40061-54-9

Basic information

• Product Name: ETHYL 2-(2-CHLOROPHENYL)ACETATE
• Synonyms: ETHYL 2-(2-CHLOROPHENYL)ACETATE;Ethyl-2-chlorophenylacetate
• CAS NO: 40061-54-9
• Molecular Formula: C₁₀H₁₁ClO₂
• Molecular Weight: 198.65
• Mol File: 40061-54-9.mol
• Article Data: 25

Chemical Properties

• Boiling Point: 258.431°C at 760 mmHg
• Flash Point: 118.312°C
• Appearance: /
• Density: 1.164g/cm³
• Vapor Pressure: 0.014mmHg at 25°C
• Refractive Index: 1.518
• Storage Temp.: Sealed in dry,Room Temperature
• CAS DataBase Reference: ETHYL 2-(2-CHLOROPHENYL)ACETATE(CAS DataBase Reference)
• NIST Chemistry Reference: ETHYL 2-(2-CHLOROPHENYL)ACETATE(40061-54-9)
• EPA Substance Registry System: ETHYL 2-(2-CHLOROPHENYL)ACETATE(40061-54-9)

Safety Data

• Hazardous Substances Data: 40061-54-9(Hazardous Substances Data)

Usage

Description

ETHYL 2-(2-CHLOROPHENYL)ACETATE is an organic compound that serves as a key intermediate in the synthesis of various pharmaceutical compounds. It is characterized by its chlorophenyl group attached to an ethyl acetate moiety, which contributes to its reactivity and utility in chemical reactions.

Uses

Used in Pharmaceutical Industry:
ETHYL 2-(2-CHLOROPHENYL)ACETATE is used as a synthetic intermediate for the preparation of clotrimazole analogs with antimalarial activities. These analogs are designed to target and inhibit the growth of Plasmodium parasites, which are responsible for causing malaria.
ETHYL 2-(2-CHLOROPHENYL)ACETATE is also used as a synthetic intermediate for the preparation of non-nucleoside adenosine kinase inhibitors of aminoarylarylethynylpyrimidines. These inhibitors play a crucial role in the development of novel therapeutic agents for the treatment of various diseases, including cancer and other adenosine-related disorders.

Synthesis Reference(s)

Synthetic Communications, 20, p. 2631, 1990 DOI: 10.1080/00397919008051471

InChI:InChI=1/C10H11ClO2/c1-2-13-10(12)7-8-5-3-4-6-9(8)11/h3-6H,2,7H2,1H3

Upstream product

• 75280-08-9 ethyl α-methylthio-(o-chlorophenyl)acetate 
• 75-03-6 ethyl iodide 
• 623-73-4 diazoacetic acid ethyl ester 
• 108-90-7 chlorobenzene 
• 1071-46-1 hydrogen ethyl malonate 
• 346656-42-6 2-(2-chlorophenyl)-5,5-dimethyl-1,3,2-dioxaborinane 
• 101-97-3 Ethyl 2-phenylethanoate 
• 611-19-8 1-chloro-2-(chloromethyl)benzene 
• 623-49-4 ethyl cyanoformate 
• 541-41-3 chloroformic acid ethyl ester 
• 609-65-4 o-chlorobenzoyl chloride 
• 201230-82-2 carbon monoxide 
• 141-52-6 sodium ethanolate 
• 64-17-5 ethanol 

Downstream Products

• 19819-95-5 2-(2-chlorophenyl)-1-ethanol 
• 402740-43-6 6-(2-chlorophenyl)-8-methyl-2-methylsulfanyl-8H-pyrido[2,3-d]pyrimidin-7-one 
• 77778-73-5 (2-chlorophenyl)(4-nitrophenyl)methanone 
• 53672-36-9 2-(2-Chloro-phenyl)-N-{2-[2-hydroxy-3-(2-nitro-phenoxy)-propylamino]-propyl}-acetamide 
• 85150-76-1 1,3-bis(2-chlorophenyl)propan-2-one 
• 83657-82-3 4-(2-Chloro-phenyl)-3-oxo-butyric acid ethyl ester 
• 1379313-44-6 C₁₁H₁₃ClO₂ 
• 2184-85-2 2-(2-chloro-phenyl)-propanoic acid 
• 614-75-5 2-Hydroxyphenylacetic acid 
• 13511-30-3 ethyl 2-(2-chlorophenyl)-2-hydroxyacetate 
• 1629188-65-3 C₁₁H₁₁ClO₂ 

Relevant articles and documents

Enantioselective Desymmetrization of 2-Aryl-1,3-propanediols by Direct O-Alkylation with a Rationally Designed Chiral Hemiboronic Acid Catalyst That Mitigates Substrate Conformational Poisoning

Enantioselective desymmetrization by direct monofunctionalization of prochiral diols is a powerful strategy to prepare valuable synthetic intermediates in high optical purity. Boron acids can activate diols toward nucleophilic additions; however, the design of stable chiral catalysts remains a challenge and highlights the need to identify new chemotypes for this purpose. Herein, the discovery and optimization of a bench-stable chiral 9-hydroxy-9,10-boroxarophenanthrene catalyst is described and applied in the highly enantioselective desymmetrization of 2-aryl-1,3-diols using benzylic electrophiles under operationally simple, ambient conditions. Nucleophilic activation and discrimination of the enantiotopic hydroxy groups on the diol substrate occurs via a defined chairlike six-membered anionic complex with the hemiboronic heterocycle. The optimal binaphthyl-based catalyst 1g features a large aryloxytrityl group to effectively shield one of the two prochiral hydroxy groups on the diol complex, whereas a strategically placed "methyl blocker"on the boroxarophenanthrene unit mitigates the deleterious effect of a competing conformation of the complexed diol that compromised the overall efficiency of the desymmetrization process. This methodology affords monoalkylated products in enantiomeric ratios equal or over 95:5 for a wide range of 1,3-propanediols with various 2-aryl/heteroaryl groups.

2-(Halogenated Phenyl) acetamides and propanamides as potent TRPV1 antagonists

A series consisting of 117 2-(halogenated phenyl) acetamide and propanamide analogs were investigated as TRPV1 antagonists. The structure–activity analysis targeting their three pharmacophoric regions indicated that halogenated phenyl A-region analogs exhibited a broad functional profile ranging from agonism to antagonism. Among the compounds, antagonists 28 and 92 exhibited potent antagonism toward capsaicin for hTRPV1 with Ki[CAP] = 2.6 and 6.9 nM, respectively. Further, antagonist 92 displayed promising analgesic activity in vivo in both phases of the formalin mouse pain model. A molecular modeling study of 92 indicated that the two fluoro groups in the A-region made hydrophobic interactions with the receptor.

OXIDATIVE COUPLING OF ARYL BORON REAGENTS WITH SP3-CARBON NUCLEOPHILES, AND AMBIENT DECARBOXYLATIVE ARYLATION OF MALONATE HALF-ESTERS VIA OXIDATIVE CATALYSIS

Described herein are methods of oxidative coupling of aryl boron reagents with sp3-carbon nucleophiles, and ambient decarboxylative arylation of malonate half-esters via oxidative catalysis.