22027-53-8

Basic information

• Product Name: METHYL (4-CHLOROBENZOYL)ACETATE
• Synonyms: Methyl p-chlorobenzoylacetate;Methyl (4-chlorobenzoyl)acetate, Methyl 3-(4-chlorophenyl)-3-oxopropionate;(p-Chlorobenzoyl)acetic acid methyl ester;Methyl 3-(4-chlorophenyl)-3-oxopropionate;Methyl 3-(4-chlorophenyl)
• CAS NO: 22027-53-8
• Molecular Formula: C₁₀H₉ClO₃
• Molecular Weight: 212.63
• Product Categories: C10 to C11;Carbonyl Compounds;Esters
• Mol File: 22027-53-8.mol
• Article Data: 45

Chemical Properties

• Melting Point: 42-46 °C(lit.)
• Boiling Point: 100-106°C 0,2mm
• Flash Point: >230 °F
• Appearance: /
• Density: 1.255g/cm³
• Vapor Pressure: 0.00123mmHg at 25°C
• Refractive Index: 1.528
• PKA: 9.54±0.25(Predicted)
• CAS DataBase Reference: METHYL (4-CHLOROBENZOYL)ACETATE(CAS DataBase Reference)
• NIST Chemistry Reference: METHYL (4-CHLOROBENZOYL)ACETATE(22027-53-8)
• EPA Substance Registry System: METHYL (4-CHLOROBENZOYL)ACETATE(22027-53-8)

Safety Data

• Hazard Codes: Xi
• Statements: 36
• Safety Statements: 26-36
• WGK Germany: 3
• Hazardous Substances Data: 22027-53-8(Hazardous Substances Data)

Usage

Description

METHYL (4-CHLOROBENZOYL)ACETATE is an organic compound that serves as a key intermediate in the synthesis of various pharmaceuticals, agrochemicals, and other specialty chemicals. It is characterized by its molecular structure, which includes a methyl ester group and a 4-chlorobenzoyl group, providing it with unique reactivity and properties that make it valuable in chemical synthesis.

Uses

Used in Pharmaceutical Industry:
METHYL (4-CHLOROBENZOYL)ACETATE is used as a reactant for the synthesis of various pharmaceutical compounds. Its unique reactivity allows for the formation of complex molecules with potential therapeutic applications.
Used in Agrochemical Industry:
METHYL (4-CHLOROBENZOYL)ACETATE is used as a building block in the development of agrochemicals, such as pesticides and herbicides. Its chemical properties enable the creation of effective compounds for crop protection and management.
Used in Specialty Chemicals:
METHYL (4-CHLOROBENZOYL)ACETATE is used as an intermediate in the production of specialty chemicals, which find applications in various industries, including plastics, coatings, and dyes.
Reactant involved in:
METHYL (4-CHLOROBENZOYL)ACETATE is involved in several chemical reactions, including:
1. Oxidative coupling with aminopyridines: This reaction allows for the formation of novel heterocyclic compounds with potential applications in various fields.
2. Enantioselective hydrogenation of unprotected β-enamine esters: This reaction enables the selective synthesis of chiral compounds, which are important in the pharmaceutical industry.
3. Intramolecular cyclization: This reaction is used to form cyclic compounds, which can have various applications depending on their specific structures.
4. Oxidative alkylation of benzylic C-H bonds: This reaction allows for the functionalization of benzylic positions, leading to the formation of new compounds with different properties and applications.
5. Tandem oxidative coupling and annulation of phenols: This reaction enables the formation of complex polycyclic structures, which can be used in the synthesis of natural products and other biologically active compounds.

InChI:InChI=1/C10H9ClO3/c1-14-10(13)6-9(12)7-2-4-8(11)5-3-7/h2-5H,6H2,1H3

Upstream product

• 74-11-3 para-chlorobenzoic acid 
• 99-91-2 para-chloroacetophenone 
• 616-38-6 carbonic acid dimethyl ester 
• 67-56-1 methanol 
• 112378-38-8 5-(4-Chloro-benzoyl)-2,2-dimethyl-[1,3]dioxane-4,6-dione 
• 122-01-0 4-chloro-benzoyl chloride 
• 124-38-9 carbon dioxide 
• 74-88-4 methyl iodide 
• 104-88-1 4-chlorobenzaldehyde 
• 6832-16-2 methyl diazoacetate 
• 105-45-3 acetoacetic acid methyl ester 

Downstream Products

• 135505-19-0 3-hydroxy-3-(4-chlorophenyl)-propionic acid methyl ester 
• 135505-19-0 3-hydroxy-3-(4-chlorophenyl)-propionic acid methyl ester 
• 25106-44-9 N-(p-Chlorphenyl)-p-chlorbenzoyl-acetamid 
• 1620519-28-9 (E)-3-benzylamino-2-(4-chlorobenzoyl)-3-phenylacrylic acid methyl ester 
• 1620519-29-0 (Z)-3-benzylamino-2-(4-chlorobenzoyl)-3-phenylacrylic acid methyl ester 
• 1186485-59-5 dimethyl 2,4-bis(4-chlorobenzoyl)pentanedioate 
• 1621176-43-9 1-(4-chlorophenyl)-3-(4,5,6,7-tetrabromo-2H-benzotriazol-2-yl)propan-1-ol 
• 171661-84-0 3-(4-chlorophenyl)-3-hydroxypropyl 4-methylbenzenesulfonate 
• 152467-43-1 1-(4-chlorophenyl)-1,3-propanediol 
• 1421922-19-1 methyl 2-(4-amino-2,5-dimethylbenzyl)-4-(4-chlorophenyl)-1,3-thiazole-5-carboxylate 
• 1421922-18-0 methyl 4-(4-chlorophenyl)-2-(2,5-dimethyl-4-nitrobenzyl)-1,3-thiazole-5-carboxylate 
• 1631153-95-1 3-(4-chlorophenyl)-2-hydroxy-3-oxopropionic acid methyl ester 
• 859190-47-9 C₁₀H₇ClO₄ 
• 1383740-57-5 methyl 2-(4-chlorophenyl)-4,5-dicyanofuran-3-carboxylate 

Relevant articles and documents

Discovery of 7-alkyloxy- [1,2,4] triazolo[1,5-a] pyrimidine derivatives as selective positive modulators of GABAA1 and GABAA4 receptors with potent antiepileptic activity

A series of 7-alkoxy - [1,2,4] triazolo [1, 5-a] pyrimidine derivatives were designed and synthesized. Maximal electroshock (MES) and pentylenetetrazole (PTZ) tests were utilized to access their anticonvulsant activity. Most of the series of compounds exhibited significant anti-seizure effects. Further studies demonstrated that the anticonvulsant activity of these compounds mainly depended on their allosteric potentiation of GABAA receptors. Among them, compound 10c was picked for the mechanism study due to its potent activity. The compound is more sensitive to subunit configurations of synaptic α1β2γ2 and extrasynaptic α4β3δ GABAA receptors, but there were no effects on NMDA receptors and Nav1.2 sodium channels. Meanwhile, 10c acted on the sites of GABAA receptors distinct from commonly used anticonvulsants benzodiazepines and barbiturates. Furthermore, studies from native neurons demonstrated that compound 10c also potentiated the activity of native GABAA receptors and reduced action potential firings in cultured cortical neurons. Such structural compounds may lay a foundation for further designing novel antiepileptic molecules.

Enantioselective decarboxylative Mannich reaction of β-keto acids withC-alkynylN-BocN,O-acetals: access to chiral β-keto propargylamines

The chiral keto-substituted propargylamines are an essential class of multifunctional compounds in the field of organic and pharmaceutical synthesis and have attracted considerable attention, but the related synthetic approaches remain limited. Therefore, a concise and efficient method for the enantioselective synthesis of β-keto propargylaminesviachiral phosphoric acid-catalyzed asymmetric Mannich reaction between β-keto acids andC-alkynylN-BocN,O-acetals as easily availableC-alkynyl imine precursors has been demonstrated here, affording a broad scope of β-ketoN-Boc-propargylamines in high yields (up to 97%) with generally high enantioselectivities (up to 97?:?3 er).

AMINOPYRIMIDINE DERIVATIVES AND THEIR USE AS ARYL HYDROCARBON RECEPTOR MODULATORS

The present invention relates to novel compounds effective as modulators Aryl hydrocarbon receptor (AhR), pharmaceutical composition comprising the compounds for the modulation of AhR, or prevention or treatment of a disease, disorder, or condition associ