2001-2002. The N-acylanilines containing variations at the acyl and aromatic domain were synthesized by condensation of substituted anilines with appropriate diesters, acid chlorides, or monoesters. The test compounds with highly electronegative groups such as F/Br at the para position of the aryl ring were identified as the most potent CHAs, causing higher induction of male sterility. A variation of N-substitution at the side chain generally furnished analogues like 4′-fluoroacetoacetanilide (7) and ethyl 4′-fluoromalonanilate (1), which induced 89.12 and 84.66% male sterility, respectively, in PBW 343. Among halogenated acetanilides, the increasing number of chlorine atoms in the side chain led to an increase in the activity of 4′-fluoro (23) and 4′-bromo (24) derivatives of trichoroacetanilides, which induced >87% male sterility. Quantitative structure-activity relationship (QSAR) models indicated the positive contributions of the field effect exemplified by the Swain-Lupton constant (Fp) and negative contributions of the Swain-Lupton resonance constant (R) for the aromatic substitution. The positive influences of parachor (P) for the acyl domain have been underlined. These leads will be significant in explaining the CHA fit in the macromolecular receptor site. The CHAs appeared to act by causing an imbalance in the acid-base equilibrium in pollen mother cells resulting in dissolution of the callose wall by premature callase secretion.

Structure elucidation of N-aryl-2-chloro-3-oxobutanamides with respect to intra- and intermolecular hydrogen bonding

In general, N-aryl-2-chloro-3-oxobutanamides form in solid state an intermolecular hydrogen bond between the anilide hydrogen and the anilide carbonyl oxygen of a neighbouring molecule, which is disrupted in solution. An intramolecular association could not be detected.

Synthesis and structural assignment of oxanilo-N-arylhydrazonoyl chlorides

Oxanilo-N-arylhydrazonoyl chlorides have been prepared from appropriate N-aryl-2-chloro-3-oxobutanamides by the Japp-Klingemann reaction. The structures of the title compounds have been established in the solid state by single-crystal X-ray structure determination and IR spectroscopy, and in solution by IR, UV, and 1H and 13C NMR spectroscopy. The results indicate that the hydrazonoyl chloride moiety adopts the (Z)-configured form. In the crystal, intramolecular hydrogen bonds generally exist between the chloride function and the hydrazone hydrogen atom, and also between the amide hydrogen atom and the double-bonded nitrogen atom of the hydrazone moiety. In solution, this intramolecular hydrogen bonding could not be detected. In compounds with an ortho-chloro-substituted NH-aryl moiety, however, the chlorine atom is involved in hydrogen bonding to the NH hydrogen atom both in the crystal and in solution. Wiley-VCH Verlag GmbH, 69451 Weinheim, Germany, 2002.