101-92-8

Basic information

• Product Name: 4'-Chloroacetoacetanilide
• Synonyms: LABOTEST-BB LT01274571;4'-CHLOROACETACETANILIDE;4'-CHLOROACETOACETANILIDE;ACETOACET-P-CHLORANILIDE;ACETOACET-P-CHLOROANILIDE;Acetoacet-d-Chloroanilide;ACETOACET-P-CHLOROAMILIDE;p-Acetoacetochloroanilide
• CAS NO: 101-92-8
• Molecular Formula: C₁₀H₁₀ClNO₂
• Molecular Weight: 211.64
• EINECS: 202-989-6
• Product Categories: Amides;Carbonyl Compounds;Organic Building Blocks;Building Blocks;C8 to C20+;Carbonyl Compounds;Chemical Synthesis;Organic Building Blocks
• Mol File: 101-92-8.mol

Chemical Properties

• Melting Point: 131-134 °C(lit.)
• Boiling Point: 303°C (rough estimate)
• Flash Point: 196 °C
• Appearance: Off-white to beige/Crystalline Powder
• Density: 1.44 g/cm3 (20℃)
• Vapor Density: 7.31
• Refractive Index: 1.5388 (estimate)
• Storage Temp.: Store below +30°C.
• Solubility: acetone: soluble25mg/mL, clear, colorless to light yellow
• PKA: 11.00±0.46(Predicted)
• CAS DataBase Reference: 4'-Chloroacetoacetanilide(CAS DataBase Reference)
• NIST Chemistry Reference: 4'-Chloroacetoacetanilide(101-92-8)
• EPA Substance Registry System: 4'-Chloroacetoacetanilide(101-92-8)

Safety Data

• Safety Statements: 24/25
• WGK Germany: 1
• RTECS: AK4375000
• Hazardous Substances Data: 101-92-8(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
4'-Chloroacetoacetanilide is used as a key intermediate in the synthesis of drugs, particularly for the development of novel therapeutic agents. Its chemical properties allow for versatile reactions and modifications, making it a valuable component in medicinal chemistry.
Used in Agrochemical Industry:
In the agrochemical sector, 4'-Chloroacetoacetanilide is utilized as a precursor for the production of various pesticides and insecticides. Its reactivity and structural features contribute to the creation of effective compounds for agricultural applications.
Used in Chemical Research:
4'-Chloroacetoacetanilide is employed in academic and industrial research settings for the investigation of novel chemical reactions and the development of new synthetic methodologies. Its unique properties make it a useful tool for exploring new avenues in organic chemistry.
Used in Recombinant Androgen Receptor Competitive Binding Assay:
4'-Chloroacetoacetanilide is used as a component in the recombinant androgen receptor competitive binding assay, which is crucial for the analysis of natural, synthetic, and environmental chemicals. This application aids in understanding the interactions and effects of various compounds on androgen receptors, contributing to the broader field of endocrine disruption research.

Safety Profile

Moderately toxic by intraperitonealroute. Combustible whenexposed to heat or flame. Dangerous: see ANILINE andCYANIDE. Can react vigorously with oxidizing materials.To fight fire, use water, foam, CO2, water mist, drychemical. When heated to decompo

Upstream product

• 110-86-1 pyridine 
• 56-23-5 tetrachloromethane 
• 141-97-9 ethyl acetoacetate 
• 106-47-8 4-chloro-aniline 
• 674-82-8 4-methyleneoxetan-2-one 
• 1197-56-4 ammonium (4-chlorophenyl)carbamodithioate 
• 30645-78-4 3-(4-chloro-phenyl)-6-methyl-[1,3]oxazine-2,4-dione 
• 141-43-5 ethanolamine 
• 109-73-9 N-butylamine 
• 121-44-8 triethylamine 
• 5394-63-8 2,2,6-trimethyl-4H-1,3-dioxin-4-one 
• 1352630-23-9 3-(4-chlorophenylamino)-2-[(4-chlorophenylimino)methyl]acrylonitrile 
• 105-45-3 acetoacetic acid methyl ester 
• 1118-84-9 allyl acetoacetate 

Downstream Products

• 2585-04-8 6-chloro-4-methyl-quinolin-2-ol 
• 34797-69-8 p-chloro-o-nitroacetoacetanilide 
• 64596-12-9 3-amino-crotonic acid-(4-chloro-anilide) 
• 42248-27-1 2-(hydroxyimino)-3-oxo-N-(4-chlorophenyl)butanamide 
• 103207-61-0 3,5-dimethyl-pyrrole-2,4-dicarboxylic acid bis-(4-chloro-anilide) 
• 51903-78-7 N-<4-Chlor-phenyl>-α.β-bis-hydroxyimino-butyramid 
• 19359-28-5 2-chloro-N-(4-chlorophenyl)-3-oxobutanamide 
• 92907-09-0 (2-Hydroxy-5-sulfamoyl-phenylazo)-4-chlor-acetoacetanilid 
• 82275-31-8 3-Methyl-3-morpholinoamino-N-(4-chlorphenyl)acrylamid 
• 112697-72-0 2-Methyl-[1,8]naphthyridine-3-carboxylic acid (4-chloro-phenyl)-amide 
• 139050-67-2 4-(4-chlorophenylcarbamoyl)-3-methyl-6,6-diphenyl-1,2-dioxan-3-ol 
• 111888-45-0 3-Methyl-1,4-dioxy-quinoxaline-2-carboxylic acid (4-chloro-phenyl)-amide 
• 139051-07-3 4-(4-chlorophenylcarbamoyl)-6,6-diethyl-3-methyl-1,2-dioxan-3-ol 
• 88267-44-1 1-anilino-N-(4-chloro-phenyl)-2-methyl-4,5-diphenyl-3-pyrrolecarboxamid 

Relevant articles and documents

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.

Antiproliferative effect, alteration of cancer cell cycle progression and potential MET kinase inhibition induced by 3,4-dihydropyrimidin-2(1H)-one C5 amide derivatives

Cancer continues to be the second leading cause of death worldwide. Discovery of novel therapeutic agents has crucial importance for improvement of our medical management capabilities. Dysregulation of the MET receptor tyrosine kinase pathway plays an important role in cancer progression, making this receptor an attractive molecular target for anticancer drug discovery. In this study, twenty-seven 3,4-dihydropyrimidin-2(1H)-one C5 amide derivatives were synthesized and their cancer cell growth inhibitory activity was examined against MCF-7, HT-29 and MOLT-4 cells and also NIH/3T3 non-cancer cells by MTT assay. The antiproliferative effect of the most potent derivatives were tested against MET-dependent EBC-1 and MKN-45, lung and gastric cancer cell lines, respectively. MET kinase inhibition was measured by a Homogenous Time Resolved Fluorescence (HTRF) Assay. The influence of the test compounds on cell cycle was examined by RNase/PI flow cytometric assay. A number of compounds exhibited considerable antiproliferative effects against breast and colon cancer and leukemia cell lines, relatively sparing non-cancer cells. Some derivatives bearing benzothiazolyl carboxamide moiety at C5 position (15, 21, 23, 31, and 37) showed the highest activities with IC50 values as low as 10.9 μM. These compounds showed antiproliferative effects also against MET-amplified cells and dose-dependently inhibited MET kinase activity. They also induced G0/G1 cell cycle arrest at lower doses and apoptosis at higher doses. Molecular docking and dynamics simulation studies confirmed the interaction of compound 23 with the active site of the MET receptor. These findings demonstrate that 3,4-dihydropyrimidin-2(1H)-one analogues may represent promising targeted anticancer agents.

Synthesis of β-Ketoamide Curcumin Analogs for Anti-Diabetic and AGEs Inhibitory Activities

Two different series of novel β-ketoamide curcumin analogs enriched in biological activities have been synthesized. The synthesized compounds were screened for their in?vitro anti-diabetic and AGEs inhibitory activities and exhibited potent to good anti-diabetic and AGEs inhibitory activities. The molecular docking study was also performed with the α-amylase enzyme.

Ru(bpy)33+ electrochemiluminescence detection of aliphatic and aromatic amines with diketene

A new derivatization method for the detection of aliphatic and aromatic amines, based on electro-chemiluminescence (ECL) with Ru(bpy)32+ is proposed. Sample amines were derivatized to acetoacetylamide-type derivatives using diketene. The derivatives were detected by reversed-phase HPLC with ECL detection using Ru(bpy)32+.

Nickel-promoted oxidative domino Csp3-H/N-H bond double-isocyanide insertion reaction to construct pyrrolin-2-ones

The first nickel-catalyzed oxidative domino Csp3-H/N-H double isocyanide insertion reaction of acetamides with isocyanides has been developed for the synthesis of pyrrolin-2-one derivatives. A wide range of acetamides bearing various functional groups are compatible with this reaction system by utilizing Ni(acac)2as a catalyst. In this transformation, isocyanide could serve as a C1 connector and insert into the inactive Csp3-H bond, representing an effective way to construct heterocycles.

Synthesis and in vitro Antidiabetic Screening of Novel Dihydropyrimidine Derivatives

Abstract: A series of N-substituted-6-methyl-4-{4-[5-(4-nitrophenyl)-1,3,4-oxadiazol-2-yl]methoxyphenyl}-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxamides have been synthesized by the condensation of newly synthesized {4-[5-(4-nitrophenyl)-1,3,4-oxadiazol-2-yl]methoxy}benzaldehyde with variously substituted acetoacetanilides and urea in the presence of ethanol. The synthesized compounds have been characterized by 1H, 13C NMR, IR spectroscopy, and mass spectrometry. All synthesized compounds were evaluated for in vitro antidiabetic activity using the α-amylase inhibition assay with the 3,5-dinitrosalicylic acid (DNSA) reagent.

Compound containing thiophene structure and application thereof in medicine

The present invention provides a compound of formula (I) and a pharmaceutically acceptable salt thereof, for use in the prevention and/or treatment of thromboembolic diseases and/or thromboembolic complications, wherein all variables are as defined in the specification.

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.

Design, synthesis, and molecular docking study of new monastrol analogues as kinesin spindle protein inhibitors

Lung, colorectal, and breast cancers are the top three types of cancer by incidence and are responsible for one-third of the cancer incidence and mortality. A series of 18 3,4-dihydropyrimidine analogues bearing a 1,2-methylenedioxybenzene component at position 4 with diverse side chains at positions 5 and 6 was designed and synthesized as inhibitors of the Eg5 kinesin enzyme. Target compounds were screened for their anticancer activity according to the NCI-USA protocol toward a panel of 60 cancer cell lines. Compounds 12a and 12b displayed the best antiproliferation activity against many cell lines. Interestingly, compound 12a displayed lethal effects against non-small-cell lung cancer NCI-H522 cells (?42.26%) and MDA-MB-468 breast cancer cells (?1.10%) at a single-dose assay concentration of 10?5 M. Compounds 11c, 11d, 11g, 12a–d, 13, 15, and 18a were assayed against the kinesin enzyme, with IC50 values ranging from 1.2 to 18.71 μM, which were more potent compared with monastrol (IC50 = 20 μM). Cell cycle analysis of NCI-H522 cells treated with compound 12a showed cell cycle arrest at the G2/M phase. Furthermore, the expression levels of active caspase-3 and -9 were measured. A molecular docking study was performed for some demonstrative compounds as well as monastrol docked into the allosteric binding site of the kinesin spindle protein.

HFIP-mediated strategy towards β-oxo amides and subsequent Friedel-Craft type cyclization to 2?quinolinones using recyclable catalyst

A simple and cost-effective 1,1,1,3,3,3-hexafluoro-2-propanol (HFIP)-mediated protocol for the synthesis of β-oxo amides has been described by using amines and β-keto esters as substrates. The reaction conditions were found to be highly efficient towards the cleavage of C[sbnd]O bond and consequent formation of the products in excellent yields and selectivity. The obtained β-oxo amides were further transformed in to the synthetically useful 2?quinolinones via intramolecular Friedel-Craft type cyclization of aromatic ring using ferrites as a recyclable catalyst. A spectrum of substrates bearing broad range of functional groups were well tolerated under the reaction conditions. The proposed mechanistic pathways were substantially verified by literature and mass-spectroscopic evidences.