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

Uses

Reactant involved in:Oxidative coupling with aminopyridinesEnantioselective hydrogenation of unprotected β-enamine estersIntramolecular cyclizationOxidative alkylation of benzylic C-H bondsTandem oxidative coupling and annulation of phenols

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

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

Downstream Products

• 63131-09-9 C₁₅H₂₀ClO₄PS₂ 
• 25106-44-9 N-(p-Chlorphenyl)-p-chlorbenzoyl-acetamid 
• 954374-37-9 methyl 3-(4-chlorophenyl)-2-(1,2,3,4-tetrahydronaphthalen-1-yl)-3-oxopropanoate 
• 954374-41-5 methyl 3-(4-chlorophenyl)-2-(2,3-dihydro-1H-inden-1-yl)-3-oxopropanoate 
• 954374-30-2 methyl 2-benzhydryl-3-(4-chlorophenyl)-3-oxopropanoate 
• 135505-19-0 3-hydroxy-3-(4-chlorophenyl)-propionic acid methyl ester 
• 1245606-54-5 (Z)-1-(4-chlorophenyl)-3-methoxy-3-oxoprop-1-en-1-amine hydrochloride 
• 1403993-86-1 methyl 2-(4-chlorobenzoyl)hept-6-ynoate 
• 810670-03-2 methyl (R)-3-acetylamino-3-(4-chlorophenyl)propionate 
• 7515-18-6 methyl 3-(p-chlorophenyl)-2-propynoate 

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